Bovine Metabolome Database: Showing metabocard for Topiramate (BMDB0005034)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:14:53 UTC

Update Date

2020-05-11 20:49:34 UTC

BMDB ID

BMDB0005034

Secondary Accession Numbers

BMDB05034

Metabolite Identification

Common Name

Topiramate

Description

Topiramate, 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2,3:4,5-Bis-O-(1-methylethylidene)-beta-D-fructopyranose sulfamate	ChEBI
2,3:4,5-Di-O-isopropylidene-beta-D-fructopyranose sulfamate	ChEBI
MCN-4853	ChEBI
RWJ-17021	ChEBI
Tipiramate	ChEBI
Tipiramato	ChEBI
Topamax	ChEBI
Topiramato	ChEBI
Topiramatum	ChEBI
TPM	ChEBI
Trokendi XR	Kegg
2,3:4,5-Bis-O-(1-methylethylidene)-b-D-fructopyranose sulfamate	Generator
2,3:4,5-Bis-O-(1-methylethylidene)-b-D-fructopyranose sulfamic acid	Generator
2,3:4,5-Bis-O-(1-methylethylidene)-b-D-fructopyranose sulphamate	Generator
2,3:4,5-Bis-O-(1-methylethylidene)-b-D-fructopyranose sulphamic acid	Generator
2,3:4,5-Bis-O-(1-methylethylidene)-beta-D-fructopyranose sulfamic acid	Generator
2,3:4,5-Bis-O-(1-methylethylidene)-beta-D-fructopyranose sulphamate	Generator
2,3:4,5-Bis-O-(1-methylethylidene)-beta-D-fructopyranose sulphamic acid	Generator
2,3:4,5-Bis-O-(1-methylethylidene)-β-D-fructopyranose sulfamate	Generator
2,3:4,5-Bis-O-(1-methylethylidene)-β-D-fructopyranose sulfamic acid	Generator
2,3:4,5-Bis-O-(1-methylethylidene)-β-D-fructopyranose sulphamate	Generator
2,3:4,5-Bis-O-(1-methylethylidene)-β-D-fructopyranose sulphamic acid	Generator
2,3:4,5-Di-O-isopropylidene-b-D-fructopyranose sulfamate	Generator
2,3:4,5-Di-O-isopropylidene-b-D-fructopyranose sulfamic acid	Generator
2,3:4,5-Di-O-isopropylidene-b-D-fructopyranose sulphamate	Generator
2,3:4,5-Di-O-isopropylidene-b-D-fructopyranose sulphamic acid	Generator
2,3:4,5-Di-O-isopropylidene-beta-D-fructopyranose sulfamic acid	Generator
2,3:4,5-Di-O-isopropylidene-beta-D-fructopyranose sulphamate	Generator
2,3:4,5-Di-O-isopropylidene-beta-D-fructopyranose sulphamic acid	Generator
2,3:4,5-Di-O-isopropylidene-β-D-fructopyranose sulfamate	Generator
2,3:4,5-Di-O-isopropylidene-β-D-fructopyranose sulfamic acid	Generator
2,3:4,5-Di-O-isopropylidene-β-D-fructopyranose sulphamate	Generator
2,3:4,5-Di-O-isopropylidene-β-D-fructopyranose sulphamic acid	Generator
Tipiramic acid	Generator
Topiramic acid	Generator
Epitomax	HMDB
Topamax sprinkle	HMDB
Topomax	HMDB
2,3-4,5-Bis-O-(1-methylethylidene)-beta-D-fructopyranose sulfamate	HMDB

Chemical Formula

C₁₂H₂₁NO₈S

Average Molecular Weight

339.362

Monoisotopic Molecular Weight

339.098787343

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 Name

topiramate

CAS Registry Number

97240-79-4

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 Key

KJADKKWYZYXHBB-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dioxolopyrans

Sub Class

Not Available

Direct Parent

Dioxolopyrans

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 Framework

Aliphatic heteropolycyclic compounds

External Descriptors

cyclic ketal (CHEBI:63631 )
sulfamate ester (CHEBI:63631 )
ketohexose derivative (CHEBI:63631 )

Ontology

Status

Expected but not Quantified

Origin

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Membrane

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	125 - 126 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.29	ALOGPS
logP	0.13	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	11.09	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	115.54 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	72.3 m³·mol⁻¹	ChemAxon
Polarizability	32.42 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-003r-5893000000-57939ef42b569234ad29	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-03di-0239000000-994a7b97e101c455a792	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-01x0-1970000000-f0e80f5cc5d6fc2b6d38	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-01q9-2960000000-a11a150bcada5055d2e9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-014i-0090000000-c1fa3d6ff15890fc1418	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-00di-0059000000-a6337903cab01edce60e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-03di-0239000000-994a7b97e101c455a792	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-01x0-1970000000-f0e80f5cc5d6fc2b6d38	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-004i-9000000000-a8df5a6ea132d69b9489	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-004i-9000000000-f76d8f2283f18dfa20be	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-004i-9000000000-316320612e65b9d317cb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-004i-9000000000-63d6b2cbde40b2bcd639	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-004i-9003000000-0b8ee634478a6f2f0eee	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-000i-0009000000-086098dbff51e692c04f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0c0r-9850000000-ae199550ba647589f088	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-004i-9000000000-eab734dd0ed786cbba6d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-1029000000-37869fd8dcd3ec0f4cc1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01po-4295000000-7cdbdca2d1d67b21879d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03fr-9810000000-9b5c3fb12c27e09cf450	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002r-4239000000-e56f7b1fecd3064e8783	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004j-9164000000-892445ea4dcd3bf9420d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9100000000-7c64b90d0daae2c6e5b8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0009000000-9a74f9cc10019d27995c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0149000000-093e852afab8097cfa0f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dm-8790000000-0a33128bbe614c27cdf7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0019000000-345311bd602424b95a49	View in MoNA
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cell membrane
Membrane

Biospecimen Locations

Brain
Prostate Tissue

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Brain	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Prostate Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0005034

DrugBank ID

DB00273

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023601

KNApSAcK ID

Not Available

Chemspider ID

4447672

KEGG Compound ID

C07502

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Topiramate

METLIN ID

Not Available

PubChem Compound

5284627

PDB ID

TOR

ChEBI ID

63631

References

Synthesis Reference

Maryanoff, 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 References

Not Available

Showing metabocard for Topiramate (BMDB0005034)

Structure for BMDB0005034 (Topiramate)