(4S)-5-[4-(benzyloxy)phenyl]-4-(7-phenylheptanamido)pentanoic acid

• ChemBase ID: 153842
• Molecular Formular: C31H37NO4
• Molecular Mass: 487.62978
• Monoisotopic Mass: 487.27225867
• SMILES: c1ccc(cc1)CCCCCCC(=O)N[C@@H](CCC(=O)O)Cc1ccc(cc1)OCc1ccccc1
• Canonical SMILES: OC(=O)CC[C@@H](Cc1ccc(cc1)OCc1ccccc1)NC(=O)CCCCCCc1ccccc1
• InChI: InChI=1S/C31H37NO4/c33-30(16-10-2-1-5-11-25-12-6-3-7-13-25)32-28(19-22-31(34)35)23-26-17-20-29(21-18-26)36-24-27-14-8-4-9-15-27/h3-4,6-9,12-15,17-18,20-21,28H,1-2,5,10-11,16,19,22-24H2,(H,32,33)(H,34,35)/t28-/m0/s1
• InChIKey: KWLUIYFCMHKLKY-NDEPHWFRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-5-[4-(benzyloxy)phenyl]-4-(7-phenylheptanamido)pentanoic acid
• IUPAC Traditional name: (4S)-5-[4-(benzyloxy)phenyl]-4-(7-phenylheptanamido)pentanoic acid
• Synonyms: 5-(4-Benzyloxyphenyl)-4S-(7-phenylheptanoylamino)pentanoic acid; sPLA2 inhibitor

Database IDs

• CAS Number: 393569-31-8
• MDL Number: MFCD06411576
• PubChem SID: 24724605; 162247981
• PubChem CID: 446400

CALCULATED PROPERTIES

• Acid pKa: 4.260861
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 5.6326337
• LogD (pH = 7.4): 3.9027698
• Log P: 6.8939314
• Molar Refractivity: 142.7421 cm^3
• Polarizability: 55.78178 Å^3
• Polar Surface Area: 75.63 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL
• Apperance: white powder
• Melting Point: 133-135 °C

Safety Information

• Storage Condition: under inert gas
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Empirical Formula (Hill Notation): C31H37NO4

DETAILS

Sigma Aldrich - S3319

Biochem/physiol Actions
Orally active, potent secretory Phospholipase A2 (sPLA2; Group IIa) inhibitor.
Packaging
Under nitrogen