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enzymes (10) Show 10 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 02:51:56 UTC

HMDB ID

HMDB0015329

Secondary Accession Numbers

HMDB15329

Metabolite Identification

Common Name

Zopiclone

Description

Zopiclone is only found in individuals that have used or taken this drug. It is a novel hypnotic agent used in the treatment of insomnia. Its mechanism of action is based on modulating benzodiazepine receptors. In addition to zopiclone's benzodiazepine pharmacological properties it also has some barbiturate like properties. Zopiclone exerts its action by binding on the benzodiazepine receptor complex and modulation of the GABA_BZ receptor chloride channel macromolecular complex. Both zopiclone and benzodiazepines act indiscriminately at the benzodiazepine binding site on α1, α2, α3 and α5 GABA_A containing receptors as full agonists causing an enhancement of the inhibitory actions of GABA to produce the therapeutic (hypnotic and anxiolytic) and adverse effects of zopiclone.

Structure

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

1198
  Mrv1652305271900332D          

 27 30  0  0  1  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
    4.5902    3.3235    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
    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
  1 27  1  0  0  0  0
  2 15  1  0  0  0  0
  2 16  1  0  0  0  0
  3 16  2  0  0  0  0
  4 20  2  0  0  0  0
  5 11  1  0  0  0  0
  5 12  1  0  0  0  0
  5 16  1  0  0  0  0
  6 13  1  0  0  0  0
  6 14  1  0  0  0  0
  6 17  1  0  0  0  0
  7 15  1  0  0  0  0
  7 20  1  0  0  0  0
  7 21  1  0  0  0  0
  8 18  2  0  0  0  0
  8 23  1  0  0  0  0
  9 19  2  0  0  0  0
  9 24  1  0  0  0  0
 10 21  2  0  0  0  0
 10 26  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 22 25  2  0  0  0  0
 23 24  2  0  0  0  0
 25 27  1  0  0  0  0
 26 27  2  0  0  0  0
M  END

HMDB0015329
     RDKit          3D
Zopiclone
 44 47  0  0  0  0  0  0  0  0999 V2000
   -5.6752    0.9957    0.7216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3925    0.5568    0.1983 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9667    1.5439   -0.7671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6922    1.1063   -1.4311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7359    0.6026   -0.4623 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5714   -0.0725   -0.8901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3711   -0.2223   -2.1297 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3969   -0.5979   -0.0478 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5352   -1.2535   -0.5901 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6151   -2.6657   -0.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7879   -3.7328   -0.2677 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1855   -4.9377    0.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4382   -5.1563    0.6595 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2765   -4.1149    0.7258 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8674   -2.9034    0.2990 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6135   -1.6619    0.3149 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8187   -1.4953    0.7214 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7604   -0.6581   -0.2052 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1441    0.7314   -0.2919 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0779    1.3150    0.5298 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4076    2.6604    0.4039 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7784    3.4015   -0.5640 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1726    5.0921   -0.7468 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.8500    2.8031   -1.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5706    1.5089   -1.2115 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0459    0.8360    0.9382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4309    0.3228    1.2488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2521    0.1722    1.1667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5599    1.8451    1.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2674    1.3962   -0.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8516    2.5365   -0.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7459    1.5649   -1.5580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2352    1.9561   -1.9989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9095    0.2885   -2.1502 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4882   -1.2428   -1.7187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5245   -5.8166    0.1147 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7941   -6.1186    1.0101 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5646    0.7405    1.2803 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1309    3.1393    1.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3438    3.3718   -2.1450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9700    1.9121    1.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3465    0.2953    1.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7736    0.7279    2.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3492   -0.7730    1.3952 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
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  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
 16 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
  5 26  1  0
 26 27  1  0
 27  2  1  0
 18  9  1  0
 25 19  1  0
 15 10  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  9 35  1  0
 12 36  1  0
 13 37  1  0
 20 38  1  0
 21 39  1  0
 24 40  1  0
 26 41  1  0
 26 42  1  0
 27 43  1  0
 27 44  1  0
M  END

