CHEBI:66672 - 2α-hydroxymaprounic acid 2,3-bis-p-hydroxybenzoate

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ChEBI Name 2α-hydroxymaprounic acid 2,3-bis-p-hydroxybenzoate
ChEBI ID CHEBI:66672
ChEBI ASCII Name 2alpha-hydroxymaprounic acid 2,3-bis-p-hydroxybenzoate
Definition A pentacyclic triterpenoid that is the diester obtained by the condensation of the hydroxy groups of 2α-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 C44H56O8
Net Charge 0
Average Mass 712.91060
Monoisotopic Mass 712.39752
InChI InChI=1S/C44H56O8/c1-39(2)22-23-44(38(49)50)21-18-32-41(5)19-16-31-40(3,4)35(52-37(48)27-10-14-29(46)15-11-27)30(51-36(47)26-8-12-28(45)13-9-26)24-43(31,7)33(41)17-20-42(32,6)34(44)25-39/h8-15,18,30-31,33-35,45-46H,16-17,19-25H2,1-7H3,(H,49,50)/t30-,31+,33+,34+,35+,41+,42-,43+,44-/m1/s1
InChIKey XPEVLOSUULAUFH-AHHVVZNJSA-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[C@@H](OC(=O)c1ccc(O)cc1)[C@H](OC(=O)c1ccc(O)cc1)C2(C)C)C(O)=O
Metabolite of Species Details
Maprounea africana (IPNI:352049-1) See: PubMed
Roles Classification
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 2α-hydroxymaprounic acid 2,3-bis-p-hydroxybenzoate (CHEBI:66672) has functional parent 4-hydroxybenzoic acid (CHEBI:30763)
2α-hydroxymaprounic acid 2,3-bis-p-hydroxybenzoate (CHEBI:66672) has functional parent maprounic acid (CHEBI:73107)
2α-hydroxymaprounic acid 2,3-bis-p-hydroxybenzoate (CHEBI:66672) has role HIV-1 reverse transcriptase inhibitor (CHEBI:53756)
2α-hydroxymaprounic acid 2,3-bis-p-hydroxybenzoate (CHEBI:66672) has role metabolite (CHEBI:25212)
2α-hydroxymaprounic acid 2,3-bis-p-hydroxybenzoate (CHEBI:66672) is a benzoate ester (CHEBI:36054)
2α-hydroxymaprounic acid 2,3-bis-p-hydroxybenzoate (CHEBI:66672) is a pentacyclic triterpenoid (CHEBI:25872)
IUPAC Name
(4aS,6bR,8aR,10R,11R,12aR,12bR,14aS,14bS)-10,11-bis[(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
D-Friedoolean-14-en-28-oic acid, 1,3-bis((4-hydroxybenzoyl)oxy)-,(1beta,3beta)- ChemIDplus
Registry Number Type Source
155510-78-4 CAS Registry Number ChemIDplus
Citation Waiting for Citations Type Source
7515410 PubMed citation Europe PMC
Last Modified
04 April 2013