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CHEBI:73107 - maprounic acid

ChEBI IDCHEBI:73107
ChEBI Namemaprounic acid
Stars
DefinitionA pentacyclic triterpenoid isolated from Maprounea africana and has been shown to exhibit inhibitory activity against HIV-1 reverse transcriptase.
Last Modified14 April 2015
Submitternamrata
DownloadsMolfile
FormulaC30H48O3
Net Charge0
Average Mass456.711
Monoisotopic Mass456.36035
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](O)CC[C@]21C
InChIInChI=1S/C30H48O3/c1-25(2)16-17-30(24(32)33)15-10-21-28(6)12-8-19-26(3,4)23(31)11-14-27(19,5)20(28)9-13-29(21,7)22(30)18-25/h10,19-20,22-23,31H,8-9,11-18H2,1-7H3,(H,32,33)/t19-,20+,22-,23-,27-,28+,29+,30+/m0/s1
InChIKeyBHHPRAFMEFGOLZ-QVUWEPBXSA-N
Species of MetaboliteComponentSourceComments
Maprounea africana (ncbitaxon:316848) - PubMed (6631436)
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
HIV-1 reverse transcriptase inhibitor  An entity which inhibits the activity of HIV-1 reverse transcriptase.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
ChEBI Ontology
Outgoing Relation(s)
maprounic acid (CHEBI:73107) has role HIV-1 reverse transcriptase inhibitor (CHEBI:53756)
maprounic acid (CHEBI:73107) has role plant metabolite (CHEBI:76924)
maprounic acid (CHEBI:73107) is a hydroxy monocarboxylic acid (CHEBI:35868)
maprounic acid (CHEBI:73107) is a pentacyclic triterpenoid (CHEBI:25872)
Incoming Relation(s)
1β-hydroxymaprounic acid 3-p-hydroxybenzoate (CHEBI:66671) has functional parent maprounic acid (CHEBI:73107)
2α-hydroxymaprounic acid 2,3-bis-p-hydroxybenzoate (CHEBI:66672) has functional parent maprounic acid (CHEBI:73107)
IUPAC Name 
(4aS,6bR,8aR,10S,12aR,12bR,14aS,14bS)-10-hydroxy-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
aleuritolic acidChEBI
Registry NumbersSources
Reaxys:2823779Reaxys
CAS:26549-17-7ChemIDplus
Citations