1198
  Mrv1652305271900332D          

 27 30  0  0  1  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
    4.5902    3.3235    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
    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
  1 27  1  0  0  0  0
  2 15  1  0  0  0  0
  2 16  1  0  0  0  0
  3 16  2  0  0  0  0
  4 20  2  0  0  0  0
  5 11  1  0  0  0  0
  5 12  1  0  0  0  0
  5 16  1  0  0  0  0
  6 13  1  0  0  0  0
  6 14  1  0  0  0  0
  6 17  1  0  0  0  0
  7 15  1  0  0  0  0
  7 20  1  0  0  0  0
  7 21  1  0  0  0  0
  8 18  2  0  0  0  0
  8 23  1  0  0  0  0
  9 19  2  0  0  0  0
  9 24  1  0  0  0  0
 10 21  2  0  0  0  0
 10 26  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 22 25  2  0  0  0  0
 23 24  2  0  0  0  0
 25 27  1  0  0  0  0
 26 27  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015329

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CCN(CC1)C(=O)OC1N(C(=O)C2=NC=CN=C12)C1=NC=C(Cl)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H17ClN6O3/c1-22-6-8-23(9-7-22)17(26)27-16-14-13(19-4-5-20-14)15(25)24(16)12-3-2-11(18)10-21-12/h2-5,10,16H,6-9H2,1H3

> <INCHI_KEY>
GBBSUAFBMRNDJC-UHFFFAOYSA-N

> <FORMULA>
C17H17ClN6O3

> <MOLECULAR_WEIGHT>
388.808

> <EXACT_MASS>
388.105066147

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
38.22177037333028

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <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 4-methylpiperazine-1-carboxylate

> <ALOGPS_LOGP>
0.97

> <JCHEM_LOGP>
0.5173320981742905

> <ALOGPS_LOGS>
-2.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.036712277413013

> <JCHEM_PKA_STRONGEST_BASIC>
6.855530816980658

> <JCHEM_POLAR_SURFACE_AREA>
91.76000000000002

> <JCHEM_REFRACTIVITY>
95.8855

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.85e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
zopiclone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015329
     RDKit          3D
Zopiclone
 44 47  0  0  0  0  0  0  0  0999 V2000
   -5.6752    0.9957    0.7216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3925    0.5568    0.1983 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9667    1.5439   -0.7671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6922    1.1063   -1.4311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7359    0.6026   -0.4623 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5714   -0.0725   -0.8901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3711   -0.2223   -2.1297 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3969   -0.5979   -0.0478 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5352   -1.2535   -0.5901 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6151   -2.6657   -0.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7879   -3.7328   -0.2677 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1855   -4.9377    0.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4382   -5.1563    0.6595 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2765   -4.1149    0.7258 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8674   -2.9034    0.2990 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6135   -1.6619    0.3149 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8187   -1.4953    0.7214 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7604   -0.6581   -0.2052 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1441    0.7314   -0.2919 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0779    1.3150    0.5298 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4076    2.6604    0.4039 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7784    3.4015   -0.5640 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1726    5.0921   -0.7468 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.8500    2.8031   -1.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5706    1.5089   -1.2115 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0459    0.8360    0.9382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4309    0.3228    1.2488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2521    0.1722    1.1667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5599    1.8451    1.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2674    1.3962   -0.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8516    2.5365   -0.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7459    1.5649   -1.5580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2352    1.9561   -1.9989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9095    0.2885   -2.1502 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4882   -1.2428   -1.7187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5245   -5.8166    0.1147 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7941   -6.1186    1.0101 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5646    0.7405    1.2803 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1309    3.1393    1.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3438    3.3718   -2.1450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9700    1.9121    1.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3465    0.2953    1.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7736    0.7279    2.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3492   -0.7730    1.3952 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
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  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
 16 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
  5 26  1  0
 26 27  1  0
 27  2  1  0
 18  9  1  0
 25 19  1  0
 15 10  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  9 35  1  0
 12 36  1  0
 13 37  1  0
 20 38  1  0
 21 39  1  0
 24 40  1  0
 26 41  1  0
 26 42  1  0
 27 43  1  0
 27 44  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1198                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         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       8.568   6.204   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.748  -2.731   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.748  -4.271   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.205  -4.740   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.644  -3.501   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.414  -2.167   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.080  -2.731   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.080  -4.271   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.954  -2.167   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.954  -4.834   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.724  -3.501   0.000  0.00  0.00           C+0
CONECT    1   27                                                            
CONECT    2   15   16                                                       
CONECT    3   16                                                            
CONECT    4   20                                                            
CONECT    5   11   12   16                                                  
CONECT    6   13   14   17                                                  
CONECT    7   15   20   21                                                  
CONECT    8   18   23                                                       
CONECT    9   19   24                                                       
CONECT   10   21   26                                                       
CONECT   11    5   13                                                       
CONECT   12    5   14                                                       
CONECT   13    6   11                                                       
CONECT   14    6   12                                                       
CONECT   15    2    7   18                                                  
CONECT   16    2    3    5                                                  
CONECT   17    6                                                            
CONECT   18    8   15   19                                                  
CONECT   19    9   18   20                                                  
CONECT   20    4    7   19                                                  
CONECT   21    7   10   22                                                  
CONECT   22   21   25                                                       
CONECT   23    8   24                                                       
CONECT   24    9   23                                                       
CONECT   25   22   27                                                       
CONECT   26   10   27                                                       
CONECT   27    1   25   26                                                  
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

