NCBI Taxonomy: 5226

Auriculariales (ncbi_taxid: 5226)

found 109 associated metabolites at order taxonomy rank level.

Ancestor: Agaricomycetes incertae sedis

Child Taxonomies: Exidiaceae, Hyaloriaceae, Auriculariaceae, Aporpiaceae, environmental samples, unclassified Auriculariales, Auriculariales incertae sedis

Tryptophol

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

C10H11NO (161.0840596)


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.

   

Patulin

(2,4-Dihydroxy-2H-pyran-3(6H)-ylidene)acetic acid, 3,4-lactone

C7H6O4 (154.0266076)


Patulin is found in pomes. Mycotoxin, found as a contaminant of foods, e.g. apple juice. Sometimes detd. in apple juice Patulin is a mycotoxin produced by a variety of molds, particularly Aspergillus and Penicillium. It is commonly found in rotting apples, and the amount of patulin in apple products is generally viewed as a measure of the quality of the apples used in production. It is not a particularly potent toxin, but a number of studies have shown that it is genotoxic, which has led to some theories that it may be a carcinogen, though animal studies have remained inconclusive. Patulin is also an antibiotic. Several countries have instituted patulin restrictions in apple products. The World Health Organization recommends a maximum concentration of 50 µg/L in apple juice Mycotoxin, found as a contaminant of foods, e.g. apple juice. Sometimes detd. in apple juice D009676 - Noxae > D011042 - Poisons > D009183 - Mycotoxins D009676 - Noxae > D009153 - Mutagens Patulin (Terinin) is a mycotoxin produced by fungi including the Aspergillus, Penicillium, and Byssochlamys species, is suspected to be clastogenic, mutagenic, teratogenic and cytotoxic. Patulin induces autophagy-dependent apoptosis through lysosomal-mitochondrial axis, and causes DNA damage[1][2][3][4].

   
   
   

Tryptophol

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

C10H11NO (161.0840596)


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.

   

ethyl 2-(2-acetyl-3,5-dihydroxyphenyl)acetate

NCGC00386069-01!ethyl 2-(2-acetyl-3,5-dihydroxyphenyl)acetate

C12H14O5 (238.08411940000002)


   

ethyl 2-(2-acetyl-3,5-dihydroxyphenyl)acetate

ethyl 2-(2-acetyl-3,5-dihydroxyphenyl)acetate

C12H14O5 (238.08411940000002)


   

patulin

patulin

C7H6O4 (154.0266076)


D009676 - Noxae > D011042 - Poisons > D009183 - Mycotoxins CONFIDENCE standard compound; INTERNAL_ID 5971 D009676 - Noxae > D009153 - Mutagens CONFIDENCE Reference Standard (Level 1) Patulin (Terinin) is a mycotoxin produced by fungi including the Aspergillus, Penicillium, and Byssochlamys species, is suspected to be clastogenic, mutagenic, teratogenic and cytotoxic. Patulin induces autophagy-dependent apoptosis through lysosomal-mitochondrial axis, and causes DNA damage[1][2][3][4].

   

methyl 1-[(3S)-3,4-dihydroxy-2-methylbutan-2-yl]indole-3-carboxylate

methyl 1-[(3S)-3,4-dihydroxy-2-methylbutan-2-yl]indole-3-carboxylate

C15H19NO4 (277.1314014)


   

4-(oxiran-2-yl)-2-[(2e)-5-oxofuran-2-ylidene]but-3-yn-1-yl acetate

4-(oxiran-2-yl)-2-[(2e)-5-oxofuran-2-ylidene]but-3-yn-1-yl acetate

C12H10O5 (234.052821)


   

(5e)-5-(1,5,6-trihydroxy-5-methylhex-3-yn-2-ylidene)furan-2-one

(5e)-5-(1,5,6-trihydroxy-5-methylhex-3-yn-2-ylidene)furan-2-one

C11H12O5 (224.06847019999998)


   

(1'r,2s,3s,3'r,5r,7'r,10'e)-5-[(1e)-3-hydroxy-2-methylprop-1-en-1-yl]-10'-(hydroxymethyl)-3,3',14'-trimethylspiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-10',13'-diene-9',12'-dione

(1'r,2s,3s,3'r,5r,7'r,10'e)-5-[(1e)-3-hydroxy-2-methylprop-1-en-1-yl]-10'-(hydroxymethyl)-3,3',14'-trimethylspiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-10',13'-diene-9',12'-dione

C25H34O5 (414.24061140000003)


   

(1s,5s,9r,11r)-14-[(2s)-7-hydroxy-6-methylhept-5-en-2-yl]-4-(hydroxymethyl)-8,11-dimethyltetracyclo[9.3.0.0¹,⁵.0⁵,⁹]tetradeca-3,7,13-trien-6-one

