NCBI Taxonomy: 36653

Penicillium commune (ncbi_taxid: 36653)

found 104 associated metabolites at species taxonomy rank level.

Ancestor: Penicillium

Child Taxonomies: none taxonomy data.

Thymidine

1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione

C10H14N2O5 (242.0903)


Deoxythymidine, also known as 2-deoxy-5-methyluridine or 5-methyl-2-deoxyuridine, is a member of the class of compounds known as pyrimidine 2-deoxyribonucleosides. Pyrimidine 2-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2. Deoxythymidine is soluble (in water) and a very weakly acidic compound (based on its pKa). Deoxythymidine can be synthesized from thymine. Deoxythymidine is also a parent compound for other transformation products, including but not limited to, tritiated thymidine, alpha-tritiated thymidine, and 5,6-dihydrothymidine. Deoxythymidine can be found in a number of food items such as butternut squash, mammee apple, catjang pea, and climbing bean, which makes deoxythymidine a potential biomarker for the consumption of these food products. Deoxythymidine can be found primarily in most biofluids, including blood, amniotic fluid, cerebrospinal fluid (CSF), and urine, as well as throughout most human tissues. Deoxythymidine exists in all living species, ranging from bacteria to humans. In humans, deoxythymidine is involved in the pyrimidine metabolism. Deoxythymidine is also involved in few metabolic disorders, which include beta ureidopropionase deficiency, dihydropyrimidinase deficiency, MNGIE (mitochondrial neurogastrointestinal encephalopathy), and UMP synthase deficiency (orotic aciduria). Moreover, deoxythymidine is found to be associated with canavan disease and degenerative disc disease. Thymidine (deoxythymidine; other names deoxyribosylthymine, thymine deoxyriboside) is a pyrimidine deoxynucleoside. Deoxythymidine is the DNA nucleoside T, which pairs with deoxyadenosine (A) in double-stranded DNA. In cell biology it is used to synchronize the cells in G1/early S phase . Thymidine, also known as deoxythymidine or deoxyribosylthymine or thymine deoxyriboside, is a pyrimidine deoxynucleoside. It consists of the nucleobase thymine attached to deoxyribose through a beta N- glycosidic bond. Thymidine also belongs to the class of organic compounds known as pyrimidine 2-deoxyribonucleosides. Pyrimidine 2-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2. Deoxythymidine (or thymidine) is the DNA nucleoside T, which pairs with deoxyadenosine (A) in double-stranded DNA. Therefore, thymidine is essential to all life. Indeed, thymidine exists in all living species, ranging from bacteria to plants to humans. Within humans, thymidine participates in a number of enzymatic reactions. In particular, thymidine can be biosynthesized from 5-thymidylic acid through its interaction with the enzyme cytosolic purine 5-nucleotidase. In addition, thymidine can be converted into 5-thymidylic acid; which is catalyzed by the enzyme thymidine kinase. Deoxythymidine can be phosphorylated with one, two or three phosphoric acid groups, creating dTMP (deoxythymidine monophosphate), dTDP, or dTTP (for the di- and tri- phosphates, respectively). dTMP can be incorporated into DNA via DNA polymerases. In cell biology, thymidine can be used to synchronize the cells in S phase. Derivatives of thymidine are used in a number of drugs, including Azidothymidine (AZT), which is used in the treatment of HIV infection. AZT inhibits the process of reverse transcription in the human immunodeficiency virus. Thymidine is a pyrimidine 2-deoxyribonucleoside having thymine as the nucleobase. It has a role as a metabolite, a human metabolite, an Escherichia coli metabolite and a mouse metabolite. It is functionally related to a thymine. It is an enantiomer of a telbivudine. Thymidine is a pyrimidine deoxynucleoside. Thymidine is the DNA nucleoside T, which pairs with deoxyadenosine (A) in double-stranded DNA. In cell biology it is used to synchronize the cells in S phase. Thymidine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Thymidine is a natural product found in Fritillaria thunbergii, Saussurea medusa, and other organisms with data available. Thymidine is a pyrimidine nucleoside that is composed of the pyrimidine base thymine attached to the sugar deoxyribose. As a constituent of DNA, thymidine pairs with adenine in the DNA double helix. (NCI04) Thymidine is a metabolite found in or produced by Saccharomyces cerevisiae. A nucleoside in which THYMINE is linked to DEOXYRIBOSE. A pyrimidine 2-deoxyribonucleoside having thymine as the nucleobase. KEIO_ID T014; [MS2] KO009272 KEIO_ID T014 Thymidine, a specific precursor of deoxyribonucleic acid, is used as a cell synchronizing agent. Thymidine is a DNA synthesis inhibitor that can arrest cell at G1/S boundary, prior to DNA replication[1][2][3]. Thymidine, a specific precursor of deoxyribonucleic acid, is used as a cell synchronizing agent. Thymidine is a DNA synthesis inhibitor that can arrest cell at G1/S boundary, prior to DNA replication[1][2][3].

   

Ergosterol

(1R,3aR,7S,9aR,9bS,11aR)-1-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1H,2H,3H,3aH,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-ol

C28H44O (396.3392)


Ergosterol is a phytosterol consisting of ergostane having double bonds at the 5,6-, 7,8- and 22,23-positions as well as a 3beta-hydroxy group. It has a role as a fungal metabolite and a Saccharomyces cerevisiae metabolite. It is a 3beta-sterol, an ergostanoid, a 3beta-hydroxy-Delta(5)-steroid and a member of phytosterols. A steroid of interest both because its biosynthesis in FUNGI is a target of ANTIFUNGAL AGENTS, notably AZOLES, and because when it is present in SKIN of animals, ULTRAVIOLET RAYS break a bond to result in ERGOCALCIFEROL. Ergosterol is a natural product found in Gladiolus italicus, Ramaria formosa, and other organisms with data available. ergosterol is a metabolite found in or produced by Saccharomyces cerevisiae. A steroid occurring in FUNGI. Irradiation with ULTRAVIOLET RAYS results in formation of ERGOCALCIFEROL (vitamin D2). See also: Reishi (part of). Ergosterol, also known as provitamin D2, belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Thus, ergosterol is considered to be a sterol lipid molecule. Ergosterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Ergosterol is the biological precursor to vitamin D2. It is turned into viosterol by ultraviolet light, and is then converted into ergocalciferol, which is a form of vitamin D. Ergosterol is a component of fungal cell membranes, serving the same function that cholesterol serves in animal cells. Ergosterol is not found in mammalian cell membranes. A phytosterol consisting of ergostane having double bonds at the 5,6-, 7,8- and 22,23-positions as well as a 3beta-hydroxy group. Ergosterol. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=57-87-4 (retrieved 2024-07-12) (CAS RN: 57-87-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Ergosterol is the primary sterol found in fungi, with antioxidative, anti-proliferative, and anti-inflammatory effects. Ergosterol is the primary sterol found in fungi, with antioxidative, anti-proliferative, and anti-inflammatory effects.

