Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (5) Show 5 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:05 UTC

HMDB ID

HMDB0015699

Secondary Accession Numbers

HMDB15699

Metabolite Identification

Common Name

Tofisopam

Description

Tofisopam (marketed under brand names Emandaxin and Grandaxin) is a 2,3-benzodiazepine drug which is a benzodiazepine derivative. In contrast to classical 1,4-benzodiazepines, the compound does not bind to the benzodiazepine binding site of the gamma-aminobutyric acid receptor and its psychopharmacological profile differs from such compounds. Although Tofisopam is not approved for sale in North America, it is approved for use in various countries worldwide, including parts of Europe. The D-enantiomer (dextofisopam) is currently in phase II trials in the U.S. for the treatment of irritable bowel syndrome.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

5502
  Mrv0541 02241214212D          

 28 30  0  0  1  0            999 V2000
    2.3920   -1.3924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9144   -2.1256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0479   -0.0257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8019   -1.6573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8910    1.8496    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4054    1.2046    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5516    1.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7352    0.4003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7473    1.3882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4785    0.0423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0660    1.8496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0178   -0.0728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2219    0.4003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5560   -0.8135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5041    2.1766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0754   -0.9302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8497   -1.3031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7080    2.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8668   -0.1141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6349    0.1873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7439   -0.9299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2799   -0.3271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3889   -1.4443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1569   -1.1429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.0315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2346   -2.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1708    0.7901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6790   -2.4731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 16  1  0  0  0  0
  1 25  1  0  0  0  0
  2 17  1  0  0  0  0
  2 26  1  0  0  0  0
  3 22  1  0  0  0  0
  3 27  1  0  0  0  0
  4 24  1  0  0  0  0
  4 28  1  0  0  0  0
  5  6  1  0  0  0  0
  5 11  2  0  0  0  0
  6 13  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 11  1  0  0  0  0
  8 10  1  0  0  0  0
  8 12  2  0  0  0  0
  9 15  1  0  0  0  0
 10 13  1  0  0  0  0
 10 14  2  0  0  0  0
 11 18  1  0  0  0  0
 12 16  1  0  0  0  0
 13 19  1  0  0  0  0
 14 17  1  0  0  0  0
 16 17  2  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 23  2  0  0  0  0
 22 24  2  0  0  0  0
 23 24  1  0  0  0  0
M  END

HMDB0251097
     RDKit          3D
Dextofisopam
 54 56  0  0  0  0  0  0  0  0999 V2000
   -4.7465    1.0940    0.8503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0588    1.5220   -0.4090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5782    1.5777   -0.3580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0268    2.4971    0.6347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9825    3.3037    1.4252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8039    2.7419    0.9435 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3546    2.1735    0.3889 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5068    1.0010   -0.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8038    0.6642   -0.6387 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0197   -0.3499   -1.5303 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2975   -0.7012   -1.9835 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3997   -0.0161   -1.5334 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6780   -0.3276   -1.9527 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9143   -1.3735   -2.8715 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2020    1.0110   -0.6353 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3203    1.6967   -0.1878 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1466    2.7523    0.7316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9461    1.3449   -0.1985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5423    0.0001   -0.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0807   -1.2876   -0.0171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9450   -2.3737   -0.0409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4214   -3.6568    0.0905 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9356   -3.9303    0.2471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2930   -2.1365   -0.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1509   -3.2215   -0.2195 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5509   -3.0938   -0.3723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7721   -0.8140   -0.3229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9193    0.2409   -0.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5973    0.3817    0.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0356    0.6664    1.5741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2718    1.9385    1.3879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4663    2.5547   -0.6382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4364    0.9474   -1.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2433    1.9853   -1.3690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2939    2.7837    2.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8134    3.7254    0.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4634    4.2294    1.8495 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2306   -0.9426   -1.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4619   -1.5009   -2.6841 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9979   -1.6086   -2.8920 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3482   -2.2602   -2.5112 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5859   -1.0430   -3.8821 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5519    2.3484    1.5754 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5086    3.5575    0.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0927    3.1863    1.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7694    2.1431    0.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9777   -1.4209    0.1560 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6057   -3.3085   -0.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1006   -4.9938   -0.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2828   -3.8985    1.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9044   -2.3090    0.3322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0763   -4.0506   -0.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7267   -2.6959   -1.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8374   -0.7537   -0.4416 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  2  0
  8 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  2  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  2  0
 28  3  1  0
 18  9  1  0
 28 19  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  3 34  1  0
  5 35  1  0
  5 36  1  0
  5 37  1  0
 10 38  1  0
 11 39  1  0
 14 40  1  0
 14 41  1  0
 14 42  1  0
 17 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 20 47  1  0
 23 48  1  0
 23 49  1  0
 23 50  1  0
 26 51  1  0
 26 52  1  0
 26 53  1  0
 27 54  1  0
M  END

