NCBI Taxonomy: 148305

Pyricularia grisea (ncbi_taxid: 148305)

found 74 associated metabolites at species taxonomy rank level.

Ancestor: Pyricularia

Child Taxonomies: Pyricularia grisea W98-20, Pyricularia grisea W97-11

Harman

1-methyl-9H-pyrido[3,4-b]indole

C12H10N2 (182.0844)


Harman is an indole alkaloid fundamental parent with a structure of 9H-beta-carboline carrying a methyl substituent at C-1. It has been isolated from the bark of Sickingia rubra, Symplocus racemosa, Passiflora incarnata, Peganum harmala, Banisteriopsis caapi and Tribulus terrestris, as well as from tobacco smoke. It is a specific, reversible inhibitor of monoamine oxidase A. It has a role as an anti-HIV agent, a plant metabolite and an EC 1.4.3.4 (monoamine oxidase) inhibitor. It is an indole alkaloid, an indole alkaloid fundamental parent and a harmala alkaloid. Harman is a natural product found in Ophiopogon, Strychnos johnsonii, and other organisms with data available. An indole alkaloid fundamental parent with a structure of 9H-beta-carboline carrying a methyl substituent at C-1. It has been isolated from the bark of Sickingia rubra, Symplocus racemosa, Passiflora incarnata, Peganum harmala, Banisteriopsis caapi and Tribulus terrestris, as well as from tobacco smoke. It is a specific, reversible inhibitor of monoamine oxidase A. Isolated from roots of Panax ginseng and Codonopsis lanceolata (todok). Struct. has now been shown to be identical with 1-Acetyl-b-carboline CHK59-M Harman is found in chicory. Harman is an alkaloid from the may pop (Passiflora incarnata, Passifloraceae) and many other Passiflora sp [Raw Data] CB042_Harman_pos_30eV_CB000019.txt [Raw Data] CB042_Harman_pos_20eV_CB000019.txt [Raw Data] CB042_Harman_pos_40eV_CB000019.txt [Raw Data] CB042_Harman_pos_10eV_CB000019.txt [Raw Data] CB042_Harman_pos_50eV_CB000019.txt [Raw Data] CB042_Harman_neg_50eV_000012.txt [Raw Data] CB042_Harman_neg_30eV_000012.txt [Raw Data] CB042_Harman_neg_40eV_000012.txt [Raw Data] CB042_Harman_neg_20eV_000012.txt [Raw Data] CB042_Harman_neg_10eV_000012.txt Harman. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=486-84-0 (retrieved 2024-06-29) (CAS RN: 486-84-0). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Harmane, a β-Carboline alkaloid (BCA), is a potent neurotoxin that causes severe action tremors and psychiatric manifestations. Harmane shows 1000-fold selectivity for I1-Imidazoline receptor (IC50=30 nM) over α2-adrenoceptor (IC50=18 μM). Harmane is also a potent and selective inhibitor of monoamine oxidase (MAO) (IC50s=0.5 and 5 μM for human MAO A/B, respectively). Harmane exhibits comutagenic effect[1][2][3][4]. Harmane, a β-Carboline alkaloid (BCA), is a potent neurotoxin that causes severe action tremors and psychiatric manifestations. Harmane shows 1000-fold selectivity for I1-Imidazoline receptor (IC50=30 nM) over α2-adrenoceptor (IC50=18 μM). Harmane is also a potent and selective inhibitor of monoamine oxidase (MAO) (IC50s=0.5 and 5 μM for human MAO A/B, respectively). Harmane exhibits comutagenic effect[1][2][3][4]. Harmane, a β-Carboline alkaloid (BCA), is a potent neurotoxin that causes severe action tremors and psychiatric manifestations. Harmane shows 1000-fold selectivity for I1-Imidazoline receptor (IC50=30 nM) over α2-adrenoceptor (IC50=18 μM). Harmane is also a potent and selective inhibitor of monoamine oxidase (MAO) (IC50s=0.5 and 5 μM for human MAO A/B, respectively). Harmane exhibits comutagenic effect[1][2][3][4].

