(2S)-2-[(1R)-2-[(2R)-2-amino-2-carboxylatoethoxy]-2-oxo-1-[2-(thiophen-2-yl)acetamido]ethyl]-5-[(E)-2-(2,4-dinitrophenyl)ethenyl]-3,6-dihydro-2H-1,3-thiazine-4-carboxylate

• ChemBase ID: 3668
• Molecular Formular: C24H21N5O11S2--
• Molecular Mass: 619.58044
• Monoisotopic Mass: 619.06789852
• SMILES: N[C@H](COC(=O)[C@@H](NC(=O)Cc1cccs1)[C@H]1NC(=C(CS1)/C=C/c1ccc(cc1[N+](=O)[O-])[N+](=O)[O-])C(=O)[O-])C(=O)[O-]
• Canonical SMILES: O=C(N[C@@H]([C@@H]1SCC(=C(N1)C(=O)[O-])/C=C/c1ccc(cc1[N+](=O)[O-])[N+](=O)[O-])C(=O)OC[C@H](C(=O)[O-])N)Cc1cccs1
• InChI: InChI=1S/C24H23N5O11S2/c25-16(22(31)32)10-40-24(35)20(26-18(30)9-15-2-1-7-41-15)21-27-19(23(33)34)13(11-42-21)4-3-12-5-6-14(28(36)37)8-17(12)29(38)39/h1-8,16,20-21,27H,9-11,25H2,(H,26,30)(H,31,32)(H,33,34)/p-2/b4-3+/t16-,20+,21+/m1/s1
• InChIKey: GPHOELDACAWWAE-OFKRYJGVSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(1R)-2-[(2R)-2-amino-2-carboxylatoethoxy]-2-oxo-1-[2-(thiophen-2-yl)acetamido]ethyl]-5-[(E)-2-(2,4-dinitrophenyl)ethenyl]-3,6-dihydro-2H-1,3-thiazine-4-carboxylate
• IUPAC Traditional name: nitrocefin acyl-serine
• Synonyms: Nitrocefin Acyl-Serine

Database IDs

• PubChem SID: 46508561; 160967106
• PubChem CID: 46936868

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.7159101
• H Acceptors: 12
• H Donor: 3
• LogD (pH = 5.5): -2.873112
• LogD (pH = 7.4): -4.0504527
• Log P: -0.75985867
• Molar Refractivity: 171.2316 cm^3
• Polarizability: 55.869156 Å^3
• Polar Surface Area: 265.35 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 2.47
• LOG S: -5.38
• Solubility (Water): 2.76e-03 g/l

DETAILS

DrugBank - DB04041

Drug information: experimental