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

ChEBI IDCHEBI:66672
ChEBI Name2α-hydroxymaprounic acid 2,3-bis-p-hydroxybenzoate
Stars
ASCII Name2alpha-hydroxymaprounic acid 2,3-bis-p-hydroxybenzoate
DefinitionA 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.
Last Modified4 April 2013
DownloadsMolfile
FormulaC44H56O8
Net Charge0
Average Mass712.924
Monoisotopic Mass712.39752
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@H](OC(=O)c3ccc(O)cc3)C[C@]21C
InChIInChI=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
InChIKeyXPEVLOSUULAUFH-AHHVVZNJSA-N
Species of MetaboliteComponentSourceComments
Maprounea africana (IPNI:352049-1) - PubMed (7515410)
Roles Classification
Biological Roles:
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.
ChEBI Ontology
Outgoing Relation(s)
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 NumbersSources
CAS:155510-78-4ChemIDplus
Citations