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enzymes (6)transporters (1) Show 7 proteins

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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:01 UTC

HMDB ID

HMDB0015559

Secondary Accession Numbers

HMDB15559

Metabolite Identification

Common Name

Thioproperazine

Description

Thioproperazine is a potent neuroleptic with antipsychotic properties. Thioproperazine has a marked cataleptic and antiapomorphine activity associated with relatively slight sedative, hypothermic and spasmolytic effects. It is virtually without antiserotonin and hypotensive action and has no antihistaminic property. It is used for the treatment of all types of acute and chronic schizophrenia, including those which did not respond to the usual neuroleptics; manic syndromes. Overdosage may result in severe extrapyramidal symptoms with dysphagia, marked sialorrhea, persistent and rapidly increasing hyperthermia, pulmonary syndrome, state of shock with pallor and profuse sweating, which may be followed by collapse and coma. LD50 in mice is 70 mg/kg I.V., 120 mg/kg I.P., 500 mg/kg S.C. and 830 mg/kg P.O.

Structure

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

1622
  Mrv0541 02231215362D          

 30 33  0  0  0  0            999 V2000
    5.2216   -2.6666    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.1336   -0.9969    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.7184   -0.2841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5488   -1.7097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929    1.4578    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641    2.2827    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -1.0169    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8463   -0.5817    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    1.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929    2.2827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073    1.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641    1.4578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    2.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073    0.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -0.1920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498    2.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9361   -1.4293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073   -1.4293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9361   -2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073   -2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6734   -0.9883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4209   -1.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7699   -0.9883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6734   -2.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4209   -2.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7699   -2.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0225   -1.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0225   -2.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8432    0.2432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5623   -0.9914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  2  0  0  0  0
  2  8  1  0  0  0  0
  2 22  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  1  0  0  0  0
  6 12  1  0  0  0  0
  6 13  1  0  0  0  0
  6 16  1  0  0  0  0
  7 15  1  0  0  0  0
  7 17  1  0  0  0  0
  7 18  1  0  0  0  0
  8 29  1  0  0  0  0
  8 30  1  0  0  0  0
  9 12  1  0  0  0  0
 10 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 17 19  2  0  0  0  0
 17 21  1  0  0  0  0
 18 20  1  0  0  0  0
 18 23  2  0  0  0  0
 19 24  1  0  0  0  0
 20 26  2  0  0  0  0
 21 22  2  0  0  0  0
 22 25  1  0  0  0  0
 23 27  1  0  0  0  0
 24 25  2  0  0  0  0
 26 28  1  0  0  0  0
 27 28  2  0  0  0  0
M  END

