(2S)-2-amino-5-{[(3S,4R)-1-[(1R)-1-carboxy-2-[(S)-methanesulfinyl]ethyl]-2-oxo-4-sulfanylazetidin-3-yl]carbamoyl}pentanoic acid

• ChemBase ID: 2711
• Molecular Formular: C13H21N3O7S2
• Molecular Mass: 395.45174
• Monoisotopic Mass: 395.08209203
• SMILES: C[S@](=O)C[C@H](N1[C@H](S)[C@@H](NC(=O)CCC[C@H](N)C(=O)O)C1=O)C(=O)O
• Canonical SMILES: O=C(N[C@@H]1[C@@H](S)N(C1=O)[C@H](C(=O)O)C[S@@](=O)C)CCC[C@@H](C(=O)O)N
• InChI: InChI=1S/C13H21N3O7S2/c1-25(23)5-7(13(21)22)16-10(18)9(11(16)24)15-8(17)4-2-3-6(14)12(19)20/h6-7,9,11,24H,2-5,14H2,1H3,(H,15,17)(H,19,20)(H,21,22)/t6-,7-,9-,11+,25-/m0/s1
• InChIKey: UFLVUEXXBDLOEJ-NBHIPWOASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-5-{[(3S,4R)-1-[(1R)-1-carboxy-2-[(S)-methanesulfinyl]ethyl]-2-oxo-4-sulfanylazetidin-3-yl]carbamoyl}pentanoic acid
• IUPAC Traditional name: (2S)-2-amino-5-{[(3S,4R)-1-[(1R)-1-carboxy-2-[(S)-methanesulfinyl]ethyl]-2-oxo-4-sulfanylazetidin-3-yl]carbamoyl}pentanoic acid
• Synonyms: 1-[(1s)-Carboxy-2-(Methylsulfinyl)Ethyl]-(3r)-[(5s)-5-Amino-5-Carboxypentanamido]-(4r)-Sulfanylazetidin-2-One

Database IDs

• PubChem SID: 160966160; 46506055
• PubChem CID: 46936551

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.8473375
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -7.4541755
• LogD (pH = 7.4): -8.738934
• Log P: -5.4874263
• Molar Refractivity: 90.0033 cm^3
• Polarizability: 35.905643 Å^3
• Polar Surface Area: 167.1 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.54
• LOG S: -2.39
• Solubility (Water): 1.63e+00 g/l

DETAILS

DrugBank - DB03004

Drug information: experimental