   

alpha-Ketoisovaleric acid

3-Methyl-2-oxobutyric acid sodium salt

C5H8O3 (116.0473)


alpha-Ketoisovaleric acid is an abnormal metabolite that arises from the incomplete breakdown of branched-chain amino acids. alpha-Ketoisovaleric acid is a neurotoxin, an acidogen, and a metabotoxin. A neurotoxin causes damage to nerve cells and nerve tissues. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of alpha-ketoisovaleric acid are associated with maple syrup urine disease. MSUD is a metabolic disorder caused by a deficiency of the branched-chain alpha-keto acid dehydrogenase complex (BCKDC), leading to a buildup of the branched-chain amino acids (leucine, isoleucine, and valine) and their toxic by-products (ketoacids) in the blood and urine. The symptoms of MSUD often show in infancy and lead to severe brain damage if untreated. MSUD may also present later depending on the severity of the disease. If left untreated in older individuals, during times of metabolic crisis, symptoms of the condition include uncharacteristically inappropriate, extreme, or erratic behaviour and moods, hallucinations, anorexia, weight loss, anemia, diarrhea, vomiting, dehydration, lethargy, oscillating hypertonia and hypotonia, ataxia, seizures, hypoglycemia, ketoacidosis, opisthotonus, pancreatitis, rapid neurological decline, and coma. In maple syrup urine disease, the brain concentration of branched-chain ketoacids can increase 10- to 20-fold. This leads to a depletion of glutamate and a consequent reduction in the concentration of brain glutamine, aspartate, alanine, and other amino acids. The result is a compromise of energy metabolism because of a failure of the malate-aspartate shuttle and a diminished rate of protein synthesis (PMID: 15930465). alpha-Ketoisovaleric acid is a keto-acid, which is a subclass of organic acids. Abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart, liver, and kidney abnormalities, seizures, coma, and possibly death. These are also the characteristic symptoms of untreated MSUD. Many affected children with organic acidemias experience intellectual disability or delayed development. Flavouring ingredient for use in butter-type flavours. Found in banana, bread, cheeses, asparagus, beer and cocoa KEIO_ID M006 3-Methyl-2-oxobutanoic acid is a precursor of pantothenic acid in Escherichia coli.

   

6-Hydroxymellein

Isocoumarin, 3,4-dihydro-6,8-dihydroxy-3-methyl-

C10H10O4 (194.0579)


   

Tenuazonic acid

3-Acetyl-1,5-dihydro-4-hydroxy-5-(1-methylpropyl)-2H-pyrrol-2-one, 9ci

C10H15NO3 (197.1052)


Tenuazonic acid is produced by Aspergillus species Causes rice leaf rot Tenuazonic acid is a mycotoxin. It is a toxic secondary metabolite, produced by Alternaria (e. g. Alternaria alternata or Alternaria tenuis) and Phoma species. It inhibits the protein synthesis machinery D000890 - Anti-Infective Agents > D000998 - Antiviral Agents D009676 - Noxae > D011042 - Poisons > D009183 - Mycotoxins Production by Aspergillus subspecies Causes rice leaf rot D000970 - Antineoplastic Agents

   

Oryzalexin A

(2R,4aR,4bS,7S,10aS)-7-ethenyl-2-hydroxy-1,1,4a,7-tetramethyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydrophenanthren-9-one

C20H30O2 (302.2246)


Oryzalexin a, also known as 3a,7-oxo-ent-sandaracopimaradiene, is a member of the class of compounds known as diterpenoids. Diterpenoids are terpene compounds formed by four isoprene units. Oryzalexin a is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Oryzalexin a can be found in rice, which makes oryzalexin a a potential biomarker for the consumption of this food product.

   

Pyriculol

Pyriculol

C14H16O4 (248.1049)


A benzaldehyde that is salicylaldehyde which is substituted at position 6 by a (3R,4S,5E)-3,4-dihydroxyhepta-1,5-dien-1-yl group. It is a phytotoxic metabolite, isolated from the rice blast fungi Magnaporthe oryzae and Magnaporthe grisea.

   

Harmalan

4,9-Dihydro-1-methyl-3H-pyrido[3,4-b]indole, 9ci

C12H12N2 (184.1)


Harmalan is found in fruits. Harmalan is an alkaloid from Elaeagnus angustifolia (Russian olive

   

5-Hydroxy-2-furoic acid

5-hydroxyfuran-2-carboxylic acid

C5H4O4 (128.011)


5-Hydroxy-2-furoic acid belongs to the family of Furoic Acid Derivatives. These are organic compounds containing a furoic acid moiety, whose structure is characterized by a furan ring bearing a carboxylic acid group at the C2 or C3 carbon atom.

   

4-hydroxy-3-nitrophenylacetate

2-(4-HYDROXY-3-nitrophenyl)acetIC ACID

C8H7NO5 (197.0324)


4-hydroxy-3-nitrophenylacetate, also known as 3-nitro-4-hydroxyphenylacetic acid, is slightly soluble (in water). It is a mildly acidic compound. This metabolite is a member of the class of compounds known as nitrophenols. Nitrophenols are compounds containing a nitrophenol moiety, which consists of a benzene ring bearing both a hydroxyl group and a nitro group on two different ring carbon atoms. Free nitrotyrosine undergoes metabolism to form 3-nitro-4-hydroxyphenylacetic acid (NHPA) which is excreted in the urine (Wikipedia). However, it is not known whether NHPA is derived exclusively from metabolism of nitrotyrosine, or whether it can be formed by nitration of circulating para -hydroxyphenylacetic acid (PHPA), a metabolite of tyrosine (PMID: 12797864). Since the plasma concentration of PHPA is markedly higher than free nitrotyrosine (approx. 400-fold), the nitration of high-circulating endogenous PHPA to form NHPA becomes very significant and accounts for the majority of NHPA excreted in urine (PMID: 12797864).

   

Oryzalexin B

(4aS,4bS,7S,9S,10aS)-7-ethenyl-9-hydroxy-1,1,4a,7-tetramethyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydrophenanthren-2-one

C20H30O2 (302.2246)


Oryzalexin b is a member of the class of compounds known as diterpenoids. Diterpenoids are terpene compounds formed by four isoprene units. Oryzalexin b is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Oryzalexin b can be found in rice, which makes oryzalexin b a potential biomarker for the consumption of this food product.

   

Oryzalexin C

(4aR,4bS,7S,10aS)-7-ethenyl-1,1,4a,7-tetramethyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydrophenanthrene-2,9-dione

C20H28O2 (300.2089)


Oryzalexin c is a member of the class of compounds known as diterpenoids. Diterpenoids are terpene compounds formed by four isoprene units. Oryzalexin c is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Oryzalexin c can be found in rice, which makes oryzalexin c a potential biomarker for the consumption of this food product.

   

Ketovaline

3-Methyl-2-oxobutanoic acid

C5H8O3 (116.0473)


3-Methyl-2-oxobutanoic acid is a precursor of pantothenic acid in Escherichia coli.

   

2,4-Dihydroxy-6-(2-oxopropyl)benzoic acid

2,4-Dihydroxy-6-(2-oxopropyl)benzoic acid

C10H10O5 (210.0528)


   

Terrestric acid

Terrestric acid

C11H14O4 (210.0892)


   

dihydropyriculol

dihydropyriculol

C14H18O4 (250.1205)


A member of the class of benzyl alcohols resulting from the formal reduction of the aldehyde group of pyriculol. Produced by the rice blast fungus Magnaporthe oryzae.

