4-{[(3S)-1-(4-tert-butylphenyl)-5-oxopyrrolidin-3-yl]methoxy}benzoic acid

• ChemBase ID: 154538
• Molecular Formular: C22H25NO4
• Molecular Mass: 367.4382
• Monoisotopic Mass: 367.17835829
• SMILES: CC(C)(C)c1ccc(cc1)N1C[C@H](CC1=O)COc1ccc(cc1)C(=O)O
• Canonical SMILES: OC(=O)c1ccc(cc1)OC[C@@H]1CN(C(=O)C1)c1ccc(cc1)C(C)(C)C
• InChI: InChI=1S/C22H25NO4/c1-22(2,3)17-6-8-18(9-7-17)23-13-15(12-20(23)24)14-27-19-10-4-16(5-11-19)21(25)26/h4-11,15H,12-14H2,1-3H3,(H,25,26)/t15-/m0/s1
• InChIKey: YZADMDZNVOBYGR-HNNXBMFYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[(3S)-1-(4-tert-butylphenyl)-5-oxopyrrolidin-3-yl]methoxy}benzoic acid
• IUPAC Traditional name: 4-{[(3S)-1-(4-tert-butylphenyl)-5-oxopyrrolidin-3-yl]methoxy}benzoic acid
• Synonyms: (S)-(+)-4-[1-(4-tert-Butylphenyl)-2-oxo-pyrrolidin-4-yl]methoxybenzoic acid; S-2E

Database IDs

• CAS Number: 155730-92-0
• MDL Number: MFCD06407742
• PubChem SID: 24724620; 162248677
• PubChem CID: 9864020

CALCULATED PROPERTIES

• Acid pKa: 4.362014
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.6419296
• LogD (pH = 7.4): 0.891676
• Log P: 3.808667
• Molar Refractivity: 103.4157 cm^3
• Polarizability: 39.883976 Å^3
• Polar Surface Area: 66.84 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble11 mg/mL; H2O: insoluble
• Apperance: white powder

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C22H25NO4

DETAILS

Sigma Aldrich - S6445

Packaging
Shipped ambient under nitrogen.
Biochem/physiol Actions
HMG-CoA reductase and acetyl-CoA carboxylase inhibitor. In the liver, S-2E is converted into its active metabolite, S-2E-CoA. S-2E-CoA noncompetitively inhibited the enzymatic activities of both 3-hydroxy-3-methylglutaryl coenzyme-A (HMG-CoA) reductase and acetyl-CoA carboxylase at K(i)=18.11 microM and K(i)=69.2 microM, respectively.