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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:18:38 UTC
Update Date2017-12-07 18:50:37 UTC
HMDB IDHMDB0061103
Secondary Accession Numbers
  • HMDB61103
Metabolite Identification
Common Namelamotrigine-2-N-glucuronide
Descriptionlamotrigine-2-N-glucuronide is a metabolite of lamotrigine. Lamotrigine, marketed in the US and most of Europe as Lamictal by GlaxoSmithKline, is an anticonvulsant drug used in the treatment of epilepsy and bipolar disorder. It is also used as an adjunct in treating depression, though this is considered off-label usage. For epilepsy, it is used to treat focal seizures, primary and secondary tonic-clonic seizures, and seizures associated with Lennox-Gastaut syndrome. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC16H18Cl2N5O5
Average Molecular Weight431.251
Monoisotopic Molecular Weight430.068499125
IUPAC Name2-[(1R,2S,3S,4R,5S)-5-carboxy-2,3,4-trihydroxycyclohexyl]-6-(2,3-dichlorophenyl)-3,5-diiminiumyl-2,3,4,5-tetrahydro-1,2,4-triazin-4-ide
Traditional Name2-[(1R,2S,3S,4R,5S)-5-carboxy-2,3,4-trihydroxycyclohexyl]-6-(2,3-dichlorophenyl)-3,5-diiminio-4H-1,2,4-triazin-4-ide
CAS Registry NumberNot Available
SMILES
O[C@@H]1[C@@H](O)[C@@H](C[C@@H]([C@H]1O)C(O)=O)N1N=C(C(=[NH2+])[N-]C1=[NH2+])C1=C(Cl)C(Cl)=CC=C1
InChI Identifier
InChI=1S/C16H17Cl2N5O5/c17-7-3-1-2-5(9(7)18)10-14(19)21-16(20)23(22-10)8-4-6(15(27)28)11(24)13(26)12(8)25/h1-3,6,8,11-13,24-26H,4H2,(H4,19,20,21,27,28)/p+1/t6-,8+,11+,12-,13-/m0/s1
InChI KeyNTBZZMYXLUYLSU-ZDTMJCMYSA-O
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as dichlorobenzenes. These are compounds containing a benzene with exactly two chlorine atoms attached to it.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentDichlorobenzenes
Alternative Parents
Substituents
  • 1,2-dichlorobenzene
  • Beta-hydroxy acid
  • Cyclohexanol
  • Cyclitol or derivatives
  • Aryl chloride
  • Aryl halide
  • 1,2,4-triazine
  • Hydroxy acid
  • Triazine
  • Cyclic alcohol
  • Heteroaromatic compound
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Polyol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Alcohol
  • Carbonyl group
  • Organopnictogen compound
  • Organohalogen compound
  • Organochloride
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.073 g/LALOGPS
logP0.07ALOGPS
logP-1.4ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)3.51ChemAxon
pKa (Strongest Basic)6.13ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area174 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity120.41 m³·mol⁻¹ChemAxon
Polarizability39.93 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
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, Positivesplash10-08fr-5906600000-8896cf1fb3313dea4cb3View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-001i-3312049000-d616ac0ef1af23e4e50fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0004900000-9dcf654a1a76a798a2f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ec-1029500000-8dfb248330343e5ebce9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0390000000-3ee197e0152299919951View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00466
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available