   

oryzalexin B

oryzalexin B

C20H30O2 (302.2246)


   

Harman

Harmane

C12H10N2 (182.0844)


relative retention time with respect to 9-anthracene Carboxylic Acid is 0.504 D009676 - Noxae > D009498 - Neurotoxins D009676 - Noxae > D009153 - Mutagens relative retention time with respect to 9-anthracene Carboxylic Acid is 0.500 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.495 IPB_RECORD: 461; CONFIDENCE confident structure Harmane, a β-Carboline alkaloid (BCA), is a potent neurotoxin that causes severe action tremors and psychiatric manifestations. Harmane shows 1000-fold selectivity for I1-Imidazoline receptor (IC50=30 nM) over α2-adrenoceptor (IC50=18 μM). Harmane is also a potent and selective inhibitor of monoamine oxidase (MAO) (IC50s=0.5 and 5 μM for human MAO A/B, respectively). Harmane exhibits comutagenic effect[1][2][3][4]. Harmane, a β-Carboline alkaloid (BCA), is a potent neurotoxin that causes severe action tremors and psychiatric manifestations. Harmane shows 1000-fold selectivity for I1-Imidazoline receptor (IC50=30 nM) over α2-adrenoceptor (IC50=18 μM). Harmane is also a potent and selective inhibitor of monoamine oxidase (MAO) (IC50s=0.5 and 5 μM for human MAO A/B, respectively). Harmane exhibits comutagenic effect[1][2][3][4]. Harmane, a β-Carboline alkaloid (BCA), is a potent neurotoxin that causes severe action tremors and psychiatric manifestations. Harmane shows 1000-fold selectivity for I1-Imidazoline receptor (IC50=30 nM) over α2-adrenoceptor (IC50=18 μM). Harmane is also a potent and selective inhibitor of monoamine oxidase (MAO) (IC50s=0.5 and 5 μM for human MAO A/B, respectively). Harmane exhibits comutagenic effect[1][2][3][4].

   

Harmane

Harmane

C12H10N2 (182.0844)


Annotation level-1 Acquisition and generation of the data is financially supported by the Max-Planck-Society IPB_RECORD: 2281; CONFIDENCE confident structure IPB_RECORD: 2961; CONFIDENCE confident structure

   

α-Ketoisovaleric acid

3-Methyl-2-oxobutanoic acid

C5H8O3 (116.0473)


A 2-oxo monocarboxylic acid that is the 2-oxo derivative of isovaleric acid. 3-Methyl-2-oxobutanoic acid is a precursor of pantothenic acid in Escherichia coli.

   

3-Methyl-2-oxobutanoic acid

3-Methyl-2-oxobutanoic acid

C5H8O3 (116.0473)


   

Harmalan

4,9-Dihydro-1-methyl-3H-pyrido[3,4-b]indole, 9ci

C12H12N2 (184.1)


   

Aribin

InChI=1\C12H10N2\c1-8-12-10(6-7-13-8)9-4-2-3-5-11(9)14-12\h2-7,14H,1H

C12H10N2 (182.0844)


D009676 - Noxae > D009498 - Neurotoxins D009676 - Noxae > D009153 - Mutagens Harmane, a β-Carboline alkaloid (BCA), is a potent neurotoxin that causes severe action tremors and psychiatric manifestations. Harmane shows 1000-fold selectivity for I1-Imidazoline receptor (IC50=30 nM) over α2-adrenoceptor (IC50=18 μM). Harmane is also a potent and selective inhibitor of monoamine oxidase (MAO) (IC50s=0.5 and 5 μM for human MAO A/B, respectively). Harmane exhibits comutagenic effect[1][2][3][4]. Harmane, a β-Carboline alkaloid (BCA), is a potent neurotoxin that causes severe action tremors and psychiatric manifestations. Harmane shows 1000-fold selectivity for I1-Imidazoline receptor (IC50=30 nM) over α2-adrenoceptor (IC50=18 μM). Harmane is also a potent and selective inhibitor of monoamine oxidase (MAO) (IC50s=0.5 and 5 μM for human MAO A/B, respectively). Harmane exhibits comutagenic effect[1][2][3][4]. Harmane, a β-Carboline alkaloid (BCA), is a potent neurotoxin that causes severe action tremors and psychiatric manifestations. Harmane shows 1000-fold selectivity for I1-Imidazoline receptor (IC50=30 nM) over α2-adrenoceptor (IC50=18 μM). Harmane is also a potent and selective inhibitor of monoamine oxidase (MAO) (IC50s=0.5 and 5 μM for human MAO A/B, respectively). Harmane exhibits comutagenic effect[1][2][3][4].

