N-[(1S)-3-amino-1-{[(1S,2R)-1-{[(1S)-3-amino-1-{[(3S,6S,9S,12S,15R,18S,21S)-6,9,18-tris(2-aminoethyl)-3-[(1R)-1-hydroxyethyl]-12,15-bis(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptaazacyclotricosan-21-yl]carbamoyl}propyl]carbamoyl}-2-hydroxypropyl]carbamoyl}propyl]-5-methylheptanamide

• ChemBase ID: 130485
• Molecular Formular: C52H98N16O13
• Molecular Mass: 1155.43392
• Monoisotopic Mass: 1154.74992728
• SMILES: O=C(N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H]1C(=O)N[C@@H](C(=O)N[C@@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)NCC1)[C@H](O)C)CCN)CCN)CC(C)C)CC(C)C)CCN)CCN)[C@H](O)C)CCN)CCCC(C)CC
• Canonical SMILES: NCC[C@@H](C(=O)N[C@@H]1CCNC(=O)[C@H](NC(=O)[C@H](CCN)NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@H](NC(=O)[C@H](NC1=O)CCN)CC(C)C)CC(C)C)CCN)[C@H](O)C)NC(=O)[C@H]([C@H](O)C)NC(=O)[C@@H](NC(=O)CCCC(CC)C)CCN
• InChI: InChI=1S/C52H98N16O13/c1-9-29(6)11-10-12-40(71)59-32(13-19-53)47(76)68-42(31(8)70)52(81)64-35(16-22-56)44(73)63-37-18-24-58-51(80)41(30(7)69)67-48(77)36(17-23-57)61-43(72)33(14-20-54)62-49(78)38(25-27(2)3)66-50(79)39(26-28(4)5)65-45(74)34(15-21-55)60-46(37)75/h27-39,41-42,69-70H,9-26,53-57H2,1-8H3,(H,58,80)(H,59,71)(H,60,75)(H,61,72)(H,62,78)(H,63,73)(H,64,81)(H,65,74)(H,66,79)(H,67,77)(H,68,76)/t29?,30-,31-,32+,33+,34+,35+,36+,37+,38+,39-,41+,42+/m1/s1
• InChIKey: YKQOSKADJPQZHB-QNPLFGSASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(1S)-3-amino-1-{[(1S,2R)-1-{[(1S)-3-amino-1-{[(3S,6S,9S,12S,15R,18S,21S)-6,9,18-tris(2-aminoethyl)-3-[(1R)-1-hydroxyethyl]-12,15-bis(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptaazacyclotricosan-21-yl]carbamoyl}propyl]carbamoyl}-2-hydroxypropyl]carbamoyl}propyl]-5-methylheptanamide
• IUPAC Traditional name: colistin
• Brand Name: Coly-mycinm
• Synonyms: Colistin; Polymyxin E. Sulfate; Belcomycine; Colomycin; Colistin Sulfate

Database IDs

• CAS Number: 1264-72-8
• PubChem SID: 162224764
• PubChem CID: 5311054
• ATC CODE: QJ51XB01; J01XB01; A07AA10
• CHEMBL: 501505
• Chemspider ID: 4470591
• DrugBank ID: DB00803
• KEGG ID: D02138
• Unique Ingredient Identifier: WP15DXU577
• Wikipedia Title: Colistin

CALCULATED PROPERTIES

• Acid pKa: 11.595611
• H Acceptors: 18
• H Donor: 18
• LogD (pH = 5.5): -23.059572
• LogD (pH = 7.4): -18.565655
• Log P: -8.095956
• Molar Refractivity: 297.6691 cm^3
• Polarizability: 118.19399 Å^3
• Polar Surface Area: 490.66 Å^2
• Rotatable Bonds: 28
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Off-White Solid
• Melting Point: >230°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

Pharmacology Properties

• Admin Routes: topical, oral, intravenous
• Bioavailability: 0%
• Half Life: 5 hours
• Legal Status: PoM (UK), not available in US
• Pregnancy Category: C

DETAILS

Toronto Research Chemicals - C641500

Cyclic polypeptide antibiotic produced by Bacillus polymyxa. Complex mixture of at least 30 components, primarily colistins A and B.[α]D= -65° (c= 1, Water) LOD: 3%

REFERENCES

• Suzuki, T., et al.: J. Biochem., 54, 25 (1963)
• Barnett, M., et al.: Br. J. Pharmacol. Chemother., 23, 552 (1963)
• Littlewood, J, M., et al.: Respir. Med., 94, 632 (1963)
• Li, J., et al.: Int. J. Antimicrob. Ag., 25, 11 (1963)