Tyrosol

4-hydroxy-Benzeneethanol;4-Hydroxyphenylethanol;beta-(4-Hydroxyphenyl)ethanol

C8H10O2 (138.0681)


Tyrosol is a phenolic compound present in two of the traditional components of the Mediterranean diet: wine and virgin olive oil. The presence of tyrosol has been described in red and white wines. Tyrosol is also present in vermouth and beer. Tyrosol has been shown to be able to exert antioxidant activity in vitro studies. Oxidation of low-density lipoprotein (LDL) appears to occur predominantly in arterial intimae in microdomains sequestered from antioxidants of plasma. The antioxidant content of the LDL particle is critical for its protection. The ability of tyrosol to bind human LDL has been reported. The bioavailability of tyrosol in humans from virgin olive oil in its natural form has been demonstrated. Urinary tyrosol increases, reaching a peak at 0-4 h after virgin olive oil administration. Men and women show a different pattern of urinary excretion of tyrosol. Moreover, tyrosol is absorbed in a dose-dependent manner after sustained and moderate doses of virgin olive oil. Tyrosol from wine or virgin olive oil could exert beneficial effects on human health in vivo if its biological properties are confirmed (PMID 15134375). Tyrosol is a microbial metabolite found in Bifidobacterium, Escherichia and Lactobacillus (PMID:28393285). 2-(4-hydroxyphenyl)ethanol is a phenol substituted at position 4 by a 2-hydroxyethyl group. It has a role as an anti-arrhythmia drug, an antioxidant, a cardiovascular drug, a protective agent, a fungal metabolite, a geroprotector and a plant metabolite. It is functionally related to a 2-phenylethanol. 2-(4-Hydroxyphenyl)ethanol is a natural product found in Thalictrum petaloideum, Casearia sylvestris, and other organisms with data available. Tyrosol is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Sedum roseum root (part of); Rhodiola crenulata root (part of). D002317 - Cardiovascular Agents > D000889 - Anti-Arrhythmia Agents A phenol substituted at position 4 by a 2-hydroxyethyl group. D020011 - Protective Agents > D000975 - Antioxidants Tyrosol is a derivative of phenethyl alcohol. Tyrosol attenuates pro-inflammatory cytokines from cultured astrocytes and NF-κB activation. Anti-oxidative and anti-inflammatory effects[1]. Tyrosol is a derivative of phenethyl alcohol. Tyrosol attenuates pro-inflammatory cytokines from cultured astrocytes and NF-κB activation. Anti-oxidative and anti-inflammatory effects[1].

   

Tryptophol

3-(2-Hydroxyethyl)-1H-indole

C10H11NO (161.0841)


Tryptophol, also known as indole-3-ethanol, is an indolyl alcohol that is ethanol substituted by a 1H-indol-3-yl group at position 2. It has a role as a Saccharomyces cerevisiae metabolite, an auxin and a plant metabolite. Tryptophol 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). Tryptophol production was negatively associated with interferon-gamma production (IFNγ) which suggests that tryptophol has anti-inflammatory properties (PMID:27814509). Tryptophol has also been identified as the hypnotic agent in trypanosomal sleeping sickness, and because it is formed in vivo after ethanol or disulfiram treatment, it is also associated with the study of alcoholism (PMID:7241135). Indole-3-ethanol is a dietary indole present in cruciferous vegetables that has been shown to influence estradiol metabolism in humans and may provide a new chemopreventive approach to estrogen-dependent diseases. (PMID 2342128) Tryptophol. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=526-55-6 (retrieved 2024-06-29) (CAS RN: 526-55-6). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Tryptophol (Indole-3-ethanol) is an endogenous metabolite. Tryptophol (Indole-3-ethanol) is an endogenous metabolite.

   

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.

