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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 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 02:51:53 UTC

HMDB ID

HMDB0015172

Secondary Accession Numbers

HMDB15172

Metabolite Identification

Common Name

Carphenazine

Description

Carphenazine is only found in individuals that have used or taken this drug. It is an antipsychotic drug, used in hospitalized patients in the management of chronic schizophrenic psychoses.A yellow, powdered, phenothiazine antipsychotic agent used in the treatment of acute or chronic schizophrenia. The term "phenothiazines" is used to describe the largest of the five main classes of neuroleptic antipsychotic drugs. These drugs have antipsychotic and, often, antiemetic properties, although they may also cause severe side effects such as akathisia, tardive dyskinesia and extrapyramidal symptoms. Carphenazine blocks postsynaptic mesolimbic dopaminergic D1 and D2 receptors in the brain; depresses the release of hypothalamic and hypophyseal hormones and is believed to depress the reticular activating system thus affecting basal metabolism, body temperature, wakefulness, vasomotor tone, and emesis.

Structure

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


  Mrv0541 04191212162D          

 29 32  0  0  0  0            999 V2000
   -2.2688   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9832   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6977   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6977   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9832   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2688   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5543   -2.4750    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8398   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8398   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5543   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1253   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1253   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5892   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5892   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5543    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8398    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8398    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8398    2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5543    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5543    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1254    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1254    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8398    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1254    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5891    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3036   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3036    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5892    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0181   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  1 10  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9 10  1  0  0  0  0
 11  9  1  0  0  0  0
  8  9  2  0  0  0  0
  8 12  1  0  0  0  0
 11 14  2  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 20 17  1  0  0  0  0
 17 21  1  0  0  0  0
 18 19  1  0  0  0  0
 18 22  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 14 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 29  2  0  0  0  0
M  END

HMDB0015172
     RDKit          3D
Carphenazine
 58 61  0  0  0  0  0  0  0  0999 V2000
   -4.3484   -0.3294    5.1592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6885   -0.3254    3.7081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5112   -0.0859    2.8463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3956    0.1086    3.3715 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6634   -0.0812    1.4053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9000   -0.2928    0.8380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0316   -0.2872   -0.5248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9059   -0.0678   -1.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6557    0.1472   -0.8005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5473    0.1377    0.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5168    0.3784   -1.6018 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2028    0.5760   -0.9650 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4438   -0.6845   -0.5158 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7331   -0.4205    0.0101 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7041    0.0067   -0.9378 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0691   -0.3071   -0.3697 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2685    0.5078    0.8065 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1624   -0.0675    1.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5907   -0.1381    1.2684 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1340    1.0901    0.9697 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0650    0.9110    1.4486 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9327   -0.1218    1.3447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5219    0.4199   -3.0317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3393    0.6469   -3.7213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2577    0.6988   -5.1095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3906    0.5175   -5.8554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5552    0.2935   -5.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6219    0.2455   -3.8312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1910   -0.0697   -3.0483 S   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2966   -0.6028    5.7053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0571    0.6626    5.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6100   -1.1285    5.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5119    0.4055    3.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0939   -1.3554    3.4719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7538   -0.4636    1.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0045   -0.4536   -0.9714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5994    0.3051    1.0420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3441    1.2020   -0.0284 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4880    1.2086   -1.5377 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6012   -1.3985   -1.3867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1369   -1.2722    0.2048 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5350   -0.5001   -1.9027 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6427    1.0892   -1.1190 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8070   -0.0205   -1.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1685   -1.4002   -0.1660 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8701   -1.1153    2.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1418    0.5041    2.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6845   -0.8802    0.4370 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1902   -0.5670    2.1018 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8238    1.0679    0.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6598    1.8341    0.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1939    1.1019    2.5333 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2745   -1.0540    1.8897 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0594    0.3454    1.8467 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5977    0.7833   -3.2333 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6760    0.8794   -5.6132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4008    0.5461   -6.9432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4638    0.1457   -5.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 17 21  1  0
 21 22  1  0
 11 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 10  5  1  0
 22 14  1  0
 28 23  1  0
 29  8  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  6 35  1  0
  7 36  1  0
 10 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 22 54  1  0
 24 55  1  0
 25 56  1  0
 26 57  1  0
 27 58  1  0
M  END