5502
  Mrv0541 02241214212D          

 28 30  0  0  1  0            999 V2000
    2.3920   -1.3924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9144   -2.1256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0479   -0.0257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8019   -1.6573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8910    1.8496    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4054    1.2046    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5516    1.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7352    0.4003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7473    1.3882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4785    0.0423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0660    1.8496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0178   -0.0728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2219    0.4003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5560   -0.8135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5041    2.1766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0754   -0.9302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8497   -1.3031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7080    2.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8668   -0.1141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6349    0.1873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7439   -0.9299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2799   -0.3271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3889   -1.4443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1569   -1.1429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.0315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2346   -2.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1708    0.7901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6790   -2.4731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 16  1  0  0  0  0
  1 25  1  0  0  0  0
  2 17  1  0  0  0  0
  2 26  1  0  0  0  0
  3 22  1  0  0  0  0
  3 27  1  0  0  0  0
  4 24  1  0  0  0  0
  4 28  1  0  0  0  0
  5  6  1  0  0  0  0
  5 11  2  0  0  0  0
  6 13  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 11  1  0  0  0  0
  8 10  1  0  0  0  0
  8 12  2  0  0  0  0
  9 15  1  0  0  0  0
 10 13  1  0  0  0  0
 10 14  2  0  0  0  0
 11 18  1  0  0  0  0
 12 16  1  0  0  0  0
 13 19  1  0  0  0  0
 14 17  1  0  0  0  0
 16 17  2  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 23  2  0  0  0  0
 22 24  2  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015699

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC1C2=CC(OC)=C(OC)C=C2C(=NN=C1C)C1=CC(OC)=C(OC)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H26N2O4/c1-7-15-13(2)23-24-22(14-8-9-18(25-3)19(10-14)26-4)17-12-21(28-6)20(27-5)11-16(15)17/h8-12,15H,7H2,1-6H3

> <INCHI_KEY>
RUJBDQSFYCKFAA-UHFFFAOYSA-N

> <FORMULA>
C22H26N2O4

> <MOLECULAR_WEIGHT>
382.4528

> <EXACT_MASS>
382.18925733

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
42.14405698268847

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(3,4-dimethoxyphenyl)-5-ethyl-7,8-dimethoxy-4-methyl-5H-2,3-benzodiazepine

> <ALOGPS_LOGP>
4.29

> <JCHEM_LOGP>
3.8256045320000003

> <ALOGPS_LOGS>
-5.21

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.2382082211651433

> <JCHEM_POLAR_SURFACE_AREA>
61.64

> <JCHEM_REFRACTIVITY>
109.03469999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.39e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
seriel

