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

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ChEBI Name 1β-hydroxymaprounic acid 3-p-hydroxybenzoate
ChEBI ID CHEBI:66671
ChEBI ASCII Name 1beta-hydroxymaprounic acid 3-p-hydroxybenzoate
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C37H52O6
Net Charge 0
Average Mass 592.80520
Monoisotopic Mass 592.37639
InChI InChI=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
InChIKey VGODRAUARQJBJM-FCWPOGGHSA-N
SMILES [H][C@@]12CC[C@@]3(C)C4=CC[C@]5(CCC(C)(C)C[C@@]5([H])[C@]4(C)CC[C@]3([H])[C@@]1(C)[C@H](O)C[C@H](OC(=O)c1ccc(O)cc1)C2(C)C)C(O)=O
Metabolite of Species Details
Maprounea africana (IPNI:352049-1) Found in root (BTO:0001188). 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): HIV-1 reverse transcriptase inhibitor
An entity which inhibits the activity of HIV-1 reverse transcriptase.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Number Type Source
155510-77-3 CAS Registry Number ChemIDplus
Citation Waiting for Citations Type Source
7515410 PubMed citation Europe PMC
Last Modified
04 April 2013