(2S,4S)-2-[(1S)-1-[(2S)-2-amino-2-(4-hydroxyphenyl)acetamido]-2-oxoethyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid

• ChemBase ID: 3315
• Molecular Formular: C16H21N3O5S
• Molecular Mass: 367.42004
• Monoisotopic Mass: 367.12019179
• SMILES: CC1(C)S[C@H](N[C@H]1C(=O)O)[C@@H](NC(=O)[C@@H](N)c1ccc(O)cc1)C=O
• Canonical SMILES: O=C[C@@H]([C@H]1N[C@H](C(S1)(C)C)C(=O)O)NC(=O)[C@H](c1ccc(cc1)O)N
• InChI: InChI=1S/C16H21N3O5S/c1-16(2)12(15(23)24)19-14(25-16)10(7-20)18-13(22)11(17)8-3-5-9(21)6-4-8/h3-7,10-12,14,19,21H,17H2,1-2H3,(H,18,22)(H,23,24)/t10-,11-,12-,14-/m0/s1
• InChIKey: SMLJDSWXGVMNTH-MNXVOIDGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S)-2-[(1S)-1-[(2S)-2-amino-2-(4-hydroxyphenyl)acetamido]-2-oxoethyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
• IUPAC Traditional name: (2S,4S)-2-[(1S)-1-[(2S)-2-amino-2-(4-hydroxyphenyl)acetamido]-2-oxoethyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
• Synonyms: 2-{1-[2-Amino-2-(4-Hydroxy-Phenyl)-Acetylamino]-2-Oxo-Ethyl}-5,5-Dimethyl-Thiazolidine-4-Carboxylic Acid

Database IDs

• PubChem SID: 160966756; 46505457
• PubChem CID: 46936747

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.8631303
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -3.1761303
• LogD (pH = 7.4): -2.5310845
• Log P: -2.4610953
• Molar Refractivity: 91.6568 cm^3
• Polarizability: 36.60833 Å^3
• Polar Surface Area: 141.75 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.05
• LOG S: -2.92
• Solubility (Water): 4.45e-01 g/l

DETAILS

DrugBank - DB03658

Drug information: experimental