NPs Basic Information

Name
Topiramate
Molecular Formula C12H21NO8S
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
SMILES
CC1(O[C@@H]2CO[C@@]3([C@H]([C@@H]2O1)OC(O3)(C)C)COS(=O)(=O)N)C
InChI
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
InChIKey
KJADKKWYZYXHBB-XBWDGYHZSA-N
Synonyms
topiramate; 97240-79-4; Topamax; Epitomax; Topamax Sprinkle; Topina; McN-4853; Tipiramate; Topiramatum; Topimax; Topomax; Tipiramato; Topiramato; Epitoma; Topamac; McN 4853; RWJ-17021; RWJ-17021-000; C12H21NO8S; 2,3:4,5-Bis-O-(1-methylethylidene)-beta-D-fructopyranose sulfamate; Sincronil; USL255; Qudexy; USL-255; 2,3:4,5-Di-O-isopropylidene-beta-D-fructopyranose sulfamate; (-)-topiramate; EPRONTIA; [(3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyltetrahydro-3aH-bis[1,3]dioxolo[4,5-b:4',5'-d]pyran-3a-yl]methyl sulfamate; ((3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran-3a-yl)methyl sulfamate; CHEBI:63631; Tipiramate [French]; Tipiramato [Spanish]; 0H73WJJ391; Topiramatum [INN-Latin]; topiramatum [Latin]; Topiramato [INN-Spanish]; MFCD00865320; DSSTox_CID_3688; DSSTox_RID_77148; DSSTox_GSID_23688; ((3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyltetrahydro-3aH-bis[1,3]dioxolo[4,5-b:4',5'-d]pyran-3a-yl)methyl sulfamate; TPM; Topiragen; Topax; Trokendi XR; Qudexy XR; [(1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.0^{2,6}]dodecan-6-yl]methyl sulfamate; SMR000466325; Topiramate (TPM); TOR; Topamax (TN); CAS-97240-79-4; RWJ 17021; BRN 5988957; UNII-0H73WJJ391; HSDB 7531; Sulfamate 7; 3hku; 3lxe; USL 255; Topiramate [USAN:USP:INN:BAN]; NCGC00095181-01; [(3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyl-5,5a,8a,8b-tetrahydrodi[1,3]dioxolo[5,4-b:5',3'-d]pyran-3a-yl]methyl sulfamate; Topiramate- Bio-X; Trokendi xr (TN); KS-1122; TOPIRAMATE [MI]; TOPIRAMATE [INN]; TOPIRAMATE [JAN]; Spectrum2_001128; TOPIRAMATE [HSDB]; TOPIRAMATE [INCI]; TOPIRAMATE [USAN]; beta-D-Fructopyranose, 2,3:4,5-bis-O-(1-methylethylidene)-, sulfamate; TOPIRAMATE [VANDF]; CBChromo1_000352; TOPIRAMATE [MART.]; TOPIRAMATE [USP-RS]; TOPIRAMATE [WHO-DD]; BIDD:PXR0127; SCHEMBL34631; BSPBio_002306; Topiramate (JAN/USP/INN); Eprontia (liquid formulation); MLS000759431; MLS001424070; BIDD:GT0854; SPECTRUM1505801; SPBio_000995; CHEMBL220492; GTPL6849; DTXSID8023688; TOPIRAMATE [ORANGE BOOK]; BDBM10887; 2,3:4,5-Di-O-isopropylidene-b-D-fructopyranose sulfamate; TOPIRAMATE [EP MONOGRAPH]; TOPIRAMATE [USP IMPURITY]; QSYMIA COMPONENT TOPIRAMATE; HMS1922H06; HMS2051L09; HMS2093D20; HMS2232H21; HMS3414C15; HMS3678C15; HMS3715I12; HMS3884C17; Pharmakon1600-01505801; TOPIRAMATE [USP MONOGRAPH]; [(3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyltetrahydro-3aH-bis[1,3]dioxolo[4,5-b:4',5'-d]pyran-3a-yl]methyl sulfamate (non-preferred name); ACT09031; ALBB-022457; HY-B0122; Tox21_111472; Tox21_302401; HB0618; NSC759251; s1438; ZINC95616603; TOPIRAMATE COMPONENT OF QSYMIA; .beta.-D-Fructopyranose, 2,3:4,5-bis-O-(1-methylethylidene)-, sulfamate; AKOS000424547; Topiramate 1.0 mg/ml in Acetonitrile; Topiramate, >=98% (HPLC), solid; Tox21_111472_1; CCG-100940; CS-1885; DB00273; NC00190; NSC 759251; NSC-759251; NCGC00178714-01; NCGC00178714-04; NCGC00178714-18; NCGC00255221-01; BT167048; SBI-0206907.P001; SW197570-3; C07502; D00537; EN300-118319; F20536; AB00639961-06; AB00639961-08; AB00639961_09; AB00639961_10; 240T794; A900173; Q221174; SR-01000759409; W-60376; Q-201845; SR-01000759409-4; Z1511495258; Topiramate, United States Pharmacopeia (USP) Reference Standard; 2,3:4,5-Bis-O-(1-methylethylidene)-?-D-fructopyranose sulfamate; 2,3:4,5-DI-O-ISOPROPYLIDENE-.BETA.-D-FRUCTOPYRANOSE SULFAMATE; Topiramate, Pharmaceutical Secondary Standard; Certified Reference Material; .beta.-D-Fructopyranose, 2,3:4,5-bis-O-(1-methylethylidene)-, 1-sulfamate; [(1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.0,2,6]dodecan-6-yl]methyl sulfamate; [(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; [(3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyl-5,5a,8a,8b-tetrahydrodi[1,3]dioxolo[4,5-a:5',3'-d]pyran-3a-yl]methyl sulfamate; 2,3:4,5-bis-O-(1-methylethylidene)-beta-D-fructopyranose 1-sulfamate;2,3:4,5-di-O-isopropylidene-beta-D-fructopyranose sulfamate; Topamax; Tracrium; Toiramate:
CAS 97240-79-4
PubChem CID 5284627
ChEMBL ID CHEMBL220492
*Note: the IUPAC Name was collected from PubChem.
Chemical Classification:
  • Kingdom: Organic compounds
    • Superclass: Organoheterocyclic compou
      • Class: Dioxolopyrans
        • Subclass: No Rank at Level Subclass
          • Direct Parent: Dioxolopyrans

