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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (11) Show 11 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:49 UTC

HMDB ID

HMDB0014988

Secondary Accession Numbers

HMDB14988

Metabolite Identification

Common Name

Perphenazine

Description

Perphenazine is only found in individuals that have used or taken this drug. It is an antipsychotic phenothiazine derivative with actions and uses similar to those of chlorpromazine. [PubChem]Binds to the dopamine D1 and dopamine D2 receptors and inhibits their activity. The mechanism of the anti-emetic effect is due predominantly to blockage of the dopamine D2 neurotransmitter receptors in the chemoreceptor trigger zone and vomiting centre. Perphenazine also binds the alpha andrenergic receptor. This receptor's action is mediated by association with G proteins that activate a phosphatidylinositol-calcium second messenger system.

Structure

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

850
  Mrv0541 02231215032D          

 27 30  0  0  0  0            999 V2000
    8.8480   -1.8712    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.9361   -3.5410    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498    3.0581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073    0.5834    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    1.4083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9361   -1.8912    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929    0.1710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073    1.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929    1.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216    0.1710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641    1.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9361   -1.0664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641    2.6456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6504   -2.3037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -2.3037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6504   -3.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -3.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3878   -1.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4843   -1.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3878   -3.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4843   -3.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1352   -2.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7368   -2.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1352   -3.1457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7368   -3.1457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 24  1  0  0  0  0
  2 18  1  0  0  0  0
  2 19  1  0  0  0  0
  3 15  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  4 11  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 13  1  0  0  0  0
  6 14  1  0  0  0  0
  6 16  1  0  0  0  0
  6 17  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
 11 12  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 16 18  2  0  0  0  0
 16 20  1  0  0  0  0
 17 19  1  0  0  0  0
 17 21  2  0  0  0  0
 18 22  1  0  0  0  0
 19 23  2  0  0  0  0
 20 24  2  0  0  0  0
 21 25  1  0  0  0  0
 22 26  2  0  0  0  0
 23 27  1  0  0  0  0
 24 26  1  0  0  0  0
 25 27  2  0  0  0  0
M  END

HMDB0014988
     RDKit          3D
Perphenazine
 53 56  0  0  0  0  0  0  0  0999 V2000
    6.3486    0.4915    0.2364 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1918   -0.5114   -0.6960 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3678   -1.6846   -0.1754 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0793   -1.3804    0.2122 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7877   -0.5839    1.3314 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8919    0.5507    0.8199 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5632    0.0269    0.5111 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9875    0.8038   -0.5899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4772    0.5538   -0.7930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2759    0.9594    0.4307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7060    0.6883    0.3064 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1129   -0.6661    0.4993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1318   -1.6098    0.8095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4419   -2.9506    1.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7421   -3.3742    0.9267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7332   -2.4679    0.6232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3837   -1.1512    0.4218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7233   -0.0163    0.0452 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9795    1.5694   -0.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7891    2.6135   -0.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3326    3.8966   -0.6261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9845    4.0812   -0.4852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3268    5.6827   -0.6997 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1300    3.0406   -0.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6214    1.7392   -0.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6452   -1.3780    0.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9510   -1.7324   -0.5537 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4146    1.3916   -0.1299 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7631   -0.0874   -1.6116 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2068   -0.8770   -0.9737 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9547   -2.0923    0.7008 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4204   -2.4743   -0.9742 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2466   -1.1960    2.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7124   -0.1484    1.7569 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8591    1.3827    1.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3309    0.8877   -0.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2568    1.8477   -0.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5015    0.4704   -1.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6494   -0.4474   -1.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7788    1.2429   -1.6374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0270    2.0227    0.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8960    0.4701    1.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1016   -1.3486    0.9048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6817   -3.6819    1.2580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0078   -4.4143    1.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7776   -2.7590    0.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8713    2.4573   -0.5543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9436    4.7370   -0.8588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0862    3.2915   -0.1020 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4760   -2.0617    0.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8521   -1.5832   -0.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9323   -2.8585   -0.6336 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9714   -1.3625   -1.6005 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  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  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
 17 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
  7 26  1  0
 26 27  1  0
 27  4  1  0
 25 11  1  0
 17 12  1  0
 25 19  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  0
 16 46  1  0
 20 47  1  0
 21 48  1  0
 24 49  1  0
 26 50  1  0
 26 51  1  0
 27 52  1  0
 27 53  1  0
M  END

