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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6) Show 6 proteins XML

enzymes (6) Show 6 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:52 UTC

HMDB ID

HMDB0015097

Secondary Accession Numbers

HMDB15097

Metabolite Identification

Common Name

Zaleplon

Description

Zaleplon, also known as sonata or dea no. 2781, belongs to the class of organic compounds known as phenylpyrimidines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrimidine ring through a CC or CN bond. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. Zaleplon is a drug which is used for the treatment of short-term treatment of insomnia in adults. Zaleplon is an extremely weak basic (essentially neutral) compound (based on its pKa). Zaleplon is a potentially toxic compound. A pyrazolopyrimidine having a nitrile group at position 3 and a 3-(N-ethylacetamido)phenyl substituent at the 7-position.

Structure

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

HMDB0015097
     RDKit          3D
Zaleplon
 38 40  0  0  0  0  0  0  0  0999 V2000
   -4.8085   -0.9676    0.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9080   -0.2848    1.1896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7572    0.3380    0.4820 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9391    1.6539    0.0724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0846    2.5342   -0.7328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0562    2.2039    0.4623 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6315   -0.4791    0.2752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7403   -1.8674    0.4704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6731   -2.6982    0.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5390   -2.1827   -0.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7033   -0.8373   -0.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9687   -0.3076   -0.7881 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1588   -0.1577   -2.1701 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3385    0.3182   -2.6832 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3221    0.6431   -1.8348 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1528    0.5045   -0.5277 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0489    0.7851    0.4923 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3947    1.2932    0.3875 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4798    1.6803    0.3067 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3548    0.4584    1.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1270    0.0131    1.3111 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9957    0.0374   -0.0068 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3990   -0.0287   -0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5735   -0.2467   -0.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1984   -1.2440   -0.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3691   -1.8094    0.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5191    0.5144    1.6560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6060   -0.9765    1.9701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3060    2.9734   -0.0790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7120    3.4172   -1.1032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6710    2.0173   -1.6224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6865   -2.2730    0.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7740   -3.7932    0.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3789   -2.8435   -0.2803 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3583   -0.4194   -2.8434 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5361    0.4554   -3.7457 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7536    0.5505    2.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1979    1.0256   -0.2725 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
  3  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  3  0
 17 20  1  0
 20 21  2  0
 21 22  1  0
 11 23  2  0
 23  7  1  0
 22 12  1  0
 22 16  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  5 29  1  0
  5 30  1  0
  5 31  1  0
  8 32  1  0
  9 33  1  0
 10 34  1  0
 13 35  1  0
 14 36  1  0
 20 37  1  0
 23 38  1  0
M  END

962
  Mrv0541 02231215082D          

 23 25  0  0  0  0            999 V2000
    3.0791    3.3850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.1474    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.7401    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597   -0.4887    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.9777    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3723   -3.3850    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.7349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.9099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.7349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.9099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.1474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.5651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.7349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.9725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.1474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597   -1.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.5651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3412   -1.1526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    3.3850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1159   -2.6008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 17  2  0  0  0  0
  2  8  1  0  0  0  0
  2 11  1  0  0  0  0
  2 17  1  0  0  0  0
  3  4  1  0  0  0  0
  3  9  1  0  0  0  0
  3 14  1  0  0  0  0
  4 21  2  0  0  0  0
  5 14  1  0  0  0  0
  5 20  2  0  0  0  0
  6 23  3  0  0  0  0
  7  9  1  0  0  0  0
  7 10  2  0  0  0  0
  7 12  1  0  0  0  0
  8 10  1  0  0  0  0
  8 13  2  0  0  0  0
  9 16  2  0  0  0  0
 11 18  1  0  0  0  0
 12 15  2  0  0  0  0
 13 15  1  0  0  0  0
 14 19  2  0  0  0  0
 16 20  1  0  0  0  0
 17 22  1  0  0  0  0
 19 21  1  0  0  0  0
 19 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015097

