(4aR,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-hydroxy-2,2,6a,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: 175835
• 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)(CCC(C1)(C)C)C(=O)O)C)C)C)(C)C)O
• Canonical SMILES: O[C@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@]1([C@H]2CC(C)(C)CC1)C(=O)O)C)C
• InChI: InChI=1S/C30H48O3/c1-25(2)14-16-30(24(32)33)17-15-28(6)19(20(30)18-25)8-9-22-27(5)12-11-23(31)26(3,4)21(27)10-13-29(22,28)7/h8,20-23,31H,9-18H2,1-7H3,(H,32,33)/t20-,21-,22+,23-,27-,28+,29+,30+/m0/s1
• InChIKey: MIJYXULNPSFWEK-ZZAAMMQTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4aR,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-hydroxy-2,2,6a,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: (4aR,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid
• Synonyms: (3β)-3-hydroxyolean-12-en-28-oic Acid; (+)-Oleanolic Acid; 3β-Hydroxyolean-12-en-28-oic Αcid; Astrantiagenin C; Caryophyllin; Giganteumgenin C; Gledigenin 1; NSC 114945; Oleonolic acid; Virgaureagenin B; Oleanolic Acid

Database IDs

• CAS Number: 508-02-1
• PubChem SID: 164231745
• PubChem CID: 45483610

CALCULATED PROPERTIES

• Acid pKa: 4.7442603
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 5.7696033
• LogD (pH = 7.4): 3.992649
• Log P: 6.5948334
• Molar Refractivity: 133.6245 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: Chloroform
• Apperance: White Solid
• Melting Point: 295-297°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - O521000

A triterpenoid known for its anti-inflammatory properties, is commonly present in several medicinal plants. Inhibits secretory phospholipase A2.

REFERENCES

• Andrikopoulos, N., et al.: J. Med. Food, 5, 1 (2002)
• Lanteri, S., et al.: Food Chem., 76, 501 (2002)
• Rodriguez-Rodriguez, R., et al.: Br. J. Pharmacol., 155, 535 (2002)
• Sotiroudis, T., et al.: Eur. J. Nutr, 47, 69 (2002)