   

Methyl indole-3-acetate

(1H-Indol-3-yl)acetic acid methyl ester

C11H11NO2 (189.079)


Indole-3-methyl acetate, also known as methyl indole-3-acetate (methyl-IAA), is a catabolite of tryptophan converted by the gut microbiota. After absorption through the intestinal epithelium, tryptophan catabolites enter the bloodstream and are later excreted in the urine (PMID: 30120222). Pediatric enthesitis-related arthritis (ERA) patients (i.e. spondyloarthropathy associated with inflammatory bowel disease) have intestinal inflammation and decreased gut microbial diversity. Such alterations in the gut microbiota resulted in the reduction of tryptophan metabolism and several tryptophan metabolites in pediatric ERA fecal samples, including indole-3-methyl acetate (PMID: 27786174). Indole-3-methyl acetate is found in apple, and has been isolated from immature seeds of beach pea (Lathyrus maritimus), Vicia amurensis, wild soybean (Glycine soja), lobiya (Vigna catiang var. sinensis) and hyacinth bean (Dolichos lablab). Isolated from immature seeds of beach pea (Lathyrus maritimus), Vicia amurensis, wild soybean (Glycine soja), lobiya (Vigna catiang variety sinensis) and hyacinth bean (Dolichos lablab). Indole-3-methyl acetate is found in many foods, some of which are gram bean, yellow wax bean, common bean, and sweet orange. Methyl 2-(1H-indol-3-yl)acetate is an endogenous metabolite.

   

Thymine

5-Methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

C5H6N2O2 (126.0429)


Thymine, also known as 5-methyluracil, belongs to the class of organic compounds known as hydroxypyrimidines. These are organic compounds containing a hydroxyl group attached to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. Thymine was first isolated in 1893 by Albrecht Kossel and Albert Neumann from calves thymus glands, hence its name. Thymine is one of the 4 nuelcoebases found in DNA and is essential to all life. Thymine exists in all living species, ranging from bacteria to plants to humans. Thymine combined with deoxyribose creates the nucleoside deoxythymidine (also called thymidine) which when phosphorylated to dTDP can be incorporated into DNA via DNA polymerases. Thymidine can be phosphorylated with up to three phosphoric acid groups, producing dTMP (deoxythymidine monophosphate) dTDP and/or dTTP. In RNA thymine is replaced with uracil in most cases. In DNA, thymine binds to adenine via two hydrogen bonds to assist in stabilizing the nucleic acid structures. Within humans, thymine participates in a number of enzymatic reactions. In particular, thymine and deoxyribose 1-phosphate can be biosynthesized from thymidine through its interaction with the enzyme thymidine phosphorylase. In addition, thymine can be converted into dihydrothymine; which is mediated by the enzyme dihydropyrimidine dehydrogenase [NADP(+)]. One of the pyrimidine bases of living matter. Derivation: Hydrolysis of deoxyribonucleic acid, from methylcyanoacetylurea by catalytic reduction. Use: Biochemical research. (Hawleys Condensed Chemical Dictionary) Acquisition and generation of the data is financially supported in part by CREST/JST. COVID info from COVID-19 Disease Map Corona-virus KEIO_ID T015 Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Thymine is one of the four nucleobases in the nucleic acid of DNA and can be a target for actions of 5-fluorouracil (5-FU) in cancer treatment, with a Km of 2.3 μM. Thymine is one of the four nucleobases in the nucleic acid of DNA and can be a target for actions of 5-fluorouracil (5-FU) in cancer treatment, with a Km of 2.3 μM. Thymine is one of the four nucleobases in the nucleic acid of DNA and can be a target for actions of 5-fluorouracil (5-FU) in cancer treatment, with a Km of 2.3 μM.

   

N-Acetyltryptophan

(2S)-2-[(1-hydroxyethylidene)amino]-3-(1H-indol-3-yl)propanoic acid

C13H14N2O3 (246.1004)


N-Acetyl-L-tryptophan or N-Acetyltryptophan, belongs to the class of organic compounds known as N-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. N-Acetyltryptophan can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-Acetyltryptophan is a biologically available N-terminal capped form of the proteinogenic alpha amino acid L-tryptophan. N-acetyl amino acids can be produced either via direct synthesis of specific N-acetyltransferases or via the proteolytic degradation of N-acetylated proteins by specific hydrolases. N-terminal acetylation of proteins is a widespread and highly conserved process in eukaryotes that is involved in protection and stability of proteins (PMID: 16465618). About 85\\\\\% of all human proteins and 68\\\\\% of all yeast proteins are acetylated at their N-terminus (PMID: 21750686). Several proteins from prokaryotes and archaea are also modified by N-terminal acetylation. The majority of eukaryotic N-terminal-acetylation reactions occur through N-acetyltransferase enzymes or NAT’s (PMID: 30054468). These enzymes consist of three main oligomeric complexes NatA, NatB, and NatC, which are composed of at least a unique catalytic subunit and one unique ribosomal anchor. The substrate specificities of different NAT enzymes are mainly determined by the identities of the first two N-terminal residues of the target protein. The human NatA complex co-translationally acetylates N-termini that bear a small amino acid (A, S, T, C, and occasionally V and G) (PMID: 30054468). NatA also exists in a monomeric state and can post-translationally acetylate acidic N-termini residues (D-, E-). NatB and NatC acetylate N-terminal methionine with further specificity determined by the identity of the second amino acid. N-acetylated amino acids, such as N-acetyltryptophan can be released by an N-acylpeptide hydrolase from peptides generated by proteolytic degradation (PMID: 16465618). In addition to the NAT enzymes and protein-based acetylation, N-acetylation of free tryptophan can also occur. Many N-acetylamino acids, including N-acetyltryptophan are classified as uremic toxins if present in high abundance in the serum or plasma (PMID: 26317986; PMID: 20613759). Uremic toxins are a diverse group of endogenously produced molecules that, if not properly cleared or eliminated by the kidneys, can cause kidney damage, cardiovascular disease and neurological deficits (PMID: 18287557). N-Acetyltryptophan has also been used as a protein stabilizer. It prevents protein molecules from oxidative degradation by scavenging oxygen dissolved in protein solutions (PMID: 21903216 ). N-Acetyltryptophan has been identified as a catabolite of tryptophan generated by the gut microbiota. After absorption through the intestinal epithelium, tryptophan catabolites enter the bloodstream and are later excreted in the urine (PMID: 28916042). N-Acetyltryptophan is an inhibitor of cytochrome c release and an antagonist of the neurokinin 1 receptor (NK-1R). These inhibitory effects are thought have a useful role in neuroprotection. For instance, in mouse models of amyotrophic lateral sclerosis (ALS) the administration of N-Acetyltryptophan has been shown delay disease onset, extend survival, and ameliorate deterioration in motor performance ALS transgenic mice (PMID: 25986728). N-acetyltryptophan has been shown to significantly reduce blood-brain barrier permeability and improve functional outcome in rat models of traumatic brain injury (PMID: 29256408). N-Acetyltryptophan has also been shown to have a role in preventing hepatic ischemia-reperfusion injury. This is thought to occur through de-activation of the RIP2/caspase/IL-1beta signaling pathway (PMID: 31184936). D004791 - Enzyme Inhibitors > D011480 - Protease Inhibitors Ac-DL-Trp-OH is an endogenous metabolite. Ac-DL-Trp-OH is an endogenous metabolite. N-Acetyl-L-tryptophan is an endogenous metabolite.