> <DATABASE_NAME>
hmdb

> <SMILES>
CCN(C(C)=O)C1=CC=CC(=C1)C1=CC=NC2=C(C=NN12)C#N

> <INCHI_IDENTIFIER>
InChI=1S/C17H15N5O/c1-3-21(12(2)23)15-6-4-5-13(9-15)16-7-8-19-17-14(10-18)11-20-22(16)17/h4-9,11H,3H2,1-2H3

> <INCHI_KEY>
HUNXMJYCHXQEGX-UHFFFAOYSA-N

> <FORMULA>
C17H15N5O

> <MOLECULAR_WEIGHT>
305.3339

> <EXACT_MASS>
305.127660127

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
32.09341454372763

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-(3-{3-cyanopyrazolo[1,5-a]pyrimidin-7-yl}phenyl)-N-ethylacetamide

> <ALOGPS_LOGP>
2.00

> <JCHEM_LOGP>
1.5348796856666667

> <ALOGPS_LOGS>
-3.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
0.3021576634174695

> <JCHEM_POLAR_SURFACE_AREA>
74.28999999999999

> <JCHEM_REFRACTIVITY>
97.23639999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.03e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
zaleplon

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015097
     RDKit          3D
Zaleplon
 38 40  0  0  0  0  0  0  0  0999 V2000
   -4.8085   -0.9676    0.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9080   -0.2848    1.1896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7572    0.3380    0.4820 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9391    1.6539    0.0724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0846    2.5342   -0.7328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0562    2.2039    0.4623 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6315   -0.4791    0.2752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7403   -1.8674    0.4704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6731   -2.6982    0.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5390   -2.1827   -0.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7033   -0.8373   -0.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9687   -0.3076   -0.7881 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1588   -0.1577   -2.1701 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3385    0.3182   -2.6832 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3221    0.6431   -1.8348 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1528    0.5045   -0.5277 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0489    0.7851    0.4923 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3947    1.2932    0.3875 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4798    1.6803    0.3067 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3548    0.4584    1.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1270    0.0131    1.3111 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9957    0.0374   -0.0068 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3990   -0.0287   -0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5735   -0.2467   -0.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1984   -1.2440   -0.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3691   -1.8094    0.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5191    0.5144    1.6560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6060   -0.9765    1.9701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3060    2.9734   -0.0790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7120    3.4172   -1.1032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6710    2.0173   -1.6224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6865   -2.2730    0.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7740   -3.7932    0.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3789   -2.8435   -0.2803 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3583   -0.4194   -2.8434 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5361    0.4554   -3.7457 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7536    0.5505    2.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1979    1.0256   -0.2725 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
  3  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  3  0
 17 20  1  0
 20 21  2  0
 21 22  1  0
 11 23  2  0
 23  7  1  0
 22 12  1  0
 22 16  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  5 29  1  0
  5 30  1  0
  5 31  1  0
  8 32  1  0
  9 33  1  0
 10 34  1  0
 13 35  1  0
 14 36  1  0
 20 37  1  0
 23 38  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 962                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       5.748   6.319   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       7.081   4.008   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       5.748  -1.382   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       7.205  -0.912   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       4.414  -3.692   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       8.162  -6.319   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       4.414   0.928   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.748   3.238   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414  -0.612   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.748   1.698   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.415   3.238   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.080   1.698   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414   4.008   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.748  -2.922   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.080   3.238   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.080  -1.382   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.081   5.549   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.748   4.008   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.205  -3.391   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.080  -2.922   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.104  -2.152   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.415   6.319   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.683  -4.855   0.000  0.00  0.00           C+0
