(1S,2R,4aR,6aS,6bR,8aR,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

• ChemBase ID: 179410
• 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]1[C@](CC2)(CC[C@H]([C@@H]1C)C)C(=O)O)C)C)C)(C)C)O
• Canonical SMILES: C[C@@H]1CC[C@@]2([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)C(=O)O
• 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-XUTPQDOASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,4aR,6aS,6bR,8aR,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
• IUPAC Traditional name: (1S,2R,4aR,6aS,6bR,8aR,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
• Synonyms: (3β)-3-Hydroxy-urs-12-en-28-oic Acid; (+)-Ursolic Acid; Bungeolic Acid; Malol; Merotaine; Neoage UR; Prunol; NSC 167406; NSC 4060; β-Ursolic Acid; Ursolic Acid

Database IDs

• CAS Number: 77-52-1
• PubChem SID: 164235320
• PubChem CID: 45483617

CALCULATED PROPERTIES

• Acid pKa: 4.744127
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 5.7564616
• LogD (pH = 7.4): 3.9795034
• Log P: 6.581805
• Molar Refractivity: 133.698 cm^3
• Polarizability: 53.23124 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Pyridine
• Apperance: White Solid
• Melting Point: >273°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - U850100

A Triterpene acid used in cosmetics, that also has STAT3 pathway inhibiting properties.

REFERENCES

• Lee, C., et al.: Bioorg. Med. Chem. Lett., 20, 7354 (2010)
• Lee, A., et al.: J. Agric. Food Chem., 58, 12941 (2010)
• Pethakamsetty, L., et al.: J. Pharm. Res., 3, 193 (2010)