9-Hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
PubChem CID: 2371
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| Compound Synonyms | 3-epi-betulinic acid, 38736-77-5, 9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid, Lup-20(29)-en-28-oic acid, 3.beta.-hydroxy-, NSC113090, Lup-20(29)-en-28-oic acid, 3-hydroxy-, (3.beta.)-, SCHEMBL4143519, QGJZLNKBHJESQX-UHFFFAOYSA-N, BDBM512883, acs.jmedchem.1c00409_ST.478, BCP08998, AKOS025295351, LS-15294, NCI60_000293, 3-Hydroxylup-20(29)-en-28-oic acid #, 1H-Cyclopenta[a]chrysene, lup-20(29)-en-28-oic acid deriv., Lupatic acid, Betulic acid, Mairin, ALS357, ALS 357, ALS-357 |
|---|---|
| Topological Polar Surface Area | 57.5 |
| Hydrogen Bond Donor Count | 2.0 |
| Heavy Atom Count | 33.0 |
| Description | Betulinic acid is a naturally occurring pentacyclic triterpenoid which has anti-retroviral, anti-malarial, and anti-inflammatory properties, as well as a more recently discovered potential as an anticancer agent, by inhibition of topoisomerase. It is found in the bark of several species of plants, principally the white birch (Betula pubescens) from which it gets its name, but also the Ber tree (Ziziphus mauritiana), the tropical carnivorous plants Triphyophyllum peltatum and Ancistrocladus heyneanus, Diospyros leucomelas a member of the persimmon family, Tetracera boiviniana, the jambul (Syzygium formosanum), flowering quince (Chaenomeles sinensis), Rosemary, and Pulsatilla chinensis., Controversial is a role of p53 in betulinic acid-induced apoptosis. Fulda suggested p53-independent mechanism of the apoptosis, basing on fact of no accumulation of wild-type p53 detected upon treatment with the betulinic acid, whereas wild-type p53 protein strongly increased after treatment with doxorubicin. The suggestion is supported by study of Raisova. On the other hand Rieber suggested that betulinic acid exerts its inhibitory effect on human metastatic melanoma partly by increasing p53. |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 861.0 |
| Database Name | cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;pubchem |
| Defined Atom Stereocenter Count | 0.0 |
| Iupac Name | 9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid |
| Prediction Hob | 1.0 |
| Class | Prenol lipids |
| Xlogp | 8.2 |
| Superclass | Lipids and lipid-like molecules |
| Subclass | Triterpenoids |
| Molecular Formula | C30H48O3 |
| Prediction Swissadme | 0.0 |
| Inchi Key | QGJZLNKBHJESQX-UHFFFAOYSA-N |
| Fcsp3 | 0.9 |
| Logs | -4.434 |
| Rotatable Bond Count | 2.0 |
| Logd | 5.459 |
| Synonyms | 3-Hydroxy-(3beta)-lup-20(29)-en-28-Oic acid, 3-Hydroxylup-20(29)-en-28-oic acid, 3beta-Hydroxy-20(29)-lupaene-28-oic acid, 3beta-Hydroxy-lup-20(29)-en-28-Oic acid, Betulic acid, Lup-20(29)-en-28-oic acid, 3-hydroxy-, (3beta)-, Lup-20(29)-en-28-oic acid, 3&beta, -hydroxy-, Lup-20(29)-en-28-oic acid, 3beta-hydroxy-, Mairin, Epibetulinate, Betulinate, 3-Hydroxylup-20(29)-en-28-Oic acid, 3beta-Hydroxy-20(29)-lupaene-28-Oic acid |
| Substituent Name | Lupane triterpenoid, 18-hydroxysteroid, 18-oxosteroid, Oxosteroid, Hydroxysteroid, Steroid, Cyclic alcohol, Secondary alcohol, Monocarboxylic acid or derivatives, Carboxylic acid, Carboxylic acid derivative, Hydrocarbon derivative, Organooxygen compound, Carbonyl group, Alcohol, Aliphatic homopolycyclic compound |
| Compound Name | 9-Hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid |
| Kingdom | Organic compounds |
| Prediction Hob Swissadme | 0.0 |
| Exact Mass | 456.36 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 456.36 |
| Hydrogen Bond Acceptor Count | 3.0 |
| Molecular Weight | 456.7 |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 10.0 |
| Total Bond Stereocenter Count | 0.0 |
| Molecular Framework | Aliphatic homopolycyclic compounds |
| Esol | -7.7119082000000025 |
| 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) |
| Smiles | CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)O)C)C(=O)O |
| Nring | 5.0 |
| Defined Bond Stereocenter Count | 0.0 |
| Taxonomy Direct Parent | Triterpenoids |
- 1. Outgoing r'ship
FOUND_INto/from Anemone Raddeana (Plant) Rel Props:Source_db:cmaup_ingredients - 2. Outgoing r'ship
FOUND_INto/from Artocarpus Heterophyllus (Plant) Rel Props:Source_db:fooddb_chem_all - 3. Outgoing r'ship
FOUND_INto/from Cichorium Intybus (Plant) Rel Props:Source_db:fooddb_chem_all - 4. Outgoing r'ship
FOUND_INto/from Crateva Religiosa (Plant) Rel Props:Source_db:fooddb_chem_all - 5. Outgoing r'ship
FOUND_INto/from Diospyros Kaki (Plant) Rel Props:Source_db:fooddb_chem_all - 6. Outgoing r'ship
FOUND_INto/from Diospyros Virginiana (Plant) Rel Props:Source_db:fooddb_chem_all - 7. Outgoing r'ship
FOUND_INto/from Eugenia Jambolana (Plant) Rel Props:Source_db:fooddb_chem_all - 8. Outgoing r'ship
FOUND_INto/from Juglans Regia (Plant) Rel Props:Source_db:cmaup_ingredients;fooddb_chem_all - 9. Outgoing r'ship
FOUND_INto/from Ocimum Basilicum (Plant) Rel Props:Source_db:fooddb_chem_all - 10. Outgoing r'ship
FOUND_INto/from Olea Europaea (Plant) Rel Props:Source_db:fooddb_chem_all - 11. Outgoing r'ship
FOUND_INto/from Psophocarpus Tetragonolobus (Plant) Rel Props:Source_db:fooddb_chem_all - 12. Outgoing r'ship
FOUND_INto/from Punica Granatum (Plant) Rel Props:Source_db:cmaup_ingredients;fooddb_chem_all - 13. Outgoing r'ship
FOUND_INto/from Rosmarinus Officinalis (Plant) Rel Props:Source_db:fooddb_chem_all - 14. Outgoing r'ship
FOUND_INto/from Sambucus Nigra (Plant) Rel Props:Source_db:fooddb_chem_all - 15. Outgoing r'ship
FOUND_INto/from Syzygium Cumini (Plant) Rel Props:Source_db:cmaup_ingredients;fooddb_chem_all - 16. Outgoing r'ship
FOUND_INto/from Vitis Vinifera (Plant) Rel Props:Source_db:fooddb_chem_all - 17. Outgoing r'ship
FOUND_INto/from Ziziphus Jujuba (Plant) Rel Props:Source_db:cmaup_ingredients