CHEBI:3087 - betulinic acid

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ChEBI Name betulinic acid
Definition A pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3β-hydroxy and 28-carboxy substituents. It is found in the bark and other plant parts of several species of plants including Syzygium claviflorum. It exhibits anti-HIV, antimalarial, antineoplastic and anti-inflammatory properties.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:65491
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Formula C30H48O3
Net Charge 0
Average Mass 456.70030
Monoisotopic Mass 456.36035
InChI InChI=1S/C30H48O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1
SMILES [H][C@]12CC[C@]3([H])[C@@]4(C)CC[C@H](O)C(C)(C)[C@]4([H])CC[C@@]3(C)[C@]1(C)CC[C@]1(CC[C@@H](C(C)=C)[C@]21[H])C(O)=O
Metabolite of Species Details
Hypericum chinense (IPNI:433315-1) Found in leaf (BTO:0000713). 95% EtOH extract of dried, chopped leaves See: PubMed
Breynia fruticosa (NCBI:txid296042) Found in root (BTO:0001188). 90% Methanolic extract of air-dried, crushed roots. See: PubMed
Diospyros kaki (NCBI:txid35925) Found in calyx (BTO:0000169). See: PubMed
Paeonia rockii subsp. rockii (NCBI:txid459179) Found in root (BTO:0001188). Isolated from chloroform soluble extract of air-dried and powdered roots See: PubMed
Mimosa diplotricha (NCBI:txid512270) Found in aerial part (BTO:0001658). Ethanolic extract of aerial parts See: PubMed
Syzygium claviflorum (NCBI:txid219860) Found in leaf (BTO:0000713). 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): EC [DNA topoisomerase (ATP-hydrolysing)] inhibitor
A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC (also known as topoisomerase II and as DNA gyrase), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.
anti-HIV agent
An antiviral agent that destroys or inhibits the replication of the human immunodeficiency virus.
A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application(s): antimalarial
A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
anti-inflammatory agent
Any compound that has anti-inflammatory effects.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing betulinic acid (CHEBI:3087) has parent hydride lupane (CHEBI:36485)
betulinic acid (CHEBI:3087) has role anti-HIV agent (CHEBI:64946)
betulinic acid (CHEBI:3087) has role anti-inflammatory agent (CHEBI:67079)
betulinic acid (CHEBI:3087) has role antimalarial (CHEBI:38068)
betulinic acid (CHEBI:3087) has role antineoplastic agent (CHEBI:35610)
betulinic acid (CHEBI:3087) has role EC [DNA topoisomerase (ATP-hydrolysing)] inhibitor (CHEBI:50750)
betulinic acid (CHEBI:3087) has role plant metabolite (CHEBI:76924)
betulinic acid (CHEBI:3087) is a hydroxy monocarboxylic acid (CHEBI:35868)
betulinic acid (CHEBI:3087) is a pentacyclic triterpenoid (CHEBI:25872)
Incoming 2α,3β-dihydroxy-20(29)-lupen-28-oic acid (CHEBI:67600) has functional parent betulinic acid (CHEBI:3087)
bevirimat (CHEBI:65484) has functional parent betulinic acid (CHEBI:3087)
3β-hydroxylup-20(29)-en-28-oic acid
Synonyms Sources
Betulinic acid KEGG COMPOUND
Mairin ChemIDplus
Manual Xrefs Databases
Betulinic_acid Wikipedia
C00003741 KNApSAcK
HMDB0030094 HMDB
RU2445317 Patent
RU2458933 Patent
US2012237629 Patent
View more database links
Registry Numbers Types Sources
2711110 Reaxys Registry Number Reaxys
472-15-1 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
14595673 PubMed citation Europe PMC
15083202 PubMed citation Europe PMC
20075711 PubMed citation Europe PMC
7489361 PubMed citation Europe PMC
8176401 PubMed citation Europe PMC
Last Modified
01 June 2015