ClassyFire Version 1.0
PMID:27867422

NPs Species Source

Endophyte ID Endophyte Name Family Genus Taxonomy ID GenBank ID Closest GenBank ID Reference
Endophyte ID Endophyte Name Family Genus Taxonomy ID GenBank ID Closest GenBank ID Reference

NPs Content

*Note: The vaules in Content Percentage are calculated by dividing the content value by the maximum content value in NP Content.
**Note: The units with different NP content, due to their incomparable values, are separated into different tables.

NPs Biological Activity

Bioactivity Name Target ID Target Name Target Type Target Organism Target Organism ID Potency of Bioactivity Activity Type Value Unit Endophyte ID Endophyte Name
Bioactivity Name Target ID Target Name Target Type Target Organism Target Organism ID Potency of Bioactivity Activity Type Value Unit Endophyte ID Endophyte Name

NPs Physi-Chem Properties

Molecular Weight: 339.36 ALogp: -0.8
HBD: 1 HBA: 9
Rotatable Bonds: 3 Lipinski's rule of five: Accepted
Polar Surface Area: 124.0 Aromatic Rings: 3
Heavy Atoms: 22 QED Weighted: 0.766

NPs ADMET Properties*

ADMET: Absorption

Caco-2 Permeability: -5.06 MDCK Permeability: 0.00005390
Pgp-inhibitor: 0.001 Pgp-substrate: 0
Human Intestinal Absorption (HIA): 0.002 20% Bioavailability (F20%): 0.35
30% Bioavailability (F30%): 0.023

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB): 0.979 Plasma Protein Binding (PPB): 29.29%
Volume Distribution (VD): 0.878 Fu: 59.66%

ADMET: Metabolism

CYP1A2-inhibitor: 0.003 CYP1A2-substrate: 0.732
CYP2C19-inhibitor: 0.014 CYP2C19-substrate: 0.828
CYP2C9-inhibitor: 0.005 CYP2C9-substrate: 0.01
CYP2D6-inhibitor: 0.005 CYP2D6-substrate: 0.089
CYP3A4-inhibitor: 0.006 CYP3A4-substrate: 0.269

ADMET: Excretion

Clearance (CL): 9.79 Half-life (T1/2): 0.448

ADMET: Toxicity

hERG Blockers: 0.23 Human Hepatotoxicity (H-HT): 0.976
Drug-inuced Liver Injury (DILI): 0.996 AMES Toxicity: 0.986
Rat Oral Acute Toxicity: 0.043 Maximum Recommended Daily Dose: 0.163
Skin Sensitization: 0.549 Carcinogencity: 0.954
Eye Corrosion: 0.003 Eye Irritation: 0.195
Respiratory Toxicity: 0.03
*Note: the ADMET properties was calculated by ADMETlab 2.0. Reference: PMID: 33893803.

Similar Compounds*

Compounds similar to EMNPD with top10 similarity:

Similar NPs Similar Drugs
NPs ID NPs 2D Structure Similarity Score TTD ID Drug 2D Structure Similarity Score
ENC001209 0.420 D07VDZ 1.000
ENC005558 0.217 D02JNM 0.205
ENC004900 0.208 D0Y2YP 0.202
ENC005785 0.208 D06IIB 0.202
ENC001193 0.207 D02QJH 0.198
ENC001444 0.203 D03ZZK 0.195
ENC004129 0.202 D0Y5ZA 0.175
ENC005627 0.202 D0D4JO 0.165
ENC003257 0.198 D0S3WH 0.162
ENC002424 0.194 D02PCR 0.159
*Note: the compound similarity was calculated by RDKIT.