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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:15:32 UTC

Update Date

2019-07-23 07:15:40 UTC

HMDB ID

HMDB0061055

Secondary Accession Numbers

HMDB61055

Metabolite Identification

Common Name

desethylzaleplon

Description

desethylzaleplon is a metabolite of zaleplon. Zaleplon (marketed under the brand names Sonata and Starnoc) is a sedative/hypnotic, mainly used for insomnia. It is a nonbenzodiazepine hypnotic from the pyrazolopyrimidine class. In terms of adverse effects zaleplon appears to offer little improvement compared to both benzodiazepines and other non-benzodiazepine Z-drugs. Sonata (US) is manufactured by King Pharm. of Bristol, TN; Starnoc has been discontinued in Canada. (Wikipedia)

Structure

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

HMDB0061055
     RDKit          3D
desethylzaleplon
 33 35  0  0  0  0  0  0  0  0999 V2000
   -4.8977    0.2251    2.1561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1590    0.2473    0.8553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7332    0.1439    1.0299 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9031    0.1525   -0.1301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4345    0.2567   -1.3960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6557    0.2672   -2.5279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2801    0.1666   -2.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3172    0.0593   -1.1046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7633   -0.0586   -1.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5054   -0.3016   -2.1673 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9021   -0.4012   -2.1334 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4936   -0.2487   -0.9397 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8135   -0.0129    0.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2448    0.1735    1.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5641    0.1630    2.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6324    0.1694    2.4550 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1011    0.3841    2.2244 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0812    0.3156    1.3565 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4647    0.0804    0.1283 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5181    0.0550   -0.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3512    0.8025    2.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9988   -0.8134    2.5539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9002    0.7018    2.0744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3605    1.2538    0.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5479   -0.4936    0.1459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3253    0.0661    1.9659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5185    0.3313   -1.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0686    0.3477   -3.5038 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2966    0.1877   -3.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0814   -0.4430   -3.1673 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4777   -0.5914   -3.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0325    0.5700    3.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1191   -0.0317    0.9760 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  3  0
 14 17  1  0
 17 18  2  0
 18 19  1  0
  8 20  2  0
 20  4  1  0
 19  9  1  0
 19 13  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  5 27  1  0
  6 28  1  0
  7 29  1  0
 10 30  1  0
 11 31  1  0
 17 32  1  0
 20 33  1  0
M  END

  Mrv0541 07091309152D          

 20 22  0  0  0  0            999 V2000
    0.4944   -3.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2089   -2.6021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.7771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6288    3.7596    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2089   -1.7771    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  7  6  1  0  0  0  0
 11  4  1  0  0  0  0
 11  8  2  0  0  0  0
 12  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13  5  2  0  0  0  0
 13  8  1  0  0  0  0
 14  6  2  0  0  0  0
 14 11  1  0  0  0  0
 15 12  2  0  0  0  0
 16  9  3  0  0  0  0
 17  2  1  0  0  0  0
 17 13  1  0  0  0  0
 18  7  2  0  0  0  0
 18 15  1  0  0  0  0
 19 10  2  0  0  0  0
 20 14  1  0  0  0  0
 20 15  1  0  0  0  0
 20 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061055

> <DATABASE_NAME>
hmdb

> <SMILES>
CCNC1=CC=CC(=C1)C1=CC=NC2=C(C=NN12)C#N

> <INCHI_IDENTIFIER>
InChI=1S/C15H13N5/c1-2-17-13-5-3-4-11(8-13)14-6-7-18-15-12(9-16)10-19-20(14)15/h3-8,10,17H,2H2,1H3

> <INCHI_KEY>
QIBDHPGCTQWVTR-UHFFFAOYSA-N

> <FORMULA>
C15H13N5

> <MOLECULAR_WEIGHT>
263.2972

> <EXACT_MASS>
263.117095441

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
28.409409769504926

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-[3-(ethylamino)phenyl]pyrazolo[1,5-a]pyrimidine-3-carbonitrile

> <ALOGPS_LOGP>
2.40

> <JCHEM_LOGP>
1.905881377

> <ALOGPS_LOGS>
-3.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
4.508106940381391

> <JCHEM_POLAR_SURFACE_AREA>
66.01

> <JCHEM_REFRACTIVITY>
89.45130000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.57e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-[3-(ethylamino)phenyl]pyrazolo[1,5-a]pyrimidine-3-carbonitrile

