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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-12 17:32:58 UTC

Update Date

2021-09-14 15:48:21 UTC

HMDB ID

HMDB0060541

Secondary Accession Numbers

HMDB60541

Metabolite Identification

Common Name

N-Desmethylzopiclone

Description

N-Desmethylzopiclone is a metabolite of Eszopiclone. Eszopiclone, marketed by Sepracor under the brand-name Lunesta, is a nonbenzodiazepine hypnotic which is slightly effective for insomnia. Eszopiclone is the active dextrorotatory stereoisomer of zopiclone, and belongs to the class of drugs known as cyclopyrrolones. (Wikipedia)

Structure

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

[NO NAME]
  Mrv0541 06121310322D          
Created with ChemWriter - http://chemwriter.com
 26 29  0  0  0  0            999 V2000
    7.6412   -1.8754    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.1159   -0.4273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7577    0.0166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1159   -3.3235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8213    0.9710    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3339    2.5393    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3412   -1.8754    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0504    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.7004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5787   -2.5899    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2703    1.5850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6286    1.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8848    1.9253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0791   -2.2879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597   -2.5393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1662   -1.8754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5787   -1.1610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.4629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.2879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4037   -1.1610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4037   -2.5899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8162   -1.8754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 24 26  1  0  0  0  0
 25 26  2  0  0  0  0
M  END

HMDB0060541
     RDKit          3D
N-Desmethylzopiclone
 41 44  0  0  0  0  0  0  0  0999 V2000
   -1.0971   -0.4177    1.8242 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1843   -0.3361    0.5728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1032   -0.8027   -0.1581 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0523   -1.3485    0.4536 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3217   -2.7116   -0.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0536   -4.9880   -0.5808 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3203   -5.0732   -1.1173 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5846   -2.7881   -0.5782 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1740   -1.4675   -0.4489 C   0  0  0  0  0  0  0  0  0  0  0  0
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 13  4  1  0
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 10  5  1  0
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 26 41  1  0
M  END

[NO NAME]
  Mrv0541 06121310322D          
Created with ChemWriter - http://chemwriter.com
 26 29  0  0  0  0            999 V2000
    7.6412   -1.8754    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.1159   -0.4273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7577    0.0166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1159   -3.3235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8213    0.9710    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3339    2.5393    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3412   -1.8754    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0504    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.7004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5787   -2.5899    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2703    1.5850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6286    1.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5266    2.3692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8848    1.9253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597   -1.2115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5650    0.1868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.4629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.2879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597   -2.5393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1662   -1.8754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5787   -1.1610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 10 20  2  0  0  0  0
 10 25  1  0  0  0  0
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 21 24  2  0  0  0  0
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 25 26  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060541

> <DATABASE_NAME>
hmdb

> <SMILES>
ClC1=CN=C(C=C1)N1C(OC(=O)N2CCNCC2)C2=NC=CN=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H15ClN6O3/c17-10-1-2-11(21-9-10)23-14(24)12-13(20-4-3-19-12)15(23)26-16(25)22-7-5-18-6-8-22/h1-4,9,15,18H,5-8H2

> <INCHI_KEY>
CGSFZSTXVVJLIX-UHFFFAOYSA-N

> <FORMULA>
C16H15ClN6O3

> <MOLECULAR_WEIGHT>
374.782

> <EXACT_MASS>
374.089416083

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
36.06580795265205

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-(5-chloropyridin-2-yl)-7-oxo-5H,6H,7H-pyrrolo[3,4-b]pyrazin-5-yl piperazine-1-carboxylate

> <ALOGPS_LOGP>
0.66

> <JCHEM_LOGP>
0.4234950956666667

> <ALOGPS_LOGS>
-3.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.03831072581141