850
  Mrv0541 02231215032D          

 27 30  0  0  0  0            999 V2000
    8.8480   -1.8712    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.9361   -3.5410    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498    3.0581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073    0.5834    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    1.4083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9361   -1.8912    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929    0.1710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073    1.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929    1.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216    0.1710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641    1.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9361   -1.0664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641    2.6456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6504   -2.3037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -2.3037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6504   -3.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -3.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3878   -1.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4843   -1.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3878   -3.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4843   -3.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1352   -2.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7368   -2.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1352   -3.1457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7368   -3.1457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 24  1  0  0  0  0
  2 18  1  0  0  0  0
  2 19  1  0  0  0  0
  3 15  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  4 11  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 13  1  0  0  0  0
  6 14  1  0  0  0  0
  6 16  1  0  0  0  0
  6 17  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
 11 12  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 16 18  2  0  0  0  0
 16 20  1  0  0  0  0
 17 19  1  0  0  0  0
 17 21  2  0  0  0  0
 18 22  1  0  0  0  0
 19 23  2  0  0  0  0
 20 24  2  0  0  0  0
 21 25  1  0  0  0  0
 22 26  2  0  0  0  0
 23 27  1  0  0  0  0
 24 26  1  0  0  0  0
 25 27  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014988

> <DATABASE_NAME>
hmdb

> <SMILES>
OCCN1CCN(CCCN2C3=CC=CC=C3SC3=C2C=C(Cl)C=C3)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C21H26ClN3OS/c22-17-6-7-21-19(16-17)25(18-4-1-2-5-20(18)27-21)9-3-8-23-10-12-24(13-11-23)14-15-26/h1-2,4-7,16,26H,3,8-15H2

> <INCHI_KEY>
RGCVKNLCSQQDEP-UHFFFAOYSA-N

> <FORMULA>
C21H26ClN3OS

> <MOLECULAR_WEIGHT>
403.969

> <EXACT_MASS>
403.148510866

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
44.77499972085428

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{4-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]piperazin-1-yl}ethan-1-ol