COMPND    HMDB0015329
HETATM    1  C1  UNL     1      -5.675   0.996   0.722  1.00  0.00           C  
HETATM    2  N1  UNL     1      -4.392   0.557   0.198  1.00  0.00           N  
HETATM    3  C2  UNL     1      -3.967   1.544  -0.767  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.692   1.106  -1.431  1.00  0.00           C  
HETATM    5  N2  UNL     1      -1.736   0.603  -0.462  1.00  0.00           N  
HETATM    6  C4  UNL     1      -0.571  -0.072  -0.890  1.00  0.00           C  
HETATM    7  O1  UNL     1      -0.371  -0.222  -2.130  1.00  0.00           O  
HETATM    8  O2  UNL     1       0.397  -0.598  -0.048  1.00  0.00           O  
HETATM    9  C5  UNL     1       1.535  -1.254  -0.590  1.00  0.00           C  
HETATM   10  C6  UNL     1       1.615  -2.666  -0.212  1.00  0.00           C  
HETATM   11  N3  UNL     1       0.788  -3.733  -0.268  1.00  0.00           N  
HETATM   12  C7  UNL     1       1.186  -4.938   0.154  1.00  0.00           C  
HETATM   13  C8  UNL     1       2.438  -5.156   0.660  1.00  0.00           C  
HETATM   14  N4  UNL     1       3.277  -4.115   0.726  1.00  0.00           N  
HETATM   15  C9  UNL     1       2.867  -2.903   0.299  1.00  0.00           C  
HETATM   16  C10 UNL     1       3.613  -1.662   0.315  1.00  0.00           C  
HETATM   17  O3  UNL     1       4.819  -1.495   0.721  1.00  0.00           O  
HETATM   18  N5  UNL     1       2.760  -0.658  -0.205  1.00  0.00           N  
HETATM   19  C11 UNL     1       3.144   0.731  -0.292  1.00  0.00           C  
HETATM   20  C12 UNL     1       4.078   1.315   0.530  1.00  0.00           C  
HETATM   21  C13 UNL     1       4.408   2.660   0.404  1.00  0.00           C  
HETATM   22  C14 UNL     1       3.778   3.402  -0.564  1.00  0.00           C  
HETATM   23 CL1  UNL     1       4.173   5.092  -0.747  1.00  0.00          CL  
HETATM   24  C15 UNL     1       2.850   2.803  -1.375  1.00  0.00           C  
HETATM   25  N6  UNL     1       2.571   1.509  -1.211  1.00  0.00           N  
HETATM   26  C16 UNL     1      -2.046   0.836   0.938  1.00  0.00           C  
HETATM   27  C17 UNL     1      -3.431   0.323   1.249  1.00  0.00           C  
HETATM   28  H1  UNL     1      -6.252   0.172   1.167  1.00  0.00           H  
HETATM   29  H2  UNL     1      -5.560   1.845   1.449  1.00  0.00           H  
HETATM   30  H3  UNL     1      -6.267   1.396  -0.127  1.00  0.00           H  
HETATM   31  H4  UNL     1      -3.852   2.537  -0.314  1.00  0.00           H  
HETATM   32  H5  UNL     1      -4.746   1.565  -1.558  1.00  0.00           H  
HETATM   33  H6  UNL     1      -2.235   1.956  -1.999  1.00  0.00           H  
HETATM   34  H7  UNL     1      -2.910   0.288  -2.150  1.00  0.00           H  
HETATM   35  H8  UNL     1       1.488  -1.243  -1.719  1.00  0.00           H  
HETATM   36  H9  UNL     1       0.525  -5.817   0.115  1.00  0.00           H  
HETATM   37  H10 UNL     1       2.794  -6.119   1.010  1.00  0.00           H  
HETATM   38  H11 UNL     1       4.565   0.740   1.280  1.00  0.00           H  
HETATM   39  H12 UNL     1       5.131   3.139   1.032  1.00  0.00           H  
HETATM   40  H13 UNL     1       2.344   3.372  -2.145  1.00  0.00           H  
HETATM   41  H14 UNL     1      -1.970   1.912   1.200  1.00  0.00           H  
HETATM   42  H15 UNL     1      -1.347   0.295   1.618  1.00  0.00           H  
HETATM   43  H16 UNL     1      -3.774   0.728   2.225  1.00  0.00           H  
HETATM   44  H17 UNL     1      -3.349  -0.773   1.395  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3   27
CONECT    3    4   31   32
CONECT    4    5   33   34
CONECT    5    6   26
CONECT    6    7    7    8
CONECT    8    9
CONECT    9   10   18   35
CONECT   10   11   11   15
CONECT   11   12
CONECT   12   13   13   36
CONECT   13   14   37
CONECT   14   15   15
CONECT   15   16
CONECT   16   17   17   18
CONECT   18   19
CONECT   19   20   20   25
CONECT   20   21   38
CONECT   21   22   22   39
CONECT   22   23   24
CONECT   24   25   25   40
CONECT   26   27   41   42
CONECT   27   43   44
END

