N-{3-[(2S,5S,8S)-5,8-bis[3-(N-hydroxyacetamido)propyl]-3,6,9,12,15,18-hexaoxo-1,4,7,10,13,16-hexaazacyclooctadecan-2-yl]propyl}-N-hydroxyacetamide

• ChemBase ID: 166248
• Molecular Formular: C27H45N9O12
• Molecular Mass: 687.6993
• Monoisotopic Mass: 687.31876793
• SMILES: C1NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC(=O)CNC1=O)CCCN(O)C(=O)C)CCCN(O)C(=O)C)CCCN(O)C(=O)C
• Canonical SMILES: O=C1NCC(=O)NCC(=O)N[C@@H](CCCN(C(=O)C)O)C(=O)N[C@H](C(=O)N[C@@H](C(=O)NC1)CCCN(C(=O)C)O)CCCN(C(=O)C)O
• InChI: InChI=1S/C27H45N9O12/c1-16(37)34(46)10-4-7-19-25(43)30-14-23(41)28-13-22(40)29-15-24(42)31-20(8-5-11-35(47)17(2)38)26(44)33-21(27(45)32-19)9-6-12-36(48)18(3)39/h19-21,46-48H,4-15H2,1-3H3,(H,28,41)(H,29,40)(H,30,43)(H,31,42)(H,32,45)(H,33,44)/t19-,20-,21-/m0/s1
• InChIKey: ZFDAUYPBCXMSBF-ACRUOGEOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{3-[(2S,5S,8S)-5,8-bis[3-(N-hydroxyacetamido)propyl]-3,6,9,12,15,18-hexaoxo-1,4,7,10,13,16-hexaazacyclooctadecan-2-yl]propyl}-N-hydroxyacetamide
• IUPAC Traditional name: N-{3-[(2S,5S,8S)-5,8-bis[3-(N-hydroxyacetamido)propyl]-3,6,9,12,15,18-hexaoxo-1,4,7,10,13,16-hexaazacyclooctadecan-2-yl]propyl}-N-hydroxyacetamide
• Synonyms: Cyclo(glycylglycylglycyl-N5-acetyl-N5-hydroxy-L-ornithyl-N5-acetyl-N5-hydroxy-L-ornithyl-N5-acetyl-N5-hydroxy-L-ornithyl); Deferrichrome; Deferriferrichrome; Desferriferrichrome; Desferrichrome

Database IDs

• CAS Number: 34787-28-5
• PubChem SID: 162260381
• PubChem CID: 169636

CALCULATED PROPERTIES

• Acid pKa: 7.933105
• H Acceptors: 12
• H Donor: 9
• LogD (pH = 5.5): -7.209414
• LogD (pH = 7.4): -7.3286843
• Log P: -7.20782
• Molar Refractivity: 162.0615 cm^3
• Polarizability: 63.03933 Å^3
• Polar Surface Area: 296.22 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D289850

Growth-promoting iron chelator. Ferrichrome iron-free from Ustilago sphaerogena.

REFERENCES

• Karpowich, N., et al.: J. Biol. Chem., 278, 8429 (2003)
• Hvorup, R., et al.: Science, 317, 1387 (2003)
• Zawadzka, A., et al.: Biochemistry, 48, 3645 (2003)