(1s,5s,9r,11r)-14-[(2s)-7-hydroxy-6-methylhept-5-en-2-yl]-4-(hydroxymethyl)-8,11-dimethyltetracyclo[9.3.0.0¹,⁵.0⁵,⁹]tetradeca-3,7,13-trien-6-one

C25H34O3 (382.25078140000005)


   

n-(1,3-dihydroxy-3-methyl-4-oxopentan-2-yl)-6,8-dimethyldeca-2,4,6-trienamide

n-(1,3-dihydroxy-3-methyl-4-oxopentan-2-yl)-6,8-dimethyldeca-2,4,6-trienamide

C18H29NO4 (323.20964740000005)


   

(1'r,2s,3s,3'r,5r,7'r,10'z)-5-[(1e)-3-hydroxy-2-methylprop-1-en-1-yl]-10'-(hydroxymethyl)-3,3',14'-trimethylspiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-10',13'-dien-12'-one

(1'r,2s,3s,3'r,5r,7'r,10'z)-5-[(1e)-3-hydroxy-2-methylprop-1-en-1-yl]-10'-(hydroxymethyl)-3,3',14'-trimethylspiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-10',13'-dien-12'-one

C25H36O4 (400.2613456)


   

[(1r,4r,6r,8r)-8-(hydroxymethyl)-4-isopropyl-1-methyl-7-methylidenebicyclo[3.2.1]octan-6-yl]methanol

[(1r,4r,6r,8r)-8-(hydroxymethyl)-4-isopropyl-1-methyl-7-methylidenebicyclo[3.2.1]octan-6-yl]methanol

C15H26O2 (238.1932696)


   

(2s,3r,4r)-2-[(2r,4ar,4br,10ar,12ar)-6,9-dihydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-5-oxo-3,4,4b,11,12,12a-hexahydro-2h-1,10-dioxatetraphen-8-yl]-4-methylhexan-3-yl acetate

(2s,3r,4r)-2-[(2r,4ar,4br,10ar,12ar)-6,9-dihydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-5-oxo-3,4,4b,11,12,12a-hexahydro-2h-1,10-dioxatetraphen-8-yl]-4-methylhexan-3-yl acetate

C30H44O8 (532.3036024)


   

(1'r,2s,3s,3'r,5r,7'r,9'e,11's,12'r,14'r)-10'-(hydroxymethyl)-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)spiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecan]-9'-ene-1',12'-diol

(1'r,2s,3s,3'r,5r,7'r,9'e,11's,12'r,14'r)-10'-(hydroxymethyl)-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)spiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecan]-9'-ene-1',12'-diol

C25H40O4 (404.29264400000005)


   

(3r,4r,5s,6r,10z)-3,4,6-trihydroxy-2-methoxy-3-methyl-10-propylidene-2-azaspiro[4.5]dec-8-ene-1,7-dione

(3r,4r,5s,6r,10z)-3,4,6-trihydroxy-2-methoxy-3-methyl-10-propylidene-2-azaspiro[4.5]dec-8-ene-1,7-dione

C14H19NO6 (297.1212314)


   

(1's,2s,3s,3'r,5r,7'r,11'r)-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)-12'-oxospiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-9',13'-diene-10'-carboxylic acid

(1's,2s,3s,3'r,5r,7'r,11'r)-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)-12'-oxospiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-9',13'-diene-10'-carboxylic acid

C25H34O4 (398.24569640000004)


   

(1r,4r,5s)-6-formyl-4-isopropyl-1,7-dimethylbicyclo[3.2.1]oct-6-ene-8-carboxylic acid

(1r,4r,5s)-6-formyl-4-isopropyl-1,7-dimethylbicyclo[3.2.1]oct-6-ene-8-carboxylic acid

C15H22O3 (250.1568862)


   

6-formyl-4-isopropyl-1,7-dimethylbicyclo[3.2.1]oct-6-ene-8-carboxylic acid

6-formyl-4-isopropyl-1,7-dimethylbicyclo[3.2.1]oct-6-ene-8-carboxylic acid

C15H22O3 (250.1568862)


   

(1's,2s,3s,3'r,5r,7's,8's,9'e,11'r)-8'-hydroxy-10'-(hydroxymethyl)-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)spiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-9',13'-dien-12'-one

(1's,2s,3s,3'r,5r,7's,8's,9'e,11'r)-8'-hydroxy-10'-(hydroxymethyl)-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)spiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-9',13'-dien-12'-one

C25H36O4 (400.2613456)


   

methyl 7-[(4-hydroxyphenyl)carbamoyl]heptanoate

methyl 7-[(4-hydroxyphenyl)carbamoyl]heptanoate

C15H21NO4 (279.1470506)


   
   

(4s,7e,10s,13e,16s)-4,10,16-trimethyl-1,5,11-trioxacyclohexadeca-7,13-diene-2,6,12-trione

