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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2017-10-23 19:06:25 UTC
HMDB IDHMDB0014919
Secondary Accession Numbers
  • HMDB14919
Metabolite Identification
Common NamePolymyxin B Sulfate
DescriptionPolymyxin B sulfate is a mixture of polymyxins B1 and B2, obtained from Bacillus polymyxa strains. They are basic polypeptides of about eight amino acids and have cationic detergent action on cell membranes. Polymyxin B is used for infections with gram-negative organisms, but may be neurotoxic and nephrotoxic. All gram-positive bacteria, fungi, and the gram-negative cocci, N. gonorrhea and N. menigitidis, are resistant. It is appropriate for treatment of infections of the urinary tract, meninges, and blood stream, caused by susceptible strains of Pseudomonas aeruginosa.
Structure
Thumb
Synonyms
ValueSource
Polymixin b sulfateHMDB
Polymixin b sulphateHMDB
Polymyxin b sulfate saltHMDB
Polymyxin b sulphateHMDB
Polymyxin b sulphate saltHMDB
Sulfate, polymyxin bMeSH
Polymyxin bMeSH
Chemical FormulaC56H98N16O13
Average Molecular Weight1203.4767
Monoisotopic Molecular Weight1202.749927302
IUPAC NameN-[3-amino-1-({1-[(3-amino-1-{[6,9,18-tris(2-aminoethyl)-15-benzyl-3-(1-hydroxyethyl)-12-(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]-6-methyloctanamide
Traditional Namepolymyxin B sulfate
CAS Registry Number1405-20-5
SMILES
CCC(C)CCCCC(=O)NC(CCN)C(=O)NC(C(C)O)C(=O)NC(CCN)C(=O)NC1CCNC(=O)C(NC(=O)C(CCN)NC(=O)C(CCN)NC(=O)C(CC(C)C)NC(=O)C(CC2=CC=CC=C2)NC(=O)C(CCN)NC1=O)C(C)O
InChI Identifier
InChI=1S/C56H98N16O13/c1-7-32(4)13-11-12-16-44(75)63-36(17-23-57)51(80)72-46(34(6)74)56(85)68-39(20-26-60)48(77)67-41-22-28-62-55(84)45(33(5)73)71-52(81)40(21-27-61)65-47(76)37(18-24-58)66-53(82)42(29-31(2)3)69-54(83)43(30-35-14-9-8-10-15-35)70-49(78)38(19-25-59)64-50(41)79/h8-10,14-15,31-34,36-43,45-46,73-74H,7,11-13,16-30,57-61H2,1-6H3,(H,62,84)(H,63,75)(H,64,79)(H,65,76)(H,66,82)(H,67,77)(H,68,85)(H,69,83)(H,70,78)(H,71,81)(H,72,80)
InChI KeyWQVJHHACXVLGBL-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Monocyclic benzene moiety
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Benzenoid
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Amino acid or derivatives
  • Carboxamide group
  • Lactam
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Carbonyl group
  • Alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Biofluid and excreta:

Route of exposure:

  Parenteral:

Role

Industrial application:

  Pharmaceutical industry:

    Antimicrobial agent:

Indirect biological role:

Physiological effect

Health effect:

  Health condition:

    Nervous system disorders:

    General disorders and administration site conditions:

    Respiratory, thoracic and mediastinal disorders:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.074 g/LNot Available
LogP-4.861Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.074 g/LALOGPS
logP-0.89ALOGPS
logP-7.2ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)11.57ChemAxon
pKa (Strongest Basic)10.23ChemAxon
Physiological Charge5ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count18ChemAxon
Polar Surface Area490.66 ŲChemAxon
Rotatable Bond Count29ChemAxon
Refractivity313.22 m³·mol⁻¹ChemAxon
Polarizability129.71 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0900000000-2fc106a8849095860948View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-4910000111-09aa17c0c5e9e1d3a251View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9420000000-50618abf83d40012137dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-1159-0941000000-9241d7871d46b3a90d91View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bu9-1910000111-2dc8c378fec3170a9d1cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08fu-5921000300-2f55ebc350da3657d7e3View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00781 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00781 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-1 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-0 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00781
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4702
KEGG Compound IDC11613
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPolymyxin_B
METLIN IDNot Available
PubChem Compound5702105
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Zavascki AP, Goldani LZ, Li J, Nation RL: Polymyxin B for the treatment of multidrug-resistant pathogens: a critical review. J Antimicrob Chemother. 2007 Dec;60(6):1206-15. Epub 2007 Sep 17. [PubMed:17878146 ]
  2. Yuan Z, Tam VH: Polymyxin B: a new strategy for multidrug-resistant Gram-negative organisms. Expert Opin Investig Drugs. 2008 May;17(5):661-8. doi: 10.1517/13543784.17.5.661 . [PubMed:18447592 ]