   

oryzalexin A

oryzalexin A

C20H30O2 (302.2246)


A tricyclic diterpenoid that is ent-sandaracopimaradiene bearing additional hydroxy and oxo substituents at the 3alpha- and 7-positions respectively.

   

(5S)-3-acetyl-5-[(2S)-butan-2-yl]pyrrolidine-2,4-dione

(5S)-3-acetyl-5-[(2S)-butan-2-yl]pyrrolidine-2,4-dione

C10H15NO3 (197.1052)


   

4-Hydroxy-3-nitrophenylacetic acid

4-Hydroxy-3-nitrophenylacetic acid

C8H7NO5 (197.0324)


   

5-hydroxyfuran-2-carboxylic acid

5-hydroxyfuran-2-carboxylic acid

C5H4O4 (128.011)


A hydroxy monocarboxylic acid that is furan substituted by a hydroxy group at position 5 and a carboxy group at position 2 respectively.

   

2-[(1e,3e,5r,6s)-5,6-dihydroxyhepta-1,3-dien-1-yl]-6-hydroxybenzaldehyde

2-[(1e,3e,5r,6s)-5,6-dihydroxyhepta-1,3-dien-1-yl]-6-hydroxybenzaldehyde

C14H16O4 (248.1049)


   

(2s,4r)-4-acetyl-5-hydroxy-2-isopropyl-2,4-dihydropyrrol-3-one

(2s,4r)-4-acetyl-5-hydroxy-2-isopropyl-2,4-dihydropyrrol-3-one

C9H13NO3 (183.0895)


   

3-(penta-1,3-dien-1-yl)-3,4-dihydro-1h-2-benzopyran-4,8-diol

3-(penta-1,3-dien-1-yl)-3,4-dihydro-1h-2-benzopyran-4,8-diol

C14H16O3 (232.1099)


   

2-[(1e,3s,4s,5e)-3,4-dihydroxyhepta-1,5-dien-1-yl]-6-hydroxybenzaldehyde

2-[(1e,3s,4s,5e)-3,4-dihydroxyhepta-1,5-dien-1-yl]-6-hydroxybenzaldehyde

C14H16O4 (248.1049)


   

2-amino-4-methylpentanoyl pyrrolidine-2-carboxylate

2-amino-4-methylpentanoyl pyrrolidine-2-carboxylate

C11H20N2O3 (228.1474)


   

(1e,3s,4s,5e)-1-[3-hydroxy-2-(hydroxymethyl)phenyl]hepta-1,5-diene-3,4-diol

(1e,3s,4s,5e)-1-[3-hydroxy-2-(hydroxymethyl)phenyl]hepta-1,5-diene-3,4-diol

C14H18O4 (250.1205)


   

(3s,4s)-3,4,8-trihydroxy-3,4-dihydro-2h-naphthalen-1-one

(3s,4s)-3,4,8-trihydroxy-3,4-dihydro-2h-naphthalen-1-one

C10H10O4 (194.0579)


   

7-ethenyl-1,1,4a,7-tetramethyl-4,4b,5,6,10,10a-hexahydro-3h-phenanthrene-2,9-dione

7-ethenyl-1,1,4a,7-tetramethyl-4,4b,5,6,10,10a-hexahydro-3h-phenanthrene-2,9-dione

C20H28O2 (300.2089)


   

(3s,3ar,4s,6s,6ar,10s,12r,15r,15ar)-1,6,12-trihydroxy-3-[(4-methoxyphenyl)methyl]-4,10,12-trimethyl-5-methylidene-3h,3ah,4h,6h,6ah,9h,10h,11h,15h-cycloundeca[d]isoindol-15-yl acetate

(3s,3ar,4s,6s,6ar,10s,12r,15r,15ar)-1,6,12-trihydroxy-3-[(4-methoxyphenyl)methyl]-4,10,12-trimethyl-5-methylidene-3h,3ah,4h,6h,6ah,9h,10h,11h,15h-cycloundeca[d]isoindol-15-yl acetate

