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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (15)transporters (1) Show 16 proteins XML

enzymes (15)transporters (1) Show 16 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:41 UTC

HMDB ID

HMDB0014645

Secondary Accession Numbers

HMDB14645

Metabolite Identification

Common Name

Haloperidol

Description

A phenyl-piperidinyl-butyrophenone that is used primarily to treat schizophrenia and other psychoses. It is also used in schizoaffective disorder, delusional disorders, ballism, and tourette syndrome (a drug of choice) and occasionally as adjunctive therapy in mental retardation and the chorea of huntington disease. It is a potent antiemetic and is used in the treatment of intractable hiccups. (From AMA Drug Evaluations Annual, 1994, p279)

Structure

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

502
  Mrv1652305271900142D          

 26 28  0  0  0  0            999 V2000
    5.4436    5.1416    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -5.1416    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.3810    2.9981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.4290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.6335    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.2836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.8711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.8711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.0460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.0460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2060    2.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    3.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0310    2.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2060    4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4436    3.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.8415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0310    4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.6665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -3.0791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -3.0791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -3.9041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -3.9041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -4.3166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  1  0  0  0  0
  2 26  1  0  0  0  0
  3  6  1  0  0  0  0
  4 19  2  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6 12  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  2  0  0  0  0
 12 15  1  0  0  0  0
 13 16  1  0  0  0  0
 14 17  1  0  0  0  0
 15 18  2  0  0  0  0
 16 19  1  0  0  0  0
 17 20  2  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
 23 25  2  0  0  0  0
 24 26  2  0  0  0  0
 25 26  1  0  0  0  0
M  END

HMDB0014645
     RDKit          3D
Haloperidol
 49 51  0  0  0  0  0  0  0  0999 V2000
   -3.5892    1.9149    0.1150 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9473    0.7203    0.0644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9068   -0.3399    0.0611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5073    0.2410    0.1206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5215   -0.8968    0.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8299   -0.5228    0.1080 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4026    0.1691   -0.9582 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2826    1.3158   -0.6382 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2284    0.9606    0.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6741    2.2227    0.9683 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4728    0.2928   -0.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5105   -1.0596   -0.2591 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6669   -1.6901   -0.7084 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8232   -0.9776   -0.9213 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2901   -1.7895   -1.4867 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.8046    0.3758   -0.6803 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6510    0.9777   -0.2373 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6196    0.2292    1.6188 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4817   -0.6478    1.3380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3429    0.3352    0.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3490    1.2626   -0.0285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7023    0.9152   -0.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9771   -0.4385   -0.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3003   -0.8121   -0.1349 F   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0037   -1.4114   -0.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6755   -1.0205   -0.0044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9667   -0.9122   -0.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0801   -1.1025    0.8618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3643    0.9026    1.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4140    0.9060   -0.7658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7066   -1.3833   -0.9435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7308   -1.6791    0.8163 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9336   -0.5405   -1.6593 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5687    0.5724   -1.6223 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8726    1.6076   -1.5344 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6580    2.1636   -0.2744 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0864    2.4581    1.7420 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6430   -1.6709   -0.1124 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6899   -2.7528   -0.8967 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7333    0.9185   -0.8593 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6320    2.0461   -0.0366 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4476   -0.3232    2.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2970    0.9707    2.4115 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8246   -1.7209    1.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6997   -0.5724    2.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1336    2.3184   -0.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4360    1.6760   -0.1058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2828   -2.4375   -0.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8869   -1.7709    0.0228 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  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
  9 18  1  0
 18 19  1  0
  2 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 19  6  1  0
 26 20  1  0
 17 11  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
 10 37  1  0
 12 38  1  0
 13 39  1  0
 16 40  1  0
 17 41  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  0
 19 45  1  0
 21 46  1  0
 22 47  1  0
 25 48  1  0
 26 49  1  0
M  END

502
  Mrv1652305271900142D          

 26 28  0  0  0  0            999 V2000
    5.4436    5.1416    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -5.1416    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.3810    2.9981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.4290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.6335    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.2836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.8711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.8711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.0460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.0460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2060    2.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    3.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0310    2.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2060    4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4436    3.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.8415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0310    4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.6665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -3.0791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -3.0791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -3.9041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -3.9041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -4.3166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  1  0  0  0  0
  2 26  1  0  0  0  0
  3  6  1  0  0  0  0
  4 19  2  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6 12  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  2  0  0  0  0
 12 15  1  0  0  0  0
 13 16  1  0  0  0  0
 14 17  1  0  0  0  0
 15 18  2  0  0  0  0
 16 19  1  0  0  0  0
 17 20  2  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
 23 25  2  0  0  0  0
 24 26  2  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014645