  Mrv0541 04191212162D          

 29 32  0  0  0  0            999 V2000
   -2.2688   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9832   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6977   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6977   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9832   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2688   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5543   -2.4750    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8398   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8398   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5543   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1253   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1253   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5892   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5892   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5543    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8398    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8398    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8398    2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5543    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5543    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1254    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1254    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8398    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1254    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5891    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3036   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3036    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5892    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0181   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  1 10  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9 10  1  0  0  0  0
 11  9  1  0  0  0  0
  8  9  2  0  0  0  0
  8 12  1  0  0  0  0
 11 14  2  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 20 17  1  0  0  0  0
 17 21  1  0  0  0  0
 18 19  1  0  0  0  0
 18 22  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 14 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 29  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015172

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(=O)C1=CC2=C(SC3=C(C=CC=C3)N2CCN2CCN(CCO)CC2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C23H29N3O2S/c1-2-21(28)18-7-8-23-20(17-18)26(19-5-3-4-6-22(19)29-23)14-13-24-9-11-25(12-10-24)15-16-27/h3-8,17,27H,2,9-16H2,1H3

> <INCHI_KEY>
DYCNETKPCXPXNW-UHFFFAOYSA-N

> <FORMULA>
C23H29N3O2S

> <MOLECULAR_WEIGHT>
411.56

> <EXACT_MASS>
411.198047877

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
47.251332837209375

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(10-{2-[4-(2-hydroxyethyl)piperazin-1-yl]ethyl}-10H-phenothiazin-2-yl)propan-1-one

> <ALOGPS_LOGP>
2.84

> <JCHEM_LOGP>
3.286196759666667

> <ALOGPS_LOGS>
-3.66

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
16.679742568328034

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.555981666593063

> <JCHEM_PKA_STRONGEST_BASIC>
8.00235250344538

> <JCHEM_POLAR_SURFACE_AREA>
47.02

> <JCHEM_REFRACTIVITY>
121.45819999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.05e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
carfenazina

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015172
     RDKit          3D
Carphenazine
 58 61  0  0  0  0  0  0  0  0999 V2000
   -4.3484   -0.3294    5.1592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6885   -0.3254    3.7081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5112   -0.0859    2.8463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3956    0.1086    3.3715 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6634   -0.0812    1.4053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9000   -0.2928    0.8380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0316   -0.2872   -0.5248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9059   -0.0678   -1.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6557    0.1472   -0.8005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5473    0.1377    0.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5168    0.3784   -1.6018 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2028    0.5760   -0.9650 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4438   -0.6845   -0.5158 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7331   -0.4205    0.0101 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7041    0.0067   -0.9378 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0691   -0.3071   -0.3697 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2685    0.5078    0.8065 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1624   -0.0675    1.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5907   -0.1381    1.2684 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1340    1.0901    0.9697 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0650    0.9110    1.4486 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9327   -0.1218    1.3447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5219    0.4199   -3.0317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3393    0.6469   -3.7213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2577    0.6988   -5.1095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3906    0.5175   -5.8554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5552    0.2935   -5.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6219    0.2455   -3.8312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1910   -0.0697   -3.0483 S   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2966   -0.6028    5.7053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0571    0.6626    5.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6100   -1.1285    5.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5119    0.4055    3.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0939   -1.3554    3.4719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7538   -0.4636    1.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0045   -0.4536   -0.9714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5994    0.3051    1.0420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3441    1.2020   -0.0284 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4880    1.2086   -1.5377 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6012   -1.3985   -1.3867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1369   -1.2722    0.2048 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5350   -0.5001   -1.9027 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6427    1.0892   -1.1190 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8070   -0.0205   -1.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1685   -1.4002   -0.1660 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8701   -1.1153    2.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1418    0.5041    2.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6845   -0.8802    0.4370 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1902   -0.5670    2.1018 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8238    1.0679    0.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6598    1.8341    0.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1939    1.1019    2.5333 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2745   -1.0540    1.8897 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0594    0.3454    1.8467 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5977    0.7833   -3.2333 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6760    0.8794   -5.6132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4008    0.5461   -6.9432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4638    0.1457   -5.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 17 21  1  0
 21 22  1  0
 11 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 10  5  1  0
 22 14  1  0
 28 23  1  0
 29  8  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  6 35  1  0
  7 36  1  0
 10 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 22 54  1  0
 24 55  1  0
 25 56  1  0
 26 57  1  0
 27 58  1  0
M  END