> <JCHEM_PKA_STRONGEST_BASIC>
7.814938144450361

> <JCHEM_POLAR_SURFACE_AREA>
100.55000000000001

> <JCHEM_REFRACTIVITY>
90.59079999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.79e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-(5-chloropyridin-2-yl)-7-oxo-5H-pyrrolo[3,4-b]pyrazin-5-yl piperazine-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060541
     RDKit          3D
N-Desmethylzopiclone
 41 44  0  0  0  0  0  0  0  0999 V2000
   -1.0971   -0.4177    1.8242 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1843   -0.3361    0.5728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1032   -0.8027   -0.1581 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0523   -1.3485    0.4536 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3217   -2.7116   -0.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5643   -3.8551   -0.0626 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0536   -4.9880   -0.5808 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3203   -5.0732   -1.1173 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0640   -3.9571   -1.1026 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5846   -2.7881   -0.5782 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1740   -1.4675   -0.4489 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4938    0.7923    0.4435 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4171    1.2892    1.7230 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6584    2.6334    2.0016 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9782    3.4667    0.9674 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3011    5.1912    1.2338 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0507    2.9552   -0.3030 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8106    1.6447   -0.5396 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3501    0.2143   -0.0386 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5049    0.3316   -1.4645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7685    1.1737   -1.6865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6512    2.4155   -0.9295 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8885    2.0757    0.4609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4286    0.6778    0.8043 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9539   -1.3456    1.5723 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4272   -5.8837   -0.5806 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1601    0.5897    2.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5982    3.0233    3.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3080    3.6441   -1.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7280   -0.6573   -1.9343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6718    0.8575   -1.9453 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4351    2.8320    1.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3226    0.0190    0.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1456    0.6206    1.8895 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  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
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
  2 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 13  4  1  0
 20 14  1  0
 26 21  1  0
 10  5  1  0
  4 27  1  0
  7 28  1  0
  8 29  1  0
 15 30  1  0
 16 31  1  0
 19 32  1  0
 22 33  1  0
 22 34  1  0
 23 35  1  0
 23 36  1  0
 24 37  1  0
 25 38  1  0
 25 39  1  0
 26 40  1  0
 26 41  1  0
M  END

HEADER    PROTEIN                                 12-JUN-13   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: [NO NAME]                                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-JUN-13         0                                  
HETATM    1 Cl   UNK     0      14.264  -3.501   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0       7.683  -0.798   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       5.148   0.031   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       7.683  -6.204   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       7.133   1.813   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       8.090   4.740   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       8.104  -3.501   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       4.414  -1.961   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       4.414  -5.041   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      10.414  -4.834   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       6.105   2.959   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.640   2.130   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.583   4.423   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.118   3.594   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.205  -2.261   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.655   0.349   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.748  -2.731   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.748  -4.271   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.205  -4.740   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.644  -3.501   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.414  -2.167   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.080  -2.731   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.080  -4.271   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.954  -2.167   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.954  -4.834   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.724  -3.501   0.000  0.00  0.00           C+0
CONECT    1   26                                                            
CONECT    2   15   16                                                       
CONECT    3   16                                                            
CONECT    4   19                                                            
CONECT    5   11   12   16                                                  
CONECT    6   13   14                                                       
CONECT    7   15   19   20                                                  
CONECT    8   17   22                                                       
CONECT    9   18   23                                                       
CONECT   10   20   25                                                       
CONECT   11    5   13                                                       
CONECT   12    5   14                                                       
CONECT   13    6   11                                                       
CONECT   14    6   12                                                       
CONECT   15    2    7   17                                                  
CONECT   16    2    3    5                                                  
CONECT   17    8   15   18                                                  
CONECT   18    9   17   19                                                  
CONECT   19    4    7   18                                                  
CONECT   20    7   10   21                                                  
CONECT   21   20   24                                                       
CONECT   22    8   23                                                       
CONECT   23    9   22                                                       
CONECT   24   21   26                                                       
CONECT   25   10   26                                                       
CONECT   26    1   24   25                                                  
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