   

Indole-3-carboxylic acid

1H-Indole-3-carboxylic acid

C9H7NO2 (161.0477)


Indole-3-carboxylic acid, also known as 3-carboxyindole or 3-indolecarboxylate, belongs to the class of organic compounds known as indolecarboxylic acids and derivatives. Indolecarboxylic acids and derivatives are compounds containing a carboxylic acid group (or a derivative thereof) linked to an indole. Naphthylmethylindoles: Any compound containing a 1H-indol-3-yl-(1-naphthyl)methane structure with substitution at the nitrogen atom of the indole ring by an alkyl, haloalkyl, alkenyl, cycloalkylmethyl, cycloalkylethyl, 1-(N-methyl-2-piperidinyl)methyl, or 2-(4-morpholinyl)ethyl group whether or not further substituted in the indole ring to any extent and whether or not substituted in the naphthyl ring to any extent. One example given is JWH-250. Outside of the human body, indole-3-carboxylic acid has been detected, but not quantified in several different foods, such as brassicas, broccoli, pulses, common beets, and barley. This could make indole-3-carboxylic acid a potential biomarker for the consumption of these foods. Notice the pentyl group substituted onto the nitrogen atom of the indole ring. Note that this definition encompasses only those compounds that have OH groups attached to both the phenyl and the cyclohexyl rings, and so does not include compounds such as O-1871 which lacks the cyclohexyl OH group, or compounds such as JWH-337 or JWH-344 which lack the phenolic OH group. Present in plants, e.g. apple (Pyrus malus), garden pea (Pisum sativum) and brassicas Indole-3-carboxylic acid is a normal urinary indolic tryptophan metabolite and has been found elevated in patients with liver diseases[1][2]. Indole-3-carboxylic acid is a normal urinary indolic tryptophan metabolite and has been found elevated in patients with liver diseases[1][2].

   

Modiolide B

4R-hydroxy-2Z,5E-decadien-9R-olide

C10H14O3 (182.0943)


   

1H-Indole-3-carboxylic acid

1H-Indole-3-carboxylic acid

C9H7NO2 (161.0477)


IPB_RECORD: 302; CONFIDENCE confident structure CONFIDENCE confident structure; IPB_RECORD: 302

   

3-Indolecarboxylic acid

Indole-3-carboxylic acid_120169

C9H7NO2 (161.0477)


An indole-3-carboxylic acid carrying a carboxy group at position 3. Acquisition and generation of the data is financially supported in part by CREST/JST. IPB_RECORD: 2301; CONFIDENCE confident structure Indole-3-carboxylic acid is a normal urinary indolic tryptophan metabolite and has been found elevated in patients with liver diseases[1][2]. Indole-3-carboxylic acid is a normal urinary indolic tryptophan metabolite and has been found elevated in patients with liver diseases[1][2].

   

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.

   

Tryptophol

5-21-03-00061 (Beilstein Handbook Reference)

C10H11NO (161.0841)


An indolyl alcohol that is ethanol substituted by a 1H-indol-3-yl group at position 2. Tryptophol (Indole-3-ethanol) is an endogenous metabolite. Tryptophol (Indole-3-ethanol) is an endogenous metabolite.

   

Modiolide A

4R,7S,dihydroxy-2Z,5E-decadien-9R-olide

C10H14O4 (198.0892)


   

771-50-6

InChI=1\C9H7NO2\c11-9(12)7-5-10-8-4-2-1-3-6(7)8\h1-5,10H,(H,11,12

C9H7NO2 (161.0477)


Indole-3-carboxylic acid is a normal urinary indolic tryptophan metabolite and has been found elevated in patients with liver diseases[1][2]. Indole-3-carboxylic acid is a normal urinary indolic tryptophan metabolite and has been found elevated in patients with liver diseases[1][2].

   

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.