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1(CCN(CCCC(=O)C2=CC=C(F)C=C2)CC1)C1=CC=C(Cl)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H23ClFNO2/c22-18-7-5-17(6-8-18)21(26)11-14-24(15-12-21)13-1-2-20(25)16-3-9-19(23)10-4-16/h3-10,26H,1-2,11-15H2

> <INCHI_KEY>
LNEPOXFFQSENCJ-UHFFFAOYSA-N

> <FORMULA>
C21H23ClFNO2

> <MOLECULAR_WEIGHT>
375.864

> <EXACT_MASS>
375.140134897

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
39.147554540280176

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-1-(4-fluorophenyl)butan-1-one

> <ALOGPS_LOGP>
3.70

> <JCHEM_LOGP>
3.6611138006666666

> <ALOGPS_LOGS>
-4.93

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
16.398188334958146

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.963255005315197

> <JCHEM_PKA_STRONGEST_BASIC>
8.045287776980366

> <JCHEM_POLAR_SURFACE_AREA>
40.54

> <JCHEM_REFRACTIVITY>
102.59190000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.46e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
haloperidol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014645
     RDKit          3D
Haloperidol
 49 51  0  0  0  0  0  0  0  0999 V2000
   -3.5892    1.9149    0.1150 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9473    0.7203    0.0644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9068   -0.3399    0.0611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5073    0.2410    0.1206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5215   -0.8968    0.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8299   -0.5228    0.1080 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4026    0.1691   -0.9582 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2826    1.3158   -0.6382 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2284    0.9606    0.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6741    2.2227    0.9683 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4728    0.2928   -0.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5105   -1.0596   -0.2591 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6669   -1.6901   -0.7084 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8232   -0.9776   -0.9213 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2901   -1.7895   -1.4867 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.8046    0.3758   -0.6803 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6510    0.9777   -0.2373 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6196    0.2292    1.6188 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4817   -0.6478    1.3380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3429    0.3352    0.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3490    1.2626   -0.0285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7023    0.9152   -0.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9771   -0.4385   -0.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3003   -0.8121   -0.1349 F   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0037   -1.4114   -0.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6755   -1.0205   -0.0044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9667   -0.9122   -0.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0801   -1.1025    0.8618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3643    0.9026    1.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4140    0.9060   -0.7658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7066   -1.3833   -0.9435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7308   -1.6791    0.8163 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9336   -0.5405   -1.6593 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5687    0.5724   -1.6223 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8726    1.6076   -1.5344 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6580    2.1636   -0.2744 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0864    2.4581    1.7420 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6430   -1.6709   -0.1124 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6899   -2.7528   -0.8967 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7333    0.9185   -0.8593 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6320    2.0461   -0.0366 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4476   -0.3232    2.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2970    0.9707    2.4115 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8246   -1.7209    1.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6997   -0.5724    2.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1336    2.3184   -0.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4360    1.6760   -0.1058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2828   -2.4375   -0.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8869   -1.7709    0.0228 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  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
  9 18  1  0
 18 19  1  0
  2 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 19  6  1  0
 26 20  1  0
 17 11  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
 10 37  1  0
 12 38  1  0
 13 39  1  0
 16 40  1  0
 17 41  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  0
 19 45  1  0
 21 46  1  0
 22 47  1  0
 25 48  1  0
 26 49  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 502                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1 Cl   UNK     0      10.161   9.598   0.000  0.00  0.00          Cl+0
HETATM    2  F   UNK     0       4.414  -9.598   0.000  0.00  0.00           F+0
HETATM    3  O   UNK     0       6.311   5.596   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.080  -2.667   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       7.081   1.183   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       7.081   4.263   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.748   3.493   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.415   3.493   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.748   1.953   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.415   1.953   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081  -0.357   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.851   5.596   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.748  -1.127   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.081   6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.391   5.596   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.748  -2.667   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.851   8.264   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.161   6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.414  -3.437   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.391   8.264   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.414  -4.977   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.748  -5.748   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.080  -5.748   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.748  -7.288   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.080  -7.288   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.414  -8.058   0.000  0.00  0.00           C+0
CONECT    1   20                                                            
CONECT    2   26                                                            
CONECT    3    6                                                            
CONECT    4   19                                                            
CONECT    5    9   10   11                                                  
CONECT    6    3    7    8   12                                             
CONECT    7    6    9                                                       
CONECT    8    6   10                                                       
CONECT    9    5    7                                                       
CONECT   10    5    8                                                       
CONECT   11    5   13                                                       
CONECT   12    6   14   15                                                  
CONECT   13   11   16                                                       
CONECT   14   12   17                                                       
CONECT   15   12   18                                                       
CONECT   16   13   19                                                       
CONECT   17   14   20                                                       
CONECT   18   15   20                                                       
CONECT   19    4   16   21                                                  
CONECT   20    1   17   18                                                  
CONECT   21   19   22   23                                                  
CONECT   22   21   24                                                       
CONECT   23   21   25                                                       
CONECT   24   22   26                                                       
CONECT   25   23   26                                                       
CONECT   26    2   24   25                                                  
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

