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CHEBI:65783 - 2α,19α-dihydroxy-3-oxo-12-ursen-28-oic acid

ChEBI IDCHEBI:65783
ChEBI Name2α,19α-dihydroxy-3-oxo-12-ursen-28-oic acid
Stars
ASCII Name2alpha,19alpha-dihydroxy-3-oxo-12-ursen-28-oic acid
DefinitionA pentacyclic triterpenoid that is urs-12-ene substituted by a carboxy group at position 28, α-configured hydroxy groups at positions 2 and 19 and an oxo group at position 3. Isolated from the whole plants of Geum japonicum, it exhibits activity against HIV-1 protease.
Last Modified6 February 2018
DownloadsMolfile
FormulaC30H46O5
Net Charge0
Average Mass486.693
Monoisotopic Mass486.33452
SMILES[H][C@]12CC=C3[C@@]4([H])[C@](C(=O)O)(CC[C@@H](C)[C@@]4(C)O)CC[C@@]3(C)[C@]1(C)CC[C@@]1([H])C(C)(C)C(=O)[C@H](O)C[C@]21C
InChIInChI=1S/C30H46O5/c1-17-10-13-30(24(33)34)15-14-27(5)18(22(30)29(17,7)35)8-9-21-26(4)16-19(31)23(32)25(2,3)20(26)11-12-28(21,27)6/h8,17,19-22,31,35H,9-16H2,1-7H3,(H,33,34)/t17-,19-,20+,21-,22-,26+,27-,28-,29-,30+/m1/s1
InChIKeyLJORXTIGOHMBOS-OTRVPSFMSA-N
Species of MetaboliteComponentSourceComments
Geum japonicum (ncbitaxon:321607) whole plant (BTO:0001461) PubMed (8759159)
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 protease inhibitor  An inhibitor of HIV protease, an enzyme required for production of proteins needed for viral assembly.
ChEBI Ontology
Outgoing Relation(s)
2α,19α-dihydroxy-3-oxo-12-ursen-28-oic acid (CHEBI:65783) has parent hydride ursane (CHEBI:35711)
2α,19α-dihydroxy-3-oxo-12-ursen-28-oic acid (CHEBI:65783) has role HIV protease inhibitor (CHEBI:35660)
2α,19α-dihydroxy-3-oxo-12-ursen-28-oic acid (CHEBI:65783) has role metabolite (CHEBI:25212)
2α,19α-dihydroxy-3-oxo-12-ursen-28-oic acid (CHEBI:65783) is a diol (CHEBI:23824)
2α,19α-dihydroxy-3-oxo-12-ursen-28-oic acid (CHEBI:65783) is a oxo monocarboxylic acid (CHEBI:35871)
2α,19α-dihydroxy-3-oxo-12-ursen-28-oic acid (CHEBI:65783) is a pentacyclic triterpenoid (CHEBI:25872)
2α,19α-dihydroxy-3-oxo-12-ursen-28-oic acid (CHEBI:65783) is a secondary α-hydroxy ketone (CHEBI:2468)
IUPAC Name 
(2α)-2,19-dihydroxy-3-oxours-12-en-28-oic acid
Manual XrefsDatabases
552868ChemSpider
Registry NumbersSources
Reaxys:8885609Reaxys
Citations