   

Tyrosol

InChI=1\C8H10O2\c9-6-5-7-1-3-8(10)4-2-7\h1-4,9-10H,5-6H

C8H10O2 (138.0681)


Tyrosol, also known as 4-hydroxyphenylethanol or 4-(2-hydroxyethyl)phenol, is a member of the class of compounds known as tyrosols. Tyrosols are organic aromatic compounds containing a phenethyl alcohol moiety that carries a hydroxyl group at the 4-position of the benzene group. Tyrosol is soluble (in water) and a very weakly acidic compound (based on its pKa). Tyrosol can be synthesized from 2-phenylethanol. Tyrosol is also a parent compound for other transformation products, including but not limited to, hydroxytyrosol, crosatoside B, and oleocanthal. Tyrosol is a mild, sweet, and floral tasting compound and can be found in a number of food items such as breadnut tree seed, sparkleberry, loquat, and savoy cabbage, which makes tyrosol a potential biomarker for the consumption of these food products. Tyrosol can be found primarily in feces and urine, as well as in human prostate tissue. Tyrosol exists in all eukaryotes, ranging from yeast to humans. Tyrosol present in wine is also shown to be cardioprotective. Samson et al. has shown that tyrosol-treated animals showed significant increase in the phosphorylation of Akt, eNOS and FOXO3a. In addition, tyrosol also induced the expression of longevity protein SIRT1 in the heart after myocardial infarction in a rat MI model. Hence tyrosols SIRT1, Akt and eNOS activating power adds another dimension to the wine research, because it adds a great link to the French paradox. In conclusion these findings suggest that tyrosol induces myocardial protection against ischemia related stress by inducing survival and longevity proteins that may be considered as anti-aging therapy for the heart . D002317 - Cardiovascular Agents > D000889 - Anti-Arrhythmia Agents D020011 - Protective Agents > D000975 - Antioxidants Tyrosol is a derivative of phenethyl alcohol. Tyrosol attenuates pro-inflammatory cytokines from cultured astrocytes and NF-κB activation. Anti-oxidative and anti-inflammatory effects[1]. Tyrosol is a derivative of phenethyl alcohol. Tyrosol attenuates pro-inflammatory cytokines from cultured astrocytes and NF-κB activation. Anti-oxidative and anti-inflammatory effects[1].

   

(3s)-6-hydroxy-8-methoxy-3-methyl-3,4-dihydro-1h-2-benzopyran-7-carbaldehyde

(3s)-6-hydroxy-8-methoxy-3-methyl-3,4-dihydro-1h-2-benzopyran-7-carbaldehyde

C12H14O4 (222.0892)


   

6-hydroxy-8-methoxy-3-methyl-1h-isochromene-7-carbaldehyde

6-hydroxy-8-methoxy-3-methyl-1h-isochromene-7-carbaldehyde

C12H12O4 (220.0736)


   

(2r)-2,7-dihydroxy-2,4-dimethyl-1-benzofuran-3-one

(2r)-2,7-dihydroxy-2,4-dimethyl-1-benzofuran-3-one

C10H10O4 (194.0579)


   

1-[(3s,4r)-3,4-dihydroxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]ethanone

1-[(3s,4r)-3,4-dihydroxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]ethanone

C13H16O4 (236.1049)


   

4-hydroxy-2-methoxy-3-methyl-6-(2-oxopropyl)benzaldehyde

4-hydroxy-2-methoxy-3-methyl-6-(2-oxopropyl)benzaldehyde

C12H14O4 (222.0892)


   

(2r,3r,4r,5r)-4-{[(3r,4ar,5s,8as)-3-hydroxy-5-(hydroxymethyl)-2,5,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]methoxy}hexane-1,2,3,5,6-pentol

(2r,3r,4r,5r)-4-{[(3r,4ar,5s,8as)-3-hydroxy-5-(hydroxymethyl)-2,5,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]methoxy}hexane-1,2,3,5,6-pentol

C21H38O8 (418.2567)


   

(1s,4s,5s)-5-hydroxy-5-methyl-6,8-dioxo-4-pentyl-3-oxa-12-thia-9-azatricyclo[7.4.0.0²,⁷]trideca-2(7),10-diene-10-carboxylic acid

(1s,4s,5s)-5-hydroxy-5-methyl-6,8-dioxo-4-pentyl-3-oxa-12-thia-9-azatricyclo[7.4.0.0²,⁷]trideca-2(7),10-diene-10-carboxylic acid

C17H21NO6S (367.109)


   

