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CHEBI:65455 - asprellic acid A

ChEBI IDCHEBI:65455
ChEBI Nameasprellic acid A
Stars
DefinitionA pentacyclic triterpenoid that is the diester obtained by the global condensation of the hydroxy groups of (3β)-3,27-dihydroxyolean-12-en-28-oic acid with trans-4-coumaric acid. It is isolated from the dried leaves of Ilex asprella and exhibits significant toxicity against KB (epidermoid carcinoma of the nasopharynx) and RPMI-7951 (melanoma) cell lines.
Last Modified16 November 2012
DownloadsMolfile
FormulaC48H60O8
Net Charge0
Average Mass765.000
Monoisotopic Mass764.42882
SMILES[H][C@]12CC=C3[C@@](COC(=O)/C=C/c4ccc(O)cc4)(CC[C@@]4(C(=O)O)CCC(C)(C)C[C@@]34[H])[C@]1(C)CC[C@@]1([H])C(C)(C)[C@@H](OC(=O)/C=C/c3ccc(O)cc3)CC[C@]21C
InChIInChI=1S/C48H60O8/c1-43(2)25-26-47(42(53)54)27-28-48(30-55-40(51)19-11-31-7-13-33(49)14-8-31)35(36(47)29-43)17-18-38-45(5)23-22-39(44(3,4)37(45)21-24-46(38,48)6)56-41(52)20-12-32-9-15-34(50)16-10-32/h7-17,19-20,36-39,49-50H,18,21-30H2,1-6H3,(H,53,54)/b19-11+,20-12+/t36-,37-,38+,39-,45-,46+,47-,48-/m0/s1
InChIKeyYBOIBOWMTWFCEG-MVYRAAOISA-N
Species of MetaboliteComponentSourceComments
Ilex asprella (ncbitaxon:185493) leaf (BTO:0000713) PubMed (8133297)
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)
asprellic acid A (CHEBI:65455) has functional parent (3β)-3,27-dihydroxyolean-12-en-28-oic acid (CHEBI:71171)
asprellic acid A (CHEBI:65455) has functional parent trans-4-coumaric acid (CHEBI:32374)
asprellic acid A (CHEBI:65455) has role antineoplastic agent (CHEBI:35610)
asprellic acid A (CHEBI:65455) has role metabolite (CHEBI:25212)
asprellic acid A (CHEBI:65455) is a diester (CHEBI:51307)
asprellic acid A (CHEBI:65455) is a monocarboxylic acid (CHEBI:25384)
asprellic acid A (CHEBI:65455) is a pentacyclic triterpenoid (CHEBI:25872)
IUPAC Name 
(3β)-3,27-bis{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}olean-12-en-28-oic acid
Synonym  Source
3,27-di-O-trans-p-coumaroyl-3β,27-dihydroxy-olean-12-en-28-oic acidChEBI
Registry NumbersSources
CAS:152509-92-7ChemIDplus
Citations