HMDB0015329
     RDKit          3D
Zopiclone
 44 47  0  0  0  0  0  0  0  0999 V2000
   -5.6752    0.9957    0.7216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3925    0.5568    0.1983 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9667    1.5439   -0.7671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6922    1.1063   -1.4311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7359    0.6026   -0.4623 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5714   -0.0725   -0.8901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3711   -0.2223   -2.1297 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3969   -0.5979   -0.0478 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5352   -1.2535   -0.5901 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6151   -2.6657   -0.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7879   -3.7328   -0.2677 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1855   -4.9377    0.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4382   -5.1563    0.6595 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2765   -4.1149    0.7258 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8674   -2.9034    0.2990 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6135   -1.6619    0.3149 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8187   -1.4953    0.7214 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7604   -0.6581   -0.2052 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1441    0.7314   -0.2919 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0779    1.3150    0.5298 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4076    2.6604    0.4039 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7784    3.4015   -0.5640 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1726    5.0921   -0.7468 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.8500    2.8031   -1.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5706    1.5089   -1.2115 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0459    0.8360    0.9382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4309    0.3228    1.2488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2521    0.1722    1.1667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5599    1.8451    1.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2674    1.3962   -0.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8516    2.5365   -0.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7459    1.5649   -1.5580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2352    1.9561   -1.9989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9095    0.2885   -2.1502 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4882   -1.2428   -1.7187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5245   -5.8166    0.1147 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7941   -6.1186    1.0101 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5646    0.7405    1.2803 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1309    3.1393    1.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3438    3.3718   -2.1450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9700    1.9121    1.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3465    0.2953    1.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7736    0.7279    2.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3492   -0.7730    1.3952 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
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  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
 16 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
  5 26  1  0
 26 27  1  0
 27  2  1  0
 18  9  1  0
 25 19  1  0
 15 10  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  9 35  1  0
 12 36  1  0
 13 37  1  0
 20 38  1  0
 21 39  1  0
 24 40  1  0
 26 41  1  0
 26 42  1  0
 27 43  1  0
 27 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+-)-Zopiclone	ChEBI
6-(5-Chloro-2-pyridinyl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-yl 4-methyl-1-piperazinecarboxylate	ChEBI
Zopiclona	ChEBI
Zopiclonum	ChEBI
Amoban	Kegg
6-(5-Chloro-2-pyridinyl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-yl 4-methyl-1-piperazinecarboxylic acid	Generator
Limovan	HMDB
Nu-zopiclone	HMDB
Zileze	HMDB
Zimovane	HMDB
Zopicalm	HMDB
Zopiclon al	HMDB
Zopiclon stada	HMDB
Zopiclon tad	HMDB
Zopiclon-teva	HMDB
Zopiclon-neuraxpharm	HMDB
Zorclone	HMDB
Ratio-zopiclone	HMDB
Siaten	HMDB
Somnosan	HMDB
Ximovan	HMDB
Zopiclon azu	HMDB
Zopiclon abz	HMDB
Zopiclodura	HMDB
Rhovane	HMDB
Zimoclone	HMDB
Zopiclon beta	HMDB
Zopitan	HMDB
6-(5-Chloro-2-pyridyl)-6,7-dihydro- 7-oxo-5H-pyrrolo(3,4-b)pyrazin-5-yl 4-methyl-1- piperazinecarboxylate	HMDB
Imovane	HMDB
Optidorm	HMDB
Zop	HMDB
Zopi-puren	HMDB
Zopicalma	HMDB
Zopiclon-ratiopharm	HMDB
Zopiclon von CT	HMDB

Chemical Formula

C₁₇H₁₇ClN₆O₃

Average Molecular Weight

388.808

Monoisotopic Molecular Weight

388.105066147

IUPAC Name

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

Traditional Name

zopiclone

CAS Registry Number

43200-80-2

SMILES

CN1CCN(CC1)C(=O)OC1N(C(=O)C2=NC=CN=C12)C1=NC=C(Cl)C=C1

InChI Identifier

InChI=1S/C17H17ClN6O3/c1-22-6-8-23(9-7-22)17(26)27-16-14-13(19-4-5-20-14)15(25)24(16)12-3-2-11(18)10-21-12/h2-5,10,16H,6-9H2,1H3

InChI Key

GBBSUAFBMRNDJC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thienothiazines. These are heterocyclic compounds containing a thiophene ring fused to a thiazine. Thiophene is 5-membered ring consisting of four carbon atoms and one sulfur atom. Thiazine is a 6-membered ring consisting of four carbon, one nitrogen and one sulfur atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Thienothiazines

Sub Class

Not Available

Direct Parent

Thienothiazines

Alternative Parents

Substituents

Thienothiazine
2,3,5-trisubstituted thiophene
Aralkylamine
Ortho-thiazine
Organosulfonic acid amide
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Sulfonyl
Heteroaromatic compound
Aminosulfonyl compound
Thiophene
Dialkyl ether
Secondary aliphatic amine
Ether
Secondary amine
Azacycle
Organic nitrogen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

sulfonamide (CHEBI:41212 )
thienothiazine (CHEBI:41212 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

central nervous system depressant (HMDB: HMDB0015329)
sedative (HMDB: HMDB0015329)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	178 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.88 g/L	Not Available
LogP	0.8	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	188.5	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.88 g/L	ALOGPS
logP	0.97	ALOGPS
logP	0.52	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	8.04	ChemAxon
pKa (Strongest Basic)	6.86	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	91.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	95.89 m³·mol⁻¹	ChemAxon
Polarizability	38.22 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-2H]-	219.504	30932474
DeepCCS	[M+Na]+	194.733	30932474
AllCCS	[M+H]+	187.1	32859911
AllCCS	[M+H-H2O]+	184.3	32859911
AllCCS	[M+NH4]+	189.6	32859911
AllCCS	[M+Na]+	190.3	32859911
AllCCS	[M-H]-	186.1	32859911
AllCCS	[M+Na-2H]-	186.0	32859911
AllCCS	[M+HCOO]-	185.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Zopiclone	CN1CCN(CC1)C(=O)OC1N(C(=O)C2=NC=CN=C12)C1=NC=C(Cl)C=C1	3800.4	Standard polar	33892256
Zopiclone	CN1CCN(CC1)C(=O)OC1N(C(=O)C2=NC=CN=C12)C1=NC=C(Cl)C=C1	3236.6	Standard non polar	33892256
Zopiclone	CN1CCN(CC1)C(=O)OC1N(C(=O)C2=NC=CN=C12)C1=NC=C(Cl)C=C1	3226.6	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 - Zopiclone GC-MS (Non-derivatized) - 70eV, Positive	splash10-05bb-9212000000-b3e4c2874ff86d2544e1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zopiclone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0007-6950000000-c1583a92e3cbc5066186	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 - Zopiclone LC-ESI-QTOF , positive-QTOF	splash10-00kb-0090000000-9d80e08080f406848221	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zopiclone LC-ESI-QFT , positive-QTOF	splash10-0002-0092000000-977d45f9a516242be80f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zopiclone LC-ESI-QFT , positive-QTOF	splash10-0002-0090000000-397a508c11f66c161327	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zopiclone LC-ESI-QFT , positive-QTOF	splash10-014j-0090000000-abc6a676659114a83d08	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zopiclone LC-ESI-QFT , positive-QTOF	splash10-014i-0790000000-74d7c73e854e61700433	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zopiclone LC-ESI-QFT , positive-QTOF	splash10-00lr-0920000000-2c17f6282d1031cb4d50	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zopiclone LC-ESI-QFT , positive-QTOF	splash10-001i-0900000000-c0f92aba9374337ff737	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zopiclone LC-ESI-QFT , positive-QTOF	splash10-003r-5900000000-46755df8b5cfb7f46bf9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zopiclone LC-ESI-QFT , positive-QTOF	splash10-004i-9300000000-091d5434bc674d5bf9a4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zopiclone LC-ESI-QFT , positive-QTOF	splash10-004i-9000000000-87365fa01fb0854897ca	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zopiclone 45V, Positive-QTOF	splash10-014j-0090000000-10c3fa2d80a8abbefd55	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zopiclone 30V, Positive-QTOF	splash10-0002-0090000000-1867bce03fb895923ceb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zopiclone 60V, Positive-QTOF	splash10-014i-0790000000-462830e768acf8704d81	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zopiclone 75V, Positive-QTOF	splash10-00lr-0920000000-6c00112af341c07aba1b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zopiclone 15V, Positive-QTOF	splash10-0002-0092000000-b9948d590c2d56a477e8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zopiclone -1V, Positive-QTOF	splash10-00kb-0090000000-66a3d681838796c245d3	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zopiclone 10V, Positive-QTOF	splash10-000i-0009000000-58198ad5b8e6fb5075fc	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zopiclone 20V, Positive-QTOF	splash10-004i-5917000000-fed7a3a68ceccd2f26be	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zopiclone 40V, Positive-QTOF	splash10-0ac0-9000000000-ef1623aed48bd5073d7b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zopiclone 10V, Negative-QTOF	splash10-000i-0309000000-e2a958d8569e44198c06	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zopiclone 20V, Negative-QTOF	splash10-004i-1901000000-d74484c0d625330ab7cd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zopiclone 40V, Negative-QTOF	splash10-056r-9510000000-15dec99e5a9537957558	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zopiclone 10V, Positive-QTOF	splash10-000i-0009000000-8fbf9af9d2708ba6bc8c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zopiclone 20V, Positive-QTOF	splash10-000j-0049000000-0d0bcaed2a13fc359e64	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zopiclone 40V, Positive-QTOF	splash10-03e9-2695000000-54c5cabfed200237305e	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

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 DB01198	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01198	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

DB01198

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5533

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Zopiclone

METLIN ID

Not Available

PubChem Compound

5735

PDB ID

Not Available

ChEBI ID

32315

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

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 ]
Liu HJ, Sato K, Shih HC, Shibuya T, Kawamoto H, Kitagawa H: Pharmacologic studies of the central action of zopiclone: effects on locomotor activity and brain monoamines in rats. Int J Clin Pharmacol Ther Toxicol. 1985 Mar;23(3):121-8. [PubMed:2581904 ]
Sato K, Hong YL, Yang MS, Shibuya T, Kawamoto H, Kitagawa H: Pharmacologic studies of central actions of zopiclone: influence on brain monoamines in rats under stressful condition. Int J Clin Pharmacol Ther Toxicol. 1985 Apr;23(4):204-10. [PubMed:2860074 ]
Julou L, Bardone MC, Blanchard JC, Garret C, Stutzmann JM: Pharmacological studies on zopiclone. Pharmacology. 1983;27 Suppl 2:46-58. [PubMed:6142468 ]
Blanchard JC, Julou L: Suriclone: a new cyclopyrrolone derivative recognizing receptors labeled by benzodiazepines in rat hippocampus and cerebellum. J Neurochem. 1983 Mar;40(3):601-7. [PubMed:6298365 ]

Enzymes

Enzyme Details

1. Prostaglandin G/H synthase 1

General function:: Involved in peroxidase activity
Specific function:: May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:: PTGS1
Uniprot ID:: P23219
Molecular weight:: 68685.82

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]

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

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
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 ]
Lalovic B, Phillips B, Risler LL, Howald W, Shen DD: Quantitative contribution of CYP2D6 and CYP3A to oxycodone metabolism in human liver and intestinal microsomes. Drug Metab Dispos. 2004 Apr;32(4):447-54. [PubMed:15039299 ]

Enzyme Details

3. Cytochrome P450 2C9

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. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
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

4. Cytochrome P450 2E1

General function:: Involved in monooxygenase activity
Specific function:: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:: CYP2E1
Uniprot ID:: P05181
Molecular weight:: 56848.42

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

5. Cytochrome P450 2C8

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. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:: CYP2C8
Uniprot ID:: P10632
Molecular weight:: 55824.275

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
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 ]
Lalovic B, Phillips B, Risler LL, Howald W, Shen DD: Quantitative contribution of CYP2D6 and CYP3A to oxycodone metabolism in human liver and intestinal microsomes. Drug Metab Dispos. 2004 Apr;32(4):447-54. [PubMed:15039299 ]

Enzyme Details

6. 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

7. 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

Nutt DJ, Stahl SM: Searching for perfect sleep: the continuing evolution of GABAA receptor modulators as hypnotics. J Psychopharmacol. 2010 Nov;24(11):1601-12. doi: 10.1177/0269881109106927. Epub 2009 Nov 26. [PubMed:19942638 ]
Hanson SM, Morlock EV, Satyshur KA, Czajkowski C: Structural requirements for eszopiclone and zolpidem binding to the gamma-aminobutyric acid type-A (GABAA) receptor are different. J Med Chem. 2008 Nov 27;51(22):7243-52. doi: 10.1021/jm800889m. [PubMed:18973287 ]
Sanger DJ: The pharmacology and mechanisms of action of new generation, non-benzodiazepine hypnotic agents. CNS Drugs. 2004;18 Suppl 1:9-15; discussion 41, 43-5. [PubMed:15291009 ]
Skerritt JH, Johnston GA: Enhancement of GABA binding by benzodiazepines and related anxiolytics. Eur J Pharmacol. 1983 May 6;89(3-4):193-8. [PubMed:6135616 ]
Ramerstorfer J, Furtmuller R, Vogel E, Huck S, Sieghart W: The point mutation gamma 2F77I changes the potency and efficacy of benzodiazepine site ligands in different GABAA receptor subtypes. Eur J Pharmacol. 2010 Jun 25;636(1-3):18-27. doi: 10.1016/j.ejphar.2010.03.015. Epub 2010 Mar 19. [PubMed:20303942 ]

Enzyme Details

8. Gamma-aminobutyric acid receptor subunit alpha-2

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:: GABRA2
Uniprot ID:: P47869
Molecular weight:: 51325.9

References

Nutt DJ, Stahl SM: Searching for perfect sleep: the continuing evolution of GABAA receptor modulators as hypnotics. J Psychopharmacol. 2010 Nov;24(11):1601-12. doi: 10.1177/0269881109106927. Epub 2009 Nov 26. [PubMed:19942638 ]
Hanson SM, Morlock EV, Satyshur KA, Czajkowski C: Structural requirements for eszopiclone and zolpidem binding to the gamma-aminobutyric acid type-A (GABAA) receptor are different. J Med Chem. 2008 Nov 27;51(22):7243-52. doi: 10.1021/jm800889m. [PubMed:18973287 ]
Ramerstorfer J, Furtmuller R, Vogel E, Huck S, Sieghart W: The point mutation gamma 2F77I changes the potency and efficacy of benzodiazepine site ligands in different GABAA receptor subtypes. Eur J Pharmacol. 2010 Jun 25;636(1-3):18-27. doi: 10.1016/j.ejphar.2010.03.015. Epub 2010 Mar 19. [PubMed:20303942 ]

Enzyme Details

9. Gamma-aminobutyric acid receptor subunit alpha-3

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:: GABRA3
Uniprot ID:: P34903
Molecular weight:: 55164.1

References

Nutt DJ, Stahl SM: Searching for perfect sleep: the continuing evolution of GABAA receptor modulators as hypnotics. J Psychopharmacol. 2010 Nov;24(11):1601-12. doi: 10.1177/0269881109106927. Epub 2009 Nov 26. [PubMed:19942638 ]
Hanson SM, Morlock EV, Satyshur KA, Czajkowski C: Structural requirements for eszopiclone and zolpidem binding to the gamma-aminobutyric acid type-A (GABAA) receptor are different. J Med Chem. 2008 Nov 27;51(22):7243-52. doi: 10.1021/jm800889m. [PubMed:18973287 ]
Ramerstorfer J, Furtmuller R, Vogel E, Huck S, Sieghart W: The point mutation gamma 2F77I changes the potency and efficacy of benzodiazepine site ligands in different GABAA receptor subtypes. Eur J Pharmacol. 2010 Jun 25;636(1-3):18-27. doi: 10.1016/j.ejphar.2010.03.015. Epub 2010 Mar 19. [PubMed:20303942 ]

Enzyme Details

10. Gamma-aminobutyric acid receptor subunit alpha-5

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:: GABRA5
Uniprot ID:: P31644
Molecular weight:: 52145.6

References

Nutt DJ, Stahl SM: Searching for perfect sleep: the continuing evolution of GABAA receptor modulators as hypnotics. J Psychopharmacol. 2010 Nov;24(11):1601-12. doi: 10.1177/0269881109106927. Epub 2009 Nov 26. [PubMed:19942638 ]
Hanson SM, Morlock EV, Satyshur KA, Czajkowski C: Structural requirements for eszopiclone and zolpidem binding to the gamma-aminobutyric acid type-A (GABAA) receptor are different. J Med Chem. 2008 Nov 27;51(22):7243-52. doi: 10.1021/jm800889m. [PubMed:18973287 ]
Skerritt JH, Johnston GA: Enhancement of GABA binding by benzodiazepines and related anxiolytics. Eur J Pharmacol. 1983 May 6;89(3-4):193-8. [PubMed:6135616 ]
Ramerstorfer J, Furtmuller R, Vogel E, Huck S, Sieghart W: The point mutation gamma 2F77I changes the potency and efficacy of benzodiazepine site ligands in different GABAA receptor subtypes. Eur J Pharmacol. 2010 Jun 25;636(1-3):18-27. doi: 10.1016/j.ejphar.2010.03.015. Epub 2010 Mar 19. [PubMed:20303942 ]

Showing metabocard for Zopiclone (HMDB0015329)

MOL for HMDB0015329 (Zopiclone)

3D MOL for HMDB0015329 (Zopiclone)

3D SDF for HMDB0015329 (Zopiclone)

3D-SDF for HMDB0015329 (Zopiclone)

PDB for HMDB0015329 (Zopiclone)

3D PDB for HMDB0015329 (Zopiclone)

SMILES for HMDB0015329 (Zopiclone)

INCHI for HMDB0015329 (Zopiclone)

Structure for HMDB0015329 (Zopiclone)

3D Structure for HMDB0015329 (Zopiclone)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References

References

References

References

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References