COMPND    HMDB0014645
HETATM    1  O1  UNL     1      -3.589   1.915   0.115  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.947   0.720   0.064  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.907  -0.340   0.061  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.507   0.241   0.121  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.522  -0.897   0.062  1.00  0.00           C  
HETATM    6  N1  UNL     1       0.830  -0.523   0.108  1.00  0.00           N  
HETATM    7  C5  UNL     1       1.403   0.169  -0.958  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.283   1.316  -0.638  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.228   0.961   0.469  1.00  0.00           C  
HETATM   10  O2  UNL     1       3.674   2.223   0.968  1.00  0.00           O  
HETATM   11  C8  UNL     1       4.473   0.293  -0.011  1.00  0.00           C  
HETATM   12  C9  UNL     1       4.510  -1.060  -0.259  1.00  0.00           C  
HETATM   13  C10 UNL     1       5.667  -1.690  -0.708  1.00  0.00           C  
HETATM   14  C11 UNL     1       6.823  -0.978  -0.921  1.00  0.00           C  
HETATM   15 CL1  UNL     1       8.290  -1.789  -1.487  1.00  0.00          CL  
HETATM   16  C12 UNL     1       6.805   0.376  -0.680  1.00  0.00           C  
HETATM   17  C13 UNL     1       5.651   0.978  -0.237  1.00  0.00           C  
HETATM   18  C14 UNL     1       2.620   0.229   1.619  1.00  0.00           C  
HETATM   19  C15 UNL     1       1.482  -0.648   1.338  1.00  0.00           C  
HETATM   20  C16 UNL     1      -5.343   0.335   0.008  1.00  0.00           C  
HETATM   21  C17 UNL     1      -6.349   1.263  -0.029  1.00  0.00           C  
HETATM   22  C18 UNL     1      -7.702   0.915  -0.077  1.00  0.00           C  
HETATM   23  C19 UNL     1      -7.977  -0.438  -0.087  1.00  0.00           C  
HETATM   24  F1  UNL     1      -9.300  -0.812  -0.135  1.00  0.00           F  
HETATM   25  C20 UNL     1      -7.004  -1.411  -0.053  1.00  0.00           C  
HETATM   26  C21 UNL     1      -5.675  -1.020  -0.004  1.00  0.00           C  
HETATM   27  H1  UNL     1      -2.967  -0.912  -0.898  1.00  0.00           H  
HETATM   28  H2  UNL     1      -3.080  -1.102   0.862  1.00  0.00           H  
HETATM   29  H3  UNL     1      -1.364   0.903   1.000  1.00  0.00           H  
HETATM   30  H4  UNL     1      -1.414   0.906  -0.766  1.00  0.00           H  
HETATM   31  H5  UNL     1      -0.707  -1.383  -0.943  1.00  0.00           H  
HETATM   32  H6  UNL     1      -0.731  -1.679   0.816  1.00  0.00           H  
HETATM   33  H7  UNL     1       1.934  -0.540  -1.659  1.00  0.00           H  
HETATM   34  H8  UNL     1       0.569   0.572  -1.622  1.00  0.00           H  
HETATM   35  H9  UNL     1       2.873   1.608  -1.534  1.00  0.00           H  
HETATM   36  H10 UNL     1       1.658   2.164  -0.274  1.00  0.00           H  
HETATM   37  H11 UNL     1       3.086   2.458   1.742  1.00  0.00           H  
HETATM   38  H12 UNL     1       3.643  -1.671  -0.112  1.00  0.00           H  
HETATM   39  H13 UNL     1       5.690  -2.753  -0.897  1.00  0.00           H  
HETATM   40  H14 UNL     1       7.733   0.919  -0.859  1.00  0.00           H  
HETATM   41  H15 UNL     1       5.632   2.046  -0.037  1.00  0.00           H  
HETATM   42  H16 UNL     1       3.448  -0.323   2.124  1.00  0.00           H  
HETATM   43  H17 UNL     1       2.297   0.971   2.412  1.00  0.00           H  
HETATM   44  H18 UNL     1       1.825  -1.721   1.440  1.00  0.00           H  
HETATM   45  H19 UNL     1       0.700  -0.572   2.161  1.00  0.00           H  
HETATM   46  H20 UNL     1      -6.134   2.318  -0.026  1.00  0.00           H  
HETATM   47  H21 UNL     1      -8.436   1.676  -0.106  1.00  0.00           H  
HETATM   48  H22 UNL     1      -7.283  -2.438  -0.064  1.00  0.00           H  
HETATM   49  H23 UNL     1      -4.887  -1.771   0.023  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   20
CONECT    3    4   27   28
CONECT    4    5   29   30
CONECT    5    6   31   32
CONECT    6    7   19
CONECT    7    8   33   34
CONECT    8    9   35   36
CONECT    9   10   11   18
CONECT   10   37
CONECT   11   12   12   17
CONECT   12   13   38
CONECT   13   14   14   39
CONECT   14   15   16
CONECT   16   17   17   40
CONECT   17   41
CONECT   18   19   42   43
CONECT   19   44   45
CONECT   20   21   21   26
CONECT   21   22   46
CONECT   22   23   23   47
CONECT   23   24   25
CONECT   25   26   26   48
CONECT   26   49
END