COMPND    HMDB0060541
HETATM    1  O1  UNL     1      -1.097  -0.418   1.824  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.184  -0.336   0.573  1.00  0.00           C  
HETATM    3  O2  UNL     1      -0.103  -0.803  -0.158  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.052  -1.349   0.454  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.322  -2.712  -0.046  1.00  0.00           C  
HETATM    6  N1  UNL     1       0.564  -3.855  -0.063  1.00  0.00           N  
HETATM    7  C4  UNL     1       1.054  -4.988  -0.581  1.00  0.00           C  
HETATM    8  C5  UNL     1       2.320  -5.073  -1.117  1.00  0.00           C  
HETATM    9  N2  UNL     1       3.064  -3.957  -1.103  1.00  0.00           N  
HETATM   10  C6  UNL     1       2.585  -2.788  -0.578  1.00  0.00           C  
HETATM   11  C7  UNL     1       3.174  -1.467  -0.449  1.00  0.00           C  
HETATM   12  O3  UNL     1       4.360  -1.155  -0.841  1.00  0.00           O  
HETATM   13  N3  UNL     1       2.239  -0.608   0.168  1.00  0.00           N  
HETATM   14  C8  UNL     1       2.494   0.792   0.444  1.00  0.00           C  
HETATM   15  C9  UNL     1       2.417   1.289   1.723  1.00  0.00           C  
HETATM   16  C10 UNL     1       2.658   2.633   2.002  1.00  0.00           C  
HETATM   17  C11 UNL     1       2.978   3.467   0.967  1.00  0.00           C  
HETATM   18 CL1  UNL     1       3.301   5.191   1.234  1.00  0.00          CL  
HETATM   19  C12 UNL     1       3.051   2.955  -0.303  1.00  0.00           C  
HETATM   20  N4  UNL     1       2.811   1.645  -0.540  1.00  0.00           N  
HETATM   21  N5  UNL     1      -2.350   0.214  -0.039  1.00  0.00           N  
HETATM   22  C13 UNL     1      -2.505   0.332  -1.464  1.00  0.00           C  
HETATM   23  C14 UNL     1      -3.769   1.174  -1.687  1.00  0.00           C  
HETATM   24  N6  UNL     1      -3.651   2.415  -0.930  1.00  0.00           N  
HETATM   25  C15 UNL     1      -3.888   2.076   0.461  1.00  0.00           C  
HETATM   26  C16 UNL     1      -3.429   0.678   0.804  1.00  0.00           C  
HETATM   27  H1  UNL     1       0.954  -1.346   1.572  1.00  0.00           H  
HETATM   28  H2  UNL     1       0.427  -5.884  -0.581  1.00  0.00           H  
HETATM   29  H3  UNL     1       2.632  -6.028  -1.513  1.00  0.00           H  
HETATM   30  H4  UNL     1       2.160   0.590   2.509  1.00  0.00           H  
HETATM   31  H5  UNL     1       2.598   3.023   3.004  1.00  0.00           H  
HETATM   32  H6  UNL     1       3.308   3.644  -1.106  1.00  0.00           H  
HETATM   33  H7  UNL     1      -2.728  -0.657  -1.934  1.00  0.00           H  
HETATM   34  H8  UNL     1      -1.672   0.858  -1.945  1.00  0.00           H  
HETATM   35  H9  UNL     1      -4.654   0.638  -1.290  1.00  0.00           H  
HETATM   36  H10 UNL     1      -3.927   1.419  -2.735  1.00  0.00           H  
HETATM   37  H11 UNL     1      -2.663   2.734  -1.068  1.00  0.00           H  
HETATM   38  H12 UNL     1      -4.998   2.185   0.611  1.00  0.00           H  
HETATM   39  H13 UNL     1      -3.435   2.832   1.137  1.00  0.00           H  
HETATM   40  H14 UNL     1      -4.323   0.019   0.694  1.00  0.00           H  
HETATM   41  H15 UNL     1      -3.146   0.621   1.889  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   21
CONECT    3    4
CONECT    4    5   13   27
CONECT    5    6    6   10
CONECT    6    7
CONECT    7    8    8   28
CONECT    8    9   29
CONECT    9   10   10
CONECT   10   11
CONECT   11   12   12   13
CONECT   13   14
CONECT   14   15   15   20
CONECT   15   16   30
CONECT   16   17   17   31
CONECT   17   18   19
CONECT   19   20   20   32
CONECT   21   22   26
CONECT   22   23   33   34
CONECT   23   24   35   36
CONECT   24   25   37
CONECT   25   26   38   39
CONECT   26   40   41
END

