(1S,2R,4R,6aS,6bR,8aR,10S,12aR,12bR,14bR)-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-4-carboxylic acid

• ChemBase ID: 72994
• Molecular Formular: C30H48O3
• Molecular Mass: 456.70032
• Monoisotopic Mass: 456.3603454
• SMILES: C1[C@@H](C([C@H]2[C@](C1)([C@@H]1[C@@](CC2)([C@]2(C(=CC1)[C@H]1C(CC2)[C@@H](C[C@H]([C@@H]1C)C)C(=O)O)C)C)C)(C)C)O
• Canonical SMILES: C[C@@H]1C[C@@H](C(=O)O)C2[C@@H]([C@H]1C)C1=CC[C@H]3[C@@]([C@@]1(CC2)C)(C)CC[C@@H]1[C@]3(C)CC[C@@H](C1(C)C)O
• InChI: InChI=1S/C30H48O3/c1-17-16-20(26(32)33)19-10-14-29(6)21(25(19)18(17)2)8-9-23-28(5)13-12-24(31)27(3,4)22(28)11-15-30(23,29)7/h8,17-20,22-25,31H,9-16H2,1-7H3,(H,32,33)/t17-,18+,19?,20-,22+,23-,24+,25-,28+,29-,30-/m1/s1
• InChIKey: FZRIRHAXJWMMFP-UTQWFWGYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,4R,6aS,6bR,8aR,10S,12aR,12bR,14bR)-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-4-carboxylic acid
• IUPAC Traditional name: (1S,2R,4R,6aS,6bR,8aR,10S,12aR,12bR,14bR)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,4a,5,6,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-1H-picene-4-carboxylic acid
• Synonyms: Malol; Prunol; Urson; Ursolic acid

Database IDs

• CAS Number: 77-52-1
• PubChem SID: 162037914
• PubChem CID: 49867942

CALCULATED PROPERTIES

• Acid pKa: 4.6561365
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 5.4116936
• LogD (pH = 7.4): 3.6340525
• Log P: 6.3128104
• Molar Refractivity: 133.7456 cm^3
• Polarizability: 53.23124 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S2370

Research Area: Cancer
Biological Activity:
Ursolic acid(Malol) 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. As medicine, it is well tolerated and can be used topically and orally. Ursolic acid can also serve as a starting material for synthesis of more potent bioactive derivatives, such as anti-tumor agents. [1]

REFERENCES

• http://en.wikipedia.org/wiki/Ursolic_acid