HMDB0014645
     RDKit          3D
Haloperidol
 49 51  0  0  0  0  0  0  0  0999 V2000
   -3.5892    1.9149    0.1150 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9473    0.7203    0.0644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9068   -0.3399    0.0611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5073    0.2410    0.1206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5215   -0.8968    0.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8299   -0.5228    0.1080 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4026    0.1691   -0.9582 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2826    1.3158   -0.6382 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2284    0.9606    0.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6741    2.2227    0.9683 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4728    0.2928   -0.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5105   -1.0596   -0.2591 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6669   -1.6901   -0.7084 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8232   -0.9776   -0.9213 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2901   -1.7895   -1.4867 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.8046    0.3758   -0.6803 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6510    0.9777   -0.2373 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6196    0.2292    1.6188 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4817   -0.6478    1.3380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3429    0.3352    0.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3490    1.2626   -0.0285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7023    0.9152   -0.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9771   -0.4385   -0.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3003   -0.8121   -0.1349 F   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0037   -1.4114   -0.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6755   -1.0205   -0.0044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9667   -0.9122   -0.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0801   -1.1025    0.8618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3643    0.9026    1.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4140    0.9060   -0.7658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7066   -1.3833   -0.9435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7308   -1.6791    0.8163 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9336   -0.5405   -1.6593 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5687    0.5724   -1.6223 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8726    1.6076   -1.5344 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6580    2.1636   -0.2744 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0864    2.4581    1.7420 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6430   -1.6709   -0.1124 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6899   -2.7528   -0.8967 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7333    0.9185   -0.8593 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6320    2.0461   -0.0366 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4476   -0.3232    2.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2970    0.9707    2.4115 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8246   -1.7209    1.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6997   -0.5724    2.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1336    2.3184   -0.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4360    1.6760   -0.1058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2828   -2.4375   -0.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8869   -1.7709    0.0228 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  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
  9 18  1  0
 18 19  1  0
  2 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 19  6  1  0
 26 20  1  0
 17 11  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
 10 37  1  0
 12 38  1  0
 13 39  1  0
 16 40  1  0
 17 41  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  0
 19 45  1  0
 21 46  1  0
 22 47  1  0
 25 48  1  0
 26 49  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(3-p-Fluorobenzoylpropyl)-4-p-chlorophenyl-4-hydroxypiperidine	ChEBI
4'-Fluoro-4-(4-(p-chlorophenyl)-4-hydroxypiperidinyl)butyrophenone	ChEBI
4'-Fluoro-4-(4-hydroxy-4-(4'-chlorophenyl)piperidino)butyrophenone	ChEBI
4-(4-(Para-chlorophenyl)-4-hydroxypiperidino)-4'-fluorobutyrophenone	ChEBI
4-[4-(4-Chlorophenyl)-4-hydroxy-1-piperidyl]-1-(4-fluorophenyl)-butan-1-one	ChEBI
gamma-(4-(p-Chlorophenyl)-4-hydroxpiperidino)-p-fluorbutyrophenone	ChEBI
Haldol	ChEBI
Haloperidolum	ChEBI
g-(4-(p-Chlorophenyl)-4-hydroxpiperidino)-p-fluorbutyrophenone	Generator
Γ-(4-(p-chlorophenyl)-4-hydroxpiperidino)-p-fluorbutyrophenone	Generator

