ContaminantDB: lamotigrin-N2-glucuronide

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-06-03 10:51:31 UTC

Update Date

2016-11-09 01:22:54 UTC

Accession Number

CHEM043372

Identification

Common Name

lamotigrin-N2-glucuronide

Class

Small Molecule

Description

lamotrigine-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)

Contaminant Sources

STOFF IDENT Compounds

Contaminant Type

Not Available

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Lamotrigine 2-N-glucuronide	HMDB

Chemical Formula

C₁₅H₁₆Cl₂N₅O₆

Average Molecular Mass

433.220 g/mol

Monoisotopic Mass

432.047 g/mol

CAS Registry Number

133310-19-7

IUPAC Name

3,5-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 Name

3,5-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

SMILES

[H][C@@]1(O)[C@@]([H])(O)[C@@]([H])(O[C@]([H])(C(O)=O)[C@@]1([H])O)N1N=C(C(=[NH2+])[N-]C1=[NH2+])C1=C(Cl)C(Cl)=CC=C1

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 Key

IEVMENHZPOWVGO-XPORZQOISA-O

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

N-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
Monocyclic benzene moiety
Imidolactam
Benzenoid
Triazine
Pyran
Heteroaromatic compound
Amino acid
Secondary alcohol
Amino acid or derivatives
Oxacycle
Azacycle
Carboxylic acid derivative
Carboxylic acid
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Organopnictogen compound
Organic nitrogen compound
Carbonyl group
Amine
Alcohol
Primary amine
Organic oxide
Organonitrogen compound
Organochloride
Hydrocarbon derivative
Organohalogen compound
Organic cation
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.35 g/L	ALOGPS
logP	0.68	ALOGPS
logP	-3	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	3.03	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	188.92 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	108.59 m³·mol⁻¹	ChemAxon
Polarizability	38.89 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0090200000-daa4fe8cfa7178444d0e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-1191200000-90a10076192bb849e564	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0bt9-0590000000-3ea2534cb8cde012fe71	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01q9-0010900000-2f145999d0e59fb170aa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0090000000-a40135c7a506bd54a0ee	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0bti-0490000000-e7ce0ca1f39688b2dca9	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0061103

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

164342

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

lamotigrin-N2-glucuronide (CHEM043372)

Structure for CHEM043372: lamotigrin-N2-glucuronide