(4s,7e,10s,13e,16s)-4,10,16-trimethyl-1,5,11-trioxacyclohexadeca-7,13-diene-2,6,12-trione

C16H22O6 (310.1416312)


   

10'-(hydroxymethyl)-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)spiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecan]-9'-en-14'-ol

10'-(hydroxymethyl)-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)spiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecan]-9'-en-14'-ol

C25H40O3 (388.297729)


   

9'-hydroxy-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)-12'-oxospiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-10',13'-diene-10'-carboxylic acid

9'-hydroxy-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)-12'-oxospiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-10',13'-diene-10'-carboxylic acid

C25H34O5 (414.24061140000003)


   

9'-hydroxy-5-(3-hydroxy-2-methylprop-1-en-1-yl)-10'-(hydroxymethyl)-3,3',14'-trimethylspiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-10',13'-dien-12'-one

9'-hydroxy-5-(3-hydroxy-2-methylprop-1-en-1-yl)-10'-(hydroxymethyl)-3,3',14'-trimethylspiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-10',13'-dien-12'-one

C25H36O5 (416.2562606)


   

(1'r,2s,3s,4's,5r,5'r,7'r,11'r,14'r)-4'-hydroxy-5-(3-hydroxy-2-methylprop-1-en-1-yl)-16'-(2-hydroxyethyl)-3,4',7'-trimethyl-2'-oxa-16'-azaspiro[oxolane-2,10'-tetracyclo[12.3.0.0¹,⁵.0⁷,¹¹]heptadecane]-15',17'-dione

(1'r,2s,3s,4's,5r,5'r,7'r,11'r,14'r)-4'-hydroxy-5-(3-hydroxy-2-methylprop-1-en-1-yl)-16'-(2-hydroxyethyl)-3,4',7'-trimethyl-2'-oxa-16'-azaspiro[oxolane-2,10'-tetracyclo[12.3.0.0¹,⁵.0⁷,¹¹]heptadecane]-15',17'-dione

C27H41NO7 (491.28828760000005)


   

6,8-dimethyldeca-2,4,6-trienamide

6,8-dimethyldeca-2,4,6-trienamide

C12H19NO (193.14665639999998)


   

methyl 1-(3,4-dihydroxy-2-methylbutan-2-yl)indole-3-carboxylate

methyl 1-(3,4-dihydroxy-2-methylbutan-2-yl)indole-3-carboxylate

C15H19NO4 (277.1314014)


   

4-[(2r)-oxiran-2-yl]-2-[(2e)-5-oxofuran-2-ylidene]but-3-yn-1-yl acetate

4-[(2r)-oxiran-2-yl]-2-[(2e)-5-oxofuran-2-ylidene]but-3-yn-1-yl acetate

C12H10O5 (234.052821)


   

(2r,4ar,4bs,5s,10ar,12ar)-5-hydroxy-2-(2-hydroxypropan-2-yl)-7-methoxy-4a,10a-dimethyl-8-[(2s,4e)-4-methyl-3-oxohex-4-en-2-yl]-2,3,4,4b,5,11,12,12a-octahydro-1,10-dioxatetraphene-6,9-dione

(2r,4ar,4bs,5s,10ar,12ar)-5-hydroxy-2-(2-hydroxypropan-2-yl)-7-methoxy-4a,10a-dimethyl-8-[(2s,4e)-4-methyl-3-oxohex-4-en-2-yl]-2,3,4,4b,5,11,12,12a-octahydro-1,10-dioxatetraphene-6,9-dione

C29H40O8 (516.2723040000001)


   

5-(3-hydroxy-2-methylprop-1-en-1-yl)-3,3',14'-trimethyl-12'-oxospiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-9',13'-diene-10'-carbaldehyde

5-(3-hydroxy-2-methylprop-1-en-1-yl)-3,3',14'-trimethyl-12'-oxospiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-9',13'-diene-10'-carbaldehyde

C25H34O4 (398.24569640000004)


   

(1's,2s,3s,3'r,5r,7'r,13's,15'r)-15'-hydroxy-12'-(2-hydroxyethyl)-3,3',15'-trimethyl-5-(2-methylprop-1-en-1-yl)-12'-azaspiro[oxolane-2,6'-tetracyclo[8.5.1.0³,⁷.0¹³,¹⁶]hexadecan]-10'(16')-en-11'-one

(1's,2s,3s,3'r,5r,7'r,13's,15'r)-15'-hydroxy-12'-(2-hydroxyethyl)-3,3',15'-trimethyl-5-(2-methylprop-1-en-1-yl)-12'-azaspiro[oxolane-2,6'-tetracyclo[8.5.1.0³,⁷.0¹³,¹⁶]hexadecan]-10'(16')-en-11'-one

