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CHEBI:65846 - 20-epi-bryonolic acid

ChEBI IDCHEBI:65846
ChEBI Name20-epi-bryonolic acid
Stars
ASCII Name20-epi-bryonolic acid
DefinitionA 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.
Last Modified21 January 2013
DownloadsMolfile
FormulaC30H48O3
Net Charge0
Average Mass456.711
Monoisotopic Mass456.36035
SMILES[H][C@@]12C[C@@](C)(C(=O)O)CC[C@]1(C)CC[C@]1(C)C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@]1([H])CC3
InChIInChI=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
InChIKeyBHVJSLPLFOAMEV-UHIFYLTQSA-N
Species of MetaboliteComponentSourceComments
Macaranga conifera (ncbitaxon:109817) leaf (BTO:0000713) DOI (10.1016/S0031-9422(02)00378-3)
Coriaria intermedia (ncbitaxon:79756) - DOI (10.1016/0031-9422(95)00935-3)
Lagenaria siceraria (ncbitaxon:3668) stem (BTO:0001300) PubMed (18310955)
Celtis philippinensis (ncbitaxon:213552) twig (BTO:0001411) PubMed (12482456)
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
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 NumbersSources
Reaxys:8176385Reaxys
Citations