CONECT    1   17                                                            
CONECT    2    8   11   17                                                  
CONECT    3    4    9   14                                                  
CONECT    4    3   21                                                       
CONECT    5   14   20                                                       
CONECT    6   23                                                            
CONECT    7    9   10   12                                                  
CONECT    8    2   10   13                                                  
CONECT    9    3    7   16                                                  
CONECT   10    7    8                                                       
CONECT   11    2   18                                                       
CONECT   12    7   15                                                       
CONECT   13    8   15                                                       
CONECT   14    3    5   19                                                  
CONECT   15   12   13                                                       
CONECT   16    9   20                                                       
CONECT   17    1    2   22                                                  
CONECT   18   11                                                            
CONECT   19   14   21   23                                                  
CONECT   20    5   16                                                       
CONECT   21    4   19                                                       
CONECT   22   17                                                            
CONECT   23    6   19                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0015097
HETATM    1  C1  UNL     1      -4.809  -0.968   0.173  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.908  -0.285   1.190  1.00  0.00           C  
HETATM    3  N1  UNL     1      -2.757   0.338   0.482  1.00  0.00           N  
HETATM    4  C3  UNL     1      -2.939   1.654   0.072  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.085   2.534  -0.733  1.00  0.00           C  
HETATM    6  O1  UNL     1      -4.056   2.204   0.462  1.00  0.00           O  
HETATM    7  C5  UNL     1      -1.632  -0.479   0.275  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.740  -1.867   0.470  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.673  -2.698   0.273  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.539  -2.183  -0.126  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.703  -0.837  -0.331  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.969  -0.308  -0.788  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.159  -0.158  -2.170  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.338   0.318  -2.683  1.00  0.00           C  
HETATM   15  N2  UNL     1       4.322   0.643  -1.835  1.00  0.00           N  
HETATM   16  C13 UNL     1       4.153   0.504  -0.528  1.00  0.00           C  
HETATM   17  C14 UNL     1       5.049   0.785   0.492  1.00  0.00           C  
HETATM   18  C15 UNL     1       6.395   1.293   0.388  1.00  0.00           C  
HETATM   19  N3  UNL     1       7.480   1.680   0.307  1.00  0.00           N  
HETATM   20  C16 UNL     1       4.355   0.458   1.651  1.00  0.00           C  
HETATM   21  N4  UNL     1       3.127   0.013   1.311  1.00  0.00           N  
HETATM   22  N5  UNL     1       2.996   0.037  -0.007  1.00  0.00           N  
HETATM   23  C17 UNL     1      -0.399  -0.029  -0.119  1.00  0.00           C  
HETATM   24  H1  UNL     1      -5.574  -0.247  -0.244  1.00  0.00           H  
HETATM   25  H2  UNL     1      -4.198  -1.244  -0.725  1.00  0.00           H  
HETATM   26  H3  UNL     1      -5.369  -1.809   0.605  1.00  0.00           H  
HETATM   27  H4  UNL     1      -4.519   0.514   1.656  1.00  0.00           H  
HETATM   28  H5  UNL     1      -3.606  -0.977   1.970  1.00  0.00           H  
HETATM   29  H6  UNL     1      -1.306   2.973  -0.079  1.00  0.00           H  
HETATM   30  H7  UNL     1      -2.712   3.417  -1.103  1.00  0.00           H  
HETATM   31  H8  UNL     1      -1.671   2.017  -1.622  1.00  0.00           H  
HETATM   32  H9  UNL     1      -2.687  -2.273   0.779  1.00  0.00           H  
HETATM   33  H10 UNL     1      -0.774  -3.793   0.434  1.00  0.00           H  
HETATM   34  H11 UNL     1       1.379  -2.844  -0.280  1.00  0.00           H  
HETATM   35  H12 UNL     1       1.358  -0.419  -2.843  1.00  0.00           H  
HETATM   36  H13 UNL     1       3.536   0.455  -3.746  1.00  0.00           H  
HETATM   37  H14 UNL     1       4.754   0.550   2.667  1.00  0.00           H  
HETATM   38  H15 UNL     1      -0.198   1.026  -0.273  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   27   28
CONECT    3    4    7
CONECT    4    5    6    6
CONECT    5   29   30   31
CONECT    7    8    8   23
CONECT    8    9   32
CONECT    9   10   10   33
CONECT   10   11   34
CONECT   11   12   23   23
CONECT   12   13   13   22
CONECT   13   14   35
CONECT   14   15   15   36
CONECT   15   16
CONECT   16   17   17   22
CONECT   17   18   20
CONECT   18   19   19   19
CONECT   20   21   21   37
CONECT   21   22
CONECT   23   38
END

