Showing metabocard for Topiramate (BMDB0005034)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:14:53 UTC
Update Date2020-05-11 20:49:34 UTC
BMDB IDBMDB0005034
Secondary Accession Numbers
  • BMDB05034
Metabolite Identification
Common NameTopiramate
DescriptionTopiramate, also known as topamax or MCN-4853, belongs to the class of organic compounds known as dioxolopyrans. Dioxolopyrans are compounds containing a dioxolopyran moiety, which consists of a dioxole ring fused to a pyran ring. Topiramate is an extremely weak basic (essentially neutral) compound (based on its pKa). Topiramate is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2,3:4,5-Bis-O-(1-methylethylidene)-beta-D-fructopyranose sulfamateChEBI
2,3:4,5-Di-O-isopropylidene-beta-D-fructopyranose sulfamateChEBI
MCN-4853ChEBI
RWJ-17021ChEBI
TipiramateChEBI
TipiramatoChEBI
TopamaxChEBI
TopiramatoChEBI
TopiramatumChEBI
TPMChEBI
Trokendi XRKegg
2,3:4,5-Bis-O-(1-methylethylidene)-b-D-fructopyranose sulfamateGenerator
2,3:4,5-Bis-O-(1-methylethylidene)-b-D-fructopyranose sulfamic acidGenerator
2,3:4,5-Bis-O-(1-methylethylidene)-b-D-fructopyranose sulphamateGenerator
2,3:4,5-Bis-O-(1-methylethylidene)-b-D-fructopyranose sulphamic acidGenerator
2,3:4,5-Bis-O-(1-methylethylidene)-beta-D-fructopyranose sulfamic acidGenerator
2,3:4,5-Bis-O-(1-methylethylidene)-beta-D-fructopyranose sulphamateGenerator
2,3:4,5-Bis-O-(1-methylethylidene)-beta-D-fructopyranose sulphamic acidGenerator
2,3:4,5-Bis-O-(1-methylethylidene)-β-D-fructopyranose sulfamateGenerator
2,3:4,5-Bis-O-(1-methylethylidene)-β-D-fructopyranose sulfamic acidGenerator
2,3:4,5-Bis-O-(1-methylethylidene)-β-D-fructopyranose sulphamateGenerator
2,3:4,5-Bis-O-(1-methylethylidene)-β-D-fructopyranose sulphamic acidGenerator
2,3:4,5-Di-O-isopropylidene-b-D-fructopyranose sulfamateGenerator
2,3:4,5-Di-O-isopropylidene-b-D-fructopyranose sulfamic acidGenerator
2,3:4,5-Di-O-isopropylidene-b-D-fructopyranose sulphamateGenerator
2,3:4,5-Di-O-isopropylidene-b-D-fructopyranose sulphamic acidGenerator
2,3:4,5-Di-O-isopropylidene-beta-D-fructopyranose sulfamic acidGenerator
2,3:4,5-Di-O-isopropylidene-beta-D-fructopyranose sulphamateGenerator
2,3:4,5-Di-O-isopropylidene-beta-D-fructopyranose sulphamic acidGenerator
2,3:4,5-Di-O-isopropylidene-β-D-fructopyranose sulfamateGenerator
2,3:4,5-Di-O-isopropylidene-β-D-fructopyranose sulfamic acidGenerator
2,3:4,5-Di-O-isopropylidene-β-D-fructopyranose sulphamateGenerator
2,3:4,5-Di-O-isopropylidene-β-D-fructopyranose sulphamic acidGenerator
Tipiramic acidGenerator
Topiramic acidGenerator
EpitomaxHMDB
Topamax sprinkleHMDB
TopomaxHMDB
2,3-4,5-Bis-O-(1-methylethylidene)-beta-D-fructopyranose sulfamateHMDB
Chemical FormulaC12H21NO8S
Average Molecular Weight339.362
Monoisotopic Molecular Weight339.098787343
IUPAC Name[(1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.0²,⁶]dodecan-6-yl]methyl sulfamate
Traditional Nametopiramate
CAS Registry Number97240-79-4
SMILES
[H][C@@]12CO[C@@]3(COS(N)(=O)=O)OC(C)(C)O[C@@]3([H])[C@]1([H])OC(C)(C)O2
InChI Identifier
InChI=1S/C12H21NO8S/c1-10(2)18-7-5-16-12(6-17-22(13,14)15)9(8(7)19-10)20-11(3,4)21-12/h7-9H,5-6H2,1-4H3,(H2,13,14,15)/t7-,8-,9+,12+/m1/s1
InChI KeyKJADKKWYZYXHBB-XBWDGYHZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dioxolopyrans. Dioxolopyrans are compounds containing a dioxolopyran moiety, which consists of a dioxole ring fused to a pyran ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDioxolopyrans
Sub ClassNot Available
Direct ParentDioxolopyrans
Alternative Parents
Substituents
  • Dioxolopyran
  • Ketal
  • Oxane
  • Monosaccharide
  • Organic sulfuric acid or derivatives
  • Meta-dioxolane
  • Oxacycle
  • Acetal
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point125 - 126 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.29ALOGPS
logP0.13ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)11.09ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area115.54 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity72.3 m³·mol⁻¹ChemAxon
Polarizability32.42 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen Locations
  • Brain
  • Prostate Tissue
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0005034
DrugBank IDDB00273
Phenol Explorer Compound IDNot Available
FooDB IDFDB023601
KNApSAcK IDNot Available
Chemspider ID4447672
KEGG Compound IDC07502
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTopiramate
METLIN IDNot Available
PubChem Compound5284627
PDB IDTOR
ChEBI ID63631
References
Synthesis ReferenceMaryanoff, Bruce E.; Gardocki, Joseph F. Anticonvulsant sulfamate derivatives. U.S. (1985), CODEN: USXXAM US 4513006 A 19850423 CAN 103:37701 AN 1985:437701
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available