CHEBI:65846 - 20-epi-bryonolic acid

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ChEBI Name 20-epi-bryonolic acid
ChEBI ID CHEBI:65846
ChEBI ASCII Name 20-epi-bryonolic acid
Definition A pentacyclic triterpenoid of D:C-friedooleanane-type triterpenoids isolated from the stems of Lagenaria siceraria and roots of Coriaria intermedia and has been found to exhibit antineoplastic activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C30H48O3
Net Charge 0
Average Mass 456.70030
Monoisotopic Mass 456.36035
InChI InChI=1S/C30H48O3/c1-25(2)21-9-8-20-19(28(21,5)12-11-23(25)31)10-13-30(7)22-18-27(4,24(32)33)15-14-26(22,3)16-17-29(20,30)6/h21-23,31H,8-18H2,1-7H3,(H,32,33)/t21-,22+,23-,26+,27-,28+,29+,30-/m0/s1
InChIKey BHVJSLPLFOAMEV-UHIFYLTQSA-N
SMILES [H][C@@]12CCC3=C(CC[C@@]4(C)[C@]5([H])C[C@](C)(CC[C@]5(C)CC[C@]34C)C(O)=O)[C@@]1(C)CC[C@H](O)C2(C)C
Metabolite of Species Details
Macaranga conifera (NCBI:txid109817) Found in leaf (BTO:0000713). See: DOI
Celtis philippinensis (NCBI:txid213552) Found in twig (BTO:0001411). See: PubMed
Lagenaria siceraria (NCBI:txid3668) Found in stem (BTO:0001300). See: PubMed
Coriaria intermedia (NCBI:txid79756) See: DOI
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 20-epi-bryonolic acid (CHEBI:65846) has role antineoplastic agent (CHEBI:35610)
20-epi-bryonolic acid (CHEBI:65846) has role metabolite (CHEBI:25212)
20-epi-bryonolic acid (CHEBI:65846) is a hydroxy monocarboxylic acid (CHEBI:35868)
20-epi-bryonolic acid (CHEBI:65846) is a pentacyclic triterpenoid (CHEBI:25872)
IUPAC Name
(2S,4aS,6aS,8aR,10S,12aS,14aS,14bR)-10-hydroxy-2,4a,6a,9,9,12a,14a-heptamethyl-1,2,3,4,4a,5,6,6a,7,8,8a,9,10,11,12,12a,13,14,14a,14b-icosahydropicene-2-carboxylic acid
Registry Number Type Source
8176385 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
12482456 PubMed citation Europe PMC
18310955 PubMed citation Europe PMC
Last Modified
21 January 2013