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0251097
     RDKit          3D
Dextofisopam
 54 56  0  0  0  0  0  0  0  0999 V2000
   -4.7465    1.0940    0.8503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0588    1.5220   -0.4090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5782    1.5777   -0.3580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0268    2.4971    0.6347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9825    3.3037    1.4252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8039    2.7419    0.9435 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3546    2.1735    0.3889 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5068    1.0010   -0.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8038    0.6642   -0.6387 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0197   -0.3499   -1.5303 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2975   -0.7012   -1.9835 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3997   -0.0161   -1.5334 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6780   -0.3276   -1.9527 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9143   -1.3735   -2.8715 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2020    1.0110   -0.6353 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3203    1.6967   -0.1878 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1466    2.7523    0.7316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9461    1.3449   -0.1985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5423    0.0001   -0.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0807   -1.2876   -0.0171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9450   -2.3737   -0.0409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4214   -3.6568    0.0905 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9356   -3.9303    0.2471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2930   -2.1365   -0.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1509   -3.2215   -0.2195 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5509   -3.0938   -0.3723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7721   -0.8140   -0.3229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9193    0.2409   -0.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5973    0.3817    0.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0356    0.6664    1.5741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2718    1.9385    1.3879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4663    2.5547   -0.6382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4364    0.9474   -1.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2433    1.9853   -1.3690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2939    2.7837    2.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8134    3.7254    0.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4634    4.2294    1.8495 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2306   -0.9426   -1.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4619   -1.5009   -2.6841 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9979   -1.6086   -2.8920 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3482   -2.2602   -2.5112 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5859   -1.0430   -3.8821 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5519    2.3484    1.5754 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5086    3.5575    0.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0927    3.1863    1.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7694    2.1431    0.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9777   -1.4209    0.1560 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6057   -3.3085   -0.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1006   -4.9938   -0.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2828   -3.8985    1.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9044   -2.3090    0.3322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0763   -4.0506   -0.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7267   -2.6959   -1.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8374   -0.7537   -0.4416 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  2  0
  8 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  2  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  2  0
 28  3  1  0
 18  9  1  0
 28 19  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  3 34  1  0
  5 35  1  0
  5 36  1  0
  5 37  1  0
 10 38  1  0
 11 39  1  0
 14 40  1  0
 14 41  1  0
 14 42  1  0
 17 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 20 47  1  0
 23 48  1  0
 23 49  1  0
 23 50  1  0
 26 51  1  0
 26 52  1  0
 26 53  1  0
 27 54  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 5502                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       4.465  -2.599   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       7.307  -3.968   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      15.023  -0.048   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      14.564  -3.094   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       9.130   3.453   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      10.090   2.249   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       6.630   2.249   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.972   0.747   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.128   2.591   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.360   0.079   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.590   3.453   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.633  -0.136   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.748   0.747   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.505  -1.519   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.674   4.063   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.741  -1.736   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.186  -2.432   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.922   4.840   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.951  -0.213   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.385   0.350   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.722  -1.736   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.589  -0.611   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.926  -2.696   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.360  -2.133   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.080  -1.925   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.038  -4.840   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.252   1.475   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.334  -4.616   0.000  0.00  0.00           C+0
CONECT    1   16   25                                                       
CONECT    2   17   26                                                       
CONECT    3   22   27                                                       
CONECT    4   24   28                                                       
CONECT    5    6   11                                                       
CONECT    6    5   13                                                       
CONECT    7    8    9   11                                                  
CONECT    8    7   10   12                                                  
CONECT    9    7   15                                                       
CONECT   10    8   13   14                                                  
CONECT   11    5    7   18                                                  
CONECT   12    8   16                                                       
CONECT   13    6   10   19                                                  
CONECT   14   10   17                                                       
CONECT   15    9                                                            
CONECT   16    1   12   17                                                  
CONECT   17    2   14   16                                                  
CONECT   18   11                                                            
CONECT   19   13   20   21                                                  
CONECT   20   19   22                                                       
CONECT   21   19   23                                                       
CONECT   22    3   20   24                                                  
CONECT   23   21   24                                                       
CONECT   24    4   22   23                                                  
CONECT   25    1                                                            
CONECT   26    2                                                            
CONECT   27    3                                                            
CONECT   28    4                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

