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

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ChEBI Name 2α,19α-dihydroxy-3-oxo-12-ursen-28-oic acid
ChEBI ID CHEBI:65783
ChEBI ASCII Name 2alpha,19alpha-dihydroxy-3-oxo-12-ursen-28-oic acid
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C30H46O5
Net Charge 0
Average Mass 486.68320
Monoisotopic Mass 486.33452
InChI InChI=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
InChIKey LJORXTIGOHMBOS-OTRVPSFMSA-N
SMILES [H][C@@]12CC[C@]3(C)[C@]([H])(CC=C4[C@]5([H])[C@](C)(O)[C@H](C)CC[C@@]5(CC[C@@]34C)C(O)=O)[C@@]1(C)C[C@@H](O)C(=O)C2(C)C
Metabolite of Species Details
Geum japonicum (NCBI:txid321607) Found in whole plant (BTO:0001461). 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 protease inhibitor
An inhibitor of HIV protease, an enzyme required for production of proteins needed for viral assembly.
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,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 Xref Database
552868 ChemSpider
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Registry Number Type Source
8885609 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
8759159 PubMed citation Europe PMC
Last Modified
06 February 2018