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0      -4.235  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.569  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.902  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.902  -3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.569  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.235  -3.850   0.000  0.00  0.00           C+0
HETATM    7  S   UNK     0      -2.901  -4.620   0.000  0.00  0.00           S+0
HETATM    8  C   UNK     0      -1.568  -3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.568  -2.310   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -2.901  -1.540   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -0.234  -1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.234  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.100  -3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.100  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.901   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.568   0.770   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      -1.568   2.310   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0      -1.568   5.390   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      -2.901   4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.901   3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.234   3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.234   4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.568   6.930   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.234   7.700   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.100   6.930   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.433  -1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.433   0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.100   0.770   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.767  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2    6   10                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9   10   11    8                                                  
CONECT   10    1    9   15                                                  
CONECT   11    9   14                                                       
CONECT   12    8   13                                                       
CONECT   13   12   14                                                       
CONECT   14   11   13   26                                                  
CONECT   15   10   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   20   21                                                  
CONECT   18   19   22   23                                                  
CONECT   19   18   20                                                       
CONECT   20   17   19                                                       
CONECT   21   17   22                                                       
CONECT   22   18   21                                                       
CONECT   23   18   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   14   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

COMPND    HMDB0015172
HETATM    1  C1  UNL     1      -4.348  -0.329   5.159  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.689  -0.325   3.708  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.511  -0.086   2.846  1.00  0.00           C  
HETATM    4  O1  UNL     1      -2.396   0.109   3.372  1.00  0.00           O  
HETATM    5  C4  UNL     1      -3.663  -0.081   1.405  1.00  0.00           C  
HETATM    6  C5  UNL     1      -4.900  -0.293   0.838  1.00  0.00           C  
HETATM    7  C6  UNL     1      -5.032  -0.287  -0.525  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.906  -0.068  -1.293  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.656   0.147  -0.800  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.547   0.138   0.591  1.00  0.00           C  
HETATM   11  N1  UNL     1      -1.517   0.378  -1.602  1.00  0.00           N  
HETATM   12  C10 UNL     1      -0.203   0.576  -0.965  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.444  -0.685  -0.516  1.00  0.00           C  
HETATM   14  N2  UNL     1       1.733  -0.420   0.010  1.00  0.00           N  