C31H41NO6 (523.2934)


   

1-[2,4-dihydroxy-5-(sec-butyl)-5h-pyrrol-3-yl]ethanone

1-[2,4-dihydroxy-5-(sec-butyl)-5h-pyrrol-3-yl]ethanone

C10H15NO3 (197.1052)


   

(4s,5z)-4-[(1s,2e)-1-hydroxybut-2-en-1-yl]-1,4-dihydro-2,3-benzodioxocin-10-ol

(4s,5z)-4-[(1s,2e)-1-hydroxybut-2-en-1-yl]-1,4-dihydro-2,3-benzodioxocin-10-ol

C14H16O4 (248.1049)


   

2-hydroxy-6-[(1e,3s)-4-hydroxy-3-[(1e)-prop-1-en-1-yl]but-1-en-1-yl]benzaldehyde

2-hydroxy-6-[(1e,3s)-4-hydroxy-3-[(1e)-prop-1-en-1-yl]but-1-en-1-yl]benzaldehyde

C14H16O3 (232.1099)


   

(4z)-5-hydroxy-4-(1-hydroxyethylidene)-2-(sec-butyl)-2h-pyrrol-3-one; 1-[2,4-dihydroxy-5-(sec-butyl)-5h-pyrrol-3-yl]ethanone

(4z)-5-hydroxy-4-(1-hydroxyethylidene)-2-(sec-butyl)-2h-pyrrol-3-one; 1-[2,4-dihydroxy-5-(sec-butyl)-5h-pyrrol-3-yl]ethanone

C20H30N2O6 (394.2104)


   

(z,5s,5'r)-5-ethyl-5'-methyl-4,5-dihydro-3h,5'h-[2,3'-bioxolylidene]-2',4'-dione

(z,5s,5'r)-5-ethyl-5'-methyl-4,5-dihydro-3h,5'h-[2,3'-bioxolylidene]-2',4'-dione

C11H14O4 (210.0892)


   

7-ethenyl-9-hydroxy-1,1,4a,7-tetramethyl-3,4,4b,5,6,9,10,10a-octahydrophenanthren-2-one

7-ethenyl-9-hydroxy-1,1,4a,7-tetramethyl-3,4,4b,5,6,9,10,10a-octahydrophenanthren-2-one

C20H30O2 (302.2246)


   

2-hydroxy-6-[4-hydroxy-3-(prop-1-en-1-yl)but-1-en-1-yl]benzaldehyde

2-hydroxy-6-[4-hydroxy-3-(prop-1-en-1-yl)but-1-en-1-yl]benzaldehyde

C14H16O3 (232.1099)


   

2-hydroxy-6-[(1e,3r)-4-hydroxy-3-[(1e)-prop-1-en-1-yl]but-1-en-1-yl]benzaldehyde

2-hydroxy-6-[(1e,3r)-4-hydroxy-3-[(1e)-prop-1-en-1-yl]but-1-en-1-yl]benzaldehyde

C14H16O3 (232.1099)


   

(2r,4e)-2-[(2r)-butan-2-yl]-5-hydroxy-4-(1-hydroxyethylidene)-2h-pyrrol-3-one

(2r,4e)-2-[(2r)-butan-2-yl]-5-hydroxy-4-(1-hydroxyethylidene)-2h-pyrrol-3-one

C10H15NO3 (197.1052)


   

(1e,3r,4s,5e)-1-[3-hydroxy-2-(hydroxymethyl)phenyl]hepta-1,5-diene-3,4-diol

(1e,3r,4s,5e)-1-[3-hydroxy-2-(hydroxymethyl)phenyl]hepta-1,5-diene-3,4-diol

C14H18O4 (250.1205)


   

(1s,2r,6r,9s,10s,13r,14r)-6-hydroxy-13-[(2r,5e)-5-isopropylhept-5-en-2-yl]-2,14-dimethyl-5-oxatetracyclo[7.7.0.0²,⁶.0¹⁰,¹⁴]hexadecan-4-one

