EMBL-EBI | Chemical Biology | ChEBI
Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search
CHEBI:3087 - betulinic acid
| Formula | C30H48O3 |
| Net Charge | 0 |
| Average Mass | 456.711 |
| Monoisotopic Mass | 456.36035 |
| SMILES | [H][C@]12CC[C@@]3([H])[C@@](C)(CC[C@@]4(C(=O)O)CC[C@@H](C(=C)C)[C@@]43[H])[C@]1(C)CC[C@@]1([H])C(C)(C)[C@@H](O)CC[C@]21C |
| 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 |
| InChIKey | QGJZLNKBHJESQX-FZFNOLFKSA-N |
| Wikipedia |
|---|
| Species of Metabolite | Component | Source | Comments |
|---|---|---|---|
| Syzygium claviflorum (ncbitaxon:219860) | leaf (BTO:0000713) | PubMed (8176401) | |
| Breynia fruticosa (ncbitaxon:296042) | root (BTO:0001188) | PubMed (21428418) | 90% Methanolic extract of air-dried, crushed roots. |
| Diospyros kaki (ncbitaxon:35925) | calyx (BTO:0000169) | PubMed (21561086) | |
| Mimosa diplotricha (ncbitaxon:512270) | aerial part (BTO:0001658) | PubMed (21875046) | Ethanolic extract of aerial parts |
| Paeonia rockii subsp. rockii (ncbitaxon:459179) | root (BTO:0001188) | PubMed (21954959) | Isolated from chloroform soluble extract of air-dried and powdered roots |
| Hypericum chinense (IPNI:433315-1) | leaf (BTO:0000713) | PubMed (21043475) | 95% EtOH extract of dried, chopped leaves |
| Roles Classification |
|---|
| Chemical Role: | Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Brønsted base). |
| Biological Roles: | 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. 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. anti-HIV agent An antiviral agent that destroys or inhibits the replication of the human immunodeficiency virus. plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. |
| Applications: | 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. antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. anti-inflammatory agent Any compound that has anti-inflammatory effects. |
| ChEBI Ontology |
|---|
| Outgoing Relation(s) |
| 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 5.99.1.3 [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 Relation(s) |
| 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) |
| IUPAC Name |
|---|
| 3β-hydroxylup-20(29)-en-28-oic acid |
| Synonyms | Source |
|---|---|
| Betulinic acid | KEGG COMPOUND |
| Mairin | ChemIDplus |
| Manual Xrefs | Databases |
|---|---|
| C08619 | KEGG COMPOUND |
| Betulinic_acid | Wikipedia |
| LMPR0106140004 | LIPID MAPS |
| RU2458933 | Patent |
| US2012237629 | Patent |
| RU2445317 | Patent |
| HMDB0030094 | HMDB |
| C00003741 | KNApSAcK |
| Registry Numbers | Sources |
|---|---|
| Reaxys:2711110 | Reaxys |
| CAS:472-15-1 | KEGG COMPOUND |
| CAS:472-15-1 | ChemIDplus |
| Citations |
|---|