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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:06:26 UTC

Update Date

2019-07-23 07:15:21 UTC

HMDB ID

HMDB0060905

Secondary Accession Numbers

HMDB60905

Metabolite Identification

Common Name

Haloperidol 1,2,3,6-tetrahydropyridine

Description

Haloperidol 1,2,3,6-tetrahydropyridine belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. It is in the butyrophenone class of antipsychotic medications and has pharmacological effects similar to the phenothiazines. Haloperidol 1,2,3,6-tetrahydropyridine is a very strong basic compound (based on its pKa). Haloperidol 1,2,3,6-tetrahydropyridine is a metabolite of haloperidol. Haloperidol is a typical antipsychotic. Haloperidol is an older antipsychotic used in the treatment of schizophrenia and acute psychotic states and delirium.

Structure

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


  Mrv0541 07091309062D          

 25 27  0  0  0  0            999 V2000
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 13  1  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16  3  2  0  0  0  0
 16  4  1  0  0  0  0
 17 11  2  0  0  0  0
 17 12  1  0  0  0  0
 17 16  1  0  0  0  0
 18  5  2  0  0  0  0
 18  6  1  0  0  0  0
 19  7  2  0  0  0  0
 19  8  1  0  0  0  0
 20  9  2  0  0  0  0
 20 10  1  0  0  0  0
 21  2  1  0  0  0  0
 21 18  1  0  0  0  0
 22 19  1  0  0  0  0
 23 20  1  0  0  0  0
 24 13  1  0  0  0  0
 24 14  1  0  0  0  0
 24 15  1  0  0  0  0
 25 21  2  0  0  0  0
M  END

HMDB0060905
     RDKit          3D
Haloperidol 1,2,3,6-tetrahydropyridine
 46 48  0  0  0  0  0  0  0  0999 V2000
   -2.5728   -0.3410    2.2224 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2574   -0.4057    1.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2760   -1.6466    0.3781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0810   -1.7253   -0.5491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7781   -1.7099    0.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2897   -1.7868   -0.7040 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5334   -0.6770   -1.5530 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7016    0.1183   -1.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7457   -0.5059   -0.5696 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9101    0.2137   -0.0723 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9178    1.6084   -0.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0126    2.3366    0.4215 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1482    1.7017    0.8581 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5420    2.6289    1.4406 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.1621    0.3371    0.8282 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0683   -0.3826    0.3734 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7584   -1.9898   -0.4996 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3878   -2.6076   -0.3996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0186    0.7519    0.7509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9788    1.9250    1.5189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6818    3.0560    1.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4552    3.0675    0.0585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1575    4.1603   -0.3039 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5337    1.9243   -0.7485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8075    0.8053   -0.3673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2359   -2.5565    1.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1741   -1.7568   -0.2326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1297   -0.9358   -1.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1376   -2.7068   -1.0770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7355   -2.6129    0.8677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7241   -0.8448    0.9149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3567   -0.0564   -1.6603 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8430   -1.0745   -2.5460 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6145    1.1805   -1.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0511    2.1659   -0.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0134    3.4170    0.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0280   -0.2079    1.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1200   -1.4740    0.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2249   -2.3305   -1.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3915   -2.2860    0.3620 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3638   -3.5285   -1.0345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2791   -2.9929    0.6482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3714    1.9525    2.4175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6154    3.9477    1.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1474    1.9254   -1.6396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8804   -0.0813   -1.0160 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
  9 17  1  0
 17 18  1  0
  2 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
 18  6  1  0
 25 19  1  0
 16 10  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
 11 35  1  0
 12 36  1  0
 15 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 20 43  1  0
 21 44  1  0
 24 45  1  0
 25 46  1  0
M  END


  Mrv0541 07091309062D          

 25 27  0  0  0  0            999 V2000
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 13  1  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16  3  2  0  0  0  0
 16  4  1  0  0  0  0
 17 11  2  0  0  0  0
 17 12  1  0  0  0  0
 17 16  1  0  0  0  0
 18  5  2  0  0  0  0
 18  6  1  0  0  0  0
 19  7  2  0  0  0  0
 19  8  1  0  0  0  0
 20  9  2  0  0  0  0
 20 10  1  0  0  0  0
 21  2  1  0  0  0  0
 21 18  1  0  0  0  0
 22 19  1  0  0  0  0
 23 20  1  0  0  0  0
 24 13  1  0  0  0  0
 24 14  1  0  0  0  0
 24 15  1  0  0  0  0
 25 21  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060905

