CHEBI:67600 - 2α,3β-dihydroxy-20(29)-lupen-28-oic acid

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ChEBI Name 2α,3β-dihydroxy-20(29)-lupen-28-oic acid
ChEBI ID CHEBI:67600
ChEBI ASCII Name 2alpha,3beta-dihydroxy-20(29)-lupen-28-oic acid
Definition A pentacyclic triterpenoid that is betulinic acid carrying an additional α-hydroxy group at position 2. It has been isolated from Breynia fruticosa.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C30H48O4
Net Charge 0
Average Mass 472.69970
Monoisotopic Mass 472.35526
InChI InChI=1S/C30H48O4/c1-17(2)18-10-13-30(25(33)34)15-14-28(6)19(23(18)30)8-9-22-27(5)16-20(31)24(32)26(3,4)21(27)11-12-29(22,28)7/h18-24,31-32H,1,8-16H2,2-7H3,(H,33,34)/t18-,19+,20+,21-,22+,23+,24-,27-,28+,29+,30-/m0/s1
InChIKey PFCVZKFJHRCLCC-PGOIBATFSA-N
SMILES CC(=C)[C@@H]1CC[C@@]2(CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)C[C@@H](O)[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]12)C(O)=O
Metabolite of Species Details
Breynia fruticosa (NCBI:txid296042) Found in root (BTO:0001188). 90% Methanolic extract of air-dried, crushed roots. 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): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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ChEBI Ontology
Outgoing 2α,3β-dihydroxy-20(29)-lupen-28-oic acid (CHEBI:67600) has functional parent betulinic acid (CHEBI:3087)
2α,3β-dihydroxy-20(29)-lupen-28-oic acid (CHEBI:67600) has parent hydride lupane (CHEBI:36485)
2α,3β-dihydroxy-20(29)-lupen-28-oic acid (CHEBI:67600) has role plant metabolite (CHEBI:76924)
2α,3β-dihydroxy-20(29)-lupen-28-oic acid (CHEBI:67600) is a dihydroxy monocarboxylic acid (CHEBI:35972)
2α,3β-dihydroxy-20(29)-lupen-28-oic acid (CHEBI:67600) is a pentacyclic triterpenoid (CHEBI:25872)
IUPAC Name
2α,3β-dihydroxylup-20(29)-en-28-oic acid
Synonym Source
2α-hydroxybetulinic acid ChEBI
Manual Xref Database
C16912 KEGG COMPOUND
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Registry Numbers Types Sources
19533-92-7 CAS Registry Number ChemIDplus
5648545 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
21428418 PubMed citation Europe PMC
Last Modified
01 June 2015