> <ALOGPS_LOGP>
4.15

> <JCHEM_LOGP>
3.6920178093333327

> <ALOGPS_LOGS>
-4.23

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.593098118515542

> <JCHEM_PKA_STRONGEST_BASIC>
8.210900734200099

> <JCHEM_POLAR_SURFACE_AREA>
29.950000000000003

> <JCHEM_REFRACTIVITY>
116.09870000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.37e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
perphenazine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014988
     RDKit          3D
Perphenazine
 53 56  0  0  0  0  0  0  0  0999 V2000
    6.3486    0.4915    0.2364 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1918   -0.5114   -0.6960 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3678   -1.6846   -0.1754 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0793   -1.3804    0.2122 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7877   -0.5839    1.3314 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8919    0.5507    0.8199 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5632    0.0269    0.5111 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9875    0.8038   -0.5899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4772    0.5538   -0.7930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2759    0.9594    0.4307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7060    0.6883    0.3064 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1129   -0.6661    0.4993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1318   -1.6098    0.8095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4419   -2.9506    1.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7421   -3.3742    0.9267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7332   -2.4679    0.6232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3837   -1.1512    0.4218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7233   -0.0163    0.0452 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9795    1.5694   -0.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7891    2.6135   -0.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3326    3.8966   -0.6261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9845    4.0812   -0.4852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3268    5.6827   -0.6997 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1300    3.0406   -0.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6214    1.7392   -0.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6452   -1.3780    0.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9510   -1.7324   -0.5537 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4146    1.3916   -0.1299 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7631   -0.0874   -1.6116 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2068   -0.8770   -0.9737 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9547   -2.0923    0.7008 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4204   -2.4743   -0.9742 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2466   -1.1960    2.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7124   -0.1484    1.7569 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8591    1.3827    1.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3309    0.8877   -0.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2568    1.8477   -0.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5015    0.4704   -1.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6494   -0.4474   -1.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7788    1.2429   -1.6374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0270    2.0227    0.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8960    0.4701    1.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1016   -1.3486    0.9048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6817   -3.6819    1.2580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0078   -4.4143    1.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7776   -2.7590    0.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8713    2.4573   -0.5543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9436    4.7370   -0.8588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0862    3.2915   -0.1020 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4760   -2.0617    0.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8521   -1.5832   -0.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9323   -2.8585   -0.6336 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9714   -1.3625   -1.6005 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  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  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
 17 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
  7 26  1  0
 26 27  1  0
 27  4  1  0
 25 11  1  0
 17 12  1  0
 25 19  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  0
 16 46  1  0
 20 47  1  0
 21 48  1  0
 24 49  1  0
 26 50  1  0
 26 51  1  0
 27 52  1  0
 27 53  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 850                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0      16.516  -3.493   0.000  0.00  0.00          Cl+0
HETATM    2  S   UNK     0      11.081  -6.610   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0       3.080   5.708   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       8.414   1.089   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       5.747   2.629   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      11.081  -3.530   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       7.080   0.319   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.414   2.629   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.747   1.089   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.080   3.399   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.747   0.319   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.747  -1.221   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.413   3.399   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.081  -1.991   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.413   4.939   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.414  -4.300   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.747  -4.300   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.414  -5.840   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.747  -5.840   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.791  -3.477   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.371  -3.477   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.791  -6.663   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.371  -6.663   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.186  -4.268   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.975  -4.268   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      15.186  -5.872   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.975  -5.872   0.000  0.00  0.00           C+0
CONECT    1   24                                                            
CONECT    2   18   19                                                       
CONECT    3   15                                                            
CONECT    4    7    8   11                                                  
CONECT    5    9   10   13                                                  
CONECT    6   14   16   17                                                  
CONECT    7    4    9                                                       
CONECT    8    4   10                                                       
CONECT    9    5    7                                                       
CONECT   10    5    8                                                       
CONECT   11    4   12                                                       
CONECT   12   11   14                                                       
CONECT   13    5   15                                                       
CONECT   14    6   12                                                       
CONECT   15    3   13                                                       
CONECT   16    6   18   20                                                  
CONECT   17    6   19   21                                                  
CONECT   18    2   16   22                                                  
CONECT   19    2   17   23                                                  
CONECT   20   16   24                                                       
CONECT   21   17   25                                                       
CONECT   22   18   26                                                       
CONECT   23   19   27                                                       
CONECT   24    1   20   26                                                  
CONECT   25   21   27                                                       
CONECT   26   22   24                                                       
CONECT   27   23   25                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

