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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2020-02-26 21:41:14 UTC
HMDB IDHMDB0015243
Secondary Accession Numbers
  • HMDB15243
Metabolite Identification
Common NameColistimethate
DescriptionColistimethate is an antibiotic that has been shown to have bactericidal activity against aerobic gram-negative microorganisms. Colistimethate is particularly indicated when the infection is caused by sensitive strains of Pseudomonas aeruginosa.
Structure
Data?1582753274
Synonyms
ValueSource
Colistimethic acidGenerator
N-[1-({1-[(1-{[2,5,8,11,14,17,20-heptahydroxy-3-(1-hydroxyethyl)-12,15-bis(2-methylpropyl)-6,9,18-tris({2-[(sulfomethyl)amino]ethyl})-1,4,7,10,13,16,19-heptaazacyclotricosa-1,4,7,10,13,16,19-heptaen-21-yl]-C-hydroxycarbonimidoyl}-3-[(sulfomethyl)amino]propyl)-C-hydroxycarbonimidoyl]-2-hydroxypropyl}-C-hydroxycarbonimidoyl)-3-[(sulfomethyl)amino]propyl]-6-methyloctanimidateGenerator
N-[1-({1-[(1-{[2,5,8,11,14,17,20-heptahydroxy-3-(1-hydroxyethyl)-12,15-bis(2-methylpropyl)-6,9,18-tris({2-[(sulphomethyl)amino]ethyl})-1,4,7,10,13,16,19-heptaazacyclotricosa-1,4,7,10,13,16,19-heptaen-21-yl]-C-hydroxycarbonimidoyl}-3-[(sulphomethyl)amino]propyl)-C-hydroxycarbonimidoyl]-2-hydroxypropyl}-C-hydroxycarbonimidoyl)-3-[(sulphomethyl)amino]propyl]-6-methyloctanimidateGenerator
N-[1-({1-[(1-{[2,5,8,11,14,17,20-heptahydroxy-3-(1-hydroxyethyl)-12,15-bis(2-methylpropyl)-6,9,18-tris({2-[(sulphomethyl)amino]ethyl})-1,4,7,10,13,16,19-heptaazacyclotricosa-1,4,7,10,13,16,19-heptaen-21-yl]-C-hydroxycarbonimidoyl}-3-[(sulphomethyl)amino]propyl)-C-hydroxycarbonimidoyl]-2-hydroxypropyl}-C-hydroxycarbonimidoyl)-3-[(sulphomethyl)amino]propyl]-6-methyloctanimidic acidGenerator
Colistin sodium methanesulfonateMeSH
Colistimethate sodiumMeSH
Colistinmethanesulfonic acidMeSH
Colistimethate, disodium saltMeSH
Chemical FormulaC58H110N16O28S5
Average Molecular Weight1639.909
Monoisotopic Molecular Weight1638.627900466
IUPAC Name[(3-{3-hydroxy-2-[2-(6-methyloctanamido)-4-[(sulfomethyl)amino]butanamido]butanamido}-3-{[3-(1-hydroxyethyl)-12,15-bis(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-6,9,18-tris({2-[(sulfomethyl)amino]ethyl})-1,4,7,10,13,16,19-heptaazacyclotricosan-21-yl]carbamoyl}propyl)amino]methanesulfonic acid
Traditional Name[(3-{3-hydroxy-2-[2-(6-methyloctanamido)-4-[(sulfomethyl)amino]butanamido]butanamido}-3-{[3-(1-hydroxyethyl)-12,15-bis(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-6,9,18-tris({2-[(sulfomethyl)amino]ethyl})-1,4,7,10,13,16,19-heptaazacyclotricosan-21-yl]carbamoyl}propyl)amino]methanesulfonic acid
CAS Registry Number8068-28-8
SMILES
CCC(C)CCCCC(=O)NC(CCNCS(O)(=O)=O)C(=O)NC(C(C)O)C(=O)NC(CCNCS(O)(=O)=O)C(=O)NC1CCNC(=O)C(NC(=O)C(CCNCS(O)(=O)=O)NC(=O)C(CCNCS(O)(=O)=O)NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=O)C(CCNCS(O)(=O)=O)NC1=O)C(C)O
InChI Identifier
InChI=1S/C58H110N16O28S5/c1-9-35(6)12-10-11-13-46(77)65-38(14-20-59-28-103(88,89)90)53(82)74-48(37(8)76)58(87)70-41(17-23-62-31-106(97,98)99)50(79)68-43-19-25-64-57(86)47(36(7)75)73-54(83)42(18-24-63-32-107(100,101)102)67-49(78)39(15-21-60-29-104(91,92)93)69-55(84)44(26-33(2)3)72-56(85)45(27-34(4)5)71-52(81)40(66-51(43)80)16-22-61-30-105(94,95)96/h33-45,47-48,59-63,75-76H,9-32H2,1-8H3,(H,64,86)(H,65,77)(H,66,80)(H,67,78)(H,68,79)(H,69,84)(H,70,87)(H,71,81)(H,72,85)(H,73,83)(H,74,82)(H,88,89,90)(H,91,92,93)(H,94,95,96)(H,97,98,99)(H,100,101,102)
InChI KeyBSSIRFLGSWHWDE-UHFFFAOYSA-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
  • N-acyl-alpha amino acid or derivatives
  • Macrolactam
  • Alpha-amino acid amide
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • N-acyl-amine
  • Fatty acyl
  • Fatty amide
  • Alkanesulfonic acid
  • Sulfonyl
  • Organosulfonic acid
  • Organosulfonic acid or derivatives
  • Organic sulfonic acid or derivatives
  • Lactam
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Amino acid or derivatives
  • Carboxylic acid derivative
  • Azacycle
  • Secondary aliphatic amine
  • Organoheterocyclic compound
  • Secondary amine
  • Organic nitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Amine
  • Organic oxygen compound
  • Organopnictogen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen 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 PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility4.17 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.17 g/LALOGPS
logP-2.2ALOGPS
logP-17ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)-4.3ChemAxon
pKa (Strongest Basic)6.46ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count33ChemAxon
Hydrogen Donor Count23ChemAxon
Polar Surface Area692.56 ŲChemAxon
Rotatable Bond Count44ChemAxon
Refractivity375.79 m³·mol⁻¹ChemAxon
Polarizability164.59 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, Positivesplash10-0fki-1101229000-e09876a3535ac59eb23aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02tj-0201791000-7e893f27f4da1f81879aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-2911121000-aaa56c5b09a0d54eaa0bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05o9-3000093000-5a10468fb03f4828d604Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-5000090000-1216f649ff7a273137e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9101170000-51fd014171a76c8d41c1Spectrum
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 DB01111 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01111 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDBSALT000415
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkColistin
METLIN IDNot Available
PubChem Compound216259
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