HMDB0015559
     RDKit          3D
Thioproperazine
 60 63  0  0  0  0  0  0  0  0999 V2000
    5.2770   -3.0171   -0.1240 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3615   -1.9186   -0.1191 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6069   -0.9755    0.9611 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3576   -0.7642    1.7914 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2222   -0.3330    0.9927 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3635    1.0893    0.7419 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2099    1.6756   -0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0965    1.5312    0.6800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2249    2.1213   -0.0369 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3450    3.5520   -0.0141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4091    4.2941    0.7112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4760    5.6909    0.7763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4556    6.3766    0.1355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3692    5.6264   -0.5739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3135    4.2687   -0.6438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5680    3.4733   -1.5838 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2209    1.7006   -1.4727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0558    0.8426   -2.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8208   -0.5039   -2.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7544   -1.0113   -1.3708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4579   -2.7399   -1.3042 S   0  0  0  0  0  6  0  0  0  0  0  0
   -2.9095   -3.4109   -2.5707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9907   -2.9550   -1.0672 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3148   -3.3567    0.0498 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8267   -2.7535    1.2587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3017   -4.7838    0.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9520   -0.1058   -0.7289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1414    1.2854   -0.7452 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1485   -1.0666   -0.2601 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9666   -2.3306   -0.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2578   -2.7060    0.2830 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4533   -3.3284   -1.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8722   -3.8903    0.4199 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3576   -1.4392    1.6325 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0190   -0.0138    0.6186 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5953    0.0446    2.5235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0808   -1.6492    2.3690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4364    1.5638    1.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2917    1.2264    0.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2000    1.0438   -0.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4010    2.6877   -0.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3454    0.5111    0.9850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0499    2.0553    1.6697 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3930    3.8694    1.2571 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2727    6.2344    1.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5102    7.4539    0.1835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1526    6.2113   -1.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8879    1.2543   -2.6867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4735   -1.2086   -2.5999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8320   -3.4569    2.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7752   -2.4312    1.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4269   -1.8694    1.5709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2396   -5.1309    1.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2632   -5.1880   -0.2613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4963   -5.2131   -0.4786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1251   -0.5417   -0.1971 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6840   -0.4386   -1.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1102   -1.2673   -0.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6977   -2.8954    0.8018 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8462   -2.9896   -1.0122 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  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  2  0
 21 24  1  0
 24 25  1  0
 24 26  1  0
 20 27  1  0
 27 28  2  0
  5 29  1  0
 29 30  1  0
 30  2  1  0
 28  9  1  0
 15 10  1  0
 28 17  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
 11 44  1  0
 12 45  1  0
 13 46  1  0
 14 47  1  0
 18 48  1  0
 19 49  1  0
 25 50  1  0
 25 51  1  0
 25 52  1  0
 26 53  1  0
 26 54  1  0
 26 55  1  0
 27 56  1  0
 29 57  1  0
 29 58  1  0
 30 59  1  0
 30 60  1  0
M  END

1622
  Mrv0541 02231215362D          

 30 33  0  0  0  0            999 V2000
    5.2216   -2.6666    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.1336   -0.9969    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.7184   -0.2841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5488   -1.7097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929    1.4578    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641    2.2827    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -1.0169    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8463   -0.5817    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    1.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929    2.2827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073    1.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641    1.4578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    2.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073    0.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -0.1920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498    2.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9361   -1.4293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073   -1.4293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9361   -2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073   -2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6734   -0.9883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4209   -1.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7699   -0.9883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6734   -2.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4209   -2.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7699   -2.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0225   -1.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0225   -2.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8432    0.2432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5623   -0.9914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  2  0  0  0  0
  2  8  1  0  0  0  0
  2 22  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  1  0  0  0  0
  6 12  1  0  0  0  0
  6 13  1  0  0  0  0
  6 16  1  0  0  0  0
  7 15  1  0  0  0  0
  7 17  1  0  0  0  0
  7 18  1  0  0  0  0
  8 29  1  0  0  0  0
  8 30  1  0  0  0  0
  9 12  1  0  0  0  0
 10 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 17 19  2  0  0  0  0
 17 21  1  0  0  0  0
 18 20  1  0  0  0  0
 18 23  2  0  0  0  0
 19 24  1  0  0  0  0
 20 26  2  0  0  0  0
 21 22  2  0  0  0  0
 22 25  1  0  0  0  0
 23 27  1  0  0  0  0
 24 25  2  0  0  0  0
 26 28  1  0  0  0  0
 27 28  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015559

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)S(=O)(=O)C1=CC2=C(SC3=CC=CC=C3N2CCCN2CCN(C)CC2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H30N4O2S2/c1-23(2)30(27,28)18-9-10-22-20(17-18)26(19-7-4-5-8-21(19)29-22)12-6-11-25-15-13-24(3)14-16-25/h4-5,7-10,17H,6,11-16H2,1-3H3

> <INCHI_KEY>
VZYCZNZBPPHOFY-UHFFFAOYSA-N

> <FORMULA>
C22H30N4O2S2

> <MOLECULAR_WEIGHT>
446.629

> <EXACT_MASS>
446.181017604

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
49.623029021872085

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N,N-dimethyl-10-[3-(4-methylpiperazin-1-yl)propyl]-10H-phenothiazine-2-sulfonamide