COMPND    HMDB0251097
HETATM    1  C1  UNL     1      -4.747   1.094   0.850  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.059   1.522  -0.409  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.578   1.578  -0.358  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.027   2.497   0.635  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.982   3.304   1.425  1.00  0.00           C  
HETATM    6  N1  UNL     1      -0.804   2.742   0.944  1.00  0.00           N  
HETATM    7  N2  UNL     1       0.355   2.174   0.389  1.00  0.00           N  
HETATM    8  C6  UNL     1       0.507   1.001  -0.131  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.804   0.664  -0.639  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.020  -0.350  -1.530  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.297  -0.701  -1.984  1.00  0.00           C  
HETATM   12  C10 UNL     1       4.400  -0.016  -1.533  1.00  0.00           C  
HETATM   13  O1  UNL     1       5.678  -0.328  -1.953  1.00  0.00           O  
HETATM   14  C11 UNL     1       5.914  -1.374  -2.872  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.202   1.011  -0.635  1.00  0.00           C  
HETATM   16  O2  UNL     1       5.320   1.697  -0.188  1.00  0.00           O  
HETATM   17  C13 UNL     1       5.147   2.752   0.732  1.00  0.00           C  
HETATM   18  C14 UNL     1       2.946   1.345  -0.198  1.00  0.00           C  
HETATM   19  C15 UNL     1      -0.542   0.000  -0.146  1.00  0.00           C  
HETATM   20  C16 UNL     1      -0.081  -1.288  -0.017  1.00  0.00           C  
HETATM   21  C17 UNL     1      -0.945  -2.374  -0.041  1.00  0.00           C  
HETATM   22  O3  UNL     1      -0.421  -3.657   0.090  1.00  0.00           O  
HETATM   23  C18 UNL     1       0.936  -3.930   0.247  1.00  0.00           C  
HETATM   24  C19 UNL     1      -2.293  -2.137  -0.195  1.00  0.00           C  
HETATM   25  O4  UNL     1      -3.151  -3.222  -0.220  1.00  0.00           O  
HETATM   26  C20 UNL     1      -4.551  -3.094  -0.372  1.00  0.00           C  
HETATM   27  C21 UNL     1      -2.772  -0.814  -0.323  1.00  0.00           C  
HETATM   28  C22 UNL     1      -1.919   0.241  -0.298  1.00  0.00           C  
HETATM   29  H1  UNL     1      -5.597   0.382   0.645  1.00  0.00           H  
HETATM   30  H2  UNL     1      -4.036   0.666   1.574  1.00  0.00           H  
HETATM   31  H3  UNL     1      -5.272   1.938   1.388  1.00  0.00           H  
HETATM   32  H4  UNL     1      -4.466   2.555  -0.638  1.00  0.00           H  
HETATM   33  H5  UNL     1      -4.436   0.947  -1.311  1.00  0.00           H  
HETATM   34  H6  UNL     1      -2.243   1.985  -1.369  1.00  0.00           H  
HETATM   35  H7  UNL     1      -3.294   2.784   2.378  1.00  0.00           H  
HETATM   36  H8  UNL     1      -3.813   3.725   0.854  1.00  0.00           H  
HETATM   37  H9  UNL     1      -2.463   4.229   1.850  1.00  0.00           H  
HETATM   38  H10 UNL     1       1.231  -0.943  -1.996  1.00  0.00           H  
HETATM   39  H11 UNL     1       3.462  -1.501  -2.684  1.00  0.00           H  
HETATM   40  H12 UNL     1       6.998  -1.609  -2.892  1.00  0.00           H  
HETATM   41  H13 UNL     1       5.348  -2.260  -2.511  1.00  0.00           H  
HETATM   42  H14 UNL     1       5.586  -1.043  -3.882  1.00  0.00           H  
HETATM   43  H15 UNL     1       4.552   2.348   1.575  1.00  0.00           H  
HETATM   44  H16 UNL     1       4.509   3.557   0.269  1.00  0.00           H  
HETATM   45  H17 UNL     1       6.093   3.186   1.068  1.00  0.00           H  
HETATM   46  H18 UNL     1       2.769   2.143   0.502  1.00  0.00           H  
HETATM   47  H19 UNL     1       0.978  -1.421   0.156  1.00  0.00           H  
HETATM   48  H20 UNL     1       1.606  -3.309  -0.363  1.00  0.00           H  
HETATM   49  H21 UNL     1       1.101  -4.994  -0.095  1.00  0.00           H  
HETATM   50  H22 UNL     1       1.283  -3.899   1.299  1.00  0.00           H  
HETATM   51  H23 UNL     1      -4.904  -2.309   0.332  1.00  0.00           H  
HETATM   52  H24 UNL     1      -5.076  -4.051  -0.246  1.00  0.00           H  
HETATM   53  H25 UNL     1      -4.727  -2.696  -1.396  1.00  0.00           H  
HETATM   54  H26 UNL     1      -3.837  -0.754  -0.442  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3   32   33
CONECT    3    4   28   34
CONECT    4    5    6    6
CONECT    5   35   36   37
CONECT    6    7
CONECT    7    8    8
CONECT    8    9   19
CONECT    9   10   10   18
CONECT   10   11   38
CONECT   11   12   12   39
CONECT   12   13   15
CONECT   13   14
CONECT   14   40   41   42
CONECT   15   16   18   18
CONECT   16   17
CONECT   17   43   44   45
CONECT   18   46
CONECT   19   20   20   28
CONECT   20   21   47
CONECT   21   22   24   24
CONECT   22   23
CONECT   23   48   49   50
CONECT   24   25   27
CONECT   25   26
CONECT   26   51   52   53
CONECT   27   28   28   54
END

