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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2017-10-23 19:06:26 UTC
HMDB IDHMDB0015016
Secondary Accession Numbers
  • HMDB15016
Metabolite Identification
Common NameChlorhexidine
DescriptionChlorhexidine is only found in individuals that have used or taken this drug. It is a disinfectant and topical anti-infective agent used also as mouthwash to prevent oral plaque. [PubChem]Chlorhexidine's antimicrobial effects are associated with the attractions between chlorhexidine (cation) and negatively charged bacterial cells. After chlorhexidine is absorpted onto the organism's cell wall, it disrupts the integrity of the cell membrane and causes the leakage of intracellular components of the organisms.
Structure
Thumb
Synonyms
ValueSource
1,1'-Hexamethylene bis(5-(P-chlorophenyl)biguanide)ChEBI
N,N'-bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediimidamideChEBI
CloresidinaHMDB
Chemical FormulaC22H30Cl2N10
Average Molecular Weight505.447
Monoisotopic Molecular Weight504.203196424
IUPAC NameN-(4-chlorophenyl)-1-3-(6-{N-[3-(4-chlorophenyl)carbamimidamidomethanimidoyl]amino}hexyl)carbamimidamidomethanimidamide
Traditional Namechlorhexidine
CAS Registry Number55-56-1
SMILES
ClC1=CC=C(NC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)NC2=CC=C(Cl)C=C2)C=C1
InChI Identifier
InChI=1S/C22H30Cl2N10/c23-15-5-9-17(10-6-15)31-21(27)33-19(25)29-13-3-1-2-4-14-30-20(26)34-22(28)32-18-11-7-16(24)8-12-18/h5-12H,1-4,13-14H2,(H5,25,27,29,31,33)(H5,26,28,30,32,34)
InChI KeyGHXZTYHSJHQHIJ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as chlorobenzenes. These are compounds containing one or more chlorine atoms attached to a benzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassHalobenzenes
Direct ParentChlorobenzenes
Alternative Parents
Substituents
  • Biguanide
  • Chlorobenzene
  • Aryl chloride
  • Aryl halide
  • Guanidine
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Organohalogen compound
  • Imine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organochloride
  • Organonitrogen compound
  • Organopnictogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Role

Industrial application:

  Pharmaceutical industry:

    Antimicrobial agent:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point134 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.026 g/LNot Available
LogP3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.026 g/LALOGPS
logP2.71ALOGPS
logP4.51ChemAxon
logS-4.3ALOGPS
pKa (Strongest Basic)10.52ChemAxon
Physiological Charge4ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area167.58 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity181.71 m³·mol⁻¹ChemAxon
Polarizability54.6 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-1390000000-e2087e07b387187b35e2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00yi-2912000000-109a5810a9e5d36f3105View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0ufr-2900000000-77fb2c1a85c1b39d8e91View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00yi-2912000000-109a5810a9e5d36f3105View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0624090000-0824436f86a1c2a4784bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-0922000000-b6c796459e4397e81075View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0229-2940000000-ba95a6a3988436fdde57View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0825090000-0c29f46fa3cd4527a699View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0hk9-0943010000-331d57f140196db7cca5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-2920000000-1106ffe675713cb3aa8bView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Saliva
  • 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 DB00878 details
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00878 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00878
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2612
KEGG Compound IDC06902
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkChlorhexidine
METLIN IDNot Available
PubChem Compound2713
PDB IDNot Available
ChEBI ID3614
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in histamine N-methyltransferase activity
Specific function:
Inactivates histamine by N-methylation. Plays an important role in degrading histamine and in regulating the airway response to histamine.
Gene Name:
HNMT
Uniprot ID:
P50135
Molecular weight:
6045.9
References
  1. Harle DG, Baldo BA: Structural features of potent inhibitors of rat kidney histamine N-methyltransferase. Biochem Pharmacol. 1988 Feb 1;37(3):385-8. [PubMed:3337739 ]