> <ALOGPS_LOGP>
3.09

> <JCHEM_LOGP>
2.831458045999999

> <ALOGPS_LOGS>
-3.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.36451159976591

> <JCHEM_POLAR_SURFACE_AREA>
47.10000000000001

> <JCHEM_REFRACTIVITY>
126.95290000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.69e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
thioproperazine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015559
     RDKit          3D
Thioproperazine
 60 63  0  0  0  0  0  0  0  0999 V2000
    5.2770   -3.0171   -0.1240 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3615   -1.9186   -0.1191 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6069   -0.9755    0.9611 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3576   -0.7642    1.7914 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2222   -0.3330    0.9927 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3635    1.0893    0.7419 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2099    1.6756   -0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0965    1.5312    0.6800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2249    2.1213   -0.0369 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3450    3.5520   -0.0141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4091    4.2941    0.7112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4760    5.6909    0.7763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4556    6.3766    0.1355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3692    5.6264   -0.5739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3135    4.2687   -0.6438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5680    3.4733   -1.5838 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2209    1.7006   -1.4727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0558    0.8426   -2.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8208   -0.5039   -2.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7544   -1.0113   -1.3708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4579   -2.7399   -1.3042 S   0  0  0  0  0  6  0  0  0  0  0  0
   -2.9095   -3.4109   -2.5707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9907   -2.9550   -1.0672 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3148   -3.3567    0.0498 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8267   -2.7535    1.2587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3017   -4.7838    0.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9520   -0.1058   -0.7289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1414    1.2854   -0.7452 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1485   -1.0666   -0.2601 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9666   -2.3306   -0.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2578   -2.7060    0.2830 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4533   -3.3284   -1.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8722   -3.8903    0.4199 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3576   -1.4392    1.6325 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0190   -0.0138    0.6186 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5953    0.0446    2.5235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0808   -1.6492    2.3690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4364    1.5638    1.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2917    1.2264    0.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2000    1.0438   -0.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4010    2.6877   -0.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3454    0.5111    0.9850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0499    2.0553    1.6697 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3930    3.8694    1.2571 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2727    6.2344    1.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5102    7.4539    0.1835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1526    6.2113   -1.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8879    1.2543   -2.6867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4735   -1.2086   -2.5999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8320   -3.4569    2.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7752   -2.4312    1.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4269   -1.8694    1.5709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2396   -5.1309    1.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2632   -5.1880   -0.2613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4963   -5.2131   -0.4786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1251   -0.5417   -0.1971 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6840   -0.4386   -1.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1102   -1.2673   -0.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6977   -2.8954    0.8018 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8462   -2.9896   -1.0122 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  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  2  0
 21 24  1  0
 24 25  1  0
 24 26  1  0
 20 27  1  0
 27 28  2  0
  5 29  1  0
 29 30  1  0
 30  2  1  0
 28  9  1  0
 15 10  1  0
 28 17  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
 11 44  1  0
 12 45  1  0
 13 46  1  0
 14 47  1  0
 18 48  1  0
 19 49  1  0
 25 50  1  0
 25 51  1  0
 25 52  1  0
 26 53  1  0
 26 54  1  0
 26 55  1  0
 27 56  1  0
 29 57  1  0
 29 58  1  0
 30 59  1  0
 30 60  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1622                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       9.747  -4.978   0.000  0.00  0.00           S+0
HETATM    2  S   UNK     0      15.183  -1.861   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0      14.408  -0.530   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      15.958  -3.191   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       7.080   2.721   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       4.413   4.261   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       9.747  -1.898   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      16.513  -1.086   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       5.747   1.951   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.080   4.261   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.414   1.951   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.413   2.721   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.747   5.031   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.414   0.412   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.747  -0.358   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.080   5.031   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.081  -2.668   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.414  -2.668   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.081  -4.208   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.414  -4.208   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.457  -1.845   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.852  -2.636   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.037  -1.845   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.457  -5.031   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.852  -4.240   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.037  -5.031   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.642  -2.636   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.642  -4.240   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      16.507   0.454   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      17.850  -1.851   0.000  0.00  0.00           C+0
CONECT    1   19   20                                                       
CONECT    2    3    4    8   22                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    9   10   11                                                  
CONECT    6   12   13   16                                                  
CONECT    7   15   17   18                                                  
CONECT    8    2   29   30                                                  
CONECT    9    5   12                                                       
CONECT   10    5   13                                                       
CONECT   11    5   14                                                       
CONECT   12    6    9                                                       
CONECT   13    6   10                                                       
CONECT   14   11   15                                                       
CONECT   15    7   14                                                       
CONECT   16    6                                                            
CONECT   17    7   19   21                                                  
CONECT   18    7   20   23                                                  
CONECT   19    1   17   24                                                  
CONECT   20    1   18   26                                                  
CONECT   21   17   22                                                       
CONECT   22    2   21   25                                                  
CONECT   23   18   27                                                       
CONECT   24   19   25                                                       
CONECT   25   22   24                                                       
CONECT   26   20   28                                                       
CONECT   27   23   28                                                       
CONECT   28   26   27                                                       
CONECT   29    8                                                            
CONECT   30    8                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