HMDB0060541
     RDKit          3D
N-Desmethylzopiclone
 41 44  0  0  0  0  0  0  0  0999 V2000
   -1.0971   -0.4177    1.8242 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1843   -0.3361    0.5728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1032   -0.8027   -0.1581 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0523   -1.3485    0.4536 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3217   -2.7116   -0.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5643   -3.8551   -0.0626 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0536   -4.9880   -0.5808 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3203   -5.0732   -1.1173 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0640   -3.9571   -1.1026 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5846   -2.7881   -0.5782 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1740   -1.4675   -0.4489 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3595   -1.1552   -0.8413 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2387   -0.6082    0.1684 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4938    0.7923    0.4435 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4171    1.2892    1.7230 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6584    2.6334    2.0016 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9782    3.4667    0.9674 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3011    5.1912    1.2338 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0507    2.9552   -0.3030 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8106    1.6447   -0.5396 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3501    0.2143   -0.0386 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5049    0.3316   -1.4645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7685    1.1737   -1.6865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6512    2.4155   -0.9295 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8885    2.0757    0.4609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4286    0.6778    0.8043 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9539   -1.3456    1.5723 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4272   -5.8837   -0.5806 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6318   -6.0278   -1.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1601    0.5897    2.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5982    3.0233    3.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3080    3.6441   -1.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7280   -0.6573   -1.9343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6718    0.8575   -1.9453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6542    0.6383   -1.2898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9270    1.4192   -2.7352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6631    2.7336   -1.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9983    2.1846    0.6107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4351    2.8320    1.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3226    0.0190    0.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1456    0.6206    1.8895 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  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
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
  2 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 13  4  1  0
 20 14  1  0
 26 21  1  0
 10  5  1  0
  4 27  1  0
  7 28  1  0
  8 29  1  0
 15 30  1  0
 16 31  1  0
 19 32  1  0
 22 33  1  0
 22 34  1  0
 23 35  1  0
 23 36  1  0
 24 37  1  0
 25 38  1  0
 25 39  1  0
 26 40  1  0
 26 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6-(5-Chloro-2-pyridyl)-7-((1-piperazinyl)carbonyloxy)-6,7-dihydro(5H)pyrrolo(3,4-b)pyrazin-5-one	HMDB

Chemical Formula

C₁₆H₁₅ClN₆O₃

Average Molecular Weight

374.782

Monoisotopic Molecular Weight

374.089416083

IUPAC Name

6-(5-chloropyridin-2-yl)-7-oxo-5H,6H,7H-pyrrolo[3,4-b]pyrazin-5-yl piperazine-1-carboxylate

Traditional Name

6-(5-chloropyridin-2-yl)-7-oxo-5H-pyrrolo[3,4-b]pyrazin-5-yl piperazine-1-carboxylate

CAS Registry Number

Not Available

SMILES

ClC1=CN=C(C=C1)N1C(OC(=O)N2CCNCC2)C2=NC=CN=C2C1=O

InChI Identifier

InChI=1S/C16H15ClN6O3/c17-10-1-2-11(21-9-10)23-14(24)12-13(20-4-3-19-12)15(23)26-16(25)22-7-5-18-6-8-22/h1-4,9,15,18H,5-8H2

InChI Key

CGSFZSTXVVJLIX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclopyrrolones. Cyclopyrrolones are compounds belonging to a family of pyridin-2-ylpyrrole based chemicals. The pyrrole is usually fused to a benzene, pyrimidine, or dithiin.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolopyrazines

Sub Class

Cyclopyrrolones

Direct Parent

Cyclopyrrolones

Alternative Parents

Substituents

Cyclopyrrolone
Piperazine-1-carboxylic acid
2-heteroaryl carboxamide
Aryl chloride
Aryl halide
1,4-diazinane
Piperazine
Pyrazine
Pyridine
Imidolactam
Tertiary carboxylic acid amide
Heteroaromatic compound
Carbamic acid ester
Carboxamide group
Lactam
Carbonic acid derivative
Amino acid or derivatives
Secondary aliphatic amine
Carboxylic acid derivative
Azacycle
Secondary amine
Organonitrogen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Carbonyl group
Organopnictogen compound
Organooxygen compound
Organic oxygen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (HMDB: HMDB0060541)

Non-excretory biofluid

Blood (HMDB: HMDB0060541)

Organ

Kidney (HMDB: HMDB0060541)
Liver (HMDB: HMDB0060541)

Cellular substructure

Cytoplasm (HMDB: HMDB0060541)