C27H41NO4 (443.30354260000007)


   

(1's,2s,3s,3'r,5r,7'r,9'e,11'r,14'r)-14'-hydroxy-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)-12'-oxospiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecan]-9'-ene-10'-carboxylic acid

(1's,2s,3s,3'r,5r,7'r,9'e,11'r,14'r)-14'-hydroxy-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)-12'-oxospiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecan]-9'-ene-10'-carboxylic acid

C25H36O5 (416.2562606)


   

(1'r,2s,3s,3'r,5r,7'r,9's)-9'-hydroxy-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)-12'-oxospiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-10',13'-diene-10'-carboxylic acid

(1'r,2s,3s,3'r,5r,7'r,9's)-9'-hydroxy-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)-12'-oxospiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-10',13'-diene-10'-carboxylic acid

C25H34O5 (414.24061140000003)


   

(2s,3s,3'r,5r,7'r,9'e,14'r)-5-[(1e)-3-hydroxy-2-methylprop-1-en-1-yl]-10'-(hydroxymethyl)-3,3',14'-trimethylspiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-1'(11'),9'-dien-12'-one

(2s,3s,3'r,5r,7'r,9'e,14'r)-5-[(1e)-3-hydroxy-2-methylprop-1-en-1-yl]-10'-(hydroxymethyl)-3,3',14'-trimethylspiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-1'(11'),9'-dien-12'-one

C25H36O4 (400.2613456)


   

2-[(1r,3s,7r,8s,9s)-9-isopropyl-1-methyl-2-methylidene-5-azatricyclo[5.4.0.0³,⁸]undecan-5-yl]ethanol

2-[(1r,3s,7r,8s,9s)-9-isopropyl-1-methyl-2-methylidene-5-azatricyclo[5.4.0.0³,⁸]undecan-5-yl]ethanol

C17H29NO (263.2249024)


   

(2r,4ar,4bs,5s,10ar,12ar)-5-hydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-8-[(2s,4e)-4-methyl-3-oxohex-4-en-2-yl]-2,3,4,4b,5,11,12,12a-octahydro-1,10-dioxatetraphene-6,9-dione

(2r,4ar,4bs,5s,10ar,12ar)-5-hydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-8-[(2s,4e)-4-methyl-3-oxohex-4-en-2-yl]-2,3,4,4b,5,11,12,12a-octahydro-1,10-dioxatetraphene-6,9-dione

C28H38O7 (486.2617398)


   

(5e)-5-[1-hydroxy-4-(oxiran-2-yl)but-3-yn-2-ylidene]furan-2-one

(5e)-5-[1-hydroxy-4-(oxiran-2-yl)but-3-yn-2-ylidene]furan-2-one

C10H8O4 (192.0422568)


   

(4r)-4-isopropyl-7-methyl-10-methylidenetricyclo[5.2.1.0³,⁸]decane-2,9-diol

(4r)-4-isopropyl-7-methyl-10-methylidenetricyclo[5.2.1.0³,⁸]decane-2,9-diol

C15H24O2 (236.1776204)


   

(1's,2s,3s,3'r,5r,7'r,10'r,11'r)-10'-(hydroxymethyl)-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)spiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecan]-13'-en-12'-one

(1's,2s,3s,3'r,5r,7'r,10'r,11'r)-10'-(hydroxymethyl)-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)spiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecan]-13'-en-12'-one

C25H38O3 (386.2820798)


   

(6s)-6-[(1r,3r,4s,8r,11s,12r,14s)-3-hydroxy-5-(hydroxymethyl)-1,12-dimethyl-15-oxapentacyclo[9.3.1.0³,⁸.0⁴,¹⁴.0⁸,¹²]pentadeca-5,9-dien-9-yl]-2-methylhept-2-en-4-one

(6s)-6-[(1r,3r,4s,8r,11s,12r,14s)-3-hydroxy-5-(hydroxymethyl)-1,12-dimethyl-15-oxapentacyclo[9.3.1.0³,⁸.0⁴,¹⁴.0⁸,¹²]pentadeca-5,9-dien-9-yl]-2-methylhept-2-en-4-one

C25H34O4 (398.24569640000004)


   

5-(3-hydroxy-2-methylprop-1-en-1-yl)-10'-(hydroxymethyl)-3,3',14'-trimethylspiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-10',13'-dien-12'-one

5-(3-hydroxy-2-methylprop-1-en-1-yl)-10'-(hydroxymethyl)-3,3',14'-trimethylspiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-10',13'-dien-12'-one

C25H36O4 (400.2613456)


   

5-(3-hydroxy-2-methylprop-1-en-1-yl)-3,3',10',14'-tetramethylspiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-9',13'-dien-12'-one