   

Homogentisic acid

2-(2,5-dihydroxyphenyl)acetic acid

C8H8O4 (168.0423)


Homogentisic acid, also known as melanic acid, is an intermediate in the breakdown or catabolism of tyrosine and phenylalanine. It is generated from the compound p-hydroxyphenylpyruvate through the enzyme p-hydroxyphenylpyruvate dehydrogenase. The resulting homogentisic acid is then broken down into 4-maleylacetoacetate via the enzyme homogentisate 1,2-dioxygenase. Homogentisic acid is also found in other organisms. For instance, it can found in Arbutus unedo (strawberry-tree) honey, in the bacterial plant pathogen Xanthomonas campestris as well as in the yeast Yarrowia lipolytica where it is associated with the production of brown pigments. Homogentisic acid can be oxidatively dimerized to form hipposudoric acid, one of the main constituents of the blood sweat of hippopotamuses. When present in sufficiently high levels, homogentisic acid can function as an osteotoxin and a renal toxin. An osteotoxin is a substance that causes damage to bones and/or joints. A renal toxin causes damage to the kidneys. Chronically high levels of homogentisic acid are associated with alkaptonuria (OMIM: 203500), an inborn error of metabolism. Alkaptonuria is a rare inherited genetic disorder in which the body cannot process the amino acids phenylalanine and tyrosine. It is caused by a mutation in the enzyme homogentisate 1,2-dioxygenase (EC 1.13.11.5), which leads to an accumulation of homogentisic acid in the blood and tissues. Homogentisic acid and its oxidized form benzoquinone acetic acid are excreted in the urine, giving it an unusually dark color. The accumulating homogentisic acid (and benzoquinone acetic acid) causes damage to cartilage (ochronosis, leading to osteoarthritis) and heart valves as well as precipitating as kidney stones and stones in other organs. More specifically, homogentisic acid can be converted to benzoquinone acetic acid (BQA), and the resulting BQA can be readily converted to polymers that resemble the dark skin pigment melanin. These polymers are deposited in the collagen, a connective tissue protein, of particular tissues such as cartilage. This process is called ochronosis (as the tissue looks ochre); ochronotic tissue is stiffened and unusually brittle, impairing its normal function and causing damage. Homogentisic acid is the primary precursor of melanin synthesis in Vibrio cholerae. 2-(3,6-dihydroxyphenyl)acetic acid, also known as homogentisic acid or homogentisate, is a member of the class of compounds known as 2(hydroxyphenyl)acetic acids. 2(hydroxyphenyl)acetic acids are phenylacetic acids that carry a hydroxyl group at the 2-position. 2-(3,6-dihydroxyphenyl)acetic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). 2-(3,6-dihydroxyphenyl)acetic acid can be found in a number of food items such as gooseberry, angelica, chinese broccoli, and cucumber, which makes 2-(3,6-dihydroxyphenyl)acetic acid a potential biomarker for the consumption of these food products. 2-(3,6-dihydroxyphenyl)acetic acid can be found primarily in blood, feces, and urine, as well as in human cartilage, connective tissue and kidney tissues. In humans, 2-(3,6-dihydroxyphenyl)acetic acid is involved in few metabolic pathways, which include disulfiram action pathway, phenylalanine and tyrosine metabolism, and tyrosine metabolism. 2-(3,6-dihydroxyphenyl)acetic acid is also involved in several metabolic disorders, some of which include dopamine beta-hydroxylase deficiency, tyrosinemia type 3 (TYRO3), alkaptonuria, and tyrosinemia type 2 (or richner-hanhart syndrome). Moreover, 2-(3,6-dihydroxyphenyl)acetic acid is found to be associated with alkaptonuria. 2-(3,6-dihydroxyphenyl)acetic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Apart from treatment of the complications (such as pain relief using NSAIDs and joint replacement for the cartilage damage), vitamin C has been used to reduce the ochronosis and lowering of the homogentisic acid levels may be attempted with a low-protein diet. Recently the drug nitisinone has been found to suppress homogentisic acid production. Nitrisinone inhibits the enzyme, 4-hydroxyphenylpyruvate dioxygenase, responsible for converting tyrosine to homogentisic acid, thereby blocking the production and accumulation of homogentisic acid. Nitisinone treatment has been shown to cause a 95\\\\% reduction in plasma and urinary homogentisic acid (T3DB). Acquisition and generation of the data is financially supported in part by CREST/JST. CONFIDENCE standard compound; INTERNAL_ID 118 KEIO_ID H060 Homogentisic acid is a specific metabolite in urine and serum, which is used for diagnosis of alkaptonuria. Homogentisic acid is a specific metabolite in urine and serum, which is used for diagnosis of alkaptonuria.

   

Uracil

1,2,3,4-tetrahydropyrimidine-2,4-dione

C4H4N2O2 (112.0273)


Uracil, also known as U, belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. Uracil is a common naturally occurring pyrimidine found in RNA. It base pairs with adenine and is replaced by thymine in DNA. Uracil is one of the four nucleobases in RNA that are represented by the letters A, G, C and U. Methylation of uracil produces thymine. The name "uracil" was coined in 1885 by the German chemist Robert Behrend, who was attempting to synthesize derivatives of uric acid. Originally discovered in 1900, uracil was isolated by hydrolysis of yeast nuclein that was found in bovine thymus and spleen, herring sperm, and wheat germ. Uracil exists in all living species, ranging from bacteria to plants to humans. Uracils use in the body is to help carry out the synthesis of many enzymes necessary for cell function through bonding with riboses and phosphates. Uracil serves as an allosteric regulator and a coenzyme for many important biochemical reactions. Uracil (via the nucleoside uridine) can be phosphorylated by various kinases to produce UMP, UDP and UTP. UDP and UTP regulate carbamoyl phosphate synthetase II (CPSase II) activity in animals. Uracil is also involved in the biosynthesis of polysaccharides and in the transport of sugars containing aldehydes. Within humans, uracil participates in a number of enzymatic reactions. In particular, uracil and ribose 1-phosphate can be biosynthesized from uridine; which is mediated by the enzyme uridine phosphorylase 2. In addition, uracil can be converted into dihydrouracil through the action of the enzyme dihydropyrimidine dehydrogenase [NADP(+)]. Uracil is rarely found in DNA, and this may have been an evolutionary change to increase genetic stability. This is because cytosine can deaminate spontaneously to produce uracil through hydrolytic deamination. Therefore, if there were an organism that used uracil in its DNA, the deamination of cytosine (which undergoes base pairing with guanine) would lead to formation of uracil (which would base pair with adenine) during DNA synthesis. Uracil can be used for drug delivery and as a pharmaceutical. When elemental fluorine reacts with uracil, it produces 5-fluorouracil. 5-Fluorouracil is an anticancer drug (antimetabolite) that mimics uracil during the nucleic acid (i.e. RNA) synthesis and transcription process. Because 5-fluorouracil is similar in shape to, but does not undergo the same chemistry as, uracil, the drug inhibits RNA replication enzymes, thereby blocking RNA synthesis and stopping the growth of cancerous cells. Uracil is a common and naturally occurring pyrimidine derivative. Originally discovered in 1900, it was isolated by hydrolysis of yeast nuclein that was found in bovine thymus and spleen, herring sperm, and wheat germ. It is a planar, unsaturated compound that has the ability to absorb light. Uracil. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=66-22-8 (retrieved 2024-07-01) (CAS RN: 66-22-8). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Uracil is a common and naturally occurring pyrimidine derivative and one of the four nucleobases in the nucleic acid of RNA. Uracil is a common and naturally occurring pyrimidine derivative and one of the four nucleobases in the nucleic acid of RNA. Uracil is a common and naturally occurring pyrimidine derivative and one of the four nucleobases in the nucleic acid of RNA.

