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

• ChemBase ID: 72965
• 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](CC(C1)(C)C)C(=O)O)C)C)C)(C)C)O
• Canonical SMILES: OC(=O)[C@@H]1CC(C)(C)C[C@@H]2C1CC[C@@]1(C2=CC[C@H]2[C@@]1(C)CC[C@@H]1[C@]2(C)CC[C@@H](C1(C)C)O)C
• InChI: InChI=1S/C30H48O3/c1-26(2)16-19-18(20(17-26)25(32)33)10-14-29(6)21(19)8-9-23-28(5)13-12-24(31)27(3,4)22(28)11-15-30(23,29)7/h8,18-20,22-24,31H,9-17H2,1-7H3,(H,32,33)/t18?,19-,20-,22+,23-,24+,28+,29-,30-/m1/s1
• InChIKey: AOWMBRPPHGNFDX-HPPBOAITSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,6aS,6bR,8aR,10S,12aR,12bR,14bR)-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-4-carboxylic acid
• IUPAC Traditional name: (4R,6aS,6bR,8aR,10S,12aR,12bR,14bR)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-3,4,4a,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydro-1H-picene-4-carboxylic acid
• Synonyms: Caryophyllin; Astrantiagenin C; Giganteumgenin C; Virgaureagenin B; Oleanolic Acid

Database IDs

• CAS Number: 508-02-1
• PubChem SID: 162037885
• PubChem CID: 49867939

CALCULATED PROPERTIES

• Acid pKa: 4.6560044
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 5.4246063
• LogD (pH = 7.4): 3.6469674
• Log P: 6.325838
• Molar Refractivity: 133.6721 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 - S2334

Research Area: Inflammation
Biological Activity:
Oleanolic acid(Caryophyllin) is a naturally occurring triterpenoid, widely distributed in food and medicinal plants, related to betulinic acid. It is relatively non-toxic, antitumor, and hepatoprotective, as well as exhibiting antiviral properties. An extremely potent synthetic triterpenoid analogue of oleanolic acid was found in 2005, which are powerful inhibitors of cellular inflammatory processes. [1]

REFERENCES

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