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0061055
     RDKit          3D
desethylzaleplon
 33 35  0  0  0  0  0  0  0  0999 V2000
   -4.8977    0.2251    2.1561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1590    0.2473    0.8553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7332    0.1439    1.0299 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9031    0.1525   -0.1301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4345    0.2567   -1.3960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6557    0.2672   -2.5279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2801    0.1666   -2.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3172    0.0593   -1.1046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7633   -0.0586   -1.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5054   -0.3016   -2.1673 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9021   -0.4012   -2.1334 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4936   -0.2487   -0.9397 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8135   -0.0129    0.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2448    0.1735    1.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5641    0.1630    2.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6324    0.1694    2.4550 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1011    0.3841    2.2244 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0812    0.3156    1.3565 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4647    0.0804    0.1283 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5181    0.0550   -0.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3512    0.8025    2.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9988   -0.8134    2.5539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9002    0.7018    2.0744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3605    1.2538    0.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5479   -0.4936    0.1459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3253    0.0661    1.9659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5185    0.3313   -1.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0686    0.3477   -3.5038 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2966    0.1877   -3.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0814   -0.4430   -3.1673 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4777   -0.5914   -3.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0325    0.5700    3.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1191   -0.0317    0.9760 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  3  0
 14 17  1  0
 17 18  2  0
 18 19  1  0
  8 20  2  0
 20  4  1  0
 19  9  1  0
 19 13  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  5 27  1  0
  6 28  1  0
  7 29  1  0
 10 30  1  0
 11 31  1  0
 17 32  1  0
 20 33  1  0
M  END

HEADER    PROTEIN                                 09-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JUL-13         0                                  
HETATM    1  C   UNK     0       0.923  -5.627   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.257  -4.857   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.258  -2.547   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.258  -1.007   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.924  -3.317   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.590  -1.007   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.650   5.553   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.924  -0.237   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.590  -2.547   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       1.174   7.018   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0       2.257  -3.317   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0       4.924   4.383   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0       2.126   1.597   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0       3.590   2.073   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1   17                                                       
CONECT    3    4    5                                                       
CONECT    4    3   11                                                       
CONECT    5    3   13                                                       
CONECT    6    7   14                                                       
CONECT    7    6   18                                                       
CONECT    8   11   13                                                       
CONECT    9   12   16                                                       
CONECT   10   12   19                                                       
CONECT   11    4    8   14                                                  
CONECT   12    9   10   15                                                  
CONECT   13    5    8   17                                                  
CONECT   14    6   11   20                                                  
CONECT   15   12   18   20                                                  
CONECT   16    9                                                            
CONECT   17    2   13                                                       
CONECT   18    7   15                                                       
CONECT   19   10   20                                                       
CONECT   20   14   15   19                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0061055
HETATM    1  C1  UNL     1      -4.898   0.225   2.156  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.159   0.247   0.855  1.00  0.00           C  
HETATM    3  N1  UNL     1      -2.733   0.144   1.030  1.00  0.00           N  
HETATM    4  C3  UNL     1      -1.903   0.152  -0.130  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.435   0.257  -1.396  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.656   0.267  -2.528  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.280   0.167  -2.344  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.317   0.059  -1.105  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.763  -0.059  -1.034  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.505  -0.302  -2.167  1.00  0.00           C  
HETATM   11  C10 UNL     1       3.902  -0.401  -2.133  1.00  0.00           C  
HETATM   12  N2  UNL     1       4.494  -0.249  -0.940  1.00  0.00           N  
HETATM   13  C11 UNL     1       3.814  -0.013   0.179  1.00  0.00           C  
HETATM   14  C12 UNL     1       4.245   0.173   1.484  1.00  0.00           C  
HETATM   15  C13 UNL     1       5.564   0.163   2.016  1.00  0.00           C  
HETATM   16  N3  UNL     1       6.632   0.169   2.455  1.00  0.00           N  
HETATM   17  C14 UNL     1       3.101   0.384   2.224  1.00  0.00           C  
HETATM   18  N4  UNL     1       2.081   0.316   1.357  1.00  0.00           N  
HETATM   19  N5  UNL     1       2.465   0.080   0.128  1.00  0.00           N  
HETATM   20  C15 UNL     1      -0.518   0.055  -0.021  1.00  0.00           C  
HETATM   21  H1  UNL     1      -4.351   0.802   2.929  1.00  0.00           H  
HETATM   22  H2  UNL     1      -4.999  -0.813   2.554  1.00  0.00           H  
HETATM   23  H3  UNL     1      -5.900   0.702   2.074  1.00  0.00           H  
HETATM   24  H4  UNL     1      -4.361   1.254   0.384  1.00  0.00           H  
HETATM   25  H5  UNL     1      -4.548  -0.494   0.146  1.00  0.00           H  
HETATM   26  H6  UNL     1      -2.325   0.066   1.966  1.00  0.00           H  
HETATM   27  H7  UNL     1      -3.518   0.331  -1.454  1.00  0.00           H  
HETATM   28  H8  UNL     1      -2.069   0.348  -3.504  1.00  0.00           H  
HETATM   29  H9  UNL     1       0.297   0.188  -3.268  1.00  0.00           H  
HETATM   30  H10 UNL     1       2.081  -0.443  -3.167  1.00  0.00           H  
HETATM   31  H11 UNL     1       4.478  -0.591  -3.024  1.00  0.00           H  
HETATM   32  H12 UNL     1       3.032   0.570   3.301  1.00  0.00           H  
HETATM   33  H13 UNL     1      -0.119  -0.032   0.976  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   24   25
CONECT    3    4   26
CONECT    4    5    5   20
CONECT    5    6   27
CONECT    6    7    7   28
CONECT    7    8   29
CONECT    8    9   20   20
CONECT    9   10   10   19
CONECT   10   11   30
CONECT   11   12   12   31
CONECT   12   13
CONECT   13   14   14   19
CONECT   14   15   17
CONECT   15   16   16   16
CONECT   17   18   18   32
CONECT   18   19
CONECT   20   33
END