COMPND    HMDB0014988
HETATM    1  O1  UNL     1       6.349   0.492   0.236  1.00  0.00           O  
HETATM    2  C1  UNL     1       6.192  -0.511  -0.696  1.00  0.00           C  
HETATM    3  C2  UNL     1       5.368  -1.685  -0.175  1.00  0.00           C  
HETATM    4  N1  UNL     1       4.079  -1.380   0.212  1.00  0.00           N  
HETATM    5  C3  UNL     1       3.788  -0.584   1.331  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.892   0.551   0.820  1.00  0.00           C  
HETATM    7  N2  UNL     1       1.563   0.027   0.511  1.00  0.00           N  
HETATM    8  C5  UNL     1       0.987   0.804  -0.590  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.477   0.554  -0.793  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.276   0.959   0.431  1.00  0.00           C  
HETATM   11  N3  UNL     1      -2.706   0.688   0.306  1.00  0.00           N  
HETATM   12  C8  UNL     1      -3.113  -0.666   0.499  1.00  0.00           C  
HETATM   13  C9  UNL     1      -2.132  -1.610   0.809  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.442  -2.951   1.021  1.00  0.00           C  
HETATM   15  C11 UNL     1      -3.742  -3.374   0.927  1.00  0.00           C  
HETATM   16  C12 UNL     1      -4.733  -2.468   0.623  1.00  0.00           C  
HETATM   17  C13 UNL     1      -4.384  -1.151   0.422  1.00  0.00           C  
HETATM   18  S1  UNL     1      -5.723  -0.016   0.045  1.00  0.00           S  
HETATM   19  C14 UNL     1      -4.979   1.569  -0.149  1.00  0.00           C  
HETATM   20  C15 UNL     1      -5.789   2.614  -0.447  1.00  0.00           C  
HETATM   21  C16 UNL     1      -5.333   3.897  -0.626  1.00  0.00           C  
HETATM   22  C17 UNL     1      -3.985   4.081  -0.485  1.00  0.00           C  
HETATM   23 CL1  UNL     1      -3.327   5.683  -0.700  1.00  0.00          CL  
HETATM   24  C18 UNL     1      -3.130   3.041  -0.182  1.00  0.00           C  
HETATM   25  C19 UNL     1      -3.621   1.739  -0.004  1.00  0.00           C  
HETATM   26  C20 UNL     1       1.645  -1.378   0.145  1.00  0.00           C  
HETATM   27  C21 UNL     1       2.951  -1.732  -0.554  1.00  0.00           C  
HETATM   28  H1  UNL     1       6.415   1.392  -0.130  1.00  0.00           H  
HETATM   29  H2  UNL     1       5.763  -0.087  -1.612  1.00  0.00           H  
HETATM   30  H3  UNL     1       7.207  -0.877  -0.974  1.00  0.00           H  
HETATM   31  H4  UNL     1       5.955  -2.092   0.701  1.00  0.00           H  
HETATM   32  H5  UNL     1       5.420  -2.474  -0.974  1.00  0.00           H  
HETATM   33  H6  UNL     1       3.247  -1.196   2.108  1.00  0.00           H  
HETATM   34  H7  UNL     1       4.712  -0.148   1.757  1.00  0.00           H  
HETATM   35  H8  UNL     1       2.859   1.383   1.531  1.00  0.00           H  
HETATM   36  H9  UNL     1       3.331   0.888  -0.137  1.00  0.00           H  
HETATM   37  H10 UNL     1       1.257   1.848  -0.436  1.00  0.00           H  
HETATM   38  H11 UNL     1       1.501   0.470  -1.527  1.00  0.00           H  
HETATM   39  H12 UNL     1      -0.649  -0.447  -1.169  1.00  0.00           H  
HETATM   40  H13 UNL     1      -0.779   1.243  -1.637  1.00  0.00           H  
HETATM   41  H14 UNL     1      -1.027   2.023   0.603  1.00  0.00           H  
HETATM   42  H15 UNL     1      -0.896   0.470   1.372  1.00  0.00           H  
HETATM   43  H16 UNL     1      -1.102  -1.349   0.905  1.00  0.00           H  
HETATM   44  H17 UNL     1      -1.682  -3.682   1.258  1.00  0.00           H  
HETATM   45  H18 UNL     1      -4.008  -4.414   1.088  1.00  0.00           H  
HETATM   46  H19 UNL     1      -5.778  -2.759   0.538  1.00  0.00           H  
HETATM   47  H20 UNL     1      -6.871   2.457  -0.554  1.00  0.00           H  
HETATM   48  H21 UNL     1      -5.944   4.737  -0.859  1.00  0.00           H  
HETATM   49  H22 UNL     1      -2.086   3.292  -0.102  1.00  0.00           H  
HETATM   50  H23 UNL     1       1.476  -2.062   0.996  1.00  0.00           H  
HETATM   51  H24 UNL     1       0.852  -1.583  -0.591  1.00  0.00           H  
HETATM   52  H25 UNL     1       2.932  -2.859  -0.634  1.00  0.00           H  
HETATM   53  H26 UNL     1       2.971  -1.362  -1.601  1.00  0.00           H  
CONECT    1    2   28
CONECT    2    3   29   30
CONECT    3    4   31   32
CONECT    4    5   27
CONECT    5    6   33   34
CONECT    6    7   35   36
CONECT    7    8   26
CONECT    8    9   37   38
CONECT    9   10   39   40
CONECT   10   11   41   42
CONECT   11   12   25
CONECT   12   13   13   17
CONECT   13   14   43
CONECT   14   15   15   44
CONECT   15   16   45
CONECT   16   17   17   46
CONECT   17   18
CONECT   18   19
CONECT   19   20   20   25
CONECT   20   21   47
CONECT   21   22   22   48
CONECT   22   23   24
CONECT   24   25   25   49
CONECT   26   27   50   51
CONECT   27   52   53
END