COMPND    HMDB0015559
HETATM    1  C1  UNL     1       5.277  -3.017  -0.124  1.00  0.00           C  
HETATM    2  N1  UNL     1       4.361  -1.919  -0.119  1.00  0.00           N  
HETATM    3  C2  UNL     1       4.607  -0.975   0.961  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.358  -0.764   1.791  1.00  0.00           C  
HETATM    5  N2  UNL     1       2.222  -0.333   0.993  1.00  0.00           N  
HETATM    6  C4  UNL     1       2.364   1.089   0.742  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.210   1.676  -0.040  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.096   1.531   0.680  1.00  0.00           C  
HETATM    9  N3  UNL     1      -1.225   2.121  -0.037  1.00  0.00           N  
HETATM   10  C7  UNL     1      -1.345   3.552  -0.014  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.409   4.294   0.711  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.476   5.691   0.776  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.456   6.377   0.136  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.369   5.626  -0.574  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.314   4.269  -0.644  1.00  0.00           C  
HETATM   16  S1  UNL     1      -3.568   3.473  -1.584  1.00  0.00           S  
HETATM   17  C13 UNL     1      -3.221   1.701  -1.473  1.00  0.00           C  
HETATM   18  C14 UNL     1      -4.056   0.843  -2.134  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.821  -0.504  -2.081  1.00  0.00           C  
HETATM   20  C16 UNL     1      -2.754  -1.011  -1.371  1.00  0.00           C  
HETATM   21  S2  UNL     1      -2.458  -2.740  -1.304  1.00  0.00           S  
HETATM   22  O1  UNL     1      -2.909  -3.411  -2.571  1.00  0.00           O  
HETATM   23  O2  UNL     1      -0.991  -2.955  -1.067  1.00  0.00           O  
HETATM   24  N4  UNL     1      -3.315  -3.357   0.050  1.00  0.00           N  
HETATM   25  C17 UNL     1      -2.827  -2.753   1.259  1.00  0.00           C  
HETATM   26  C18 UNL     1      -3.302  -4.784   0.144  1.00  0.00           C  
HETATM   27  C19 UNL     1      -1.952  -0.106  -0.729  1.00  0.00           C  
HETATM   28  C20 UNL     1      -2.141   1.285  -0.745  1.00  0.00           C  
HETATM   29  C21 UNL     1       2.148  -1.067  -0.260  1.00  0.00           C  
HETATM   30  C22 UNL     1       2.967  -2.331  -0.110  1.00  0.00           C  
HETATM   31  H1  UNL     1       6.258  -2.706   0.283  1.00  0.00           H  
HETATM   32  H2  UNL     1       5.453  -3.328  -1.193  1.00  0.00           H  
HETATM   33  H3  UNL     1       4.872  -3.890   0.420  1.00  0.00           H  
HETATM   34  H4  UNL     1       5.358  -1.439   1.633  1.00  0.00           H  
