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CHEBI:66671 - 1β-hydroxymaprounic acid 3-p-hydroxybenzoate

ChEBI IDCHEBI:66671
ChEBI Name1β-hydroxymaprounic acid 3-p-hydroxybenzoate
Stars
ASCII Name1beta-hydroxymaprounic acid 3-p-hydroxybenzoate
DefinitionA pentacyclic triterpenoid that is the benzoate ester obtained by the condensation of the 3-hydroxy group of 1β-hydroxymaprounic acid with p-hydroxybenzoic acid. Isolated from Maprounea africana, it exhibits inhibitory activity against HIV-1 reverse transcriptase.
Last Modified4 April 2013
DownloadsMolfile
FormulaC37H52O6
Net Charge0
Average Mass592.817
Monoisotopic Mass592.37639
SMILES[H][C@]12CC[C@]3(C)C(=CC[C@@]4(C(=O)O)CCC(C)(C)C[C@]43[H])[C@]1(C)CC[C@@]1([H])C(C)(C)[C@@H](OC(=O)c3ccc(O)cc3)C[C@@H](O)[C@]21C
InChIInChI=1S/C37H52O6/c1-32(2)18-19-37(31(41)42)17-14-25-34(5)15-12-24-33(3,4)29(43-30(40)22-8-10-23(38)11-9-22)20-28(39)36(24,7)26(34)13-16-35(25,6)27(37)21-32/h8-11,14,24,26-29,38-39H,12-13,15-21H2,1-7H3,(H,41,42)/t24-,26-,27-,28+,29-,34-,35+,36-,37+/m0/s1
InChIKeyVGODRAUARQJBJM-FCWPOGGHSA-N
Species of MetaboliteComponentSourceComments
Maprounea africana (IPNI:352049-1) root (BTO:0001188) PubMed (7515410)
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
HIV-1 reverse transcriptase inhibitor  An entity which inhibits the activity of HIV-1 reverse transcriptase.
ChEBI Ontology
Outgoing Relation(s)
1β-hydroxymaprounic acid 3-p-hydroxybenzoate (CHEBI:66671) has functional parent 4-hydroxybenzoic acid (CHEBI:30763)
1β-hydroxymaprounic acid 3-p-hydroxybenzoate (CHEBI:66671) has functional parent maprounic acid (CHEBI:73107)
1β-hydroxymaprounic acid 3-p-hydroxybenzoate (CHEBI:66671) has role HIV-1 reverse transcriptase inhibitor (CHEBI:53756)
1β-hydroxymaprounic acid 3-p-hydroxybenzoate (CHEBI:66671) has role metabolite (CHEBI:25212)
1β-hydroxymaprounic acid 3-p-hydroxybenzoate (CHEBI:66671) is a benzoate ester (CHEBI:36054)
1β-hydroxymaprounic acid 3-p-hydroxybenzoate (CHEBI:66671) is a hydroxy monocarboxylic acid (CHEBI:35868)
1β-hydroxymaprounic acid 3-p-hydroxybenzoate (CHEBI:66671) is a pentacyclic triterpenoid (CHEBI:25872)
IUPAC Name 
(4aS,6bR,8aS,10S,12R,12aR,12bS,14aS,14bS)-12-hydroxy-10-[(4-hydroxybenzoyl)oxy]-2,2,6b,9,9,12a,14a-heptamethyl-1,3,4,5,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a,14b-octadecahydropicene-4a(2H)-carboxylic acid
Synonym  Source
1-Hydroxy-3-((4-hydroxybenzoyl)oxy)-D-friedoolean-14-en-28-oic acid (1beta,3beta)-ChemIDplus
Registry NumbersSources
CAS:155510-77-3ChemIDplus
Citations