HMDB0061055
     RDKit          3D
desethylzaleplon
 33 35  0  0  0  0  0  0  0  0999 V2000
   -4.8977    0.2251    2.1561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1590    0.2473    0.8553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7332    0.1439    1.0299 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9031    0.1525   -0.1301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4345    0.2567   -1.3960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6557    0.2672   -2.5279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2801    0.1666   -2.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3172    0.0593   -1.1046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7633   -0.0586   -1.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5054   -0.3016   -2.1673 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9021   -0.4012   -2.1334 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4936   -0.2487   -0.9397 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8135   -0.0129    0.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2448    0.1735    1.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5641    0.1630    2.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6324    0.1694    2.4550 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1011    0.3841    2.2244 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0812    0.3156    1.3565 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4647    0.0804    0.1283 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5181    0.0550   -0.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3512    0.8025    2.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9988   -0.8134    2.5539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9002    0.7018    2.0744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3605    1.2538    0.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5479   -0.4936    0.1459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3253    0.0661    1.9659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5185    0.3313   -1.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0686    0.3477   -3.5038 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2966    0.1877   -3.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0814   -0.4430   -3.1673 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4777   -0.5914   -3.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0325    0.5700    3.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1191   -0.0317    0.9760 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  3  0
 14 17  1  0
 17 18  2  0
 18 19  1  0
  8 20  2  0
 20  4  1  0
 19  9  1  0
 19 13  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  5 27  1  0
  6 28  1  0
  7 29  1  0
 10 30  1  0
 11 31  1  0
 17 32  1  0
 20 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₁₃N₅

Average Molecular Weight

263.2972

Monoisotopic Molecular Weight

263.117095441

IUPAC Name

7-[3-(ethylamino)phenyl]pyrazolo[1,5-a]pyrimidine-3-carbonitrile

Traditional Name

7-[3-(ethylamino)phenyl]pyrazolo[1,5-a]pyrimidine-3-carbonitrile

CAS Registry Number

Not Available

SMILES

CCNC1=CC=CC(=C1)C1=CC=NC2=C(C=NN12)C#N

InChI Identifier

InChI=1S/C15H13N5/c1-2-17-13-5-3-4-11(8-13)14-6-7-18-15-12(9-16)10-19-20(14)15/h3-8,10,17H,2H2,1H3

InChI Key

QIBDHPGCTQWVTR-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
Pyrazolo[1,5-a]pyrimidine
Pyrazolopyrimidine
Phenylalkylamine
Aniline or substituted anilines
Secondary aliphatic/aromatic amine
Monocyclic benzene moiety
Benzenoid
Azole
Heteroaromatic compound
Pyrazole
Carbonitrile
Nitrile
Azacycle
Secondary amine
Amine
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organopnictogen 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 (HMDB: HMDB0061055)

Organ

Kidney (HMDB: HMDB0061055)
Liver (HMDB: HMDB0061055)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0061055)

Cellular substructure

Cytoplasm (HMDB: HMDB0061055)