> <DATABASE_NAME>
hmdb

> <SMILES>
FC1=CC=C(C=C1)C(=O)CCCN1CCC(=CC1)C1=CC=C(Cl)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H21ClFNO/c22-19-7-3-16(4-8-19)17-11-14-24(15-12-17)13-1-2-21(25)18-5-9-20(23)10-6-18/h3-11H,1-2,12-15H2

> <INCHI_KEY>
ZNOLNAPJKOYTHY-UHFFFAOYSA-N

> <FORMULA>
C21H21ClFNO

> <MOLECULAR_WEIGHT>
357.849

> <EXACT_MASS>
357.129570211

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
39.54090511877288

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[4-(4-chlorophenyl)-1,2,3,6-tetrahydropyridin-1-yl]-1-(4-fluorophenyl)butan-1-one

> <ALOGPS_LOGP>
5.21

> <JCHEM_LOGP>
4.855062889666667

> <ALOGPS_LOGS>
-5.22

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.392231674337562

> <JCHEM_PKA_STRONGEST_BASIC>
7.9495404262729945

> <JCHEM_POLAR_SURFACE_AREA>
20.310000000000002

> <JCHEM_REFRACTIVITY>
101.84699999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.17e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[4-(4-chlorophenyl)-3,6-dihydro-2H-pyridin-1-yl]-1-(4-fluorophenyl)butan-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0060905
     RDKit          3D
Haloperidol 1,2,3,6-tetrahydropyridine
 46 48  0  0  0  0  0  0  0  0999 V2000
   -2.5728   -0.3410    2.2224 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2574   -0.4057    1.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2760   -1.6466    0.3781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0810   -1.7253   -0.5491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7781   -1.7099    0.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2897   -1.7868   -0.7040 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5334   -0.6770   -1.5530 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7016    0.1183   -1.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7457   -0.5059   -0.5696 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9101    0.2137   -0.0723 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9178    1.6084   -0.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0126    2.3366    0.4215 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1482    1.7017    0.8581 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5420    2.6289    1.4406 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.1621    0.3371    0.8282 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0683   -0.3826    0.3734 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7584   -1.9898   -0.4996 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3878   -2.6076   -0.3996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0186    0.7519    0.7509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9788    1.9250    1.5189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6818    3.0560    1.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4552    3.0675    0.0585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1575    4.1603   -0.3039 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5337    1.9243   -0.7485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8075    0.8053   -0.3673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2359   -2.5565    1.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1741   -1.7568   -0.2326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1297   -0.9358   -1.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1376   -2.7068   -1.0770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7355   -2.6129    0.8677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7241   -0.8448    0.9149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3567   -0.0564   -1.6603 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8430   -1.0745   -2.5460 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6145    1.1805   -1.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0511    2.1659   -0.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0134    3.4170    0.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0280   -0.2079    1.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1200   -1.4740    0.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2249   -2.3305   -1.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3915   -2.2860    0.3620 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3638   -3.5285   -1.0345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2791   -2.9929    0.6482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3714    1.9525    2.4175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6154    3.9477    1.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1474    1.9254   -1.6396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8804   -0.0813   -1.0160 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
  9 17  1  0
 17 18  1  0
  2 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
 18  6  1  0
 25 19  1  0
 16 10  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
 11 35  1  0
 12 36  1  0
 15 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 20 43  1  0
 21 44  1  0
 24 45  1  0
 25 46  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       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.671  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.004   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.671   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.004   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   22 Cl   UNK     0      17.338   2.310   0.000  0.00  0.00          Cl+0
HETATM   23  F   UNK     0      -1.334  -5.390   0.000  0.00  0.00           F+0
HETATM   24  N   UNK     0       9.336  -2.310   0.000  0.00  0.00           N+0
HETATM   25  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2   13                                                       
CONECT    2    1   21                                                       
CONECT    3    7   16                                                       