HETATM   15  C12 UNL     1       2.704   0.007  -0.938  1.00  0.00           C  
HETATM   16  C13 UNL     1       4.069  -0.307  -0.370  1.00  0.00           C  
HETATM   17  N3  UNL     1       4.268   0.508   0.806  1.00  0.00           N  
HETATM   18  C14 UNL     1       5.162  -0.067   1.754  1.00  0.00           C  
HETATM   19  C15 UNL     1       6.591  -0.138   1.268  1.00  0.00           C  
HETATM   20  O2  UNL     1       7.134   1.090   0.970  1.00  0.00           O  
HETATM   21  C16 UNL     1       3.065   0.911   1.449  1.00  0.00           C  
HETATM   22  C17 UNL     1       1.933  -0.122   1.345  1.00  0.00           C  
HETATM   23  C18 UNL     1      -1.522   0.420  -3.032  1.00  0.00           C  
HETATM   24  C19 UNL     1      -0.339   0.647  -3.721  1.00  0.00           C  
HETATM   25  C20 UNL     1      -0.258   0.699  -5.110  1.00  0.00           C  
HETATM   26  C21 UNL     1      -1.391   0.518  -5.855  1.00  0.00           C  
HETATM   27  C22 UNL     1      -2.555   0.294  -5.207  1.00  0.00           C  
HETATM   28  C23 UNL     1      -2.622   0.246  -3.831  1.00  0.00           C  
HETATM   29  S1  UNL     1      -4.191  -0.070  -3.048  1.00  0.00           S  
HETATM   30  H1  UNL     1      -5.297  -0.603   5.705  1.00  0.00           H  
HETATM   31  H2  UNL     1      -4.057   0.663   5.528  1.00  0.00           H  
HETATM   32  H3  UNL     1      -3.610  -1.129   5.360  1.00  0.00           H  
HETATM   33  H4  UNL     1      -5.512   0.406   3.521  1.00  0.00           H  
HETATM   34  H5  UNL     1      -5.094  -1.355   3.472  1.00  0.00           H  
HETATM   35  H6  UNL     1      -5.754  -0.464   1.513  1.00  0.00           H  
HETATM   36  H7  UNL     1      -6.005  -0.454  -0.971  1.00  0.00           H  
HETATM   37  H8  UNL     1      -1.599   0.305   1.042  1.00  0.00           H  
HETATM   38  H9  UNL     1      -0.344   1.202  -0.028  1.00  0.00           H  
HETATM   39  H10 UNL     1       0.488   1.209  -1.538  1.00  0.00           H  
HETATM   40  H11 UNL     1       0.601  -1.398  -1.387  1.00  0.00           H  
HETATM   41  H12 UNL     1      -0.137  -1.272   0.205  1.00  0.00           H  
HETATM   42  H13 UNL     1       2.535  -0.500  -1.903  1.00  0.00           H  
HETATM   43  H14 UNL     1       2.643   1.089  -1.119  1.00  0.00           H  
HETATM   44  H15 UNL     1       4.807  -0.020  -1.173  1.00  0.00           H  
HETATM   45  H16 UNL     1       4.169  -1.400  -0.166  1.00  0.00           H  
HETATM   46  H17 UNL     1       4.870  -1.115   2.030  1.00  0.00           H  
HETATM   47  H18 UNL     1       5.142   0.504   2.703  1.00  0.00           H  
HETATM   48  H19 UNL     1       6.685  -0.880   0.437  1.00  0.00           H  
HETATM   49  H20 UNL     1       7.190  -0.567   2.102  1.00  0.00           H  
HETATM   50  H21 UNL     1       7.824   1.068   0.277  1.00  0.00           H  
HETATM   51  H22 UNL     1       2.660   1.834   0.974  1.00  0.00           H  
HETATM   52  H23 UNL     1       3.194   1.102   2.533  1.00  0.00           H  
HETATM   53  H24 UNL     1       2.275  -1.054   1.890  1.00  0.00           H  
HETATM   54  H25 UNL     1       1.059   0.345   1.847  1.00  0.00           H  
HETATM   55  H26 UNL     1       0.598   0.783  -3.233  1.00  0.00           H  
HETATM   56  H27 UNL     1       0.676   0.879  -5.613  1.00  0.00           H  
HETATM   57  H28 UNL     1      -1.401   0.546  -6.943  1.00  0.00           H  
HETATM   58  H29 UNL     1      -3.464   0.146  -5.772  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3   33   34
CONECT    3    4    4    5
CONECT    5    6    6   10
CONECT    6    7   35
CONECT    7    8    8   36
CONECT    8    9   29
CONECT    9   10   10   11
CONECT   10   37
CONECT   11   12   23
CONECT   12   13   38   39
CONECT   13   14   40   41
CONECT   14   15   22
CONECT   15   16   42   43
CONECT   16   17   44   45
CONECT   17   18   21
CONECT   18   19   46   47
CONECT   19   20   48   49
CONECT   20   50
CONECT   21   22   51   52
CONECT   22   53   54
CONECT   23   24   24   28
CONECT   24   25   55
CONECT   25   26   26   56
CONECT   26   27   57
CONECT   27   28   28   58
CONECT   28   29
END

HMDB0015172
     RDKit          3D
Carphenazine
 58 61  0  0  0  0  0  0  0  0999 V2000
   -4.3484   -0.3294    5.1592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6885   -0.3254    3.7081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5112   -0.0859    2.8463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3956    0.1086    3.3715 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6634   -0.0812    1.4053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9000   -0.2928    0.8380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0316   -0.2872   -0.5248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9059   -0.0678   -1.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6557    0.1472   -0.8005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5473    0.1377    0.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5168    0.3784   -1.6018 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2028    0.5760   -0.9650 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4438   -0.6845   -0.5158 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7331   -0.4205    0.0101 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7041    0.0067   -0.9378 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0691   -0.3071   -0.3697 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2685    0.5078    0.8065 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1624   -0.0675    1.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5907   -0.1381    1.2684 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1340    1.0901    0.9697 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0650    0.9110    1.4486 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9327   -0.1218    1.3447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5219    0.4199   -3.0317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3393    0.6469   -3.7213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2577    0.6988   -5.1095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3906    0.5175   -5.8554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5552    0.2935   -5.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6219    0.2455   -3.8312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1910   -0.0697   -3.0483 S   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2966   -0.6028    5.7053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0571    0.6626    5.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6100   -1.1285    5.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5119    0.4055    3.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0939   -1.3554    3.4719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7538   -0.4636    1.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0045   -0.4536   -0.9714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5994    0.3051    1.0420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3441    1.2020   -0.0284 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4880    1.2086   -1.5377 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6012   -1.3985   -1.3867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1369   -1.2722    0.2048 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5350   -0.5001   -1.9027 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6427    1.0892   -1.1190 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8070   -0.0205   -1.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1685   -1.4002   -0.1660 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8701   -1.1153    2.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1418    0.5041    2.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6845   -0.8802    0.4370 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1902   -0.5670    2.1018 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8238    1.0679    0.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6598    1.8341    0.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1939    1.1019    2.5333 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2745   -1.0540    1.8897 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0594    0.3454    1.8467 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5977    0.7833   -3.2333 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6760    0.8794   -5.6132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4008    0.5461   -6.9432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4638    0.1457   -5.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 17 21  1  0
 21 22  1  0
 11 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 10  5  1  0
 22 14  1  0
 28 23  1  0
 29  8  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  6 35  1  0
  7 36  1  0
 10 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 22 54  1  0
 24 55  1  0
 25 56  1  0
 26 57  1  0
 27 58  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(10-(3-(4-(2-Hydroxyethyl)-1-piperazinyl)propyl)phenothiazin-2-yl)-1-propanone	ChEBI
Carfenazina	ChEBI
Carfenazine	ChEBI
Carfenazinum	ChEBI
Carphenazin	HMDB

Chemical Formula

C₂₃H₂₉N₃O₂S

Average Molecular Weight

411.56

Monoisotopic Molecular Weight

411.198047877

IUPAC Name

1-(10-{2-[4-(2-hydroxyethyl)piperazin-1-yl]ethyl}-10H-phenothiazin-2-yl)propan-1-one

Traditional Name

carfenazina

CAS Registry Number

2622-30-2

SMILES

CCC(=O)C1=CC2=C(SC3=C(C=CC=C3)N2CCN2CCN(CCO)CC2)C=C1

InChI Identifier

InChI=1S/C23H29N3O2S/c1-2-21(28)18-7-8-23-20(17-18)26(19-5-3-4-6-22(19)29-23)14-13-24-9-11-25(12-10-24)15-16-27/h3-8,17,27H,2,9-16H2,1H3

InChI Key

DYCNETKPCXPXNW-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
Aryl alkyl ketone
Aryl ketone
N-alkylpiperazine
Para-thiazine
1,4-diazinane
Piperazine
Benzenoid
1,2-aminoalcohol
Ketone
Tertiary amine
Tertiary aliphatic amine
Thioether
Alkanolamine
Azacycle
Hydrocarbon derivative
Primary alcohol
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxygen compound
Amine
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenothiazines (CHEBI:51235 )
propanone (CHEBI:51235 )
N-alkylpiperazine (CHEBI:51235 )