   

Fumigaclavine A

4,6-Dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraen-3-yl acetic acid

C18H22N2O2 (298.1681)


Fumigaclavine A is an alkaloid from Aspergillus fumigatu Fumigaclavine A. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=6879-59-0 (retrieved 2024-08-26) (CAS RN: 6879-59-0). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

   

CYCLOPIAZONIC ACID

.alpha.-Cyclopiazonic acid

C20H20N2O3 (336.1474)


D002317 - Cardiovascular Agents > D000889 - Anti-Arrhythmia Agents D002317 - Cardiovascular Agents > D014665 - Vasodilator Agents D004791 - Enzyme Inhibitors Cyclopiazonic acid (CPA), a neurotoxic secondary metabolite (SM) made by Aspergillus flavus, is an inhibitor of endoplasmic reticulum calcium ATPase (Ca2+ATPase; SERCA) and a potent inducer of cell death in plants[1].

   

(-)-Fumigaclavine B

4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraen-3-ol

C16H20N2O (256.1576)


(-)-Fumigaclavine B is a mycotoxin from Aspergillus fumigatus and Rhizopus arrhizu

   

Ergosterol peroxide

5-[(3E)-5,6-dimethylhept-3-en-2-yl]-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0¹,⁹.0²,⁶.0¹⁰,¹⁵]nonadec-18-en-13-ol

C28H44O3 (428.329)


Ergosterol peroxide is found in fruits. Ergosterol peroxide is obtained from leaves of Ananas comosus (pineapple obtained from leaves of Ananas comosus (pineapple). Ergosterol peroxide is found in pineapple and fruits.

   

(R)-glycerol 1-acetate

(2S)-2,3-Dihydroxypropyl acetic acid

C5H10O4 (134.0579)


Glycerol acetate is the ester produced from the esterification of glycerol with acetic acid. Multiple products can be produced from this reaction; these include the monoacetylglycerols (MAG), diacetylglycerols (DAG), and triacetalglycerol (TAG) (also known as triacetin). (from wiki) [HMDB] Glycerol acetate is the ester produced from the esterification of glycerol with acetic acid. Multiple products can be produced from this reaction; these include the monoacetylglycerols (MAG), diacetylglycerols (DAG), and triacetalglycerol (TAG) (also known as triacetin). (Wikipedia).

   

Sherry lactone

dihydro-5-(1-Hydroxyethyl)-2(3H)-furanone

C6H10O3 (130.063)


Constituent of akaboshi zenmai (Osmunda japonica) fronds. Also isolated from sherry (stereochem. unspecified). Sherry lactone is found in alcoholic beverages and root vegetables. Sherry lactone is found in alcoholic beverages. Sherry lactone is a constituent of akaboshi zenmai (Osmunda japonica) fronds. Also isolated from sherry (stereochem. unspecified).

   

5,6-Epoxiergosta-8,22-diene-3,7-diol

15-[(3E)-5,6-dimethylhept-3-en-2-yl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-1(11)-ene-5,10-diol

C28H44O3 (428.329)


5,6-Epoxiergosta-8,22-diene-3,7-diol is found in mushrooms. 5,6-Epoxiergosta-8,22-diene-3,7-diol is a constituent of Tricholoma portentosum Constituent of Tricholoma portentosum. 5,6-Epoxiergosta-8,22-diene-3,7-diol is found in mushrooms.

   

2,3-Dihydroxypropyl acetate

2,3-Dihydroxypropyl acetic acid

C5H10O4 (134.0579)


   

(3S,9S,10R,13R,17R)-17-((2R,5R,E)-5,6-Dimethylhept-3-en-2-yl)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

(3S,9S,10R,13R,17R)-17-((2R,5R,E)-5,6-Dimethylhept-3-en-2-yl)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

C28H44O (396.3392)


   

Cerevisterol

(22E)-Ergosta-7,22-diene-3beta,5alpha,6beta-triol

C28H46O3 (430.3447)


An ergostanoid that is (22E)-ergosta-7,22-diene substituted by hydroxy groups at positions 3, 5 and 6 (the 3beta,5alpha,6beta stereoisomer). It has been isolated from the fungus, Xylaria species. Cerevisterol is a steroid isolated from the fruiting bodies of Agaricus blazei[1]. Cerevisterol is a steroid isolated from the fruiting bodies of Agaricus blazei[1].

   
   
   

Ergosterol peroxide

Ergosterol peroxide

C28H44O3 (428.329)


   

comazaphilone D

comazaphilone D

C21H22O7 (386.1365)


An azaphilone that is 5,6,7,8-tetrahydro-1H-isochromene substituted by a hydroxy and methyl group at position 7, an oxo group at position 8, a prop-1-en-1-yl group at position 3 and a (2,4-dihydroxy-6-methylbenzoyl)oxy group at position 6.Isolated from Penicillium commune, it exhibits antibacterial and antineoplastic activities.

   

comazaphilone A

comazaphilone A

C22H26O7 (402.1678)


An azaphilone that is 5,6,7,8-tetrahydro-1H-isochromene substituted by a hydroxy group at position 6, a methyl group at position 7, an oxo group at position 8, a propyl group at position 3 and a (4-hydroxy-2-methoxy-6-methylbenzoyl)oxy group at position 7. It has been isolated from Penicillium commune.

   

comazaphilone E

comazaphilone E

C22H24O8 (416.1471)


An azaphilone that is 5,6,7,8-tetrahydro-1H-isochromene substituted by a hydroxy group and a methyl group at position 7, an oxo group at position 8, a prop-1-en-1-yl group at position 3 and a (3,4-dihydroxy-2-methoxy-6-methylbenzoyl)oxy group at position 6. Isolated from Penicillium commune, it exhibits antibacterial and antineoplastic activities.

   

comazaphilone C

comazaphilone C

C22H24O8 (416.1471)


An azaphilone that is 5,6,7,8-tetrahydro-1H-isochromene substituted by a hydroxy group at position 6, a methyl group at position 7, an oxo group at position 8, a prop-1-en-1-yl group at position 3 and a (3,4-dihydroxy-2-methoxy-6-methylbenzoyl)oxy group at position 7. Isolated from Penicillium commune, it exhibits antibacterial activity.

   

comazaphilone F

comazaphilone F

C22H26O8 (418.1628)


An azaphilone that is 5,6,7,8-tetrahydro-1H-isochromene substituted by a hydroxy group and a methyl group at position 7, an oxo group at position 8, a propyl group at position 3 and a (3,4-dihydroxy-2-methoxy-6-methylbenzoyl)oxy group at position 6. Isolated from Penicillium commune, it exhibits antibacterial and antineoplastic activities.

   

comazaphilone B

comazaphilone B

C22H26O8 (418.1628)


An azaphilone that is 5,6,7,8-tetrahydro-1H-isochromene substituted by a hydroxy group at position 6, a methyl group at position 7, an oxo group at position 8, a propyl group at position 3 and a (3,4-dihydroxy-2-methoxy-6-methylbenzoyl)oxy group at position 7. It has been isolated from Penicillium commune.

   

3,5-dihydroxy-7-methoxy-6-methyl-1-oxo-1,3-dihydro-2-benzofuran-4-carbaldehyde

3,5-dihydroxy-7-methoxy-6-methyl-1-oxo-1,3-dihydro-2-benzofuran-4-carbaldehyde

C11H10O6 (238.0477)


   

Uracil

Uracil-5-d

C4H4N2O2 (112.0273)


A common and naturally occurring pyrimidine nucleobase in which the pyrimidine ring is substituted with two oxo groups at positions 2 and 4. Found in RNA, it base pairs with adenine and replaces thymine during DNA transcription. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; ISAKRJDGNUQOIC_STSL_0177_Uracil_8000fmol_180430_S2_LC02_MS02_198; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. Uracil is a common and naturally occurring pyrimidine derivative and one of the four nucleobases in the nucleic acid of RNA. Uracil is a common and naturally occurring pyrimidine derivative and one of the four nucleobases in the nucleic acid of RNA. Uracil is a common and naturally occurring pyrimidine derivative and one of the four nucleobases in the nucleic acid of RNA.