HMDB0251097
     RDKit          3D
Dextofisopam
 54 56  0  0  0  0  0  0  0  0999 V2000
   -4.7465    1.0940    0.8503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0588    1.5220   -0.4090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5782    1.5777   -0.3580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0268    2.4971    0.6347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9825    3.3037    1.4252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8039    2.7419    0.9435 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3546    2.1735    0.3889 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5068    1.0010   -0.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8038    0.6642   -0.6387 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0197   -0.3499   -1.5303 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2975   -0.7012   -1.9835 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3997   -0.0161   -1.5334 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6780   -0.3276   -1.9527 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9143   -1.3735   -2.8715 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2020    1.0110   -0.6353 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3203    1.6967   -0.1878 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1466    2.7523    0.7316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9461    1.3449   -0.1985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5423    0.0001   -0.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0807   -1.2876   -0.0171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9450   -2.3737   -0.0409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4214   -3.6568    0.0905 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9356   -3.9303    0.2471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2930   -2.1365   -0.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1509   -3.2215   -0.2195 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5509   -3.0938   -0.3723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7721   -0.8140   -0.3229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9193    0.2409   -0.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5973    0.3817    0.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0356    0.6664    1.5741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2718    1.9385    1.3879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4663    2.5547   -0.6382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4364    0.9474   -1.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2433    1.9853   -1.3690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2939    2.7837    2.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8134    3.7254    0.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4634    4.2294    1.8495 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2306   -0.9426   -1.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4619   -1.5009   -2.6841 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9979   -1.6086   -2.8920 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3482   -2.2602   -2.5112 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5859   -1.0430   -3.8821 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5519    2.3484    1.5754 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5086    3.5575    0.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0927    3.1863    1.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7694    2.1431    0.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9777   -1.4209    0.1560 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6057   -3.3085   -0.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1006   -4.9938   -0.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2828   -3.8985    1.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9044   -2.3090    0.3322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0763   -4.0506   -0.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7267   -2.6959   -1.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8374   -0.7537   -0.4416 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  2  0
  8 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  2  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  2  0
 28  3  1  0
 18  9  1  0
 28 19  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  3 34  1  0
  5 35  1  0
  5 36  1  0
  5 37  1  0
 10 38  1  0
 11 39  1  0
 14 40  1  0
 14 41  1  0
 14 42  1  0
 17 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 20 47  1  0
 23 48  1  0
 23 49  1  0
 23 50  1  0
 26 51  1  0
 26 52  1  0
 26 53  1  0
 27 54  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Emandaxin	Kegg
Tofizopam	HMDB
EGYT-341	MeSH, HMDB
Levotofisopam	MeSH, HMDB
Dextofisopam	MeSH, HMDB
Grandaxin	MeSH, HMDB
1-(3,4-Dimethoxyphenyl)-5-ethyl-7,8-dimethoxy-4-methyl-5H-2,3-benzodiazepine	MeSH, HMDB

Chemical Formula

C₂₂H₂₆N₂O₄

Average Molecular Weight

382.4528

Monoisotopic Molecular Weight

382.18925733

IUPAC Name

1-(3,4-dimethoxyphenyl)-5-ethyl-7,8-dimethoxy-4-methyl-5H-2,3-benzodiazepine

Traditional Name

seriel

CAS Registry Number

22345-47-7

SMILES

CCC1C2=CC(OC)=C(OC)C=C2C(=NN=C1C)C1=CC(OC)=C(OC)C=C1

InChI Identifier

InChI=1S/C22H26N2O4/c1-7-15-13(2)23-24-22(14-8-9-18(25-3)19(10-14)26-4)17-12-21(28-6)20(27-5)11-16(15)17/h8-12,15H,7H2,1-6H3