HETATM   35  H5  UNL     1       5.019  -0.014   0.619  1.00  0.00           H  
HETATM   36  H6  UNL     1       3.595   0.045   2.524  1.00  0.00           H  
HETATM   37  H7  UNL     1       3.081  -1.649   2.369  1.00  0.00           H  
HETATM   38  H8  UNL     1       2.436   1.564   1.763  1.00  0.00           H  
HETATM   39  H9  UNL     1       3.292   1.226   0.154  1.00  0.00           H  
HETATM   40  H10 UNL     1       1.200   1.044  -0.999  1.00  0.00           H  
HETATM   41  H11 UNL     1       1.401   2.688  -0.420  1.00  0.00           H  
HETATM   42  H12 UNL     1      -0.345   0.511   0.985  1.00  0.00           H  
HETATM   43  H13 UNL     1       0.050   2.055   1.670  1.00  0.00           H  
HETATM   44  H14 UNL     1       0.393   3.869   1.257  1.00  0.00           H  
HETATM   45  H15 UNL     1       0.273   6.234   1.352  1.00  0.00           H  
HETATM   46  H16 UNL     1      -1.510   7.454   0.183  1.00  0.00           H  
HETATM   47  H17 UNL     1      -3.153   6.211  -1.083  1.00  0.00           H  
HETATM   48  H18 UNL     1      -4.888   1.254  -2.687  1.00  0.00           H  
HETATM   49  H19 UNL     1      -4.474  -1.209  -2.600  1.00  0.00           H  
HETATM   50  H20 UNL     1      -2.832  -3.457   2.123  1.00  0.00           H  
HETATM   51  H21 UNL     1      -1.775  -2.431   1.131  1.00  0.00           H  
HETATM   52  H22 UNL     1      -3.427  -1.869   1.571  1.00  0.00           H  
HETATM   53  H23 UNL     1      -3.240  -5.131   1.191  1.00  0.00           H  
HETATM   54  H24 UNL     1      -4.263  -5.188  -0.261  1.00  0.00           H  
HETATM   55  H25 UNL     1      -2.496  -5.213  -0.479  1.00  0.00           H  
HETATM   56  H26 UNL     1      -1.125  -0.542  -0.197  1.00  0.00           H  
HETATM   57  H27 UNL     1       2.684  -0.439  -1.009  1.00  0.00           H  
HETATM   58  H28 UNL     1       1.110  -1.267  -0.531  1.00  0.00           H  
HETATM   59  H29 UNL     1       2.698  -2.895   0.802  1.00  0.00           H  
HETATM   60  H30 UNL     1       2.846  -2.990  -1.012  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3   30
CONECT    3    4   34   35
CONECT    4    5   36   37
CONECT    5    6   29
CONECT    6    7   38   39
CONECT    7    8   40   41
CONECT    8    9   42   43
CONECT    9   10   28
CONECT   10   11   11   15
CONECT   11   12   44
CONECT   12   13   13   45
CONECT   13   14   46
CONECT   14   15   15   47
CONECT   15   16
CONECT   16   17
CONECT   17   18   18   28
CONECT   18   19   48
CONECT   19   20   20   49
CONECT   20   21   27
CONECT   21   22   22   23   23
CONECT   21   24
CONECT   24   25   26
CONECT   25   50   51   52
CONECT   26   53   54   55
CONECT   27   28   28   56
CONECT   29   30   57   58
CONECT   30   59   60
END