(1s,2r,6r,9s,10s,13r,14r)-6-hydroxy-13-[(2r,5e)-5-isopropylhept-5-en-2-yl]-2,14-dimethyl-5-oxatetracyclo[7.7.0.0²,⁶.0¹⁰,¹⁴]hexadecan-4-one

C27H44O3 (416.329)


   

1-[3-hydroxy-2-(hydroxymethyl)phenyl]hepta-1,5-diene-3,4-diol

1-[3-hydroxy-2-(hydroxymethyl)phenyl]hepta-1,5-diene-3,4-diol

C14H18O4 (250.1205)


   

3-[(1e,3e)-penta-1,3-dien-1-yl]-3,4-dihydro-1h-2-benzopyran-4,8-diol

3-[(1e,3e)-penta-1,3-dien-1-yl]-3,4-dihydro-1h-2-benzopyran-4,8-diol

C14H16O3 (232.1099)


   

5-hydroxy-4-(1-hydroxyethylidene)-2-(sec-butyl)-2h-pyrrol-3-one

5-hydroxy-4-(1-hydroxyethylidene)-2-(sec-butyl)-2h-pyrrol-3-one

C10H15NO3 (197.1052)


   

(3s,4r)-3-[(1e,3e)-penta-1,3-dien-1-yl]-3,4-dihydro-1h-2-benzopyran-4,8-diol

(3s,4r)-3-[(1e,3e)-penta-1,3-dien-1-yl]-3,4-dihydro-1h-2-benzopyran-4,8-diol

C14H16O3 (232.1099)


   

4-[(2e)-1-hydroxybut-2-en-1-yl]-1,4-dihydro-2,3-benzodioxocin-10-ol

4-[(2e)-1-hydroxybut-2-en-1-yl]-1,4-dihydro-2,3-benzodioxocin-10-ol

C14H16O4 (248.1049)


   

4-(1-hydroxybut-2-en-1-yl)-1,4-dihydro-2,3-benzodioxocin-10-ol

4-(1-hydroxybut-2-en-1-yl)-1,4-dihydro-2,3-benzodioxocin-10-ol

C14H16O4 (248.1049)


   

1,6,12-trihydroxy-3-[(4-methoxyphenyl)methyl]-4,10,12-trimethyl-5-methylidene-3h,3ah,4h,6h,6ah,9h,10h,11h,15h-cycloundeca[d]isoindol-15-yl acetate

1,6,12-trihydroxy-3-[(4-methoxyphenyl)methyl]-4,10,12-trimethyl-5-methylidene-3h,3ah,4h,6h,6ah,9h,10h,11h,15h-cycloundeca[d]isoindol-15-yl acetate

C31H41NO6 (523.2934)


   

(4s)-4,8-dihydroxy-3,4-dihydro-2h-naphthalen-1-one

(4s)-4,8-dihydroxy-3,4-dihydro-2h-naphthalen-1-one

C10H10O3 (178.063)


   

4-(2-hydroxyethyl)-2-nitrophenol

4-(2-hydroxyethyl)-2-nitrophenol

C8H9NO4 (183.0532)


   

1-[(5s)-5-[(2r)-butan-2-yl]-2,4-dihydroxy-5h-pyrrol-3-yl]ethanone

1-[(5s)-5-[(2r)-butan-2-yl]-2,4-dihydroxy-5h-pyrrol-3-yl]ethanone

C10H15NO3 (197.1052)


   

(4s)-4,6,8-trihydroxy-3,4-dihydro-2h-naphthalen-1-one

(4s)-4,6,8-trihydroxy-3,4-dihydro-2h-naphthalen-1-one

C10H10O4 (194.0579)


   

(2s)-2-amino-4-methylpentanoyl (2s)-pyrrolidine-2-carboxylate

(2s)-2-amino-4-methylpentanoyl (2s)-pyrrolidine-2-carboxylate

C11H20N2O3 (228.1474)


   

