(2R,5S,6R)-6-[(5S)-5-amino-5-carboxypentanamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

• ChemBase ID: 3216
• Molecular Formular: C14H21N3O6S
• Molecular Mass: 359.39804
• Monoisotopic Mass: 359.11510641
• SMILES: CC1(C)S[C@H]2[C@H](NC(=O)CCC[C@H](N)C(=O)O)C(=O)N2[C@@H]1C(=O)O
• Canonical SMILES: O=C(N[C@@H]1C(=O)N2[C@H]1SC([C@H]2C(=O)O)(C)C)CCC[C@@H](C(=O)O)N
• InChI: InChI=1S/C14H21N3O6S/c1-14(2)9(13(22)23)17-10(19)8(11(17)24-14)16-7(18)5-3-4-6(15)12(20)21/h6,8-9,11H,3-5,15H2,1-2H3,(H,16,18)(H,20,21)(H,22,23)/t6-,8+,9+,11-/m0/s1
• InChIKey: MIFYHUACUWQUKT-QSKNDCFUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,5S,6R)-6-[(5S)-5-amino-5-carboxypentanamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• IUPAC Traditional name: @isopenicillin N
• Synonyms: Isopenicillin N

Database IDs

• PubChem SID: 46504620; 160966659
• PubChem CID: 46936713

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.8342174
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -5.1629453
• LogD (pH = 7.4): -6.624511
• Log P: -3.3928711
• Molar Refractivity: 83.0509 cm^3
• Polarizability: 33.33548 Å^3
• Polar Surface Area: 150.03 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.43
• LOG S: -1.6
• Solubility (Water): 8.96e+00 g/l

DETAILS

DrugBank - DB03550

Drug information: experimental