HMDB0015097
     RDKit          3D
Zaleplon
 38 40  0  0  0  0  0  0  0  0999 V2000
   -4.8085   -0.9676    0.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9080   -0.2848    1.1896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7572    0.3380    0.4820 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9391    1.6539    0.0724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0846    2.5342   -0.7328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0562    2.2039    0.4623 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6315   -0.4791    0.2752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7403   -1.8674    0.4704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6731   -2.6982    0.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5390   -2.1827   -0.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7033   -0.8373   -0.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9687   -0.3076   -0.7881 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1588   -0.1577   -2.1701 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3385    0.3182   -2.6832 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3221    0.6431   -1.8348 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1528    0.5045   -0.5277 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0489    0.7851    0.4923 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3947    1.2932    0.3875 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4798    1.6803    0.3067 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3548    0.4584    1.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1270    0.0131    1.3111 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9957    0.0374   -0.0068 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3990   -0.0287   -0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5735   -0.2467   -0.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1984   -1.2440   -0.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3691   -1.8094    0.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5191    0.5144    1.6560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6060   -0.9765    1.9701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3060    2.9734   -0.0790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7120    3.4172   -1.1032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6710    2.0173   -1.6224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6865   -2.2730    0.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7740   -3.7932    0.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3789   -2.8435   -0.2803 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3583   -0.4194   -2.8434 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5361    0.4554   -3.7457 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7536    0.5505    2.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1979    1.0256   -0.2725 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
  3  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  3  0
 17 20  1  0
 20 21  2  0
 21 22  1  0
 11 23  2  0
 23  7  1  0
 22 12  1  0
 22 16  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  5 29  1  0
  5 30  1  0
  5 31  1  0
  8 32  1  0
  9 33  1  0
 10 34  1  0
 13 35  1  0
 14 36  1  0
 20 37  1  0
 23 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3'-(3-Cyanopyrazolo(1,5-a)pyrimidin-7-yl)-N-ethylacetanilide	ChEBI
Sonata	Kegg
DEA no. 2781	HMDB
N-(3-(3-Cyanopyrazolo(1,5-a)pyrimidin-7-yl)phenyl)-N-ethylacetamide	HMDB
Zelepion	HMDB
Starnoc	HMDB
3'-(3-Cyanopyrazolo(1,5-alpha)pyrimidin-7-yl)-N-ethylacetanilide	HMDB

Chemical Formula

C₁₇H₁₅N₅O

Average Molecular Weight

305.3339

Monoisotopic Molecular Weight

305.127660127

IUPAC Name

N-(3-{3-cyanopyrazolo[1,5-a]pyrimidin-7-yl}phenyl)-N-ethylacetamide

Traditional Name

zaleplon

CAS Registry Number

151319-34-5

SMILES

CCN(C(C)=O)C1=CC=CC(=C1)C1=CC=NC2=C(C=NN12)C#N

InChI Identifier

InChI=1S/C17H15N5O/c1-3-21(12(2)23)15-6-4-5-13(9-15)16-7-8-19-17-14(10-18)11-20-22(16)17/h4-9,11H,3H2,1-2H3

InChI Key

HUNXMJYCHXQEGX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpyrimidines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrimidine ring through a CC or CN bond. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Phenylpyrimidines

Alternative Parents

Substituents

4-phenylpyrimidine
5-phenylpyrimidine
Acetanilide
Pyrazolo[1,5-a]pyrimidine
Anilide
Pyrazolopyrimidine
Monocyclic benzene moiety
Benzenoid
Azole
Heteroaromatic compound
Acetamide
Tertiary carboxylic acid amide
Pyrazole
Carboxamide group
Carboxylic acid derivative
Carbonitrile
Nitrile
Azacycle
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Carbonyl group
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

nitrile (CHEBI:10102 )
pyrazolopyrimidine (CHEBI:10102 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Blood (PMID: 21059682)

Cellular substructure

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

anticonvulsant (HMDB: HMDB0015097)
central nervous system depressant (HMDB: HMDB0015097)
sedative (HMDB: HMDB0015097)