(2s,3s)-3-hydroxy-3-methyl-2-pentyl-2h-pyrano[2,3-c]pyrrole-4,5-dione

(2s,3s)-3-hydroxy-3-methyl-2-pentyl-2h-pyrano[2,3-c]pyrrole-4,5-dione

C13H17NO4 (251.1158)


   

(2s)-2-({7-hydroxy-3,9-dimethoxy-1-methyl-6-oxobenzo[c]chromen-4-yl}oxy)-2,4-dimethyl-1-benzofuran-3-one

(2s)-2-({7-hydroxy-3,9-dimethoxy-1-methyl-6-oxobenzo[c]chromen-4-yl}oxy)-2,4-dimethyl-1-benzofuran-3-one

C26H22O8 (462.1315)


   

1-(3,4-dihydroxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl)ethanone

1-(3,4-dihydroxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl)ethanone

C13H16O4 (236.1049)


   

(2r,3r,4r,5r)-4-{[(4s,4as,8as)-4-hydroxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]methoxy}hexane-1,2,3,5,6-pentol

(2r,3r,4r,5r)-4-{[(4s,4as,8as)-4-hydroxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]methoxy}hexane-1,2,3,5,6-pentol

C21H38O7 (402.2617)


   

(2s,3r,4s)-3,4-dihydroxy-6-methoxy-3-methyl-7-methylidene-2-pentyl-2h,4h-pyrano[2,3-c]pyrrol-5-one

(2s,3r,4s)-3,4-dihydroxy-6-methoxy-3-methyl-7-methylidene-2-pentyl-2h,4h-pyrano[2,3-c]pyrrol-5-one

C15H23NO5 (297.1576)


   

(5s,6r,10s)-6-hydroxy-10-methyl-3-methylidene-2-oxaspiro[4.5]dec-8-ene-1,4,7-trione

(5s,6r,10s)-6-hydroxy-10-methyl-3-methylidene-2-oxaspiro[4.5]dec-8-ene-1,4,7-trione

C11H10O5 (222.0528)


   

5-acetyl-1-[(6,8-dihydroxy-4-methyl-3-methylidene-1-oxo-4h-2-benzopyran-5-yl)methyl]pyrrolidin-2-one

5-acetyl-1-[(6,8-dihydroxy-4-methyl-3-methylidene-1-oxo-4h-2-benzopyran-5-yl)methyl]pyrrolidin-2-one

C18H19NO6 (345.1212)


   

2,7-dihydroxy-2,4-dimethyl-1-benzofuran-3-one

2,7-dihydroxy-2,4-dimethyl-1-benzofuran-3-one

C10H10O4 (194.0579)


   

5,9-dihydroxydodec-6-enoic acid

5,9-dihydroxydodec-6-enoic acid

C12H22O4 (230.1518)


   

(2r)-2-hydroxy-2,4-dimethyl-1-benzofuran-3-one

(2r)-2-hydroxy-2,4-dimethyl-1-benzofuran-3-one

C10H10O3 (178.063)


   

3-(1-hydroxypropan-2-ylidene)-4a,5-dimethyl-2-oxo-hexahydronaphtho[1,8a-b]oxiren-8-yl 3-hydroxy-6-(hydroxymethyl)-2,4-dimethyldodec-4-enoate

3-(1-hydroxypropan-2-ylidene)-4a,5-dimethyl-2-oxo-hexahydronaphtho[1,8a-b]oxiren-8-yl 3-hydroxy-6-(hydroxymethyl)-2,4-dimethyldodec-4-enoate

C30H48O7 (520.34)


   

4-hydroxy-3-(hydroxymethyl)-2-methoxy-6-(2-oxopropyl)benzaldehyde

4-hydroxy-3-(hydroxymethyl)-2-methoxy-6-(2-oxopropyl)benzaldehyde

C12H14O5 (238.0841)


   

(2s,3r,4s)-3-methyl-7-methylidene-2-pentyl-2h,4h-pyrano[2,3-c]pyrrole-3,4,5-triol

