CHEBI:65485 - dihydrobetulinic acid

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name dihydrobetulinic acid
ChEBI ID CHEBI:65485
Definition A pentacyclic triterpenoid that is lupane having a 3β-hydroxy and 28-carboxy substituents. Isolated from the leaves of Syzygium claviflorum, it exhibits anti-HIV and antileishmanial activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C30H50O3
Net Charge 0
Average Mass 458.71620
Monoisotopic Mass 458.37600
InChI InChI=1S/C30H50O3/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/h18-24,31H,8-17H2,1-7H3,(H,32,33)/t19-,20+,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1
InChIKey PZXJOHSZQAEJFE-FZFNOLFKSA-N
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
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): anti-HIV agent
An antiviral agent that destroys or inhibits the replication of the human immunodeficiency virus.
antileishmanial agent
An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
EC 5.99.1.2 (DNA topoisomerase) inhibitor
A topoisomerase inhibitor that inhibits the bacterial enzymes of the DNA topoisomerases, Type I class (EC 5.99.1.2) that catalyze ATP-independent breakage of one of the two strands of DNA, passage of the unbroken strand through the break, and rejoining of the broken strand. These bacterial enzymes reduce the topological stress in the DNA structure by relaxing negatively, but not positively, supercoiled DNA.
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor
A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (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.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application(s): antileishmanial agent
An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing dihydrobetulinic acid (CHEBI:65485) has parent hydride lupane (CHEBI:36485)
dihydrobetulinic acid (CHEBI:65485) has role anti-HIV agent (CHEBI:64946)
dihydrobetulinic acid (CHEBI:65485) has role antileishmanial agent (CHEBI:70868)
dihydrobetulinic acid (CHEBI:65485) has role EC 5.99.1.2 (DNA topoisomerase) inhibitor (CHEBI:50276)
dihydrobetulinic acid (CHEBI:65485) has role EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor (CHEBI:50750)
dihydrobetulinic acid (CHEBI:65485) has role metabolite (CHEBI:25212)
dihydrobetulinic acid (CHEBI:65485) is a hydroxy monocarboxylic acid (CHEBI:35868)
dihydrobetulinic acid (CHEBI:65485) is a pentacyclic triterpenoid (CHEBI:25872)
IUPAC Name
(3β)-3-hydroxylupan-28-oic acid
Synonym Source
20,29-dihydrobetulinic acid ChEBI
Manual Xref Database
US5679828 Patent
View more database links
Registry Numbers Types Sources
25488-53-3 CAS Registry Number ChemIDplus
2678211 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
12765337 PubMed citation Europe PMC
8176401 PubMed citation Europe PMC
8676334 PubMed citation Europe PMC
9459011 PubMed citation Europe PMC
Last Modified
20 November 2012