methyl (2R,4aS,6aS,12bR,14aS,14bR)-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylate

• ChemBase ID: 154858
• Molecular Formular: C30H40O4
• Molecular Mass: 464.6362
• Monoisotopic Mass: 464.29265976
• SMILES: CC1=C(C(=O)C=C2C1=CC=C1[C@]2(CC[C@@]2([C@@]1(CC[C@@]1([C@H]2C[C@](CC1)(C)C(=O)OC)C)C)C)C)O
• Canonical SMILES: COC(=O)[C@]1(C)CC[C@]2([C@@H](C1)[C@]1(C)CC[C@@]3(C(=CC=C4C3=CC(=O)C(=C4C)O)[C@]1(CC2)C)C)C
• InChI: InChI=1S/C30H40O4/c1-18-19-8-9-22-28(4,20(19)16-21(31)24(18)32)13-15-30(6)23-17-27(3,25(33)34-7)11-10-26(23,2)12-14-29(22,30)5/h8-9,16,23,32H,10-15,17H2,1-7H3/t23-,26-,27-,28+,29-,30+/m1/s1
• InChIKey: JFACETXYABVHFD-WXPPGMDDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2R,4aS,6aS,12bR,14aS,14bR)-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylate
• IUPAC Traditional name: pristimerin
• Synonyms: (9b,13a,14b,20a)-3-Hydroxy-9,13-dimethyl-2-oxo-24,25,26 -trinoroleana-1(10),3,5,7-tertraen-29-oic acid methyl ester; Pristimerin

Database IDs

• CAS Number: 1258-84-0
• MDL Number: MFCD01711331
• PubChem SID: 162248996
• PubChem CID: 159516

CALCULATED PROPERTIES

• Acid pKa: 9.752585
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 5.4763436
• LogD (pH = 7.4): 5.4744444
• Log P: 5.476368
• Molar Refractivity: 137.5152 cm^3
• Polarizability: 52.83122 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: ≥5 mg/mL
• Apperance: orange powder

Safety Information

• Storage Condition: protect from light
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C30H40O4

DETAILS

Sigma Aldrich - P0020

Biochem/physiol Actions
More active than euphol against MGL, better activity with rat neurons, but less selective relative to similar enzymes. First MGL inhibitor to act reversibly, several others covalently bind to cysteine residues. Other studies involve multiply mylome, pristimerin inhibits NF-κB activation via inhibition of IKK-α or IKK-β. It is the methyl ester of celastrol (C0869).