2-[(2S)-2-benzyl-3-sulfanylpropanamido]acetic acid

• ChemBase ID: 1430
• Molecular Formular: C12H15NO3S
• Molecular Mass: 253.3174
• Monoisotopic Mass: 253.07726435
• SMILES: OC(=O)CNC(=O)[C@@H](CS)Cc1ccccc1
• Canonical SMILES: SC[C@H](C(=O)NCC(=O)O)Cc1ccccc1
• InChI: InChI=1S/C12H15NO3S/c14-11(15)7-13-12(16)10(8-17)6-9-4-2-1-3-5-9/h1-5,10,17H,6-8H2,(H,13,16)(H,14,15)/t10-/m1/s1
• InChIKey: LJJKNPQAGWVLDQ-SNVBAGLBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2S)-2-benzyl-3-sulfanylpropanamido]acetic acid
• IUPAC Traditional name: @thiorphan
• Brand Name: THIORPHAN
• Synonyms: (2-MERCAPTOMETHYL-3-PHENYL-PROPIONYL)-GLYCINE; Thiorphan

Database IDs

• CAS Number: 76721-89-6
• PubChem SID: 99445097; 160964889
• PubChem CID: 4369380

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.017452
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -0.028880706
• LogD (pH = 7.4): -1.6859314
• Log P: 1.4638641
• Molar Refractivity: 67.1479 cm^3
• Polarizability: 26.171062 Å^3
• Polar Surface Area: 66.4 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.78
• LOG S: -2.76
• Solubility (Water): 4.45e-01 g/l

DETAILS

DrugBank - DB01654

Drug information: experimental

DrugBank - DB08626

• Drug Groups: experimental
• Description: A potent inhibitor of membrane metalloendopeptidase (enkephalinase). Thiorphan potentiates morphine-induced analgesia and attenuates naloxone-precipitated withdrawal symptoms.
• External Links: Wikipedia