Pharmaceutical industry

anxiolytic drug (HMDB: HMDB0015097)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	157 - 159 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.04 g/L	Not Available
LogP	0.9	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	173.5	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.04 g/L	ALOGPS
logP	2	ALOGPS
logP	1.53	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Basic)	0.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	74.29 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	97.24 m³·mol⁻¹	ChemAxon
Polarizability	32.09 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	173.763	31661259
DarkChem	[M-H]-	174.91	31661259
DeepCCS	[M-2H]-	199.597	30932474
DeepCCS	[M+Na]+	174.824	30932474
AllCCS	[M+H]+	171.1	32859911
AllCCS	[M+H-H2O]+	167.7	32859911
AllCCS	[M+NH4]+	174.2	32859911
AllCCS	[M+Na]+	175.2	32859911
AllCCS	[M-H]-	176.0	32859911
AllCCS	[M+Na-2H]-	175.5	32859911
AllCCS	[M+HCOO]-	175.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Zaleplon	CCN(C(C)=O)C1=CC=CC(=C1)C1=CC=NC2=C(C=NN12)C#N	3581.6	Standard polar	33892256
Zaleplon	CCN(C(C)=O)C1=CC=CC(=C1)C1=CC=NC2=C(C=NN12)C#N	3046.7	Standard non polar	33892256
Zaleplon	CCN(C(C)=O)C1=CC=CC(=C1)C1=CC=NC2=C(C=NN12)C#N	3153.7	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 - Zaleplon GC-MS (Non-derivatized) - 70eV, Positive	splash10-002o-3190000000-e824b41dc4a274647c52	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zaleplon GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zaleplon GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-01ot-3391000000-78a75199aa0ab8c426be	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zaleplon , positive-QTOF	splash10-0a4i-0179000000-1ba269c717f4cb21ab11	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zaleplon 35V, Positive-QTOF	splash10-0bti-0093000000-4fa0fb440741a86e6ec0	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zaleplon 10V, Positive-QTOF	splash10-0a4i-0049000000-5aaa826ffa805612f3d8	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zaleplon 20V, Positive-QTOF	splash10-0bvr-0093000000-ee7356e7d1d88937a5a1	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zaleplon 40V, Positive-QTOF	splash10-0uy3-9070000000-ba55a55873577a61559b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zaleplon 10V, Negative-QTOF	splash10-0udi-0039000000-f5fc7839e64ab7770cbd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zaleplon 20V, Negative-QTOF	splash10-0imi-1192000000-a401fb58f718b462f3e8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zaleplon 40V, Negative-QTOF	splash10-01qc-2090000000-3a6f247edccc09a27d47	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zaleplon 10V, Positive-QTOF	splash10-0a4i-0019000000-3c4d873dc10d23983dbb	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zaleplon 20V, Positive-QTOF	splash10-0a4i-0096000000-14f38245f06af2128bbb	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zaleplon 40V, Positive-QTOF	splash10-01pa-0090000000-87387933dc3858c721b3	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zaleplon 10V, Negative-QTOF	splash10-0udi-0009000000-da3cbd45a045c0d9febd	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zaleplon 20V, Negative-QTOF	splash10-004i-0092000000-215903c9317ecf06ce4e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zaleplon 40V, Negative-QTOF	splash10-0j5l-0191000000-41735f022846556481db	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
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 DB00962	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00962	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