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: HMDB0015172)

Source

Exogenous

Exogenous (HMDB: HMDB0015172)

Process

Not Available

Role

Industrial application

Antiemetic (HMDB: HMDB0015172)

Pharmaceutical industry

Phenothiazine antipsychotic drug (HMDB: HMDB0015172)

Dopamine uptake inhibitor (HMDB: HMDB0015172)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.09 g/L	Not Available
LogP	3.3	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.09 g/L	ALOGPS
logP	2.84	ALOGPS
logP	3.29	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	15.56	ChemAxon
pKa (Strongest Basic)	8	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	47.02 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	121.46 m³·mol⁻¹	ChemAxon
Polarizability	47.25 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	194.738	31661259
DarkChem	[M-H]-	194.009	31661259
DeepCCS	[M+H]+	202.806	30932474
DeepCCS	[M-H]-	200.448	30932474
DeepCCS	[M-2H]-	234.43	30932474
DeepCCS	[M+Na]+	209.657	30932474
AllCCS	[M+H]+	199.1	32859911
AllCCS	[M+H-H2O]+	196.8	32859911
AllCCS	[M+NH4]+	201.3	32859911
AllCCS	[M+Na]+	201.9	32859911
AllCCS	[M-H]-	196.6	32859911
AllCCS	[M+Na-2H]-	196.9	32859911
AllCCS	[M+HCOO]-	197.3	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.	3.23 minutes	32390414
Predicted by Siyang on May 30, 2022	10.4132 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.88 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	99.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1064.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	185.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	168.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	178.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	82.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	343.2 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	490.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	531.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	864.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	280.3 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	1016.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	249.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	332.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	306.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	494.6 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	169.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Carphenazine	CCC(=O)C1=CC2=C(SC3=C(C=CC=C3)N2CCN2CCN(CCO)CC2)C=C1	4594.1	Standard polar	33892256
Carphenazine	CCC(=O)C1=CC2=C(SC3=C(C=CC=C3)N2CCN2CCN(CCO)CC2)C=C1	3457.3	Standard non polar	33892256
Carphenazine	CCC(=O)C1=CC2=C(SC3=C(C=CC=C3)N2CCN2CCN(CCO)CC2)C=C1	3578.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Carphenazine,1TMS,isomer #1	CCC(=O)C1=CC=C2SC3=CC=CC=C3N(CCN3CCN(CCO[Si](C)(C)C)CC3)C2=C1	3502.1	Semi standard non polar	33892256
Carphenazine,1TBDMS,isomer #1	CCC(=O)C1=CC=C2SC3=CC=CC=C3N(CCN3CCN(CCO[Si](C)(C)C(C)(C)C)CC3)C2=C1	3698.5	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 - Carphenazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-003r-1249000000-8269c1aea27b4519caf5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Carphenazine GC-MS (1 TMS) - 70eV, Positive	splash10-014i-4489800000-a2dc84d530af6c491e7e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Carphenazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Carphenazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carphenazine 10V, Positive-QTOF	splash10-03di-0326900000-6e5ae095bf0ef6084542	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carphenazine 20V, Positive-QTOF	splash10-0bu0-2792000000-1cff5a929ddf220c741b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carphenazine 40V, Positive-QTOF	splash10-0bu1-5932000000-98b40f4a2cdbae56d3ab	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carphenazine 10V, Negative-QTOF	splash10-03di-0005900000-6bb5170e920dc2485681	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carphenazine 20V, Negative-QTOF	splash10-0udm-0196100000-4cbb6b3fa5eccbfc7980	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carphenazine 40V, Negative-QTOF	splash10-0k97-9653000000-000631b921931d7be9ba	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carphenazine 10V, Positive-QTOF	splash10-03di-0000900000-94a2b7e7b061d0929453	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carphenazine 20V, Positive-QTOF	splash10-01q9-0190400000-27679b67f9c21cea78da	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carphenazine 40V, Positive-QTOF	splash10-022a-8931000000-36b009ad5cd7ac7aec2b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carphenazine 10V, Negative-QTOF	splash10-03di-0000900000-474df7b273d6c5e26ef6	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carphenazine 20V, Negative-QTOF	splash10-03di-0038900000-91fbc50a2f95f1bd7526	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carphenazine 40V, Negative-QTOF	splash10-0udi-2192000000-96e0f1beaa722034f19a	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 DB01038	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01038	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