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	0.28 g/L	ALOGPS
logP	0.66	ALOGPS
logP	0.42	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	13.04	ChemAxon
pKa (Strongest Basic)	7.81	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	100.55 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	90.59 m³·mol⁻¹	ChemAxon
Polarizability	36.07 Å³	ChemAxon
Number of Rings	4	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
DeepCCS	[M+H]+	177.107	30932474
DeepCCS	[M-H]-	174.749	30932474
DeepCCS	[M-2H]-	208.641	30932474
DeepCCS	[M+Na]+	183.868	30932474
AllCCS	[M+H]+	183.1	32859911
AllCCS	[M+H-H2O]+	180.2	32859911
AllCCS	[M+NH4]+	185.7	32859911
AllCCS	[M+Na]+	186.5	32859911
AllCCS	[M-H]-	181.6	32859911
AllCCS	[M+Na-2H]-	181.2	32859911
AllCCS	[M+HCOO]-	180.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Desmethylzopiclone	ClC1=CN=C(C=C1)N1C(OC(=O)N2CCNCC2)C2=NC=CN=C2C1=O	3789.4	Standard polar	33892256
N-Desmethylzopiclone	ClC1=CN=C(C=C1)N1C(OC(=O)N2CCNCC2)C2=NC=CN=C2C1=O	3246.7	Standard non polar	33892256
N-Desmethylzopiclone	ClC1=CN=C(C=C1)N1C(OC(=O)N2CCNCC2)C2=NC=CN=C2C1=O	3317.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Desmethylzopiclone,1TMS,isomer #1	C[Si](C)(C)N1CCN(C(=O)OC2C3=NC=CN=C3C(=O)N2C2=CC=C(Cl)C=N2)CC1	3350.7	Semi standard non polar	33892256
N-Desmethylzopiclone,1TMS,isomer #1	C[Si](C)(C)N1CCN(C(=O)OC2C3=NC=CN=C3C(=O)N2C2=CC=C(Cl)C=N2)CC1	3224.0	Standard non polar	33892256
N-Desmethylzopiclone,1TMS,isomer #1	C[Si](C)(C)N1CCN(C(=O)OC2C3=NC=CN=C3C(=O)N2C2=CC=C(Cl)C=N2)CC1	4952.8	Standard polar	33892256
N-Desmethylzopiclone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN(C(=O)OC2C3=NC=CN=C3C(=O)N2C2=CC=C(Cl)C=N2)CC1	3598.6	Semi standard non polar	33892256
N-Desmethylzopiclone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN(C(=O)OC2C3=NC=CN=C3C(=O)N2C2=CC=C(Cl)C=N2)CC1	3426.5	Standard non polar	33892256
N-Desmethylzopiclone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN(C(=O)OC2C3=NC=CN=C3C(=O)N2C2=CC=C(Cl)C=N2)CC1	5106.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Desmethylzopiclone GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-9221000000-bac00f00e0fd84e4b734	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Desmethylzopiclone 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 - N-Desmethylzopiclone 10V, Positive-QTOF	splash10-004i-4009000000-0bd32a220eccfabc0126	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylzopiclone 20V, Positive-QTOF	splash10-01p9-9623000000-d00b24de9560b1910ba9	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylzopiclone 40V, Positive-QTOF	splash10-0006-9000000000-c2ff50fc31cfa50fa58c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylzopiclone 10V, Negative-QTOF	splash10-00di-1309000000-fe6e6da79332282a7e77	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylzopiclone 20V, Negative-QTOF	splash10-03di-1901000000-f960fa539500241fdeb8	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylzopiclone 40V, Negative-QTOF	splash10-004l-9400000000-a605fd0ca597cae6491a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylzopiclone 10V, Positive-QTOF	splash10-004i-0009000000-1745c0eb8ad1b7c20787	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylzopiclone 20V, Positive-QTOF	splash10-004j-0049000000-999e4aec6f0509f6599f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylzopiclone 40V, Positive-QTOF	splash10-03xs-1590000000-1898e6c956935565949c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylzopiclone 10V, Negative-QTOF	splash10-00di-0019000000-9ed3ed02820f337f2caa	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylzopiclone 20V, Negative-QTOF	splash10-0002-0292000000-1e119fa7a0c19851dc0c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylzopiclone 40V, Negative-QTOF	splash10-0r0s-6972000000-744fce9062b8a62139f3	2021-10-12	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

162892

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 N-Desmethylzopiclone (HMDB0060541)

MOL for HMDB0060541 (N-Desmethylzopiclone)

3D MOL for HMDB0060541 (N-Desmethylzopiclone)

3D SDF for HMDB0060541 (N-Desmethylzopiclone)

3D-SDF for HMDB0060541 (N-Desmethylzopiclone)

PDB for HMDB0060541 (N-Desmethylzopiclone)

3D PDB for HMDB0060541 (N-Desmethylzopiclone)

SMILES for HMDB0060541 (N-Desmethylzopiclone)

INCHI for HMDB0060541 (N-Desmethylzopiclone)

Structure for HMDB0060541 (N-Desmethylzopiclone)

3D Structure for HMDB0060541 (N-Desmethylzopiclone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra