(2S,3R,4R,5R,7R,8S)-4,8-diamino-N-[(1S)-1-carbamoyl-2-(carbamoylamino)ethyl]-2,3,5,7,9-pentahydroxynonanamide

• ChemBase ID: 130264
• Molecular Formular: C13H28N6O8
• Molecular Mass: 396.39682
• Monoisotopic Mass: 396.19686189
• SMILES: C([C@H]([C@H](CO)N)O)[C@H]([C@H]([C@H]([C@@H](C(=O)N[C@@H](CNC(=O)N)C(=O)N)O)O)N)O
• Canonical SMILES: OC[C@@H]([C@@H](C[C@H]([C@H]([C@H]([C@@H](C(=O)N[C@H](C(=O)N)CNC(=O)N)O)O)N)O)O)N
• InChI: InChI=1S/C13H28N6O8/c14-4(3-20)6(21)1-7(22)8(15)9(23)10(24)12(26)19-5(11(16)25)2-18-13(17)27/h4-10,20-24H,1-3,14-15H2,(H2,16,25)(H,19,26)(H3,17,18,27)/t4-,5-,6+,7+,8+,9+,10-/m0/s1
• InChIKey: FYIPKJHNWFVEIR-VTAUKWRXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4R,5R,7R,8S)-4,8-diamino-N-[(1S)-1-carbamoyl-2-(carbamoylamino)ethyl]-2,3,5,7,9-pentahydroxynonanamide
• IUPAC Traditional name: (2S,3R,4R,5R,7R,8S)-4,8-diamino-N-[(1S)-1-carbamoyl-2-(carbamoylamino)ethyl]-2,3,5,7,9-pentahydroxynonanamide
• Synonyms: Zwittermicin A

Database IDs

• CAS Number: 155547-95-8
• PubChem SID: 162224544
• PubChem CID: 46884249
• Chemspider ID: 24669086
• Wikipedia Title: Zwittermicin_A

CALCULATED PROPERTIES

• Acid pKa: 11.709006
• H Acceptors: 10
• H Donor: 11
• LogD (pH = 5.5): -13.428292
• LogD (pH = 7.4): -10.5015955
• Log P: -7.83617
• Molar Refractivity: 88.8177 cm^3
• Polarizability: 35.972546 Å^3
• Polar Surface Area: 280.5 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false