Chemical Formula

C₂₁H₂₃ClFNO₂

Average Molecular Weight

375.864

Monoisotopic Molecular Weight

375.140134897

IUPAC Name

4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-1-(4-fluorophenyl)butan-1-one

Traditional Name

haloperidol

CAS Registry Number

52-86-8

SMILES

OC1(CCN(CCCC(=O)C2=CC=C(F)C=C2)CC1)C1=CC=C(Cl)C=C1

InChI Identifier

InChI=1S/C21H23ClFNO2/c22-18-7-5-17(6-8-18)21(26)11-14-24(15-12-21)13-1-2-20(25)16-3-9-19(23)10-4-16/h3-10,26H,1-2,11-15H2

InChI Key

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

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

organofluorine compound (CHEBI:5613 )
tertiary alcohol (CHEBI:5613 )
monochlorobenzenes (CHEBI:5613 )
aromatic ketone (CHEBI:5613 )
hydroxypiperidine (CHEBI:5613 )

Ontology

Physiological effect

Health effect

Circulatory system disorder

Vascular disorder

Hypertension (FooDB: )
Hypotension (FooDB: )

Hypoglycemia (FooDB: )
Jaundice (FooDB: )
Impotence (FooDB: )
Dystonia (FooDB: )
Hyperglycemia (FooDB: )

Disposition

Biological location

Cytoplasm (FooDB: )
Membrane (FooDB: )
Cell membrane (FooDB: )

Biofluid or Excreta

Blood (FooDB: )
Urine (FooDB: )

Route of exposure

Parenteral

Inhalation (FooDB: )

Enteral

Ingestion (FooDB: )

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Anti-emetic (FooDB: )

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	151.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0045 g/L	Not Available
LogP	4	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	193.7	30932474
[M+H]+	Not Available	191.693	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001318