DB00962

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5517

KEGG Compound ID

C07484

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Zaleplon

METLIN ID

Not Available

PubChem Compound

5719

PDB ID

Not Available

ChEBI ID

10102

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

Patat A, Paty I, Hindmarch I: Pharmacodynamic profile of Zaleplon, a new non-benzodiazepine hypnotic agent. Hum Psychopharmacol. 2001 Jul;16(5):369-392. [PubMed:12404558 ]
Barbera J, Shapiro C: Benefit-risk assessment of zaleplon in the treatment of insomnia. Drug Saf. 2005;28(4):301-18. [PubMed:15783240 ]
Noguchi H, Kitazumi K, Mori M, Shiba T: Electroencephalographic properties of zaleplon, a non-benzodiazepine sedative/hypnotic, in rats. J Pharmacol Sci. 2004 Mar;94(3):246-51. [PubMed:15037809 ]
Holm KJ, Goa KL: Zolpidem: an update of its pharmacology, therapeutic efficacy and tolerability in the treatment of insomnia. Drugs. 2000 Apr;59(4):865-89. [PubMed:10804040 ]
Dooley M, Plosker GL: Zaleplon: a review of its use in the treatment of insomnia. Drugs. 2000 Aug;60(2):413-45. [PubMed:10983740 ]
Dundar Y, Dodd S, Strobl J, Boland A, Dickson R, Walley T: Comparative efficacy of newer hypnotic drugs for the short-term management of insomnia: a systematic review and meta-analysis. Hum Psychopharmacol. 2004 Jul;19(5):305-22. [PubMed:15252823 ]
Ramakrishnan K, Scheid DC: Treatment options for insomnia. Am Fam Physician. 2007 Aug 15;76(4):517-26. [PubMed:17853625 ]

Enzymes

Enzyme Details

1. Aldehyde oxidase

General function:: Involved in oxidoreductase activity
Specific function:: Not Available
Gene Name:: AOX1
Uniprot ID:: Q06278
Molecular weight:: 147916.735

References

Lake BG, Ball SE, Kao J, Renwick AB, Price RJ, Scatina JA: Metabolism of zaleplon by human liver: evidence for involvement of aldehyde oxidase. Xenobiotica. 2002 Oct;32(10):835-47. [PubMed:12419014 ]
Obach RS: Potent inhibition of human liver aldehyde oxidase by raloxifene. Drug Metab Dispos. 2004 Jan;32(1):89-97. [PubMed:14709625 ]

Enzyme Details

2. 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

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Cytochrome P450 3A5

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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A5
Uniprot ID:: P20815
Molecular weight:: 57108.065

Enzyme Details

4. Cytochrome P450 3A7

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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A7
Uniprot ID:: P24462
Molecular weight:: 57525.03

Enzyme Details

5. Translocator protein

General function:: Signal transduction mechanisms
Specific function:: Responsible for the manifestation of peripheral-type benzodiazepine recognition sites and is most likely to comprise binding domains for benzodiazepines and isoquinoline carboxamides. May play a role in the transport of porphyrins and heme. Plays a role in the transport of cholesterol across mitochondrial membranes in steroidogenic cells
Gene Name:: TSPO
Uniprot ID:: P30536
Molecular weight:: 18778.7

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Enzyme Details

6. Gamma-aminobutyric acid receptor subunit alpha-1

General function:: Involved in ion transport
Specific function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:: GABRA1
Uniprot ID:: P14867
Molecular weight:: 51801.4

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Patat A, Paty I, Hindmarch I: Pharmacodynamic profile of Zaleplon, a new non-benzodiazepine hypnotic agent. Hum Psychopharmacol. 2001 Jul;16(5):369-392. [PubMed:12404558 ]
Barbera J, Shapiro C: Benefit-risk assessment of zaleplon in the treatment of insomnia. Drug Saf. 2005;28(4):301-18. [PubMed:15783240 ]
Sanger DJ, Griebel G, Perrault G, Claustre Y, Schoemaker H: Discriminative stimulus effects of drugs acting at GABA(A) receptors: differential profiles and receptor selectivity. Pharmacol Biochem Behav. 1999 Oct;64(2):269-73. [PubMed:10515302 ]
Terzano MG, Rossi M, Palomba V, Smerieri A, Parrino L: New drugs for insomnia: comparative tolerability of zopiclone, zolpidem and zaleplon. Drug Saf. 2003;26(4):261-82. [PubMed:12608888 ]

Showing metabocard for Zaleplon (HMDB0015097)

MOL for HMDB0015097 (Zaleplon)

3D MOL for HMDB0015097 (Zaleplon)

3D SDF for HMDB0015097 (Zaleplon)

3D-SDF for HMDB0015097 (Zaleplon)

PDB for HMDB0015097 (Zaleplon)

3D PDB for HMDB0015097 (Zaleplon)

SMILES for HMDB0015097 (Zaleplon)

INCHI for HMDB0015097 (Zaleplon)

Structure for HMDB0015097 (Zaleplon)

3D Structure for HMDB0015097 (Zaleplon)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References