(2s,3r,4s)-3-methyl-7-methylidene-2-pentyl-2h,4h-pyrano[2,3-c]pyrrole-3,4,5-triol

C14H21NO4 (267.1471)


   

11-hydroxy-2-methyl-6-methylidene-4,7-dioxatricyclo[6.3.0.0¹,⁵]undecane-3,10-dione

11-hydroxy-2-methyl-6-methylidene-4,7-dioxatricyclo[6.3.0.0¹,⁵]undecane-3,10-dione

C11H12O5 (224.0685)


   

(3r,4s)-6-[(1s)-1-hydroxyethyl]-2,2-dimethyl-3,4-dihydro-1-benzopyran-3,4-diol

(3r,4s)-6-[(1s)-1-hydroxyethyl]-2,2-dimethyl-3,4-dihydro-1-benzopyran-3,4-diol

C13H18O4 (238.1205)


   

(2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-{[(1s)-1,5,6,7-tetramethyl-3,4-dihydro-2h-naphthalen-1-yl]methoxy}oxane-3,4,5-triol

(2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-{[(1s)-1,5,6,7-tetramethyl-3,4-dihydro-2h-naphthalen-1-yl]methoxy}oxane-3,4,5-triol

C21H32O6 (380.2199)


   

(2r,3r,4r,5r)-4-{[(4as,8as)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]methoxy}hexane-1,2,3,5,6-pentol

(2r,3r,4r,5r)-4-{[(4as,8as)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]methoxy}hexane-1,2,3,5,6-pentol

C21H38O6 (386.2668)


   

6-hydroxy-1,8-dimethoxy-3-methyl-1h-isochromene-7-carbaldehyde

6-hydroxy-1,8-dimethoxy-3-methyl-1h-isochromene-7-carbaldehyde

C13H14O5 (250.0841)


   

(4s)-6,8-dihydroxy-5-[(4-hydroxy-6-methyl-2-oxopyran-3-yl)methyl]-4-methyl-3-methylidene-4h-2-benzopyran-1-one

(4s)-6,8-dihydroxy-5-[(4-hydroxy-6-methyl-2-oxopyran-3-yl)methyl]-4-methyl-3-methylidene-4h-2-benzopyran-1-one

C18H16O7 (344.0896)


   

ethyl (2z,4e,9r)-9-hydroxydeca-2,4-dienoate

ethyl (2z,4e,9r)-9-hydroxydeca-2,4-dienoate

C12H20O3 (212.1412)


   

6,8-dihydroxy-5-[(4-hydroxy-6-methyl-2-oxopyran-3-yl)methyl]-4-methyl-3-methylidene-4h-2-benzopyran-1-one

6,8-dihydroxy-5-[(4-hydroxy-6-methyl-2-oxopyran-3-yl)methyl]-4-methyl-3-methylidene-4h-2-benzopyran-1-one

C18H16O7 (344.0896)


   

6-(1-hydroxyethyl)-2,2-dimethyl-3,4-dihydro-1-benzopyran-3,4-diol

6-(1-hydroxyethyl)-2,2-dimethyl-3,4-dihydro-1-benzopyran-3,4-diol

C13H18O4 (238.1205)


   

(1s,4as,8s,8ar)-4,8-bis(hydroxymethyl)-3,4a,8-trimethyl-1,2,5,6,7,8a-hexahydronaphthalen-1-ol

(1s,4as,8s,8ar)-4,8-bis(hydroxymethyl)-3,4a,8-trimethyl-1,2,5,6,7,8a-hexahydronaphthalen-1-ol

C15H26O3 (254.1882)


   

6-hydroxy-10-methyl-3-methylidene-2-oxaspiro[4.5]dec-8-ene-1,4,7-trione

6-hydroxy-10-methyl-3-methylidene-2-oxaspiro[4.5]dec-8-ene-1,4,7-trione

C11H10O5 (222.0528)


   

(6e)-5,9-dihydroxydodec-6-enoic acid

(6e)-5,9-dihydroxydodec-6-enoic acid

C12H22O4 (230.1518)


   

