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CHEBI:9908 - ursolic acid
| Formula | C30H48O3 |
| Net Charge | 0 |
| Average Mass | 456.711 |
| Monoisotopic Mass | 456.36035 |
| SMILES | [H][C@]12CC=C3[C@@](C)(CC[C@@]4(C(=O)O)CC[C@@H](C)[C@H](C)[C@@]34[H])[C@]1(C)CC[C@@]1([H])C(C)(C)[C@@H](O)CC[C@]21C |
| InChI | InChI=1S/C30H48O3/c1-18-10-15-30(25(32)33)17-16-28(6)20(24(30)19(18)2)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h8,18-19,21-24,31H,9-17H2,1-7H3,(H,32,33)/t18-,19+,21+,22-,23+,24+,27+,28-,29-,30+/m1/s1 |
| InChIKey | WCGUUGGRBIKTOS-GPOJBZKASA-N |
| Wikipedia |
|---|
| Species of Metabolite | Component | Source | Comments |
|---|---|---|---|
| Crataegus laevigata (ncbitaxon:298643) | - | PubMed (21648406) | Commercial herbal preperation |
| Crataegus monogyna (ncbitaxon:140997) | - | PubMed (21648406) | |
| Eriobotrya japonica (ncbitaxon:32224) | leaf (BTO:0000713) | PubMed (21923134) | |
| Ficus mucuso (ncbitaxon:309328) | fruit (BTO:0000486) | PubMed (21619045) | Methanolic extract of air-dried and powdered figs(fruits) |
| Juglans sinensis (ncbitaxon:442437-1) | |||
| leaf (BTO:0000713) | PubMed (21309591) | 80% Methanolic extract of dried leaves and twigs | |
| twig (BTO:0001411) | PubMed (21309591) | 80% Methanolic extract of dried leaves and twigs | |
| Leonurus cardiaca (ncbitaxon:587664) | - | PubMed (21648406) | Commercial herbal preperation |
| Malus domestica (ncbitaxon:3750) | fruit (BTO:0000486) | PubMed (21648406) | |
| Prunus domestica (ncbitaxon:3758) | fruit (BTO:0000486) | PubMed (21648406) | |
| Radermachera boniana (IPNI:110489-1) | |||
| leaf (BTO:0000713) | PubMed (21469696) | Ethylacetate extract of dried and ground mixture of twigs and leaves | |
| twig (BTO:0001411) | PubMed (21469696) | Ethylacetate extract of dried and ground mixture of twigs and leaves | |
| Rhododendron (ncbitaxon:4346) | - | PubMed (21443171) | |
| Rhododendron ferrugineum (ncbitaxon:49622) | leaf (BTO:0000713) | PubMed (21443171) | MeOH extract of CHCl3 soluble fraction of air-dried,powdered leaves,ursolic & oleanolic acid mixture |
| Rosa laevigata (ncbitaxon:74652) | leaf (BTO:0000713) | PubMed (21384845) | 70% EtOH extract of dried leaves |
| Rubia yunnanensis (IPNI:765385-1) | root (BTO:0001188) | PubMed (21973054) | Methanolic extract of air dried powdered roots. |
| Symplocos lancifolia (ncbitaxon:239704) | leaf (BTO:0000713) | PubMed (21288041) | Dried, powdered leaves extracted with boiling 80% methanol |
| Terminalia catappa (ncbitaxon:39993) | leaf (BTO:0000713) | PubMed (21648406) | Chloroform extract of leaves |
| Vaccinium corymbosum (ncbitaxon:69266) | fruit (BTO:0000486) | PubMed (21648406) | |
| Vaccinium macrocarpon (ncbitaxon:13750) | fruit (BTO:0000486) | PubMed (21648406) |
| Roles Classification |
|---|
| Chemical Role: | Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Brønsted base). |
| Biological Role: | plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. |
| Applications: | antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. geroprotector Any compound that supports healthy aging, slows the biological aging process, or extends lifespan. |
| ChEBI Ontology |
|---|
| Outgoing Relation(s) |
| ursolic acid (CHEBI:9908) has parent hydride ursane (CHEBI:35711) |
| ursolic acid (CHEBI:9908) has role antineoplastic agent (CHEBI:35610) |
| ursolic acid (CHEBI:9908) has role geroprotector (CHEBI:176497) |
| ursolic acid (CHEBI:9908) has role plant metabolite (CHEBI:76924) |
| ursolic acid (CHEBI:9908) is a hydroxy monocarboxylic acid (CHEBI:35868) |
| ursolic acid (CHEBI:9908) is a organic molecular entity (CHEBI:50860) |
| ursolic acid (CHEBI:9908) is a pentacyclic triterpenoid (CHEBI:25872) |
| ursolic acid (CHEBI:9908) is a triterpenoid (CHEBI:36615) |
| ursolic acid (CHEBI:9908) is conjugate acid of ursolate (CHEBI:234081) |
| Incoming Relation(s) |
| 23-hydroxyursolic acid (CHEBI:67896) has functional parent ursolic acid (CHEBI:9908) |
| ursolate (CHEBI:234081) is conjugate base of ursolic acid (CHEBI:9908) |
| IUPAC Name |
|---|
| 3β-hydroxyurs-12-en-28-oic acid |
| Synonyms | Source |
|---|---|
| (3β)-3-hydroxyurs-12-en-28-oic acid | ChemIDplus |
| malol | ChemIDplus |
| NSC-167406 | ChEMBL |
| NSC-4060 | ChEMBL |
| prunol | ChemIDplus |
| Ursolic acid | KEGG COMPOUND |
| Manual Xrefs | Databases |
|---|---|
| 6Q5 | PDBeChem |
| C00003558 | KNApSAcK |
| C08988 | KEGG COMPOUND |
| DB15588 | DrugBank |
| FDB014373 | FooDB |
| HMDB0002395 | HMDB |
| LMPR0106180007 | LIPID MAPS |
| Ursolic_acid | Wikipedia |
| Registry Numbers | Sources |
|---|---|
| Reaxys:2228563 | Reaxys |
| CAS:77-52-1 | ChemIDplus |
| CAS:77-52-1 | KEGG COMPOUND |
| Citations |
|---|