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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 |
|---|---|---|---|
| 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) | |
| Hypericum chinense (IPNI:433315-1) | leaf (BTO:0000713) | PubMed (21043475) | 95% EtOH extract of dried, chopped leaves |
| 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 |
| Syzygium claviflorum (ncbitaxon:219860) | leaf (BTO:0000713) | PubMed (8176401) |
| Roles Classification |
|---|
| Chemical Role: | Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Brønsted base). |
| Biological Roles: | 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. 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. 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. |
| Applications: | antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. 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. |
| 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 |
|---|---|
| ALS-357 | ChEMBL |
| .beta.-betulinic acid | ChEMBL |
| Betulic acid | ChEMBL |
| Betulinic acid | KEGG COMPOUND |
| Lupatic acid | ChEMBL |
| Mairin | ChemIDplus |
| Manual Xrefs | Databases |
|---|---|
| Betulinic_acid | Wikipedia |
| C00003741 | KNApSAcK |
| C08619 | KEGG COMPOUND |
| HMDB0030094 | HMDB |
| LMPR0106140004 | LIPID MAPS |
| RU2445317 | Patent |
| RU2458933 | Patent |
| US2012237629 | Patent |
| Registry Numbers | Sources |
|---|---|
| Reaxys:2711110 | Reaxys |
| CAS:472-15-1 | KEGG COMPOUND |
| CAS:472-15-1 | ChemIDplus |
| Citations |
|---|