HMDB0014988
     RDKit          3D
Perphenazine
 53 56  0  0  0  0  0  0  0  0999 V2000
    6.3486    0.4915    0.2364 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1918   -0.5114   -0.6960 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3678   -1.6846   -0.1754 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0793   -1.3804    0.2122 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7877   -0.5839    1.3314 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8919    0.5507    0.8199 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5632    0.0269    0.5111 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9875    0.8038   -0.5899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4772    0.5538   -0.7930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2759    0.9594    0.4307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7060    0.6883    0.3064 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1129   -0.6661    0.4993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1318   -1.6098    0.8095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4419   -2.9506    1.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7421   -3.3742    0.9267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7332   -2.4679    0.6232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3837   -1.1512    0.4218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7233   -0.0163    0.0452 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9795    1.5694   -0.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7891    2.6135   -0.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3326    3.8966   -0.6261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9845    4.0812   -0.4852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3268    5.6827   -0.6997 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1300    3.0406   -0.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6214    1.7392   -0.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6452   -1.3780    0.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9510   -1.7324   -0.5537 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4146    1.3916   -0.1299 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7631   -0.0874   -1.6116 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2068   -0.8770   -0.9737 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9547   -2.0923    0.7008 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4204   -2.4743   -0.9742 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2466   -1.1960    2.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7124   -0.1484    1.7569 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8591    1.3827    1.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3309    0.8877   -0.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2568    1.8477   -0.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5015    0.4704   -1.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6494   -0.4474   -1.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7788    1.2429   -1.6374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0270    2.0227    0.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8960    0.4701    1.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1016   -1.3486    0.9048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6817   -3.6819    1.2580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0078   -4.4143    1.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7776   -2.7590    0.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8713    2.4573   -0.5543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9436    4.7370   -0.8588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0862    3.2915   -0.1020 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4760   -2.0617    0.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8521   -1.5832   -0.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9323   -2.8585   -0.6336 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9714   -1.3625   -1.6005 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  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  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
 17 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
  7 26  1  0
 26 27  1  0
 27  4  1  0
 25 11  1  0
 17 12  1  0
 25 19  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  0
 16 46  1  0
 20 47  1  0
 21 48  1  0
 24 49  1  0
 26 50  1  0
 26 51  1  0
 27 52  1  0
 27 53  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(4-[3-(2-Chloro-10H-phenothiazin-10-yl)propyl]-1-piperazinyl)ethanol	ChEBI
2-Chloro-10-(3-(4-(2-hydroxyethyl)piperazin-1-yl)propyl)phenothiazine	ChEBI
4-[3-(2-Chloro-10H-phenothiazin-10-yl)propyl]-1-piperazineethanol	ChEBI
4-[3-(2-Chlorophenothiazin-10-yl)propyl]-1-piperazineethanol	ChEBI
Chlorpiprazine	ChEBI
gamma-(4-(beta-Hydroxyethyl)piperazin-1-yl)propyl-2-chlorophenothiazine	ChEBI
Perfenazina	ChEBI
Perfenazine	ChEBI
Perphenazin	ChEBI
Perphenazinum	ChEBI
Trilafon	ChEBI
4-(3-(2-Chlorophenothiazin-10-yl)propyl)-1-piperazineethanol	Kegg
g-(4-(b-Hydroxyethyl)piperazin-1-yl)propyl-2-chlorophenothiazine	Generator
Γ-(4-(β-hydroxyethyl)piperazin-1-yl)propyl-2-chlorophenothiazine	Generator
Chlorperphenazine	HMDB
Etaperazin	HMDB
Etaperazine	HMDB
Ethaperazine	HMDB
PZC	HMDB

Chemical Formula

C₂₁H₂₆ClN₃OS

Average Molecular Weight

403.969

Monoisotopic Molecular Weight

403.148510866

IUPAC Name

2-{4-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]piperazin-1-yl}ethan-1-ol

