N-[(3S,7S,11S)-7,11-bis(2,3-dihydroxybenzamido)-2,6,10-trioxo-1,5,9-trioxacyclododecan-3-yl]-2,3-dihydroxybenzamide

• ChemBase ID: 127259
• Molecular Formular: C30H27N3O15
• Molecular Mass: 669.54648
• Monoisotopic Mass: 669.14421718
• SMILES: c1cc(c(c(c1)O)O)C(=O)N[C@@H]1COC(=O)[C@@H](COC(=O)[C@@H](COC1=O)NC(=O)c1cccc(c1O)O)NC(=O)c1cccc(c1O)O
• Canonical SMILES: O=C(c1cccc(c1O)O)N[C@@H]1COC(=O)[C@@H](COC(=O)[C@@H](COC1=O)NC(=O)c1cccc(c1O)O)NC(=O)c1cccc(c1O)O
• InChI: InChI=1S/C30H27N3O15/c34-19-7-1-4-13(22(19)37)25(40)31-16-10-46-29(44)18(33-27(42)15-6-3-9-21(36)24(15)39)12-48-30(45)17(11-47-28(16)43)32-26(41)14-5-2-8-20(35)23(14)38/h1-9,16-18,34-39H,10-12H2,(H,31,40)(H,32,41)(H,33,42)/t16-,17-,18-/m0/s1
• InChIKey: SERBHKJMVBATSJ-BZSNNMDCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(3S,7S,11S)-7,11-bis(2,3-dihydroxybenzamido)-2,6,10-trioxo-1,5,9-trioxacyclododecan-3-yl]-2,3-dihydroxybenzamide
• IUPAC Traditional name: enterobactin
• Synonyms: Enterobactin

Database IDs

• CAS Number: 28384-96-5
• PubChem SID: 162221580
• PubChem CID: 34231
• CHEBI ID: 28855
• CHEMBL: 432995
• Chemspider ID: 31543
• Wikipedia Title: Enterobactin

CALCULATED PROPERTIES

• Acid pKa: 7.822545
• H Acceptors: 12
• H Donor: 9
• LogD (pH = 5.5): 2.262172
• LogD (pH = 7.4): 2.1108859
• Log P: 2.2642207
• Molar Refractivity: 157.8747 cm^3
• Polarizability: 60.301113 Å^3
• Polar Surface Area: 287.58 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false