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0045 g/L	ALOGPS
logP	3.7	ALOGPS
logP	3.66	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	13.96	ChemAxon
pKa (Strongest Basic)	8.05	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	40.54 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	102.59 m³·mol⁻¹	ChemAxon
Polarizability	39.15 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	191.902	30932474
DeepCCS	[M-H]-	189.388	30932474
DeepCCS	[M-2H]-	223.828	30932474
DeepCCS	[M+Na]+	199.609	30932474
AllCCS	[M+H]+	187.6	32859911
AllCCS	[M+H-H2O]+	184.9	32859911
AllCCS	[M+NH4]+	190.0	32859911
AllCCS	[M+Na]+	190.7	32859911
AllCCS	[M-H]-	188.5	32859911
AllCCS	[M+Na-2H]-	188.8	32859911
AllCCS	[M+HCOO]-	189.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Haloperidol	OC1(CCN(CCCC(=O)C2=CC=C(F)C=C2)CC1)C1=CC=C(Cl)C=C1	3852.4	Standard polar	33892256
Haloperidol	OC1(CCN(CCCC(=O)C2=CC=C(F)C=C2)CC1)C1=CC=C(Cl)C=C1	2919.8	Standard non polar	33892256
Haloperidol	OC1(CCN(CCCC(=O)C2=CC=C(F)C=C2)CC1)C1=CC=C(Cl)C=C1	2934.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Haloperidol,1TMS,isomer #1	C[Si](C)(C)OC1(C2=CC=C(Cl)C=C2)CCN(CCCC(=O)C2=CC=C(F)C=C2)CC1	2924.8	Semi standard non polar	33892256
Haloperidol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1(C2=CC=C(Cl)C=C2)CCN(CCCC(=O)C2=CC=C(F)C=C2)CC1	3171.4	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 GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-3941000000-d115a40817bca84c859a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Haloperidol GC-MS (1 TMS) - 70eV, Positive	splash10-00di-5941100000-c3840be760880e2d998a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Haloperidol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0079-3290000000-cc6a990404ba7b9452a8	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 - Haloperidol LC-ESI-QTOF , positive-QTOF	splash10-004i-0009000000-cdfdd91dd85d2c1cbd3d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Haloperidol LC-ESI-QTOF , positive-QTOF	splash10-00or-0409000000-d542c35143556b83b87a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Haloperidol LC-ESI-QTOF , positive-QTOF	splash10-014i-0900000000-3985dded029c89448ebe	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Haloperidol LC-ESI-QTOF , positive-QTOF	splash10-01b9-0900000000-720c0a4f1130b4237f32	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Haloperidol LC-ESI-QTOF , positive-QTOF	splash10-00di-0900000000-772a799ebb3b949cef0c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Haloperidol LC-ESI-QFT , positive-QTOF	splash10-004i-0009000000-21c8918254235e561129	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Haloperidol LC-ESI-QFT , positive-QTOF	splash10-014i-0904000000-8c97cb39f9680dd91378	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Haloperidol LC-ESI-QFT , positive-QTOF	splash10-01b9-0900000000-571a03ebb5faa3e5cd63	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Haloperidol LC-ESI-QFT , positive-QTOF	splash10-00di-0900000000-62e233fd691121c78e96	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Haloperidol LC-ESI-QFT , positive-QTOF	splash10-00di-0900000000-91bf80d34ef94ed709f0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Haloperidol LC-ESI-QFT , positive-QTOF	splash10-00di-0900000000-46ef29917220709863a4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Haloperidol LC-ESI-QFT , positive-QTOF	splash10-00di-3900000000-26f391756d439f7dbfc8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Haloperidol LC-ESI-QFT , positive-QTOF	splash10-00b9-9600000000-404fc399b40cfb560a99	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Haloperidol LC-ESI-QFT , positive-QTOF	splash10-00b9-9100000000-8779758823471091566a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Haloperidol , positive-QTOF	splash10-004i-1619000000-27aa28ad7f91429f5ae7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Haloperidol , positive-QTOF	splash10-004i-0609000000-f7c623630d33dbd89e2b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Haloperidol , positive-QTOF	splash10-01b9-3911000000-78d5b34044714e81aec3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Haloperidol 30V, Positive-QTOF	splash10-014i-0904000000-de8db1cf24411de5c68b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Haloperidol 20V, Positive-QTOF	splash10-00or-0409000000-36213f9899b1353ed71a	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Haloperidol 10V, Positive-QTOF	splash10-0a6r-0009000000-abe4b4cad1298a753614	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Haloperidol 20V, Positive-QTOF	splash10-0a6r-0679000000-5910dd3a7977bc423000	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Haloperidol 40V, Positive-QTOF	splash10-00l6-4961000000-075c4f60c9298ff5cd1e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Haloperidol 10V, Negative-QTOF	splash10-00di-0009000000-c5a2526394d0eaf36160	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Haloperidol 20V, Negative-QTOF	splash10-00di-1329000000-8e1f1a55517bf6e11ca4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Haloperidol 40V, Negative-QTOF	splash10-03dj-3920000000-2f2c54905c928d8238fb	2016-08-03	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 DB00502	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00502	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

DB00502

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB009770

KNApSAcK ID

Not Available

Chemspider ID

3438

KEGG Compound ID

C01814

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Haloperidol

METLIN ID

Not Available

PubChem Compound

3559

PDB ID

Not Available

ChEBI ID

5613

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)

Download (PDF)

General References

Niemegeers CJ, Laduron PM: Pharmacology and biochemistry of haloperidol. Proc R Soc Med. 1976;69 suppl 1:3-8. [PubMed:14331 ]

Only showing the first 10 proteins. There are 16 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Carbonyl reductase [NADPH] 1