InChI Key

RUJBDQSFYCKFAA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzodiazepines. These are organic compounds containing a benzene ring fused to either isomers of diazepine(unsaturated seven-member heterocycle with two nitrogen atoms replacing two carbon atoms).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodiazepines

Sub Class

Not Available

Direct Parent

Benzodiazepines

Alternative Parents

Substituents

Benzodiazepine
Dimethoxybenzene
O-dimethoxybenzene
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Ether
Azacycle
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic nitrogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0251097)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	152 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0024 g/L	ALOGPS
logP	4.29	ALOGPS
logP	3.83	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Basic)	-2.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	61.64 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	109.03 m³·mol⁻¹	ChemAxon
Polarizability	42.14 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	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	193.633	31661259
DarkChem	[M-H]-	191.95	31661259
DeepCCS	[M+H]+	192.335	30932474
DeepCCS	[M-H]-	189.977	30932474
DeepCCS	[M-2H]-	224.026	30932474
DeepCCS	[M+Na]+	199.254	30932474
AllCCS	[M+H]+	192.6	32859911
AllCCS	[M+H-H2O]+	189.7	32859911
AllCCS	[M+NH4]+	195.3	32859911
AllCCS	[M+Na]+	196.0	32859911
AllCCS	[M-H]-	199.7	32859911
AllCCS	[M+Na-2H]-	200.1	32859911
AllCCS	[M+HCOO]-	200.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.62 minutes	32390414
Predicted by Siyang on May 30, 2022	15.1883 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.36 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	28.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tofisopam	CCC1C2=CC(OC)=C(OC)C=C2C(=NN=C1C)C1=CC(OC)=C(OC)C=C1	3851.1	Standard polar	33892256
Tofisopam	CCC1C2=CC(OC)=C(OC)C=C2C(=NN=C1C)C1=CC(OC)=C(OC)C=C1	3157.2	Standard non polar	33892256
Tofisopam	CCC1C2=CC(OC)=C(OC)C=C2C(=NN=C1C)C1=CC(OC)=C(OC)C=C1	3147.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tofisopam GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-0039000000-5cb577edbbc8cc8d6873	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tofisopam GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tofisopam GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tofisopam GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tofisopam GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tofisopam 10V, Positive-QTOF	splash10-001i-0009000000-37ba280ae280f0151420	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tofisopam 20V, Positive-QTOF	splash10-0006-9138000000-45b5e7b9478d1c0dcc70	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tofisopam 40V, Positive-QTOF	splash10-06vi-3935000000-4b7b313aca10282cc22a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tofisopam 10V, Negative-QTOF	splash10-001i-0009000000-6678f5bee5aedc2c1c6c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tofisopam 20V, Negative-QTOF	splash10-00lr-0009000000-c7930084c12118c44738	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tofisopam 40V, Negative-QTOF	splash10-000j-0059000000-dc272a4e40d2fd95dfa8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tofisopam 10V, Positive-QTOF	splash10-001i-0009000000-d3a09a44daea37832ae1	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tofisopam 20V, Positive-QTOF	splash10-0a59-0009000000-4014af46649ca04615c7	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tofisopam 40V, Positive-QTOF	splash10-02iw-0159000000-b6276af63dc415bf6cbb	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tofisopam 10V, Negative-QTOF	splash10-001i-0009000000-e8b11cf16a87c36881ac	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tofisopam 20V, Negative-QTOF	splash10-001i-0009000000-fd93de7d58c1e12ea9b5	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tofisopam 40V, Negative-QTOF	splash10-0079-0039000000-c61d648c1bd4562a933e	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB08811	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB08811	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB08811

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5301

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tofisopam

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Rundfeldt C, Socala K, Wlaz P: The atypical anxiolytic drug, tofisopam, selectively blocks phosphodiesterase isoenzymes and is active in the mouse model of negative symptoms of psychosis. J Neural Transm (Vienna). 2010 Nov;117(11):1319-25. doi: 10.1007/s00702-010-0507-3. Epub 2010 Oct 22. [PubMed:20967473 ]

