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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:18:38 UTC
Update Date2018-05-17 00:15:07 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
Synonyms
ValueSource
Lamotrigine 2-N-glucuronideMeSH
Chemical FormulaC15H16Cl2N5O6
Average Molecular Weight433.22
Monoisotopic Molecular Weight432.0472151
IUPAC Name3,5-diamino-2-[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]-6-(2,3-dichlorophenyl)-1,2lambda5,4-triazin-2-ylium
Traditional Name3,5-diamino-2-[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]-6-(2,3-dichlorophenyl)-1,2lambda5,4-triazin-2-ylium
CAS Registry NumberNot Available
SMILES
[H]OC(=O)[C@@]1([H])O[C@@]([H])([N+]2=NC(=C(N=C2N([H])[H])N([H])[H])C2=C(Cl)C(Cl)=C([H])C([H])=C2[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]
InChI Identifier
InChI=1S/C15H15Cl2N5O6/c16-5-3-1-2-4(6(5)17)7-12(18)20-15(19)22(21-7)13-10(25)8(23)9(24)11(28-13)14(26)27/h1-3,8-11,13,23-25H,(H4,18,19,20,26,27)/p+1/t8-,9-,10+,11-,13+/m0/s1
InChI KeyIEVMENHZPOWVGO-XPORZQOISA-O
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as n-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through a N-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentN-glucuronides
Alternative Parents
Substituents
  • N-glucuronide
  • N-glycosyl compound
  • Glycosyl compound
  • 1,2-dichlorobenzene
  • Aminotriazine
  • Halobenzene
  • Chlorobenzene
  • Beta-hydroxy acid
  • Hydroxy acid
  • Aryl chloride
  • Oxane
  • Aryl halide
  • 1,2,4-triazine
  • Imidolactam
  • Benzenoid
  • Monocyclic benzene moiety
  • Triazine
  • Pyran
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Amino acid
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Polyol
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Carbonyl group
  • Organic nitrogen compound
  • Amine
  • Primary amine
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Alcohol
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

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
logP0.68ALOGPS
logP-3ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)3.03ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area188.92 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity108.59 m³·mol⁻¹ChemAxon
Polarizability38.89 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
      Phenol Explorer Compound 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 Compound164342
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available