21865853

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Carphenazine

METLIN ID

Not Available

PubChem Compound

25137957

PDB ID

Not Available

ChEBI ID

51235

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. 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

Vinar O, Formankova M, Taussigova D, Ruzicka S: Carphenazine in the treatment of schizophrenic psychoses. Controlled clinical trial. Act Nerv Super (Praha). 1967 Nov;9(4):353-5. [PubMed:4889058 ]
Bora G: Comparison of dosage ranges of carphenazine and trifluoperazine in elderly chronic schizophrenics. Dis Nerv Syst. 1968 Oct;29(10):695-7. [PubMed:4887393 ]
Platz AR, Klett CJ, Caffey EM Jr: Selective drug action related to chronic schizophrenic subtype. (A comparative study of carphenazine, chlorpromazine, and trifluoperazine). Dis Nerv Syst. 1967 Sep;28(9):601-5. [PubMed:4861216 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

2. D(1A) 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 activate adenylyl cyclase
Gene Name:: DRD1
Uniprot ID:: P21728
Molecular weight:: 49292.8

References

Vinar O, Formankova M, Taussigova D, Ruzicka S: Carphenazine in the treatment of schizophrenic psychoses. Controlled clinical trial. Act Nerv Super (Praha). 1967 Nov;9(4):353-5. [PubMed:4889058 ]
Bora G: Comparison of dosage ranges of carphenazine and trifluoperazine in elderly chronic schizophrenics. Dis Nerv Syst. 1968 Oct;29(10):695-7. [PubMed:4887393 ]
Platz AR, Klett CJ, Caffey EM Jr: Selective drug action related to chronic schizophrenic subtype. (A comparative study of carphenazine, chlorpromazine, and trifluoperazine). Dis Nerv Syst. 1967 Sep;28(9):601-5. [PubMed:4861216 ]

Enzyme Details

3. D(1B) 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 activate adenylyl cyclase
Gene Name:: DRD5
Uniprot ID:: P21918
Molecular weight:: 52950.5

References

Vinar O, Formankova M, Taussigova D, Ruzicka S: Carphenazine in the treatment of schizophrenic psychoses. Controlled clinical trial. Act Nerv Super (Praha). 1967 Nov;9(4):353-5. [PubMed:4889058 ]
Bora G: Comparison of dosage ranges of carphenazine and trifluoperazine in elderly chronic schizophrenics. Dis Nerv Syst. 1968 Oct;29(10):695-7. [PubMed:4887393 ]
Platz AR, Klett CJ, Caffey EM Jr: Selective drug action related to chronic schizophrenic subtype. (A comparative study of carphenazine, chlorpromazine, and trifluoperazine). Dis Nerv Syst. 1967 Sep;28(9):601-5. [PubMed:4861216 ]

Showing metabocard for Carphenazine (HMDB0015172)

MOL for HMDB0015172 (Carphenazine)

3D MOL for HMDB0015172 (Carphenazine)

3D SDF for HMDB0015172 (Carphenazine)

3D-SDF for HMDB0015172 (Carphenazine)

PDB for HMDB0015172 (Carphenazine)

3D PDB for HMDB0015172 (Carphenazine)

SMILES for HMDB0015172 (Carphenazine)

INCHI for HMDB0015172 (Carphenazine)

Structure for HMDB0015172 (Carphenazine)

3D Structure for HMDB0015172 (Carphenazine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References