   

thymine

thymine

C5H6N2O2 (126.0429)


A pyrimidine nucleobase that is uracil in which the hydrogen at position 5 is replaced by a methyl group. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; RWQNBRDOKXIBIV_STSL_0176_Thymine_2000fmol_180506_S2_LC02_MS02_138; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. Thymine is one of the four nucleobases in the nucleic acid of DNA and can be a target for actions of 5-fluorouracil (5-FU) in cancer treatment, with a Km of 2.3 μM. Thymine is one of the four nucleobases in the nucleic acid of DNA and can be a target for actions of 5-fluorouracil (5-FU) in cancer treatment, with a Km of 2.3 μM. Thymine is one of the four nucleobases in the nucleic acid of DNA and can be a target for actions of 5-fluorouracil (5-FU) in cancer treatment, with a Km of 2.3 μM.

   

Homogentisic acid

Homogentisic acid

C8H8O4 (168.0423)


A dihydroxyphenylacetic acid having the two hydroxy substituents at the 2- and 5-positions. Homogentisic acid is a specific metabolite in urine and serum, which is used for diagnosis of alkaptonuria. Homogentisic acid is a specific metabolite in urine and serum, which is used for diagnosis of alkaptonuria.

   

Alcapton

InChI=1\C8H8O4\c9-6-1-2-7(10)5(3-6)4-8(11)12\h1-3,9-10H,4H2,(H,11,12

C8H8O4 (168.0423)


Homogentisic acid is a specific metabolite in urine and serum, which is used for diagnosis of alkaptonuria. Homogentisic acid is a specific metabolite in urine and serum, which is used for diagnosis of alkaptonuria.

   

N-Acetyl-DL-tryptophan

N-Acetyl-DL-tryptophan

C13H14N2O3 (246.1004)


D004791 - Enzyme Inhibitors > D011480 - Protease Inhibitors Ac-DL-Trp-OH is an endogenous metabolite. Ac-DL-Trp-OH is an endogenous metabolite.

   

Meiaa

1H-Indole-3-acetic acid, methyl ester

C11H11NO2 (189.079)


Methyl 2-(1H-indol-3-yl)acetate is an endogenous metabolite.

   

fumigaclavine B

4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraen-3-ol

C16H20N2O (256.1576)


An ergot alkaloid produced by the fungus Aspergillus fumigatus that consists of ergoline substituted by two methyl groups at the 6 and 8beta positions, and by a hydroxy group at the 9beta position.

   

Fumigaclavine A

4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraen-3-yl acetate

C18H22N2O2 (298.1681)


An ergot alkaloid produced by the fungus Aspergillus fumigatus that is ergoline which is substituted by methyl groups at the 6 and 8beta positions, and by an acetoxy group at the 9beta position.

   

Sherry lactone

dihydro-5-(1-Hydroxyethyl)-2(3H)-furanone

C6H10O3 (130.063)


   

1-[4-Hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione

2,4(1H,3H)-Pyrimidinedione,1-(2-deoxy-b-D-threo-pentofuranosyl)-5-methyl-

C10H14N2O5 (242.0903)


1-(2-Deoxy-β-D-threo-pentofuranosyl)thymine is a thymidine analog. Analogs of this series have insertional activity towards replicated DNA. They can be used to label cells and track DNA synthesis[1].

   

(22E,24R)-ergosta-5alpha,6alpha-epoxide-8,22-diene-3beta,7alpha-diol

(22E,24R)-ergosta-5alpha,6alpha-epoxide-8,22-diene-3beta,7alpha-diol

C28H44O3 (428.329)


An ergostanoid that is (22E)-ergosta-7,22-diene substituted by hydroxy groups at positions 3 and 7 and an epoxy group across positions 5 and 6 (the 3beta,5alpha,6alpha,7alpha stereoisomer). It has been isolated from Aspergillus ochraceus as well as Penicillium commune.

   

Pirod

InChI=1\C4H4N2O2\c7-3-1-2-5-4(8)6-3\h1-2H,(H2,5,6,7,8

C4H4N2O2 (112.0273)


COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Uracil is a common and naturally occurring pyrimidine derivative and one of the four nucleobases in the nucleic acid of RNA. Uracil is a common and naturally occurring pyrimidine derivative and one of the four nucleobases in the nucleic acid of RNA. Uracil is a common and naturally occurring pyrimidine derivative and one of the four nucleobases in the nucleic acid of RNA.

   

Thymin

2,4(1H,3H)-Pyrimidinedione, 5-methyl-, labeled with tritium

C5H6N2O2 (126.0429)


COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Thymine is one of the four nucleobases in the nucleic acid of DNA and can be a target for actions of 5-fluorouracil (5-FU) in cancer treatment, with a Km of 2.3 μM. Thymine is one of the four nucleobases in the nucleic acid of DNA and can be a target for actions of 5-fluorouracil (5-FU) in cancer treatment, with a Km of 2.3 μM. Thymine is one of the four nucleobases in the nucleic acid of DNA and can be a target for actions of 5-fluorouracil (5-FU) in cancer treatment, with a Km of 2.3 μM.

   

methyl 2-(1H-indol-3-yl)acetate

methyl 2-(1H-indol-3-yl)acetate

C11H11NO2 (189.079)


Methyl 2-(1H-indol-3-yl)acetate is an endogenous metabolite.

   

5-(1-hydroxyethyl)oxolan-2-one

5-(1-hydroxyethyl)oxolan-2-one

C6H10O3 (130.063)


   

(6r,7r)-6-hydroxy-7-methyl-8-oxo-3-(prop-1-en-1-yl)-5,6-dihydro-1h-isochromen-7-yl 3,4-dihydroxy-2-methoxy-6-methylbenzoate

(6r,7r)-6-hydroxy-7-methyl-8-oxo-3-(prop-1-en-1-yl)-5,6-dihydro-1h-isochromen-7-yl 3,4-dihydroxy-2-methoxy-6-methylbenzoate

C22H24O8 (416.1471)


   

3-[(2r)-2-chloro-3-hydroxypropyl]-5,8-dihydroxy-6-methoxyisochromen-1-one

3-[(2r)-2-chloro-3-hydroxypropyl]-5,8-dihydroxy-6-methoxyisochromen-1-one

C13H13ClO6 (300.0401)


   

(1r,2r,3s,5s,7r,10s,11s,12s,15r)-12-(hydroxymethyl)-2,7,12,15-tetramethyl-4-oxapentacyclo[8.6.0.0¹,⁷.0³,⁵.0¹¹,¹⁵]hexadecan-6-one

(1r,2r,3s,5s,7r,10s,11s,12s,15r)-12-(hydroxymethyl)-2,7,12,15-tetramethyl-4-oxapentacyclo[8.6.0.0¹,⁷.0³,⁵.0¹¹,¹⁵]hexadecan-6-one

C20H30O3 (318.2195)


   

3-(2,3-dihydroxypropyl)-5,8-dihydroxy-6-methoxyisochromen-1-one

3-(2,3-dihydroxypropyl)-5,8-dihydroxy-6-methoxyisochromen-1-one

C13H14O7 (282.0739)


   

3-[(2r)-2,3-dihydroxypropyl]-5,8-dihydroxy-6-methoxyisochromen-1-one

3-[(2r)-2,3-dihydroxypropyl]-5,8-dihydroxy-6-methoxyisochromen-1-one

C13H14O7 (282.0739)


   

3-(3-chloro-2-hydroxypropyl)-8-hydroxy-6-methoxyisochromen-1-one

3-(3-chloro-2-hydroxypropyl)-8-hydroxy-6-methoxyisochromen-1-one

C13H13ClO5 (284.0451)


   

1-{14-hydroxy-5,5-dimethyl-3-oxo-4,13-diazatetracyclo[6.6.1.0²,⁶.0¹²,¹⁵]pentadeca-1,6,8,10,12(15),13-hexaen-4-yl}butane-1,3-dione

1-{14-hydroxy-5,5-dimethyl-3-oxo-4,13-diazatetracyclo[6.6.1.0²,⁶.0¹²,¹⁵]pentadeca-1,6,8,10,12(15),13-hexaen-4-yl}butane-1,3-dione

C19H16N2O4 (336.111)


   

6-hydroxy-7-methyl-8-oxo-3-propyl-5,6-dihydro-1h-isochromen-7-yl 4-hydroxy-2-methoxy-6-methylbenzoate

6-hydroxy-7-methyl-8-oxo-3-propyl-5,6-dihydro-1h-isochromen-7-yl 4-hydroxy-2-methoxy-6-methylbenzoate

C22H26O7 (402.1678)


   

3-[(3-acetyloxiran-2-yl)methyl]-8-hydroxy-6-methoxyisochromen-1-one

3-[(3-acetyloxiran-2-yl)methyl]-8-hydroxy-6-methoxyisochromen-1-one

C15H14O6 (290.079)


   

7-hydroxy-7-methyl-8-oxo-3-(prop-1-en-1-yl)-5,6-dihydro-1h-isochromen-6-yl 2,4-dihydroxy-6-methylbenzoate

7-hydroxy-7-methyl-8-oxo-3-(prop-1-en-1-yl)-5,6-dihydro-1h-isochromen-6-yl 2,4-dihydroxy-6-methylbenzoate

C21H22O7 (386.1365)


   

3-[(2r)-3-chloro-2-hydroxypropyl]-8-hydroxy-6-methoxyisochromen-1-one

3-[(2r)-3-chloro-2-hydroxypropyl]-8-hydroxy-6-methoxyisochromen-1-one

C13H13ClO5 (284.0451)


   

11,14-bis(hydroxymethyl)-2,6,11-trimethyltetracyclo[7.6.0.0¹,⁶.0¹⁰,¹⁴]pentadec-3-en-5-one

11,14-bis(hydroxymethyl)-2,6,11-trimethyltetracyclo[7.6.0.0¹,⁶.0¹⁰,¹⁴]pentadec-3-en-5-one

C20H30O3 (318.2195)


   

(1r,9ar,9br,11ar)-1-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-one

(1r,9ar,9br,11ar)-1-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-one

C28H40O (392.3079)


   

6-hydroxy-4-(1h-imidazol-4-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one

6-hydroxy-4-(1h-imidazol-4-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one

C22H23N5O2 (389.1852)


   

(2r,3s,5r,6r)-3-[(1e,3e)-hepta-1,3-dien-1-yl]-5,6-dihydroxy-2-(hydroxymethyl)cyclohexan-1-one

(2r,3s,5r,6r)-3-[(1e,3e)-hepta-1,3-dien-1-yl]-5,6-dihydroxy-2-(hydroxymethyl)cyclohexan-1-one

C14H22O4 (254.1518)


   

1,3-dihydroxy-5,5,13-trimethyl-4,13-diazatetracyclo[6.6.1.0²,⁶.0¹²,¹⁵]pentadeca-3,8(15),9,11-tetraen-14-one

1,3-dihydroxy-5,5,13-trimethyl-4,13-diazatetracyclo[6.6.1.0²,⁶.0¹²,¹⁵]pentadeca-3,8(15),9,11-tetraen-14-one

C16H18N2O3 (286.1317)


   

1-(5,6-dimethylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-one

1-(5,6-dimethylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-one

C28H40O (392.3079)


   

3-[(2r)-3,3-dichloro-2-hydroxypropyl]-5,8-dihydroxy-6-methoxyisochromen-1-one

3-[(2r)-3,3-dichloro-2-hydroxypropyl]-5,8-dihydroxy-6-methoxyisochromen-1-one

C13H12Cl2O6 (334.0011)


   

5,5-dimethyl-4,13-diazatetracyclo[6.6.1.0²,⁶.0¹²,¹⁵]pentadeca-1,3,6,8,10,12(15),13-heptaene-3,14-diol

5,5-dimethyl-4,13-diazatetracyclo[6.6.1.0²,⁶.0¹²,¹⁵]pentadeca-1,3,6,8,10,12(15),13-heptaene-3,14-diol

C15H12N2O2 (252.0899)


   

15-(5,6-dimethylhept-3-en-2-yl)-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-1(11)-ene-5,10-diol

15-(5,6-dimethylhept-3-en-2-yl)-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-1(11)-ene-5,10-diol

C28H44O3 (428.329)


   

12-(hydroxymethyl)-2,7,12,15-tetramethyl-4-oxapentacyclo[8.6.0.0¹,⁷.0³,⁵.0¹¹,¹⁵]hexadecan-6-one

12-(hydroxymethyl)-2,7,12,15-tetramethyl-4-oxapentacyclo[8.6.0.0¹,⁷.0³,⁵.0¹¹,¹⁵]hexadecan-6-one

C20H30O3 (318.2195)


   

5,5-dimethyl-4,13-diazatetracyclo[6.6.1.0²,⁶.0¹²,¹⁵]pentadeca-3,8,10,12(15),13-pentaene-1,3,14-triol

5,5-dimethyl-4,13-diazatetracyclo[6.6.1.0²,⁶.0¹²,¹⁵]pentadeca-3,8,10,12(15),13-pentaene-1,3,14-triol

C15H16N2O3 (272.1161)


   

(1r,2r,3s,4r,5s,9r)-3,4,5-trihydroxy-8,8,16-trimethyl-5-(2-oxopropyl)-19-oxa-7,16-diazahexacyclo[9.6.1.1¹,⁴.0²,⁹.0³,⁷.0¹⁵,¹⁸]nonadeca-11,13,15(18)-triene-6,17-dione

(1r,2r,3s,4r,5s,9r)-3,4,5-trihydroxy-8,8,16-trimethyl-5-(2-oxopropyl)-19-oxa-7,16-diazahexacyclo[9.6.1.1¹,⁴.0²,⁹.0³,⁷.0¹⁵,¹⁸]nonadeca-11,13,15(18)-triene-6,17-dione

C22H24N2O7 (428.1583)


   

1,2-dimethyl (1r,2s,3s,4r)-3,4-bis(8-hydroxy-6-methoxy-1-oxoisochromen-3-yl)cyclobutane-1,2-dicarboxylate

1,2-dimethyl (1r,2s,3s,4r)-3,4-bis(8-hydroxy-6-methoxy-1-oxoisochromen-3-yl)cyclobutane-1,2-dicarboxylate

C28H24O12 (552.1268)


   

3-(3,3-dichloro-2-hydroxypropyl)-5,8-dihydroxy-6-methoxyisochromen-1-one

3-(3,3-dichloro-2-hydroxypropyl)-5,8-dihydroxy-6-methoxyisochromen-1-one

C13H12Cl2O6 (334.0011)


   

