2-({[(2-amino-1,3-thiazol-4-yl)({[(2S,3S)-2-methyl-4-oxo-1-sulfoazetidin-3-yl]carbamoyl})methylidene]amino}oxy)-2-methylpropanoic acid

• ChemBase ID: 157733
• Molecular Formular: C13H17N5O8S2
• Molecular Mass: 435.43278
• Monoisotopic Mass: 435.05185453
• SMILES: C[C@H]1[C@@H](C(=O)N1S(=O)(=O)O)NC(=O)/C(=N/OC(C)(C)C(=O)O)/c1csc(n1)N
• Canonical SMILES: C[C@H]1[C@H](NC(=O)/C(=N/OC(C(=O)O)(C)C)/c2csc(n2)N)C(=O)N1S(=O)(=O)O
• InChI: InChI=1S/C13H17N5O8S2/c1-5-7(10(20)18(5)28(23,24)25)16-9(19)8(6-4-27-12(14)15-6)17-26-13(2,3)11(21)22/h4-5,7H,1-3H3,(H2,14,15)(H,16,19)(H,21,22)(H,23,24,25)/t5-,7-/m0/s1
• InChIKey: WZPBZJONDBGPKJ-FSPLSTOPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-({[(2-amino-1,3-thiazol-4-yl)({[(2S,3S)-2-methyl-4-oxo-1-sulfoazetidin-3-yl]carbamoyl})methylidene]amino}oxy)-2-methylpropanoic acid
• IUPAC Traditional name: 2-({[(2-amino-1,3-thiazol-4-yl)({[(2S,3S)-2-methyl-4-oxo-1-sulfoazetidin-3-yl]carbamoyl})methylidene]amino}oxy)-2-methylpropanoic acid
• Synonyms: [2S-[2α,3β(Z)]]-2-[[[1-(2-Amino-4-thiazolyl)-2-[(2-methyl-4-oxo-1-sulfo-3-azetidinyl)amino]-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid; Aztreonam; Azactam; Azthreonam; Dynabiotic; Monobactam; Nebactam; Primbactam; Probactam; [2S-[2α,3β(Z)]]-2-[[[1-(2-氨基-4-噻唑基)-2-[(2-甲基-4-氧代-1-磺基-3-氮杂环丁烷)氨基]-2-氧代亚乙基]氨基]氧代]-2-甲基丙酸; 氨曲南

Database IDs

• CAS Number: 78110-38-0
• EC Number: 278-839-9
• MDL Number: MFCD00072145
• PubChem SID: 162251870
• PubChem CID: 5459211

CALCULATED PROPERTIES

• Acid pKa: -1.8779534
• H Acceptors: 11
• H Donor: 4
• LogD (pH = 5.5): -4.6863904
• LogD (pH = 7.4): -6.120788
• Log P: -1.9186332
• Molar Refractivity: 92.9853 cm^3
• Polarizability: 36.662426 Å^3
• Polar Surface Area: 201.58 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: solid

Safety Information

• RTECS: UA2451400
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Mechanism of Action: Inhibits mucopeptide synthesis in the bacterial cell wall

Product Information

• Grade: analytical standard, for drug analysis
• Application(s): Bactericidal antibiotic; Low acute mammalian toxicity; Shows potent and specific activity against gram-negative bacteria and high beta-lactamase stability; Used clinically (e.g. to treat urinary tract infections)
• Empirical Formula (Hill Notation): C13H17N5O8S2

DETAILS

Sigma Aldrich - A6848

Application
Antibacterial

REFERENCES

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