Traditional Name

perphenazine

CAS Registry Number

58-39-9

SMILES

OCCN1CCN(CCCN2C3=CC=CC=C3SC3=C2C=C(Cl)C=C3)CC1

InChI Identifier

InChI=1S/C21H26ClN3OS/c22-17-6-7-21-19(16-17)25(18-4-1-2-5-20(18)27-21)9-3-8-23-10-12-24(13-11-23)14-15-26/h1-2,4-7,16,26H,3,8-15H2

InChI Key

RGCVKNLCSQQDEP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiazines

Sub Class

Phenothiazines

Direct Parent

Phenothiazines

Alternative Parents

Substituents

Phenothiazine
Alkyldiarylamine
Diarylthioether
Aryl thioether
Tertiary aliphatic/aromatic amine
N-alkylpiperazine
Para-thiazine
Aryl chloride
Aryl halide
1,4-diazinane
Piperazine
Benzenoid
Tertiary amine
Tertiary aliphatic amine
1,2-aminoalcohol
Azacycle
Thioether
Alkanolamine
Organic oxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organooxygen compound
Alcohol
Organic nitrogen compound
Amine
Primary alcohol
Organopnictogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenothiazines (CHEBI:8028 )
N-(2-hydroxyethyl)piperazine (CHEBI:8028 )
organochlorine compound (CHEBI:8028 )
N-alkylpiperazine (CHEBI:8028 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014988)

Source

Exogenous

Exogenous (HMDB: HMDB0014988)

Process

Not Available

Role

Industrial application

Antiemetic (HMDB: HMDB0014988)

Pharmaceutical industry

Phenothiazine antipsychotic drug (HMDB: HMDB0014988)

Dopamine uptake inhibitor (HMDB: HMDB0014988)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	97 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.024 g/L	Not Available
LogP	3.9	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	193.2	30932474
[M+H]+	Not Available	191.979	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001061

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.024 g/L	ALOGPS
logP	4.15	ALOGPS
logP	3.69	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	15.59	ChemAxon
pKa (Strongest Basic)	8.21	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.95 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	116.1 m³·mol⁻¹	ChemAxon
Polarizability	44.77 Å³	ChemAxon
Number of Rings	4	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]+	191.726	30932474
DeepCCS	[M-H]-	189.368	30932474
DeepCCS	[M-2H]-	223.528	30932474
DeepCCS	[M+Na]+	198.88	30932474
AllCCS	[M+H]+	192.8	32859911
AllCCS	[M+H-H2O]+	190.5	32859911
AllCCS	[M+NH4]+	194.9	32859911
AllCCS	[M+Na]+	195.4	32859911
AllCCS	[M-H]-	188.2	32859911
AllCCS	[M+Na-2H]-	188.2	32859911
AllCCS	[M+HCOO]-	188.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.07 minutes	32390414
Predicted by Siyang on May 30, 2022	10.8063 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.16 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	85.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	974.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	197.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	170.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	177.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	102.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	410.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	505.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	531.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1006.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	303.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1058.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	264.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	358.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	322.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	347.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	100.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Perphenazine	OCCN1CCN(CCCN2C3=CC=CC=C3SC3=C2C=C(Cl)C=C3)CC1	4436.9	Standard polar	33892256
Perphenazine	OCCN1CCN(CCCN2C3=CC=CC=C3SC3=C2C=C(Cl)C=C3)CC1	3278.1	Standard non polar	33892256
Perphenazine	OCCN1CCN(CCCN2C3=CC=CC=C3SC3=C2C=C(Cl)C=C3)CC1	3258.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Perphenazine,1TMS,isomer #1	C[Si](C)(C)OCCN1CCN(CCCN2C3=CC=CC=C3SC3=CC=C(Cl)C=C32)CC1	3362.5	Semi standard non polar	33892256
Perphenazine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCN1CCN(CCCN2C3=CC=CC=C3SC3=CC=C(Cl)C=C32)CC1	3545.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Perphenazine EI-B (Non-derivatized)	splash10-0006-9450000000-c13808005c7ad3a43067	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Perphenazine EI-B (Non-derivatized)	splash10-0006-9450000000-c13808005c7ad3a43067	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Perphenazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0095-9657000000-60700e1919a2a347a71b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Perphenazine GC-MS (1 TMS) - 70eV, Positive	splash10-0229-9487500000-73c379ba5c6abc82840d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Perphenazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Perphenazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0002-4591100000-97d36958b3e0fe519db6	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 - Perphenazine LC-ESI-qTof , Positive-QTOF	splash10-0f6t-2930000000-57d820b40a3c2c072840	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Perphenazine , positive-QTOF	splash10-0zfr-0410900000-0910eefd789edd7f94c9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Perphenazine , positive-QTOF	splash10-006x-3940100000-e722b009e1511bd2bb57	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Perphenazine , positive-QTOF	splash10-0f6t-2930000000-57d820b40a3c2c072840	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perphenazine 10V, Positive-QTOF	splash10-0udi-0212900000-26811bdbf39c3e1f8128	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perphenazine 20V, Positive-QTOF	splash10-0fki-3948400000-a80b04752eda36cb7edb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perphenazine 40V, Positive-QTOF	splash10-0aej-8951000000-b1b95a17c6520a72fbcf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perphenazine 10V, Negative-QTOF	splash10-0udi-0004900000-610370bca54ab9e9c9d6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perphenazine 20V, Negative-QTOF	splash10-0kal-0092100000-d3e759bb26e17fa9ca6c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perphenazine 40V, Negative-QTOF	splash10-001i-6790000000-a28fc2d16e6ed9427ab6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perphenazine 10V, Positive-QTOF	splash10-0udi-0000900000-fdd66a3be8cc27f249df	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perphenazine 20V, Positive-QTOF	splash10-0udi-0311900000-06e01a3d1767fa33c605	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perphenazine 40V, Positive-QTOF	splash10-0h7r-2925000000-d9a982d7b5cbf608d58c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perphenazine 10V, Negative-QTOF	splash10-0udi-0000900000-63d2610cf91fae71d084	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perphenazine 20V, Negative-QTOF	splash10-0fk9-0019400000-5b6c925124075a568e5f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perphenazine 40V, Negative-QTOF	splash10-001i-9065100000-6329f86de2658ba85f88	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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 DB00850	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00850	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

