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Record Information
Version3.6
Creation Date2013-07-09 16:18:38 UTC
Update Date2016-02-11 08:18:32 UTC
HMDB IDHMDB61103
Secondary Accession NumbersNone
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=1/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-/s2
InChI KeyInChIKey=NTBZZMYXLUYLSU-NYJGWKISNA-O
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as aminocyclitols and derivatives. These are cyclitols with at least one hydroxyl group replace by an amino group.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassAlcohols and polyols
Sub ClassCyclic alcohols and derivatives
Direct ParentAminocyclitols and derivatives
Alternative Parents
Substituents
  • Aminocyclitol derivative
  • 1,2-dichlorobenzene
  • Halobenzene
  • Cyclohexanol
  • Chlorobenzene
  • Beta-hydroxy acid
  • Aminotriazine
  • 1,2,4-triazine
  • Benzenoid
  • Triazine
  • Hydroxy acid
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl chloride
  • Heteroaromatic compound
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic salt
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity120.41 m3·mol-1ChemAxon
Polarizability39.93 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
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
NuGOwiki LinkHMDB61103
Metagene LinkHMDB61103
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