5-(3-hydroxy-2-methylprop-1-en-1-yl)-3,3',10',14'-tetramethylspiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-9',13'-dien-12'-one

C25H36O3 (384.26643060000004)


   

2-[(1r,3r,7s,8r,9s)-9-isopropyl-1-methyl-2-methylidene-5-azatricyclo[5.4.0.0³,⁸]undecan-5-yl]ethanol

2-[(1r,3r,7s,8r,9s)-9-isopropyl-1-methyl-2-methylidene-5-azatricyclo[5.4.0.0³,⁸]undecan-5-yl]ethanol

C17H29NO (263.2249024)


   

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

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

C28H46O4 (446.3395916)


   

(5z)-5-{1-hydroxy-4-[(2s)-oxiran-2-yl]but-3-yn-2-ylidene}furan-2-one

(5z)-5-{1-hydroxy-4-[(2s)-oxiran-2-yl]but-3-yn-2-ylidene}furan-2-one

C10H8O4 (192.0422568)


   

1-[(1r,12s,13s,14r,17r,19r)-10,12-dihydroxy-17-(2-hydroxypropan-2-yl)-1,14-dimethyl-2,5,18-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,6,8,10-tetraen-7-yl]-2-methylbutan-1-one

1-[(1r,12s,13s,14r,17r,19r)-10,12-dihydroxy-17-(2-hydroxypropan-2-yl)-1,14-dimethyl-2,5,18-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,6,8,10-tetraen-7-yl]-2-methylbutan-1-one

C28H38O7 (486.2617398)


   

[(1r,4r,5s,6r,8r)-8-(hydroxymethyl)-4-isopropyl-1-methyl-7-methylidenebicyclo[3.2.1]octan-6-yl]methanol

[(1r,4r,5s,6r,8r)-8-(hydroxymethyl)-4-isopropyl-1-methyl-7-methylidenebicyclo[3.2.1]octan-6-yl]methanol

C15H26O2 (238.1932696)


   

5-[1-hydroxy-4-(oxiran-2-yl)but-3-yn-2-ylidene]furan-2-one

5-[1-hydroxy-4-(oxiran-2-yl)but-3-yn-2-ylidene]furan-2-one

C10H8O4 (192.0422568)


   

(1's,2s,3s,3'r,5r,7'r,9'e,11'r)-5-[(1e)-3-hydroxy-2-methylprop-1-en-1-yl]-3,3',14'-trimethyl-12'-oxospiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-9',13'-diene-10'-carbaldehyde

(1's,2s,3s,3'r,5r,7'r,9'e,11'r)-5-[(1e)-3-hydroxy-2-methylprop-1-en-1-yl]-3,3',14'-trimethyl-12'-oxospiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-9',13'-diene-10'-carbaldehyde

C25H34O4 (398.24569640000004)


   

methyl 1-(2-methylbut-3-en-2-yl)indole-3-carboxylate

methyl 1-(2-methylbut-3-en-2-yl)indole-3-carboxylate

C15H17NO2 (243.12592220000002)


   

(2r,4ar,4bs,5s,10ar,12ar)-5-hydroxy-2-(2-hydroxypropan-2-yl)-7-methoxy-4a,10a-dimethyl-8-[(2s,4s)-4-methyl-3-oxohexan-2-yl]-2,3,4,4b,5,11,12,12a-octahydro-1,10-dioxatetraphene-6,9-dione

(2r,4ar,4bs,5s,10ar,12ar)-5-hydroxy-2-(2-hydroxypropan-2-yl)-7-methoxy-4a,10a-dimethyl-8-[(2s,4s)-4-methyl-3-oxohexan-2-yl]-2,3,4,4b,5,11,12,12a-octahydro-1,10-dioxatetraphene-6,9-dione

C29H42O8 (518.2879532000001)


   

(2s,4e)-2-[(2r,4ar,4bs,5s,10ar,12ar)-5,6,9-trihydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-2,3,4,4b,5,11,12,12a-octahydro-1,10-dioxatetraphen-8-yl]-4-methylhex-4-en-3-one

(2s,4e)-2-[(2r,4ar,4bs,5s,10ar,12ar)-5,6,9-trihydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-2,3,4,4b,5,11,12,12a-octahydro-1,10-dioxatetraphen-8-yl]-4-methylhex-4-en-3-one

C28H40O7 (488.277389)


   

(2r,4ar,4br,10ar,12ar)-2-(2-hydroxypropan-2-yl)-7-methoxy-4a,10a-dimethyl-8-[(2s,4s)-4-methyl-3-oxohexan-2-yl]-2,3,4,4b,5,11,12,12a-octahydro-1,10-dioxatetraphene-6,9-dione