General function:: Involved in oxidoreductase activity
Specific function:: NADPH-dependent reductase with broad substrate specificity. Catalyzes the reduction of a wide variety of carbonyl compounds including quinones, prostaglandins, menadione, plus various xenobiotics. Catalyzes the reduction of the antitumor anthracyclines doxorubicin and daunorubicin to the cardiotoxic compounds doxorubicinol and daunorubicinol. Can convert prostaglandin E2 to prostaglandin F2-alpha. Can bind glutathione, which explains its higher affinity for glutathione-conjugated substrates. Catalyzes the reduction of S-nitrosoglutathione.
Gene Name:: CBR1
Uniprot ID:: P16152
Molecular weight:: 30374.73

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. UDP-glucuronosyltransferase 1-9

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:: UGT1A9
Uniprot ID:: O60656
Molecular weight:: 59940.495

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

3. 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 ]
Kalgutkar AS, Taylor TJ, Venkatakrishnan K, Isin EM: Assessment of the contributions of CYP3A4 and CYP3A5 in the metabolism of the antipsychotic agent haloperidol to its potentially neurotoxic pyridinium metabolite and effect of antidepressants on the bioactivation pathway. Drug Metab Dispos. 2003 Mar;31(3):243-9. [PubMed:12584149 ]

Enzyme Details

4. 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

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 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

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

6. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Micallef J, Fakra E, Blin O: [Use of antidepressant drugs in schizophrenic patients with depression]. Encephale. 2006 Mar-Apr;32(2 Pt 1):263-9. [PubMed:16910628 ]
Otani K, Aoshima T: Pharmacogenetics of classical and new antipsychotic drugs. Ther Drug Monit. 2000 Feb;22(1):118-21. [PubMed:10688273 ]
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

7. Cytochrome P450 3A5

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A5
Uniprot ID:: P20815
Molecular weight:: 57108.065

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

8. Cytochrome P450 1A1

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP1A1
Uniprot ID:: P04798
Molecular weight:: 58164.815

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

9. Cytochrome P450 3A7

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A7
Uniprot ID:: P24462
Molecular weight:: 57525.03

Enzyme Details

10. Cytochrome P450 1A2

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. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Tateishi T, Watanabe M, Kumai T, Tanaka M, Moriya H, Yamaguchi S, Satoh T, Kobayashi S: CYP3A is responsible for N-dealkylation of haloperidol and bromperidol and oxidation of their reduced forms by human liver microsomes. Life Sci. 2000 Nov 3;67(24):2913-20. [PubMed:11133003 ]

Transporters

Enzyme Details

1. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Mahar Doan KM, Humphreys JE, Webster LO, Wring SA, Shampine LJ, Serabjit-Singh CJ, Adkison KK, Polli JW: Passive permeability and P-glycoprotein-mediated efflux differentiate central nervous system (CNS) and non-CNS marketed drugs. J Pharmacol Exp Ther. 2002 Dec;303(3):1029-37. [PubMed:12438524 ]
Nagy H, Goda K, Fenyvesi F, Bacso Z, Szilasi M, Kappelmayer J, Lustyik G, Cianfriglia M, Szabo G Jr: Distinct groups of multidrug resistance modulating agents are distinguished by competition of P-glycoprotein-specific antibodies. Biochem Biophys Res Commun. 2004 Mar 19;315(4):942-9. [PubMed:14985103 ]
Boulton DW, DeVane CL, Liston HL, Markowitz JS: In vitro P-glycoprotein affinity for atypical and conventional antipsychotics. Life Sci. 2002 May 31;71(2):163-9. [PubMed:12031686 ]

Only showing the first 10 proteins. There are 16 proteins in total.

Show all enzymes and transporters

Showing metabocard for Haloperidol (HMDB0014645)

MOL for HMDB0014645 (Haloperidol)

3D MOL for HMDB0014645 (Haloperidol)

3D SDF for HMDB0014645 (Haloperidol)

3D-SDF for HMDB0014645 (Haloperidol)

PDB for HMDB0014645 (Haloperidol)

3D PDB for HMDB0014645 (Haloperidol)

SMILES for HMDB0014645 (Haloperidol)

INCHI for HMDB0014645 (Haloperidol)

Structure for HMDB0014645 (Haloperidol)

3D Structure for HMDB0014645 (Haloperidol)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References

References

References

References

References

References

References

References

Transporters

References