(e,5s,5'r)-5-ethyl-5'-methyl-4,5-dihydro-3h,5'h-[2,3'-bioxolylidene]-2',4'-dione

(e,5s,5'r)-5-ethyl-5'-methyl-4,5-dihydro-3h,5'h-[2,3'-bioxolylidene]-2',4'-dione

C11H14O4 (210.0892)


   

7-ethenyl-2-hydroxy-1,1,4a,7-tetramethyl-2,3,4,4b,5,6,10,10a-octahydrophenanthren-9-one

7-ethenyl-2-hydroxy-1,1,4a,7-tetramethyl-2,3,4,4b,5,6,10,10a-octahydrophenanthren-9-one

C20H30O2 (302.2246)


   

(2r,3s,4e)-1-[(1r)-1,3-dihydro-2-benzofuran-1-yl]hex-4-ene-2,3-diol

(2r,3s,4e)-1-[(1r)-1,3-dihydro-2-benzofuran-1-yl]hex-4-ene-2,3-diol

C14H18O3 (234.1256)


   

2-(3,4-dihydroxyhepta-1,5-dien-1-yl)-6-hydroxybenzaldehyde

2-(3,4-dihydroxyhepta-1,5-dien-1-yl)-6-hydroxybenzaldehyde

C14H16O4 (248.1049)


   

2-hydroxy-6-[(1e)-4-hydroxy-3-[(1e)-prop-1-en-1-yl]but-1-en-1-yl]benzaldehyde

2-hydroxy-6-[(1e)-4-hydroxy-3-[(1e)-prop-1-en-1-yl]but-1-en-1-yl]benzaldehyde

C14H16O3 (232.1099)


   

cis-4-hydroxyscytalone

cis-4-hydroxyscytalone

C10H10O5 (210.0528)


   

4-(1-hydroxyethyl)-2-nitrophenol

4-(1-hydroxyethyl)-2-nitrophenol

C8H9NO4 (183.0532)


   

(2s)-4-acetyl-2-[(2s)-butan-2-yl]-5-hydroxy-2,4-dihydropyrrol-3-one

(2s)-4-acetyl-2-[(2s)-butan-2-yl]-5-hydroxy-2,4-dihydropyrrol-3-one

C10H15NO3 (197.1052)


   

3,4,8-trihydroxy-3,4-dihydro-2h-naphthalen-1-one

3,4,8-trihydroxy-3,4-dihydro-2h-naphthalen-1-one

C10H10O4 (194.0579)


   

1-(1,3-dihydro-2-benzofuran-1-yl)hex-4-ene-2,3-diol

1-(1,3-dihydro-2-benzofuran-1-yl)hex-4-ene-2,3-diol

C14H18O3 (234.1256)


   

(3s,4r)-3,4,8-trihydroxy-3,4-dihydro-2h-naphthalen-1-one

(3s,4r)-3,4,8-trihydroxy-3,4-dihydro-2h-naphthalen-1-one

C10H10O4 (194.0579)


   

4,6,8-trihydroxy-3,4-dihydro-2h-naphthalen-1-one

4,6,8-trihydroxy-3,4-dihydro-2h-naphthalen-1-one

C10H10O4 (194.0579)


   

(3s)-6,8-dihydroxy-3-methyl-3,4-dihydro-2-benzopyran-1-one

(3s)-6,8-dihydroxy-3-methyl-3,4-dihydro-2-benzopyran-1-one

C10H10O4 (194.0579)


   

3,4,6,8-tetrahydroxy-3,4-dihydro-2h-naphthalen-1-one

3,4,6,8-tetrahydroxy-3,4-dihydro-2h-naphthalen-1-one

C10H10O5 (210.0528)


   

4-acetyl-5-hydroxy-2-isopropyl-2,4-dihydropyrrol-3-one

4-acetyl-5-hydroxy-2-isopropyl-2,4-dihydropyrrol-3-one

C9H13NO3 (183.0895)


   

4-(hydroxymethyl)-2-nitrophenol

4-(hydroxymethyl)-2-nitrophenol

C7H7NO4 (169.0375)