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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:38 UTC
HMDB IDHMDB0014941
Secondary Accession Numbers
  • HMDB14941
Metabolite Identification
Common NameColistin
DescriptionCyclic polypeptide antibiotic from Bacillus colistinus. It is composed of Polymyxins E1 and E2 (or Colistins A, B, and C) which act as detergents on cell membranes. Colistin is less toxic than Polymyxin B, but otherwise similar; the methanesulfonate is used orally. [PubChem]
Structure
Data?1582753238
Synonyms
ValueSource
ColimycinHMDB
ColisticinHMDB
Coly-mycinHMDB
Polymyxin eHMDB
Colistin sulfateHMDB
Sulfate, colistinHMDB
TotazinaHMDB
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)-2,5,8,11,14,17,20-heptahydroxy-3-[(1R)-1-hydroxyethyl]-12,15-bis(2-methylpropyl)-1,4,7,10,13,16,19-heptaazacyclotricosa-1,4,7,10,13,16,19-heptaen-21-yl]-C-hydroxycarbonimidoyl}propyl]-C-hydroxycarbonimidoyl}-2-hydroxypropyl]-C-hydroxycarbonimidoyl}propyl]-5-methylheptanimidateGenerator
ColistinMeSH
Chemical FormulaC52H98N16O13
Average Molecular Weight1155.4339
Monoisotopic Molecular Weight1154.749927302
IUPAC NameN-[(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
Traditional Namecolistin
CAS Registry Number1264-72-8
SMILES
[H][C@]1(NC(=O)[C@H](CCN)NC(=O)[C@H](CCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CCN)NC(=O)[C@H](CCNC1=O)NC(=O)[C@H](CCN)NC(=O)[C@@H](NC(=O)[C@H](CCN)NC(=O)CCCC(C)CC)[C@@H](C)O)[C@@H](C)O
InChI Identifier
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
InChI KeyYKQOSKADJPQZHB-QNPLFGSASA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as polypeptides. These are peptides containing ten or more amino acid residues.
KingdomOrganic compounds
Super ClassOrganic Polymers
ClassPolypeptides
Sub ClassNot Available
Direct ParentPolypeptides
Alternative Parents
Substituents
  • Polypeptide
  • Cyclic alpha peptide
  • Macrolactam
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxamide group
  • Lactam
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid derivative
  • Primary amine
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Primary aliphatic amine
  • Carbonyl group
  • Organonitrogen compound
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point200 - 220 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.24 g/LNot Available
LogP-2.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.24 g/LALOGPS
logP-1.3ALOGPS
logP-8.1ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)11.6ChemAxon
pKa (Strongest Basic)10.23ChemAxon
Physiological Charge5ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count18ChemAxon
Polar Surface Area490.66 ŲChemAxon
Rotatable Bond Count28ChemAxon
Refractivity297.67 m³·mol⁻¹ChemAxon
Polarizability125.93 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-0900000000-419dd200ef572768dfa0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0229-4900000111-0875f1bccf9392d6eb47Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9510000000-5266e8c4a4ae959de419Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zg0-1900000000-2a3e6d4d74cae29393efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6u-5911000221-cf40b8067f3b8d4a1e28Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-4911000201-bf381c83d760e06dd86dSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00803 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00803 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4470591
KEGG Compound IDC13768
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkColistin
METLIN IDNot Available
PubChem Compound5311054
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available