5,6,8-trihydroxy-3-(2-hydroxypropyl)isochromen-1-one

5,6,8-trihydroxy-3-(2-hydroxypropyl)isochromen-1-one

C12H12O6 (252.0634)


   

6-hydroxy-7-methyl-8-oxo-3-propyl-5,6-dihydro-1h-isochromen-7-yl 3,4-dihydroxy-2-methoxy-6-methylbenzoate

6-hydroxy-7-methyl-8-oxo-3-propyl-5,6-dihydro-1h-isochromen-7-yl 3,4-dihydroxy-2-methoxy-6-methylbenzoate

C22H26O8 (418.1628)


   

(6r,7r)-3-[(1e)-3-(acetyloxy)prop-1-en-1-yl]-7-hydroxy-7-methyl-8-oxo-5,6-dihydro-1h-isochromen-6-yl 2,4-dihydroxy-6-methylbenzoate

(6r,7r)-3-[(1e)-3-(acetyloxy)prop-1-en-1-yl]-7-hydroxy-7-methyl-8-oxo-5,6-dihydro-1h-isochromen-6-yl 2,4-dihydroxy-6-methylbenzoate

C23H24O9 (444.142)


   

3,4,5-trihydroxy-8,8,16-trimethyl-5-(2-oxopropyl)-19-oxa-7,16-diazahexacyclo[9.6.1.1¹,⁴.0²,⁹.0³,⁷.0¹⁵,¹⁸]nonadeca-11,13,15(18)-triene-6,17-dione

3,4,5-trihydroxy-8,8,16-trimethyl-5-(2-oxopropyl)-19-oxa-7,16-diazahexacyclo[9.6.1.1¹,⁴.0²,⁹.0³,⁷.0¹⁵,¹⁸]nonadeca-11,13,15(18)-triene-6,17-dione

C22H24N2O7 (428.1583)


   

(2s,3as,5's,6as)-5'-(2-hydroxyethyl)-tetrahydrospiro[furo[3,2-b]furan-2,2'-oxolan]-5-one

(2s,3as,5's,6as)-5'-(2-hydroxyethyl)-tetrahydrospiro[furo[3,2-b]furan-2,2'-oxolan]-5-one

C11H16O5 (228.0998)


   

(6r,7r)-7-hydroxy-7-methyl-8-oxo-3-(prop-1-en-1-yl)-5,6-dihydro-1h-isochromen-6-yl 2,4-dihydroxy-6-methylbenzoate

(6r,7r)-7-hydroxy-7-methyl-8-oxo-3-(prop-1-en-1-yl)-5,6-dihydro-1h-isochromen-6-yl 2,4-dihydroxy-6-methylbenzoate

C21H22O7 (386.1365)


   

2-{[(2s,3r)-1,2,3-trihydroxy-3-(4-hydroxyquinazolin-2-yl)-2-methylbutylidene]amino}benzenecarboximidic acid

2-{[(2s,3r)-1,2,3-trihydroxy-3-(4-hydroxyquinazolin-2-yl)-2-methylbutylidene]amino}benzenecarboximidic acid

C20H20N4O5 (396.1434)


   

(1r,4z,7r,9s)-6-hydroxy-4-(3h-imidazol-4-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one

(1r,4z,7r,9s)-6-hydroxy-4-(3h-imidazol-4-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one

C22H23N5O2 (389.1852)


   

(6r,7r)-6-hydroxy-3-[(1e)-3-hydroxyprop-1-en-1-yl]-7-methyl-8-oxo-5,6-dihydro-1h-isochromen-7-yl 2,4-dihydroxy-6-methylbenzoate

(6r,7r)-6-hydroxy-3-[(1e)-3-hydroxyprop-1-en-1-yl]-7-methyl-8-oxo-5,6-dihydro-1h-isochromen-7-yl 2,4-dihydroxy-6-methylbenzoate

C21H22O8 (402.1315)


   

5,9,9,17-tetramethyl-4,8,17-triazapentacyclo[10.6.1.0²,¹⁰.0³,⁸.0¹⁶,¹⁹]nonadeca-1,3,5,10,12,14,16(19)-heptaene-7,18-dione

5,9,9,17-tetramethyl-4,8,17-triazapentacyclo[10.6.1.0²,¹⁰.0³,⁸.0¹⁶,¹⁹]nonadeca-1,3,5,10,12,14,16(19)-heptaene-7,18-dione

C20H17N3O2 (331.1321)


   

3-(2-chloro-3-hydroxypropyl)-5,8-dihydroxy-6-methoxyisochromen-1-one

3-(2-chloro-3-hydroxypropyl)-5,8-dihydroxy-6-methoxyisochromen-1-one

C13H13ClO6 (300.0401)


   

3-(2-chloro-3-hydroxypropyl)-8-hydroxy-6-methoxyisochromen-1-one

3-(2-chloro-3-hydroxypropyl)-8-hydroxy-6-methoxyisochromen-1-one

C13H13ClO5 (284.0451)


   

(1r,2r,3r,5r,6r,9s,10s,11s,14r)-11-(hydroxymethyl)-2,6,11,14-tetramethyltetracyclo[7.6.0.0¹,⁶.0¹⁰,¹⁴]pentadecane-3,5-diol

(1r,2r,3r,5r,6r,9s,10s,11s,14r)-11-(hydroxymethyl)-2,6,11,14-tetramethyltetracyclo[7.6.0.0¹,⁶.0¹⁰,¹⁴]pentadecane-3,5-diol

C20H34O3 (322.2508)


   

6-hydroxy-7-methyl-8-oxo-3-(prop-1-en-1-yl)-5,6-dihydro-1h-isochromen-7-yl 3,4-dihydroxy-2-methoxy-6-methylbenzoate

6-hydroxy-7-methyl-8-oxo-3-(prop-1-en-1-yl)-5,6-dihydro-1h-isochromen-7-yl 3,4-dihydroxy-2-methoxy-6-methylbenzoate

C22H24O8 (416.1471)


   

1-(5,6-dimethylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,5ah,6h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-5,7-dione

1-(5,6-dimethylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,5ah,6h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-5,7-dione

C28H42O2 (410.3185)


   

3-{14-hydroxy-5,5-dimethyl-3-oxo-4,13-diazatetracyclo[6.6.1.0²,⁶.0¹²,¹⁵]pentadeca-1,6,8,10,12(15),13-hexaen-4-yl}butanoic acid

3-{14-hydroxy-5,5-dimethyl-3-oxo-4,13-diazatetracyclo[6.6.1.0²,⁶.0¹²,¹⁵]pentadeca-1,6,8,10,12(15),13-hexaen-4-yl}butanoic acid

C19H18N2O4 (338.1267)


   

5,6,8-trihydroxy-3-[(2s)-2-hydroxypropyl]isochromen-1-one

5,6,8-trihydroxy-3-[(2s)-2-hydroxypropyl]isochromen-1-one

C12H12O6 (252.0634)


   

11-(hydroxymethyl)-2,6,11,14-tetramethyltetracyclo[7.6.0.0¹,⁶.0¹⁰,¹⁴]pentadecane-3,5-diol

11-(hydroxymethyl)-2,6,11,14-tetramethyltetracyclo[7.6.0.0¹,⁶.0¹⁰,¹⁴]pentadecane-3,5-diol

C20H34O3 (322.2508)


   

6-hydroxy-3-(3-hydroxyprop-1-en-1-yl)-7-methyl-8-oxo-5,6-dihydro-1h-isochromen-7-yl 2,4-dihydroxy-6-methylbenzoate