CONECT    4    8   16                                                       
CONECT    5    9   18                                                       
CONECT    6   10   18                                                       
CONECT    7    3   19                                                       
CONECT    8    4   19                                                       
CONECT    9    5   20                                                       
CONECT   10    6   20                                                       
CONECT   11   14   17                                                       
CONECT   12   15   17                                                       
CONECT   13    1   24                                                       
CONECT   14   11   24                                                       
CONECT   15   12   24                                                       
CONECT   16    3    4   17                                                  
CONECT   17   11   12   16                                                  
CONECT   18    5    6   21                                                  
CONECT   19    7    8   22                                                  
CONECT   20    9   10   23                                                  
CONECT   21    2   18   25                                                  
CONECT   22   19                                                            
CONECT   23   20                                                            
CONECT   24   13   14   15                                                  
CONECT   25   21                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0060905
HETATM    1  O1  UNL     1      -2.573  -0.341   2.222  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.257  -0.406   1.168  1.00  0.00           C  
HETATM    3  C2  UNL     1      -3.276  -1.647   0.378  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.081  -1.725  -0.549  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.778  -1.710   0.214  1.00  0.00           C  
HETATM    6  N1  UNL     1       0.290  -1.787  -0.704  1.00  0.00           N  
HETATM    7  C5  UNL     1       0.533  -0.677  -1.553  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.702   0.118  -1.056  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.746  -0.506  -0.570  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.910   0.214  -0.072  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.918   1.608  -0.034  1.00  0.00           C  
HETATM   12  C10 UNL     1       5.013   2.337   0.422  1.00  0.00           C  
HETATM   13  C11 UNL     1       6.148   1.702   0.858  1.00  0.00           C  
HETATM   14 CL1  UNL     1       7.542   2.629   1.441  1.00  0.00          CL  
HETATM   15  C12 UNL     1       6.162   0.337   0.828  1.00  0.00           C  
HETATM   16  C13 UNL     1       5.068  -0.383   0.373  1.00  0.00           C  
HETATM   17  C14 UNL     1       2.758  -1.990  -0.500  1.00  0.00           C  
HETATM   18  C15 UNL     1       1.388  -2.608  -0.400  1.00  0.00           C  
HETATM   19  C16 UNL     1      -4.019   0.752   0.751  1.00  0.00           C  
HETATM   20  C17 UNL     1      -3.979   1.925   1.519  1.00  0.00           C  
HETATM   21  C18 UNL     1      -4.682   3.056   1.179  1.00  0.00           C  
HETATM   22  C19 UNL     1      -5.455   3.067   0.058  1.00  0.00           C  
HETATM   23  F1  UNL     1      -6.158   4.160  -0.304  1.00  0.00           F  
HETATM   24  C20 UNL     1      -5.534   1.924  -0.748  1.00  0.00           C  
HETATM   25  C21 UNL     1      -4.808   0.805  -0.367  1.00  0.00           C  
HETATM   26  H1  UNL     1      -3.236  -2.557   1.029  1.00  0.00           H  
HETATM   27  H2  UNL     1      -4.174  -1.757  -0.233  1.00  0.00           H  
HETATM   28  H3  UNL     1      -2.130  -0.936  -1.295  1.00  0.00           H  
HETATM   29  H4  UNL     1      -2.138  -2.707  -1.077  1.00  0.00           H  
HETATM   30  H5  UNL     1      -0.736  -2.613   0.868  1.00  0.00           H  
HETATM   31  H6  UNL     1      -0.724  -0.845   0.915  1.00  0.00           H  
HETATM   32  H7  UNL     1      -0.357  -0.056  -1.660  1.00  0.00           H  
HETATM   33  H8  UNL     1       0.843  -1.075  -2.546  1.00  0.00           H  
HETATM   34  H9  UNL     1       1.614   1.181  -1.130  1.00  0.00           H  
HETATM   35  H10 UNL     1       3.051   2.166  -0.361  1.00  0.00           H  
HETATM   36  H11 UNL     1       5.013   3.417   0.449  1.00  0.00           H  
HETATM   37  H12 UNL     1       7.028  -0.208   1.160  1.00  0.00           H  
HETATM   38  H13 UNL     1       5.120  -1.474   0.356  1.00  0.00           H  
HETATM   39  H14 UNL     1       3.225  -2.330  -1.447  1.00  0.00           H  
HETATM   40  H15 UNL     1       3.391  -2.286   0.362  1.00  0.00           H  
HETATM   41  H16 UNL     1       1.364  -3.529  -1.034  1.00  0.00           H  
HETATM   42  H17 UNL     1       1.279  -2.993   0.648  1.00  0.00           H  
HETATM   43  H18 UNL     1      -3.371   1.952   2.417  1.00  0.00           H  
HETATM   44  H19 UNL     1      -4.615   3.948   1.814  1.00  0.00           H  
HETATM   45  H20 UNL     1      -6.147   1.925  -1.640  1.00  0.00           H  
HETATM   46  H21 UNL     1      -4.880  -0.081  -1.016  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   19
CONECT    3    4   26   27
CONECT    4    5   28   29
CONECT    5    6   30   31
CONECT    6    7   18
CONECT    7    8   32   33
CONECT    8    9    9   34
CONECT    9   10   17
CONECT   10   11   11   16
CONECT   11   12   35
CONECT   12   13   13   36
CONECT   13   14   15
CONECT   15   16   16   37
CONECT   16   38
CONECT   17   18   39   40
CONECT   18   41   42
CONECT   19   20   20   25
CONECT   20   21   43
CONECT   21   22   22   44
CONECT   22   23   24
CONECT   24   25   25   45
CONECT   25   46
END

HMDB0060905
     RDKit          3D
Haloperidol 1,2,3,6-tetrahydropyridine
 46 48  0  0  0  0  0  0  0  0999 V2000
   -2.5728   -0.3410    2.2224 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2574   -0.4057    1.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2760   -1.6466    0.3781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0810   -1.7253   -0.5491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7781   -1.7099    0.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2897   -1.7868   -0.7040 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5334   -0.6770   -1.5530 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7016    0.1183   -1.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7457   -0.5059   -0.5696 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9101    0.2137   -0.0723 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9178    1.6084   -0.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0126    2.3366    0.4215 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1482    1.7017    0.8581 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5420    2.6289    1.4406 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.1621    0.3371    0.8282 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0683   -0.3826    0.3734 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7584   -1.9898   -0.4996 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3878   -2.6076   -0.3996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0186    0.7519    0.7509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9788    1.9250    1.5189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6818    3.0560    1.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4552    3.0675    0.0585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1575    4.1603   -0.3039 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5337    1.9243   -0.7485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8075    0.8053   -0.3673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2359   -2.5565    1.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1741   -1.7568   -0.2326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1297   -0.9358   -1.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1376   -2.7068   -1.0770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7355   -2.6129    0.8677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7241   -0.8448    0.9149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3567   -0.0564   -1.6603 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8430   -1.0745   -2.5460 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6145    1.1805   -1.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0511    2.1659   -0.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0134    3.4170    0.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0280   -0.2079    1.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1200   -1.4740    0.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2249   -2.3305   -1.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3915   -2.2860    0.3620 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3638   -3.5285   -1.0345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2791   -2.9929    0.6482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3714    1.9525    2.4175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6154    3.9477    1.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1474    1.9254   -1.6396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8804   -0.0813   -1.0160 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
  9 17  1  0
 17 18  1  0
  2 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
 18  6  1  0
 25 19  1  0
 16 10  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
 11 35  1  0
 12 36  1  0
 15 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 20 43  1  0
 21 44  1  0
 24 45  1  0
 25 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4(4-Chlorophenyl)-1-(4-(4-fluorophenyl)-4-oxobutyl)-1,2,3,6-tetrahydropyridine	HMDB
4(4-Chlorophenyl)-1-(4-(4-fluorophenyl)-4-oxobutyl)-1,2,3,6-tetrahydropyridine hydrochloride	HMDB
4-(4-Chlorophenyl)-1-(4-(4--fluorophenyl)-4-oxobutyl)-1,2,3,6-tetrahydropyridine	HMDB

Chemical Formula

C₂₁H₂₁ClFNO

Average Molecular Weight

357.849

Monoisotopic Molecular Weight

357.129570211

IUPAC Name

4-[4-(4-chlorophenyl)-1,2,3,6-tetrahydropyridin-1-yl]-1-(4-fluorophenyl)butan-1-one

Traditional Name

4-[4-(4-chlorophenyl)-3,6-dihydro-2H-pyridin-1-yl]-1-(4-fluorophenyl)butan-1-one

CAS Registry Number

Not Available

SMILES

FC1=CC=C(C=C1)C(=O)CCCN1CCC(=CC1)C1=CC=C(Cl)C=C1

InChI Identifier

InChI=1S/C21H21ClFNO/c22-19-7-3-16(4-8-19)17-11-14-24(15-12-17)13-1-2-21(25)18-5-9-20(23)10-6-18/h3-11H,1-2,12-15H2