(2r,4ar,4br,10ar,12ar)-2-(2-hydroxypropan-2-yl)-7-methoxy-4a,10a-dimethyl-8-[(2s,4s)-4-methyl-3-oxohexan-2-yl]-2,3,4,4b,5,11,12,12a-octahydro-1,10-dioxatetraphene-6,9-dione

C29H42O7 (502.2930382)


   

8-(hydroxymethyl)-4-isopropyl-1,7-dimethylbicyclo[3.2.1]oct-6-ene-6-carboxylic acid

8-(hydroxymethyl)-4-isopropyl-1,7-dimethylbicyclo[3.2.1]oct-6-ene-6-carboxylic acid

C15H24O3 (252.1725354)


   

(1's,2s,3s,3'r,5r,7'r)-12'-(2-hydroxyethyl)-3,3'-dimethyl-5-(2-methylprop-1-en-1-yl)-12'-azaspiro[oxolane-2,6'-tetracyclo[8.5.1.0³,⁷.0¹³,¹⁶]hexadecane]-10'(16'),13'-diene-11',15'-dione

(1's,2s,3s,3'r,5r,7'r)-12'-(2-hydroxyethyl)-3,3'-dimethyl-5-(2-methylprop-1-en-1-yl)-12'-azaspiro[oxolane-2,6'-tetracyclo[8.5.1.0³,⁷.0¹³,¹⁶]hexadecane]-10'(16'),13'-diene-11',15'-dione

C26H35NO4 (425.25659500000006)


   

(1's,2s,3s,3'r,5r,7'r,11'r)-14'-(hydroxymethyl)-3,3',10'-trimethyl-5-(2-methylprop-1-en-1-yl)spiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-9',13'-dien-12'-one

(1's,2s,3s,3'r,5r,7'r,11'r)-14'-(hydroxymethyl)-3,3',10'-trimethyl-5-(2-methylprop-1-en-1-yl)spiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-9',13'-dien-12'-one

C25H36O3 (384.26643060000004)


   

9-isopropyl-1-methyl-2-methylidene-5-oxatricyclo[5.4.0.0³,⁸]undecan-4-ol

9-isopropyl-1-methyl-2-methylidene-5-oxatricyclo[5.4.0.0³,⁸]undecan-4-ol

C15H24O2 (236.1776204)


   

14'-(hydroxymethyl)-3,3',10'-trimethyl-5-(2-methylprop-1-en-1-yl)spiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-9',13'-dien-12'-one

14'-(hydroxymethyl)-3,3',10'-trimethyl-5-(2-methylprop-1-en-1-yl)spiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-9',13'-dien-12'-one

C25H36O3 (384.26643060000004)


   

5-(1,5,6-trihydroxy-5-methylhex-3-yn-2-ylidene)furan-2-one

5-(1,5,6-trihydroxy-5-methylhex-3-yn-2-ylidene)furan-2-one

C11H12O5 (224.06847019999998)


   

3,4,6-trihydroxy-2-methoxy-3-methyl-10-propylidene-2-azaspiro[4.5]dec-8-ene-1,7-dione

3,4,6-trihydroxy-2-methoxy-3-methyl-10-propylidene-2-azaspiro[4.5]dec-8-ene-1,7-dione

C14H19NO6 (297.1212314)


   

(1's,2s,3s,3'r,5r,7'r,9'e,11'r)-10'-(hydroxymethyl)-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)spiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-9',13'-dien-12'-one

(1's,2s,3s,3'r,5r,7'r,9'e,11'r)-10'-(hydroxymethyl)-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)spiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-9',13'-dien-12'-one

C25H36O3 (384.26643060000004)


   

(1's,2s,3s,3'r,5r,7'r,11'r)-5-(3-hydroxy-2-methylprop-1-en-1-yl)-3,3',10',14'-tetramethylspiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-9',13'-dien-12'-one

(1's,2s,3s,3'r,5r,7'r,11'r)-5-(3-hydroxy-2-methylprop-1-en-1-yl)-3,3',10',14'-tetramethylspiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-9',13'-dien-12'-one

C25H36O3 (384.26643060000004)


   

(1'r,2s,3s,3'r,5r,7'r,9'r,10'e)-9'-hydroxy-5-[(1e)-3-hydroxy-2-methylprop-1-en-1-yl]-10'-(hydroxymethyl)-3,3',14'-trimethylspiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-10',13'-dien-12'-one

(1'r,2s,3s,3'r,5r,7'r,9'r,10'e)-9'-hydroxy-5-[(1e)-3-hydroxy-2-methylprop-1-en-1-yl]-10'-(hydroxymethyl)-3,3',14'-trimethylspiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-10',13'-dien-12'-one

C25H36O5 (416.2562606)


   

(2s,3s,3'r,5r,7'r,9'e,14'r)-10'-(hydroxymethyl)-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)spiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-1'(11'),9'-dien-12'-one