DB00850

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4586

KEGG Compound ID

C07427

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Perphenazine

METLIN ID

Not Available

PubChem Compound

4748

PDB ID

Not Available

ChEBI ID

8028

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

Not Available

Only showing the first 10 proteins. There are 11 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. 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

Enzyme Details

2. 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

Enzyme Details

3. 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

Enzyme Details

4. 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

Enzyme Details

5. Cytochrome P450 2C18

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:: CYP2C18
Uniprot ID:: P33260
Molecular weight:: 55710.075

References

Enzyme Details

6. Cytochrome P450 2B6

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. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:: CYP2B6
Uniprot ID:: P20813
Molecular weight:: 56277.81

References

Enzyme Details

7. 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

Enzyme Details

8. 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

Enzyme Details

9. D(2) dopamine receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:: DRD2
Uniprot ID:: P14416
Molecular weight:: 50618.9

References

Enzyme Details

10. Calmodulin

General function:: Involved in calcium ion binding
Specific function:: Calmodulin mediates the control of a large number of enzymes and other proteins by Ca(2+). Among the enzymes to be stimulated by the calmodulin-Ca(2+) complex are a number of protein kinases and phosphatases. Together with CEP110 and centrin, is involved in a genetic pathway that regulates the centrosome cycle and progression through cytokinesis
Gene Name:: CALM1
Uniprot ID:: P62158
Molecular weight:: 16837.5

References

Only showing the first 10 proteins. There are 11 proteins in total.

Show all enzymes and transporters

Showing metabocard for Perphenazine (HMDB0014988)

MOL for HMDB0014988 (Perphenazine)

3D MOL for HMDB0014988 (Perphenazine)

3D SDF for HMDB0014988 (Perphenazine)

3D-SDF for HMDB0014988 (Perphenazine)

PDB for HMDB0014988 (Perphenazine)

3D PDB for HMDB0014988 (Perphenazine)

SMILES for HMDB0014988 (Perphenazine)

INCHI for HMDB0014988 (Perphenazine)

Structure for HMDB0014988 (Perphenazine)

3D Structure for HMDB0014988 (Perphenazine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References

References

References

References

References