Source

Endogenous

Endogenous (HMDB: HMDB0061055)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.036 g/L	ALOGPS
logP	2.4	ALOGPS
logP	1.91	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Basic)	4.51	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	66.01 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	89.45 m³·mol⁻¹	ChemAxon
Polarizability	28.41 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]+	161.114	31661259
DarkChem	[M-H]-	165.073	31661259
DeepCCS	[M-2H]-	189.48	30932474
DeepCCS	[M+Na]+	164.907	30932474
AllCCS	[M+H]+	161.0	32859911
AllCCS	[M+H-H2O]+	157.2	32859911
AllCCS	[M+NH4]+	164.5	32859911
AllCCS	[M+Na]+	165.5	32859911
AllCCS	[M-H]-	166.3	32859911
AllCCS	[M+Na-2H]-	165.7	32859911
AllCCS	[M+HCOO]-	165.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
desethylzaleplon	CCNC1=CC=CC(=C1)C1=CC=NC2=C(C=NN12)C#N	3559.2	Standard polar	33892256
desethylzaleplon	CCNC1=CC=CC(=C1)C1=CC=NC2=C(C=NN12)C#N	2813.4	Standard non polar	33892256
desethylzaleplon	CCNC1=CC=CC(=C1)C1=CC=NC2=C(C=NN12)C#N	2990.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
desethylzaleplon,1TMS,isomer #1	CCN(C1=CC=CC(C2=CC=NC3=C(C#N)C=NN23)=C1)[Si](C)(C)C	2854.0	Semi standard non polar	33892256
desethylzaleplon,1TMS,isomer #1	CCN(C1=CC=CC(C2=CC=NC3=C(C#N)C=NN23)=C1)[Si](C)(C)C	2894.5	Standard non polar	33892256
desethylzaleplon,1TMS,isomer #1	CCN(C1=CC=CC(C2=CC=NC3=C(C#N)C=NN23)=C1)[Si](C)(C)C	3760.6	Standard polar	33892256
desethylzaleplon,1TBDMS,isomer #1	CCN(C1=CC=CC(C2=CC=NC3=C(C#N)C=NN23)=C1)[Si](C)(C)C(C)(C)C	3088.0	Semi standard non polar	33892256
desethylzaleplon,1TBDMS,isomer #1	CCN(C1=CC=CC(C2=CC=NC3=C(C#N)C=NN23)=C1)[Si](C)(C)C(C)(C)C	3085.1	Standard non polar	33892256
desethylzaleplon,1TBDMS,isomer #1	CCN(C1=CC=CC(C2=CC=NC3=C(C#N)C=NN23)=C1)[Si](C)(C)C(C)(C)C	3807.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - desethylzaleplon GC-MS (Non-derivatized) - 70eV, Positive	splash10-000j-3790000000-40dc7521e4239ce44c7c	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - desethylzaleplon 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 - desethylzaleplon 10V, Positive-QTOF	splash10-03di-0090000000-ec5bea23ddb45e067e1c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - desethylzaleplon 20V, Positive-QTOF	splash10-01q0-0090000000-8b2a4f1556ea9025dadd	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - desethylzaleplon 40V, Positive-QTOF	splash10-0udi-9230000000-8a11010997c19b367a49	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - desethylzaleplon 10V, Negative-QTOF	splash10-03di-0090000000-25a975590095d631b686	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - desethylzaleplon 20V, Negative-QTOF	splash10-03dr-0190000000-113d4f42858ed805a634	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - desethylzaleplon 40V, Negative-QTOF	splash10-001l-3390000000-bacbdd7fc9eb2bb2faa4	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - desethylzaleplon 10V, Negative-QTOF	splash10-03di-0090000000-26a0c7dab60618963ba0	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - desethylzaleplon 20V, Negative-QTOF	splash10-03di-0090000000-28042d5cd64b38ee9757	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - desethylzaleplon 40V, Negative-QTOF	splash10-015c-1980000000-3c8d86ef49f81e2ffb17	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - desethylzaleplon 10V, Positive-QTOF	splash10-03di-0090000000-e58102c6091766bda958	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - desethylzaleplon 20V, Positive-QTOF	splash10-03di-0090000000-e7aa154ab22fd8783586	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - desethylzaleplon 40V, Positive-QTOF	splash10-01wv-0390000000-1119d0f841c1e2b2d76c	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

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	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

90688312

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

Not Available

Showing metabocard for desethylzaleplon (HMDB0061055)

MOL for HMDB0061055 (desethylzaleplon)

3D MOL for HMDB0061055 (desethylzaleplon)

3D SDF for HMDB0061055 (desethylzaleplon)

3D-SDF for HMDB0061055 (desethylzaleplon)

PDB for HMDB0061055 (desethylzaleplon)

3D PDB for HMDB0061055 (desethylzaleplon)

SMILES for HMDB0061055 (desethylzaleplon)

INCHI for HMDB0061055 (desethylzaleplon)

Structure for HMDB0061055 (desethylzaleplon)

3D Structure for HMDB0061055 (desethylzaleplon)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra