(1S,2R,4aS,6aS,6bR,10S,12aR,12bR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid
PubChem CID: 13073350
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| Compound Synonyms | (1S,2R,4aS,6aS,6bR,10S,12aR,12bR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid, Ursolic Acid, 10, SCHEMBL70206, BDBM23197, pentacyclic triterpene compound 10, AKOS016008498, GS-6617, (1S,2R,4aS,6aR,6aS,6bR,10S,12aR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid, (1S,2R,4aS,6aS,6bR,10S,12aR,12bR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylic acid, (1S,2R,4AS,6AS,6BR,10S,12AR,12BR,14BS)-10-HYDROXY-1,2,6A,6B,9,9,12A-HEPTAMETHYL-2,3,4,5,6,7,8,8A,10,11,12,12B,13,14B-TETRADECAHYDRO-1H-PICENE-4A-CARBOXYLIC ACID |
|---|---|
| Topological Polar Surface Area | 57.5 |
| Hydrogen Bond Donor Count | 2.0 |
| Inchi Key | WCGUUGGRBIKTOS-JJWDWEPMSA-N |
| Rotatable Bond Count | 1.0 |
| State | Solid |
| Synonyms | .beta.-ursolic acid, (3 beta)-3-hydroxyurs-12-en-28-oic acid, (3b)-3-Hydroxyurs-12-en-28-Oate, (3b)-3-Hydroxyurs-12-en-28-Oic acid, (3beta)-3-hydroxy-Urs-12-en-28-oate, (3beta)-3-hydroxy-Urs-12-en-28-oic acid, (3beta)-3-Hydroxyurs-12-en-28-oate, (3beta)-3-Hydroxyurs-12-en-28-oic acid, (3β)-3-hydroxyurs-12-en-28-Oate, (3β)-3-hydroxyurs-12-en-28-Oic acid, &beta, -ursolic acid, 3-epi-ursolic acid, 3.beta.-hydroxy-urs-12-en-28-Oate, 3.beta.-hydroxy-urs-12-en-28-Oic acid, 3beta-Hydroxy-12-ursen-28-ic acid, 3beta-hydroxy-Urs-12-en-28-oate, 3beta-hydroxy-Urs-12-en-28-oic acid, 3beta-Hydroxyurs-12-en-28-oate, 3beta-Hydroxyurs-12-en-28-oic acid, Bungeolic acid, Formosolic acid, Forucosolic acid, Malol, Merotaine, Micromerol, Prunol, Urs-12-en-28-oic acid, 3-hydroxy-, (3&beta, )-, Urs-12-en-28-oic acid, 3-hydroxy-, (3beta)-, Urs-12-en-28-oic acid, 3&beta, -hydroxy-, Urs-12-en-28-oic acid, 3beta-hydroxy-, Urs-12-en-28-oic acid, 3beta-hydroxy- (8CI), Ursolate, Ursolic acid, Urson |
| Heavy Atom Count | 33.0 |
| Compound Name | (1S,2R,4aS,6aS,6bR,10S,12aR,12bR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid |
| Description | Found in wax of apples, pears and other fruits. V. widely distributed in plants Ursolic acid is a pentacyclic triterpene acid, used in cosmetics, that is also capable of inhibiting various types of cancer cells by inhibiting the STAT3 activation pathway and human fibrosarcoma cells by reducing the expression of matrix metalloproteinase-9 by acting through the glucocorticoid receptor., Ursolic acid is a ubiquitous triterpenoid in plant kingdom, medicinal herbs, and is an integral part of the human diet. During the last decade over 700 research articles have been published on triterpenoids research, reflecting tremendous interest and progress in our understanding of these compounds. This included the isolation and purification of these tritepernoids from various plants and herbs, the chemical modifications to make more effective and water soluble derivatives, the pharmacological research on their beneficial effects, the toxicity studies, and the clinical use of these triterpenoids in various diseases including anticancer chemotherapies. Ursolic acid (UA), a pentacyclic triterpene acid, has been isolated from many kinds of medicinal plants, such as Eriobotrya japonica, Rosmarinns officinalis, Melaleuca leucadendron, Ocimum sanctum and Glechoma hederaceae. UA has been reported to produce antitumor activities and antioxidant activity, and is reported to have an antioxidant activity. UA may play an important role in regulating the apoptosis induced by high glucose presumably through scavenging of ROS (reactive oxygen species). It has been found recently that ursolic acid treatment affects growth and apoptosis in cancer cells. (PMID: 15994040, 17516235, 17213663), Ursolic acid is also known as Prunol, Malol, Urson, beta-Ursolic acid, NSC4060, CCRIS 7123, CHEBI:9908, TOS-BB-0966, and 3-Beta-Hydroxy-Urs-12-En-28-Oic Acid. As medicine it is well tolerated and can be used topically and orally. |
| Exact Mass | 456.36 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 456.36 |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 874.0 |
| Hydrogen Bond Acceptor Count | 3.0 |
| Molecular Weight | 456.7 |
| Database Name | fooddb_chem_all;pubchem |
| Covalent Unit Count | 1.0 |
| Defined Atom Stereocenter Count | 9.0 |
| Iupac Name | (1S,2R,4aS,6aR,6aS,6bR,10S,12aR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid |
| Total Atom Stereocenter Count | 10.0 |
| Total Bond Stereocenter Count | 0.0 |
| 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 |
| Smiles | C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CCC5[C@@]4(CC[C@@H](C5(C)C)O)C)C)[C@@H]2[C@H]1C)C)C(=O)O |
| Xlogp | 7.3 |
| Defined Bond Stereocenter Count | 0.0 |
| Molecular Formula | C30H48O3 |
- 1. Outgoing r'ship
FOUND_INto/from Artocarpus Heterophyllus (Plant) Rel Props:Source_db:fooddb_chem_all - 2. Outgoing r'ship
FOUND_INto/from Eriobotrya Japonica (Plant) Rel Props:Source_db:fooddb_chem_all - 3. Outgoing r'ship
FOUND_INto/from Hyssopus Officinalis (Plant) Rel Props:Source_db:fooddb_chem_all - 4. Outgoing r'ship
FOUND_INto/from Malus Domestica (Plant) Rel Props:Source_db:fooddb_chem_all - 5. Outgoing r'ship
FOUND_INto/from Melissa Officinalis (Plant) Rel Props:Source_db:fooddb_chem_all - 6. Outgoing r'ship
FOUND_INto/from Mentha Spicata (Plant) Rel Props:Source_db:fooddb_chem_all - 7. Outgoing r'ship
FOUND_INto/from Ocimum Basilicum (Plant) Rel Props:Source_db:fooddb_chem_all - 8. Outgoing r'ship
FOUND_INto/from Olea Europaea (Plant) Rel Props:Source_db:fooddb_chem_all - 9. Outgoing r'ship
FOUND_INto/from Origanum Majorana (Plant) Rel Props:Source_db:fooddb_chem_all - 10. Outgoing r'ship
FOUND_INto/from Origanum Vulgare (Plant) Rel Props:Source_db:fooddb_chem_all - 11. Outgoing r'ship
FOUND_INto/from Prunus Avium (Plant) Rel Props:Source_db:fooddb_chem_all - 12. Outgoing r'ship
FOUND_INto/from Prunus Cerasus (Plant) Rel Props:Source_db:fooddb_chem_all - 13. Outgoing r'ship
FOUND_INto/from Prunus Persica (Plant) Rel Props:Source_db:fooddb_chem_all - 14. Outgoing r'ship
FOUND_INto/from Psidium Guajava (Plant) Rel Props:Source_db:fooddb_chem_all - 15. Outgoing r'ship
FOUND_INto/from Punica Granatum (Plant) Rel Props:Source_db:fooddb_chem_all - 16. Outgoing r'ship
FOUND_INto/from Pyrus Communis (Plant) Rel Props:Source_db:fooddb_chem_all - 17. Outgoing r'ship
FOUND_INto/from Rosmarinus Officinalis (Plant) Rel Props:Source_db:fooddb_chem_all - 18. Outgoing r'ship
FOUND_INto/from Salvia Officinalis (Plant) Rel Props:Source_db:fooddb_chem_all - 19. Outgoing r'ship
FOUND_INto/from Sambucus Nigra (Plant) Rel Props:Source_db:fooddb_chem_all - 20. Outgoing r'ship
FOUND_INto/from Satureja Hortensis (Plant) Rel Props:Source_db:fooddb_chem_all - 21. Outgoing r'ship
FOUND_INto/from Satureja Montana (Plant) Rel Props:Source_db:fooddb_chem_all - 22. Outgoing r'ship
FOUND_INto/from Thymus Vulgaris (Plant) Rel Props:Source_db:fooddb_chem_all - 23. Outgoing r'ship
FOUND_INto/from Vaccinium Corymbosum (Plant) Rel Props:Source_db:fooddb_chem_all - 24. Outgoing r'ship
FOUND_INto/from Vaccinium Macrocarpon (Plant) Rel Props:Source_db:fooddb_chem_all - 25. Outgoing r'ship
FOUND_INto/from Vaccinium Myrtillus (Plant) Rel Props:Source_db:fooddb_chem_all - 26. Outgoing r'ship
FOUND_INto/from Verbena Officinalis (Plant) Rel Props:Source_db:fooddb_chem_all - 27. Outgoing r'ship
FOUND_INto/from Vitis Vinifera (Plant) Rel Props:Source_db:fooddb_chem_all