InChI Key

ZNOLNAPJKOYTHY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Butyrophenone
Phenylbutylamine
Benzoyl
Aryl alkyl ketone
Chlorobenzene
Fluorobenzene
Halobenzene
Aryl chloride
Aryl fluoride
Aryl halide
Benzenoid
Monocyclic benzene moiety
Gamma-aminoketone
Hydropyridine
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Azacycle
Organofluoride
Organonitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organic nitrogen compound
Amine
Organic oxide
Organochloride
Organohalogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0060905)
Liver (HMDB: HMDB0060905)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060905)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060905)

Cellular substructure

Cytoplasm (HMDB: HMDB0060905)
Membrane (HMDB: HMDB0060905)

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	0.0022 g/L	ALOGPS
logP	5.21	ALOGPS
logP	4.86	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	16.39	ChemAxon
pKa (Strongest Basic)	7.95	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	20.31 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	101.85 m³·mol⁻¹	ChemAxon
Polarizability	39.54 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	184.936	30932474
DeepCCS	[M-H]-	182.578	30932474
DeepCCS	[M-2H]-	216.617	30932474
DeepCCS	[M+Na]+	191.969	30932474
AllCCS	[M+H]+	184.9	32859911
AllCCS	[M+H-H2O]+	182.0	32859911
AllCCS	[M+NH4]+	187.5	32859911
AllCCS	[M+Na]+	188.3	32859911
AllCCS	[M-H]-	185.0	32859911
AllCCS	[M+Na-2H]-	184.6	32859911
AllCCS	[M+HCOO]-	184.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Haloperidol 1,2,3,6-tetrahydropyridine	FC1=CC=C(C=C1)C(=O)CCCN1CCC(=CC1)C1=CC=C(Cl)C=C1	3801.2	Standard polar	33892256
Haloperidol 1,2,3,6-tetrahydropyridine	FC1=CC=C(C=C1)C(=O)CCCN1CCC(=CC1)C1=CC=C(Cl)C=C1	2928.1	Standard non polar	33892256
Haloperidol 1,2,3,6-tetrahydropyridine	FC1=CC=C(C=C1)C(=O)CCCN1CCC(=CC1)C1=CC=C(Cl)C=C1	2967.9	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 - Haloperidol 1,2,3,6-tetrahydropyridine GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fr-3940000000-10bb7a5900047f4016f5	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Haloperidol 1,2,3,6-tetrahydropyridine 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 - Haloperidol 1,2,3,6-tetrahydropyridine 10V, Positive-QTOF	splash10-0a4i-0109000000-ae6d3e75a69326e63c2f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Haloperidol 1,2,3,6-tetrahydropyridine 20V, Positive-QTOF	splash10-00di-0942000000-602bc46d142be69c2b24	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Haloperidol 1,2,3,6-tetrahydropyridine 40V, Positive-QTOF	splash10-00di-2910000000-455a4c8308385c17f6c0	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Haloperidol 1,2,3,6-tetrahydropyridine 10V, Negative-QTOF	splash10-0a4i-0009000000-2fac880365ae121b0169	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Haloperidol 1,2,3,6-tetrahydropyridine 20V, Negative-QTOF	splash10-0a4i-1119000000-8a52adb2d20c7d0578f8	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Haloperidol 1,2,3,6-tetrahydropyridine 40V, Negative-QTOF	splash10-0007-3901000000-6d07035ab687b1065038	2017-10-06	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

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

171187

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 Haloperidol 1,2,3,6-tetrahydropyridine (HMDB0060905)

MOL for HMDB0060905 (Haloperidol 1,2,3,6-tetrahydropyridine)

3D MOL for HMDB0060905 (Haloperidol 1,2,3,6-tetrahydropyridine)

3D SDF for HMDB0060905 (Haloperidol 1,2,3,6-tetrahydropyridine)

3D-SDF for HMDB0060905 (Haloperidol 1,2,3,6-tetrahydropyridine)

PDB for HMDB0060905 (Haloperidol 1,2,3,6-tetrahydropyridine)

3D PDB for HMDB0060905 (Haloperidol 1,2,3,6-tetrahydropyridine)

SMILES for HMDB0060905 (Haloperidol 1,2,3,6-tetrahydropyridine)

INCHI for HMDB0060905 (Haloperidol 1,2,3,6-tetrahydropyridine)

Structure for HMDB0060905 (Haloperidol 1,2,3,6-tetrahydropyridine)

3D Structure for HMDB0060905 (Haloperidol 1,2,3,6-tetrahydropyridine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra