CHEBI:65455 - asprellic acid A

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ChEBI Name asprellic acid A
ChEBI ID CHEBI:65455
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C48H60O8
Net Charge 0
Average Mass 764.98520
Monoisotopic Mass 764.42882
InChI InChI=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
InChIKey YBOIBOWMTWFCEG-MVYRAAOISA-N
SMILES [H][C@@]12CC(C)(C)CC[C@@]1(CC[C@]1(COC(=O)\C=C\c3ccc(O)cc3)C2=CC[C@]2([H])[C@@]3(C)CC[C@H](OC(=O)\C=C\c4ccc(O)cc4)C(C)(C)[C@]3([H])CC[C@@]12C)C(O)=O
Metabolite of Species Details
Ilex asprella (NCBI:txid185493) Found in leaf (BTO:0000713). See: PubMed
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 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 acid ChEBI
Registry Number Type Source
152509-92-7 CAS Registry Number ChemIDplus
Citation Waiting for Citations Type Source
8133297 PubMed citation Europe PMC
Last Modified
16 November 2012