(2s,3s,3'r,5r,7'r,9'e,14'r)-10'-(hydroxymethyl)-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)spiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-1'(11'),9'-dien-12'-one

C25H36O3 (384.26643060000004)


   

4-isopropyl-7-methyl-10-methylidenetricyclo[5.2.1.0³,⁸]decane-2,9-diol

4-isopropyl-7-methyl-10-methylidenetricyclo[5.2.1.0³,⁸]decane-2,9-diol

C15H24O2 (236.1776204)


   
   

(1r,3r,4s,7s,8s,9r)-9-isopropyl-1-methyl-2-methylidene-5-oxatricyclo[5.4.0.0³,⁸]undecan-4-ol

(1r,3r,4s,7s,8s,9r)-9-isopropyl-1-methyl-2-methylidene-5-oxatricyclo[5.4.0.0³,⁸]undecan-4-ol

C15H24O2 (236.1776204)


   

(2e,4e,6e)-n-[(2r,3s)-1,3-dihydroxy-3-methyl-4-oxopentan-2-yl]-6,8-dimethyldeca-2,4,6-trienimidic acid

(2e,4e,6e)-n-[(2r,3s)-1,3-dihydroxy-3-methyl-4-oxopentan-2-yl]-6,8-dimethyldeca-2,4,6-trienimidic acid

C18H29NO4 (323.20964740000005)


   

(2r,4ar,4br,10ar,12ar)-6,9-dihydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-8-[(2s,4r)-4-methyl-3-oxohexan-2-yl]-3,4,4b,11,12,12a-hexahydro-2h-1,10-dioxatetraphen-5-one

(2r,4ar,4br,10ar,12ar)-6,9-dihydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-8-[(2s,4r)-4-methyl-3-oxohexan-2-yl]-3,4,4b,11,12,12a-hexahydro-2h-1,10-dioxatetraphen-5-one

C28H40O7 (488.277389)


   

3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)-12'-oxospiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-9',13'-diene-10'-carboxylic acid

3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)-12'-oxospiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-9',13'-diene-10'-carboxylic acid

C25H34O4 (398.24569640000004)


   

1,4,5,8-tetrahydroxy-2-methylanthracene-9,10-dione

1,4,5,8-tetrahydroxy-2-methylanthracene-9,10-dione

C15H10O6 (286.047736)


   

(1r,3r,4s,8r,11s,12r,14s)-9-[(2s)-7-hydroxy-6-methylhept-5-en-2-yl]-5-(hydroxymethyl)-1,12-dimethyl-15-oxapentacyclo[9.3.1.0³,⁸.0⁴,¹⁴.0⁸,¹²]pentadeca-5,9-dien-3-ol

(1r,3r,4s,8r,11s,12r,14s)-9-[(2s)-7-hydroxy-6-methylhept-5-en-2-yl]-5-(hydroxymethyl)-1,12-dimethyl-15-oxapentacyclo[9.3.1.0³,⁸.0⁴,¹⁴.0⁸,¹²]pentadeca-5,9-dien-3-ol

C25H36O4 (400.2613456)


   

(1r,3r,7s,8s,9r)-9-isopropyl-1-methyl-2-methylidene-5-oxatricyclo[5.4.0.0³,⁸]undecan-4-one

(1r,3r,7s,8s,9r)-9-isopropyl-1-methyl-2-methylidene-5-oxatricyclo[5.4.0.0³,⁸]undecan-4-one

C15H22O2 (234.1619712)


   

(1r,4r,5s,8s)-8-(hydroxymethyl)-4-isopropyl-1,7-dimethylbicyclo[3.2.1]oct-6-ene-6-carboxylic acid

(1r,4r,5s,8s)-8-(hydroxymethyl)-4-isopropyl-1,7-dimethylbicyclo[3.2.1]oct-6-ene-6-carboxylic acid

C15H24O3 (252.1725354)


   

(1s,2r,6r,9s,10s,12r)-1-[(2s)-7-hydroxy-6-methylhept-5-en-2-yl]-5-(hydroxymethyl)-9,12-dimethyl-15-oxapentacyclo[7.5.1.0²,⁶.0²,¹².0⁶,¹⁰]pentadec-4-en-7-one

(1s,2r,6r,9s,10s,12r)-1-[(2s)-7-hydroxy-6-methylhept-5-en-2-yl]-5-(hydroxymethyl)-9,12-dimethyl-15-oxapentacyclo[7.5.1.0²,⁶.0²,¹².0⁶,¹⁰]pentadec-4-en-7-one

C25H36O4 (400.2613456)


   

(5z)-5-[(5r)-1,6-dihydroxy-5-methylhex-3-yn-2-ylidene]furan-2-one

(5z)-5-[(5r)-1,6-dihydroxy-5-methylhex-3-yn-2-ylidene]furan-2-one

C11H12O4 (208.0735552)