6-hydroxy-3-(3-hydroxyprop-1-en-1-yl)-7-methyl-8-oxo-5,6-dihydro-1h-isochromen-7-yl 2,4-dihydroxy-6-methylbenzoate

C21H22O8 (402.1315)


   

(1r,2r,6s,9r,10s,11r,14r)-11,14-bis(hydroxymethyl)-2,6,11-trimethyltetracyclo[7.6.0.0¹,⁶.0¹⁰,¹⁴]pentadec-3-en-5-one

(1r,2r,6s,9r,10s,11r,14r)-11,14-bis(hydroxymethyl)-2,6,11-trimethyltetracyclo[7.6.0.0¹,⁶.0¹⁰,¹⁴]pentadec-3-en-5-one

C20H30O3 (318.2195)


   

(1s,2r,6r)-1,3-dihydroxy-5,5,13-trimethyl-4,13-diazatetracyclo[6.6.1.0²,⁶.0¹²,¹⁵]pentadeca-3,8(15),9,11-tetraen-14-one

(1s,2r,6r)-1,3-dihydroxy-5,5,13-trimethyl-4,13-diazatetracyclo[6.6.1.0²,⁶.0¹²,¹⁵]pentadeca-3,8(15),9,11-tetraen-14-one

C16H18N2O3 (286.1317)


   

(1r,3ar,5as,9ar,9br,11ar)-1-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5ah,6h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-5,7-dione

(1r,3ar,5as,9ar,9br,11ar)-1-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5ah,6h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-5,7-dione

C28H42O2 (410.3185)


   

1,2-dimethyl 3,4-bis(8-hydroxy-6-methoxy-1-oxoisochromen-3-yl)cyclobutane-1,2-dicarboxylate

1,2-dimethyl 3,4-bis(8-hydroxy-6-methoxy-1-oxoisochromen-3-yl)cyclobutane-1,2-dicarboxylate

C28H24O12 (552.1268)


   

(6r,7r)-7-hydroxy-7-methyl-8-oxo-3-(prop-1-en-1-yl)-5,6-dihydro-1h-isochromen-6-yl 3,4-dihydroxy-2-methoxy-6-methylbenzoate

(6r,7r)-7-hydroxy-7-methyl-8-oxo-3-(prop-1-en-1-yl)-5,6-dihydro-1h-isochromen-6-yl 3,4-dihydroxy-2-methoxy-6-methylbenzoate

C22H24O8 (416.1471)


   

5-(5,6-dimethylhept-3-en-2-yl)-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0¹,⁹.0²,⁶.0¹⁰,¹⁵]nonadec-18-en-13-ol

5-(5,6-dimethylhept-3-en-2-yl)-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0¹,⁹.0²,⁶.0¹⁰,¹⁵]nonadec-18-en-13-ol

C28H44O3 (428.329)


   

8-hydroxy-1,9,12-triazatetracyclo[9.8.0.0²,⁷.0¹³,¹⁸]nonadeca-2,4,6,8,11,13,15,17-octaen-19-one

8-hydroxy-1,9,12-triazatetracyclo[9.8.0.0²,⁷.0¹³,¹⁸]nonadeca-2,4,6,8,11,13,15,17-octaen-19-one

C16H11N3O2 (277.0851)


   

3-[(2r)-2-chloro-3-hydroxypropyl]-8-hydroxy-6-methoxyisochromen-1-one

3-[(2r)-2-chloro-3-hydroxypropyl]-8-hydroxy-6-methoxyisochromen-1-one

C13H13ClO5 (284.0451)


   

3-{5,5,13-trimethyl-3,14-dioxo-4,13-diazatetracyclo[6.6.1.0²,⁶.0¹²,¹⁵]pentadeca-1,6,8,10,12(15)-pentaen-4-yl}butanoic acid

3-{5,5,13-trimethyl-3,14-dioxo-4,13-diazatetracyclo[6.6.1.0²,⁶.0¹²,¹⁵]pentadeca-1,6,8,10,12(15)-pentaen-4-yl}butanoic acid

C20H20N2O4 (352.1423)


   

(2r,5s,7r,9s,10s,12r,15r,16r)-15-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-1(11)-ene-5,10-diol

(2r,5s,7r,9s,10s,12r,15r,16r)-15-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-1(11)-ene-5,10-diol

C28H44O3 (428.329)


   

1,2-dimethyl (1r,2s,3r,4s)-3,4-bis(8-hydroxy-6-methoxy-1-oxoisochromen-3-yl)cyclobutane-1,2-dicarboxylate

1,2-dimethyl (1r,2s,3r,4s)-3,4-bis(8-hydroxy-6-methoxy-1-oxoisochromen-3-yl)cyclobutane-1,2-dicarboxylate

C28H24O12 (552.1268)


   

2-{[1,2,3-trihydroxy-3-(4-hydroxyquinazolin-2-yl)-2-methylbutylidene]amino}benzenecarboximidic acid

2-{[1,2,3-trihydroxy-3-(4-hydroxyquinazolin-2-yl)-2-methylbutylidene]amino}benzenecarboximidic acid

C20H20N4O5 (396.1434)


   

(1s,2r,6r)-5,5-dimethyl-4,13-diazatetracyclo[6.6.1.0²,⁶.0¹²,¹⁵]pentadeca-3,8,10,12(15),13-pentaene-1,3,14-triol

(1s,2r,6r)-5,5-dimethyl-4,13-diazatetracyclo[6.6.1.0²,⁶.0¹²,¹⁵]pentadeca-3,8,10,12(15),13-pentaene-1,3,14-triol

C15H16N2O3 (272.1161)


   

3-{[(2s,3s)-3-acetyloxiran-2-yl]methyl}-8-hydroxy-6-methoxyisochromen-1-one

3-{[(2s,3s)-3-acetyloxiran-2-yl]methyl}-8-hydroxy-6-methoxyisochromen-1-one

C15H14O6 (290.079)


   

7-hydroxy-7-methyl-8-oxo-3-(prop-1-en-1-yl)-5,6-dihydro-1h-isochromen-6-yl 3,4-dihydroxy-2-methoxy-6-methylbenzoate

7-hydroxy-7-methyl-8-oxo-3-(prop-1-en-1-yl)-5,6-dihydro-1h-isochromen-6-yl 3,4-dihydroxy-2-methoxy-6-methylbenzoate

C22H24O8 (416.1471)


   

3-[3-(acetyloxy)prop-1-en-1-yl]-7-hydroxy-7-methyl-8-oxo-5,6-dihydro-1h-isochromen-6-yl 2,4-dihydroxy-6-methylbenzoate

3-[3-(acetyloxy)prop-1-en-1-yl]-7-hydroxy-7-methyl-8-oxo-5,6-dihydro-1h-isochromen-6-yl 2,4-dihydroxy-6-methylbenzoate

C23H24O9 (444.142)


   

7-hydroxy-7-methyl-8-oxo-3-propyl-5,6-dihydro-1h-isochromen-6-yl 3,4-dihydroxy-2-methoxy-6-methylbenzoate

7-hydroxy-7-methyl-8-oxo-3-propyl-5,6-dihydro-1h-isochromen-6-yl 3,4-dihydroxy-2-methoxy-6-methylbenzoate

C22H26O8 (418.1628)


   

5'-(2-hydroxyethyl)-tetrahydrospiro[furo[3,2-b]furan-2,2'-oxolan]-5-one

5'-(2-hydroxyethyl)-tetrahydrospiro[furo[3,2-b]furan-2,2'-oxolan]-5-one

C11H16O5 (228.0998)