(1as,4ar,5s,8r,8ar)-3-(1-hydroxypropan-2-ylidene)-4a,5-dimethyl-2-oxo-hexahydronaphtho[1,8a-b]oxiren-8-yl (2r,3s,6s)-3-hydroxy-6-(hydroxymethyl)-2,4-dimethyldodec-4-enoate

(1as,4ar,5s,8r,8ar)-3-(1-hydroxypropan-2-ylidene)-4a,5-dimethyl-2-oxo-hexahydronaphtho[1,8a-b]oxiren-8-yl (2r,3s,6s)-3-hydroxy-6-(hydroxymethyl)-2,4-dimethyldodec-4-enoate

C30H48O7 (520.34)


   

(5r)-5-acetyl-1-{[(4s)-6,8-dihydroxy-4-methyl-3-methylidene-1-oxo-4h-2-benzopyran-5-yl]methyl}pyrrolidin-2-one

(5r)-5-acetyl-1-{[(4s)-6,8-dihydroxy-4-methyl-3-methylidene-1-oxo-4h-2-benzopyran-5-yl]methyl}pyrrolidin-2-one

C18H19NO6 (345.1212)


   

(2r,3r,4r,5r)-4-{[3,6-dimethyl-2-(4-methylpent-3-en-1-yl)phenyl]methoxy}hexane-1,2,3,5,6-pentol

(2r,3r,4r,5r)-4-{[3,6-dimethyl-2-(4-methylpent-3-en-1-yl)phenyl]methoxy}hexane-1,2,3,5,6-pentol

C21H34O6 (382.2355)


   

(2r)-2-({7-hydroxy-3,9-dimethoxy-1-methyl-6-oxobenzo[c]chromen-4-yl}oxy)-2,4-dimethyl-1-benzofuran-3-one

(2r)-2-({7-hydroxy-3,9-dimethoxy-1-methyl-6-oxobenzo[c]chromen-4-yl}oxy)-2,4-dimethyl-1-benzofuran-3-one

C26H22O8 (462.1315)


   

2-heptyl-3,4-dihydroxy-6-methoxy-3-methyl-7-methylidene-2h,4h-pyrano[2,3-c]pyrrol-5-one

2-heptyl-3,4-dihydroxy-6-methoxy-3-methyl-7-methylidene-2h,4h-pyrano[2,3-c]pyrrol-5-one

C17H27NO5 (325.1889)


   

1-[(3s,4s)-3,4-dihydroxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]ethanone

1-[(3s,4s)-3,4-dihydroxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]ethanone

C13H16O4 (236.1049)


   

2-hydroxy-2,4-dimethyl-1-benzofuran-3-one

2-hydroxy-2,4-dimethyl-1-benzofuran-3-one

C10H10O3 (178.063)


   

(3r,4s)-6-(1-hydroxyethyl)-2,2-dimethyl-3,4-dihydro-1-benzopyran-3,4-diol

(3r,4s)-6-(1-hydroxyethyl)-2,2-dimethyl-3,4-dihydro-1-benzopyran-3,4-diol

C13H18O4 (238.1205)


   

(3z,5r,6e,10r)-5-hydroxy-10-methyl-5,8,9,10-tetrahydrooxecin-2-one

(3z,5r,6e,10r)-5-hydroxy-10-methyl-5,8,9,10-tetrahydrooxecin-2-one

C10H14O3 (182.0943)


   

4-hydroxy-2-methoxy-6-(2-oxopropyl)benzene-1,3-dicarbaldehyde

4-hydroxy-2-methoxy-6-(2-oxopropyl)benzene-1,3-dicarbaldehyde

C12H12O5 (236.0685)


   

(2r,3r,4r,5r)-4-{[(4ar,5s,8as)-5-(hydroxymethyl)-2,5,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]methoxy}hexane-1,2,3,5,6-pentol

(2r,3r,4r,5r)-4-{[(4ar,5s,8as)-5-(hydroxymethyl)-2,5,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]methoxy}hexane-1,2,3,5,6-pentol

C21H38O7 (402.2617)