NP-MRD: Showing NP-Card for Topiramate (NP0334566)

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Record Information

Version

2.0

Created at

2024-09-10 18:56:00 UTC

Updated at

2024-09-10 18:56:00 UTC

NP-MRD ID

NP0334566

Secondary Accession Numbers

None

Natural Product 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 bitter tasting compound. Outside of the human body,. Topiramate was first documented in 1999 (PMID: 10025774). Topiramate is a potentially toxic compound (PMID: 22233396) (PMID: 22249827).

Structure

MOL SDF PDB SMILES InChI

273
  Mrv0541 02231214342D          

 25 27  0  0  1  0            999 V2000
    7.1521    0.8041    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.4667   -0.8226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0086    1.2167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6167   -0.1587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7990    0.1403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7990    1.4680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4376    0.3916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5646    0.0897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7396    1.5186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8666    1.2167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2941   -0.0209    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5796    0.3916    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0086    0.3916    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5796    1.2167    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2941    1.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2824   -0.9077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3175    0.8041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7231    0.8041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0361   -1.2432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1962   -1.7282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.2891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7607   -0.4095    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5098   -0.2647    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5098    1.8730    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  1  8  2  0  0  0  0
  1  9  2  0  0  0  0
  1 10  1  0  0  0  0
  2 11  1  0  0  0  0
  2 16  1  0  0  0  0
  3 13  1  0  0  0  0
  3 15  1  0  0  0  0
  4 13  1  0  0  0  0
  4 16  1  0  0  0  0
  5 12  1  0  0  0  0
  5 17  1  0  0  0  0
  6 14  1  0  0  0  0
  6 17  1  0  0  0  0
  7 18  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 23  1  6  0  0  0
 12 14  1  0  0  0  0
 12 24  1  1  0  0  0
 13 18  1  6  0  0  0
 14 15  1  0  0  0  0
 14 25  1  1  0  0  0
 16 19  1  0  0  0  0
 16 20  1  0  0  0  0
 17 21  1  0  0  0  0
 17 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334566

> <DATABASE_NAME>
NP-MRD

> <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

> <FORMULA>
C12H21NO8S

> <MOLECULAR_WEIGHT>
339.362

> <EXACT_MASS>
339.098787343

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
32.42098488706586

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(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

> <ALOGPS_LOGP>
1.29

> <JCHEM_LOGP>
0.12695973433333307

> <ALOGPS_LOGS>
-1.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.087057933607165

> <JCHEM_PKA_STRONGEST_BASIC>
-3.723039569510656

> <JCHEM_POLAR_SURFACE_AREA>
115.54

> <JCHEM_REFRACTIVITY>
72.30200000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.80e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
topiramate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 273                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0      13.351   1.501   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       8.338  -1.536   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       9.349   2.271   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      10.485  -0.296   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       5.225   0.262   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       5.225   2.740   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      12.017   0.731   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      14.121   0.167   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      12.581   2.835   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0      14.684   2.271   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       8.016  -0.039   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.682   0.731   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.349   0.731   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.682   2.271   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.016   3.041   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.860  -1.694   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.326   1.501   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.683   1.501   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.267  -2.321   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.700  -3.226   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.080   0.596   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.080   2.406   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0       7.020  -0.764   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       6.552  -0.494   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       6.552   3.496   0.000  0.00  0.00           H+0
CONECT    1    7    8    9   10                                             
CONECT    2   11   16                                                       
CONECT    3   13   15                                                       
CONECT    4   13   16                                                       
CONECT    5   12   17                                                       
CONECT    6   14   17                                                       
CONECT    7    1   18                                                       
CONECT    8    1                                                            
CONECT    9    1                                                            
CONECT   10    1                                                            
CONECT   11    2   12   13   23                                             
CONECT   12    5   11   14   24                                             
CONECT   13    3    4   11   18                                             
CONECT   14    6   12   15   25                                             
CONECT   15    3   14                                                       
CONECT   16    2    4   19   20                                             
CONECT   17    5    6   21   22                                             
CONECT   18    7   13                                                       
CONECT   19   16                                                            
CONECT   20   16                                                            
CONECT   21   17                                                            
CONECT   22   17                                                            
CONECT   23   11                                                            
CONECT   24   12                                                            
CONECT   25   14                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

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 Mass

339.3620 Da

Monoisotopic Mass

339.09879 Da

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

Not Available

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

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	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	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0005034

DrugBank ID

DB00273

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

General References

Petroff OA, Hyder F, Mattson RH, Rothman DL: Topiramate increases brain GABA, homocarnosine, and pyrrolidinone in patients with epilepsy. Neurology. 1999 Feb;52(3):473-8. [PubMed:10025774 ]
Luo N, Di W, Zhang A, Wang Y, Ding M, Qi W, Zhu Y, Massing MW, Fang Y: A randomized, one-year clinical trial comparing the efficacy of topiramate, flunarizine, and a combination of flunarizine and topiramate in migraine prophylaxis. Pain Med. 2012 Jan;13(1):80-6. doi: 10.1111/j.1526-4637.2011.01295.x. [PubMed:22233396 ]
Antel J, Hebebrand J: Weight-reducing side effects of the antiepileptic agents topiramate and zonisamide. Handb Exp Pharmacol. 2012;(209):433-66. doi: 10.1007/978-3-642-24716-3_20. [PubMed:22249827 ]

Showing NP-Card for Topiramate (NP0334566)

MOL for NP0334566 (Topiramate)

3D MOL for NP0334566 (Topiramate)

3D SDF for NP0334566 (Topiramate)

3D-SDF for NP0334566 (Topiramate)

PDB for NP0334566 (Topiramate)

3D PDB for NP0334566 (Topiramate)

SMILES for NP0334566 (Topiramate)

INCHI for NP0334566 (Topiramate)

Structure for NP0334566 (Topiramate)

3D Structure for NP0334566 (Topiramate)