(2R)-2-[(R)-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido](carboxy)methyl]-5-methylidene-5,6-dihydro-2H-1,3-thiazine-4-carboxylic acid

• ChemBase ID: 5992
• Molecular Formular: C14H15N5O6S2
• Molecular Mass: 413.4288
• Monoisotopic Mass: 413.04637523
• SMILES: O=C([C@H]([C@@H]1N=C(C(=C)CS1)C(=O)O)NC(=O)/C(=N\OC)/c1csc(n1)N)O
• Canonical SMILES: CO/N=C(/c1csc(n1)N)\C(=O)N[C@@H]([C@H]1SCC(=C)C(=N1)C(=O)O)C(=O)O
• InChI: InChI=1S/C14H15N5O6S2/c1-5-3-26-11(18-7(5)12(21)22)9(13(23)24)17-10(20)8(19-25-2)6-4-27-14(15)16-6/h4,9,11H,1,3H2,2H3,(H2,15,16)(H,17,20)(H,21,22)(H,23,24)/b19-8-/t9-,11+/m0/s1
• InChIKey: ZRDXEERHKBZJMY-KTFFUYHOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-[(R)-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido](carboxy)methyl]-5-methylidene-5,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
• IUPAC Traditional name: (2R)-2-[(R)-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido](carboxy)methyl]-5-methylidene-2,6-dihydro-1,3-thiazine-4-carboxylic acid
• Synonyms: PCNOTAXIME GROUP

Database IDs

• PubChem SID: 160969417; 99444846
• PubChem CID: 6323466

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.5663958
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): -3.0260231
• LogD (pH = 7.4): -5.505103
• Log P: 0.3325226
• Molar Refractivity: 95.5618 cm^3
• Polarizability: 36.349873 Å^3
• Polar Surface Area: 176.56 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.15
• LOG S: -3.65
• Solubility (Water): 9.24e-02 g/l

DETAILS

DrugBank - DB08375

Drug information: experimental