Enzymes

Enzyme Details

1. cGMP-inhibited 3',5'-cyclic phosphodiesterase A

General function:: Involved in catalytic activity
Specific function:: Cyclic nucleotide phosphodiesterase with a dual-specificity for the second messengers cAMP and cGMP, which are key regulators of many important physiological processes (By similarity).
Gene Name:: PDE3A
Uniprot ID:: Q14432
Molecular weight:: 124978.06

References

Rundfeldt C, Socala K, Wlaz P: The atypical anxiolytic drug, tofisopam, selectively blocks phosphodiesterase isoenzymes and is active in the mouse model of negative symptoms of psychosis. J Neural Transm (Vienna). 2010 Nov;117(11):1319-25. doi: 10.1007/s00702-010-0507-3. Epub 2010 Oct 22. [PubMed:20967473 ]

Enzyme Details

2. cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A

General function:: Involved in catalytic activity
Specific function:: Plays a role in signal transduction by regulating the intracellular concentration of cyclic nucleotides. Can hydrolyze both cAMP and cGMP, but has higher affinity for cAMP and is more efficient with cAMP as substrate.
Gene Name:: PDE10A
Uniprot ID:: Q9Y233
Molecular weight:: 89388.7

References

Rundfeldt C, Socala K, Wlaz P: The atypical anxiolytic drug, tofisopam, selectively blocks phosphodiesterase isoenzymes and is active in the mouse model of negative symptoms of psychosis. J Neural Transm (Vienna). 2010 Nov;117(11):1319-25. doi: 10.1007/s00702-010-0507-3. Epub 2010 Oct 22. [PubMed:20967473 ]

Enzyme Details

3. cGMP-dependent 3',5'-cyclic phosphodiesterase

General function:: Involved in catalytic activity
Specific function:: Cyclic nucleotide phosphodiesterase with a dual-specificity for the second messengers cAMP and cGMP, which are key regulators of many important physiological processes.
Gene Name:: PDE2A
Uniprot ID:: O00408
Molecular weight:: 105145.485

References

Rundfeldt C, Socala K, Wlaz P: The atypical anxiolytic drug, tofisopam, selectively blocks phosphodiesterase isoenzymes and is active in the mouse model of negative symptoms of psychosis. J Neural Transm (Vienna). 2010 Nov;117(11):1319-25. doi: 10.1007/s00702-010-0507-3. Epub 2010 Oct 22. [PubMed:20967473 ]

Enzyme Details

4. cAMP-specific 3',5'-cyclic phosphodiesterase 4A

General function:: Involved in 3',5'-cyclic-nucleotide phosphodiesterase activity
Specific function:: Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes.
Gene Name:: PDE4A
Uniprot ID:: P27815
Molecular weight:: 98142.155

References

Rundfeldt C, Socala K, Wlaz P: The atypical anxiolytic drug, tofisopam, selectively blocks phosphodiesterase isoenzymes and is active in the mouse model of negative symptoms of psychosis. J Neural Transm (Vienna). 2010 Nov;117(11):1319-25. doi: 10.1007/s00702-010-0507-3. Epub 2010 Oct 22. [PubMed:20967473 ]

Enzyme Details

5. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Toth M, Bajnogel J, Egyed A, Drabant S, Tomlo J, Klebovich I: [Effect of tofisopam on CYP3A4 enzyme activity on human recombinant 3A4 supersome]. Acta Pharm Hung. 2005;75(4):195-8. [PubMed:16711396 ]

Showing metabocard for Tofisopam (HMDB0015699)

MOL for HMDB0015699 (Tofisopam)

3D MOL for HMDB0015699 (Tofisopam)

3D SDF for HMDB0015699 (Tofisopam)

3D-SDF for HMDB0015699 (Tofisopam)

PDB for HMDB0015699 (Tofisopam)

3D PDB for HMDB0015699 (Tofisopam)

SMILES for HMDB0015699 (Tofisopam)

INCHI for HMDB0015699 (Tofisopam)

Structure for HMDB0015699 (Tofisopam)

3D Structure for HMDB0015699 (Tofisopam)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References