   

(2s,3r,4s)-2-[(2r,4ar,4bs,5s,10ar,12ar)-7-amino-5-hydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-6,9-dioxo-2,3,4,4b,5,11,12,12a-octahydro-1,10-dioxatetraphen-8-yl]-4-methylhexan-3-yl acetate

(2s,3r,4s)-2-[(2r,4ar,4bs,5s,10ar,12ar)-7-amino-5-hydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-6,9-dioxo-2,3,4,4b,5,11,12,12a-octahydro-1,10-dioxatetraphen-8-yl]-4-methylhexan-3-yl acetate

C30H45NO8 (547.3145010000001)


   

(2e,4e,6e)-6,8-dimethyldeca-2,4,6-trienimidic acid

(2e,4e,6e)-6,8-dimethyldeca-2,4,6-trienimidic acid

C12H19NO (193.14665639999998)


   

(1'r,2s,3s,3'r,5r,7'r,9's)-9'-hydroxy-5-(3-hydroxy-2-methylprop-1-en-1-yl)-10'-(hydroxymethyl)-3,3',14'-trimethylspiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-10',13'-dien-12'-one

(1'r,2s,3s,3'r,5r,7'r,9's)-9'-hydroxy-5-(3-hydroxy-2-methylprop-1-en-1-yl)-10'-(hydroxymethyl)-3,3',14'-trimethylspiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-10',13'-dien-12'-one

C25H36O5 (416.2562606)


   

5-(1,6-dihydroxy-5-methylhex-3-yn-2-ylidene)furan-2-one

5-(1,6-dihydroxy-5-methylhex-3-yn-2-ylidene)furan-2-one

C11H12O4 (208.0735552)


   

4-(oxiran-2-yl)-2-(5-oxofuran-2-ylidene)but-3-yn-1-yl acetate

4-(oxiran-2-yl)-2-(5-oxofuran-2-ylidene)but-3-yn-1-yl acetate

C12H10O5 (234.052821)


   

(2s,4s)-2-[(2r,4ar,4bs,5s,10ar,12ar)-5,6,9-trihydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-2,3,4,4b,5,11,12,12a-octahydro-1,10-dioxatetraphen-8-yl]-4-methylhexan-3-one

(2s,4s)-2-[(2r,4ar,4bs,5s,10ar,12ar)-5,6,9-trihydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-2,3,4,4b,5,11,12,12a-octahydro-1,10-dioxatetraphen-8-yl]-4-methylhexan-3-one

C28H42O7 (490.2930382)


   

4-hydroxy-3-[(1r)-1-hydroxy-3-methylbut-3-en-1-yl]benzoic acid

4-hydroxy-3-[(1r)-1-hydroxy-3-methylbut-3-en-1-yl]benzoic acid

C12H14O4 (222.0892044)


   

(3e)-4-[(1's,2s,3s,3'r,5r,7'r,9'e,11'r)-10'-(hydroxymethyl)-3,3',14'-trimethyl-12'-oxospiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-9',13'-dien-5-yl]-3-methylbut-3-enoic acid

(3e)-4-[(1's,2s,3s,3'r,5r,7'r,9'e,11'r)-10'-(hydroxymethyl)-3,3',14'-trimethyl-12'-oxospiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-9',13'-dien-5-yl]-3-methylbut-3-enoic acid

C26H36O5 (428.2562606)


   

(1's,2s,3s,3'r,5r,7'r,9'e,11'r)-5-[(1z)-3-hydroxy-2-methylprop-1-en-1-yl]-10'-(hydroxymethyl)-3,3',14'-trimethylspiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-9',13'-dien-12'-one

(1's,2s,3s,3'r,5r,7'r,9'e,11'r)-5-[(1z)-3-hydroxy-2-methylprop-1-en-1-yl]-10'-(hydroxymethyl)-3,3',14'-trimethylspiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-9',13'-dien-12'-one

C25H36O4 (400.2613456)


   

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

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

C28H46O3 (430.34467659999996)


   

(1's,2s,3s,3'r,5r,7'r,11's,14'r)-10'-(hydroxymethyl)-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)spiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecan]-9'-en-14'-ol

(1's,2s,3s,3'r,5r,7'r,11's,14'r)-10'-(hydroxymethyl)-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)spiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecan]-9'-en-14'-ol

C25H40O3 (388.297729)


   

(2s,4s,5r,6s)-5-hydroxy-6-methoxy-10,10-dimethyl-3,11-dioxatricyclo[5.4.0.0²,⁴]undec-1(7)-en-8-one

(2s,4s,5r,6s)-5-hydroxy-6-methoxy-10,10-dimethyl-3,11-dioxatricyclo[5.4.0.0²,⁴]undec-1(7)-en-8-one

C12H16O5 (240.0997686)