HMDB0015559
     RDKit          3D
Thioproperazine
 60 63  0  0  0  0  0  0  0  0999 V2000
    5.2770   -3.0171   -0.1240 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3615   -1.9186   -0.1191 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6069   -0.9755    0.9611 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3576   -0.7642    1.7914 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2222   -0.3330    0.9927 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3635    1.0893    0.7419 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2099    1.6756   -0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0965    1.5312    0.6800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2249    2.1213   -0.0369 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3450    3.5520   -0.0141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4091    4.2941    0.7112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4760    5.6909    0.7763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4556    6.3766    0.1355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3692    5.6264   -0.5739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3135    4.2687   -0.6438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5680    3.4733   -1.5838 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2209    1.7006   -1.4727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0558    0.8426   -2.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8208   -0.5039   -2.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7544   -1.0113   -1.3708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4579   -2.7399   -1.3042 S   0  0  0  0  0  6  0  0  0  0  0  0
   -2.9095   -3.4109   -2.5707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9907   -2.9550   -1.0672 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3148   -3.3567    0.0498 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8267   -2.7535    1.2587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3017   -4.7838    0.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9520   -0.1058   -0.7289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1414    1.2854   -0.7452 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1485   -1.0666   -0.2601 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9666   -2.3306   -0.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2578   -2.7060    0.2830 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4533   -3.3284   -1.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8722   -3.8903    0.4199 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3576   -1.4392    1.6325 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0190   -0.0138    0.6186 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5953    0.0446    2.5235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0808   -1.6492    2.3690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4364    1.5638    1.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2917    1.2264    0.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2000    1.0438   -0.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4010    2.6877   -0.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3454    0.5111    0.9850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0499    2.0553    1.6697 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3930    3.8694    1.2571 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2727    6.2344    1.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5102    7.4539    0.1835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1526    6.2113   -1.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8879    1.2543   -2.6867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4735   -1.2086   -2.5999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8320   -3.4569    2.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7752   -2.4312    1.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4269   -1.8694    1.5709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2396   -5.1309    1.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2632   -5.1880   -0.2613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4963   -5.2131   -0.4786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1251   -0.5417   -0.1971 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6840   -0.4386   -1.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1102   -1.2673   -0.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6977   -2.8954    0.8018 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8462   -2.9896   -1.0122 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
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 24 25  1  0
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 20 27  1  0
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  5 29  1  0
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 28  9  1  0
 15 10  1  0
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  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  6 38  1  0
  6 39  1  0
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 29 58  1  0
 30 59  1  0
 30 60  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(Thioproperazine)-2-dimethylsulfamido-(10-(3-1-methylpiperazinyl-4)propyl)-phenothiazine	ChEBI
2-Dimethylsulfamido-(10-(3-1-methylpiperazinyl-4)propyl)-phenothiazine	ChEBI
N,N-Dimethyl-10-[3-(4-methyl-1-piperazinyl)propyl]-10H-phenothiazine-2-sulfonamide	ChEBI
N,N-Dimethyl-10-[3-(4-methyl-1-piperazinyl)propyl]phenothiazine-2-sulfonamide	ChEBI
Thioperazine	ChEBI
Thioproperazin	ChEBI
Thioproperazinum	ChEBI
Tioproferazina	ChEBI
Tioproperazina	ChEBI
(Thioproperazine)-2-dimethylsulphamido-(10-(3-1-methylpiperazinyl-4)propyl)-phenothiazine	Generator
2-Dimethylsulphamido-(10-(3-1-methylpiperazinyl-4)propyl)-phenothiazine	Generator
N,N-Dimethyl-10-[3-(4-methyl-1-piperazinyl)propyl]-10H-phenothiazine-2-sulphonamide	Generator
N,N-Dimethyl-10-[3-(4-methyl-1-piperazinyl)propyl]phenothiazine-2-sulphonamide	Generator
Thiproperazine	HMDB
Majeptil	HMDB
Thioproperazine mesylate	HMDB

Chemical Formula

C₂₂H₃₀N₄O₂S₂

Average Molecular Weight

446.629

Monoisotopic Molecular Weight

446.181017604

IUPAC Name

N,N-dimethyl-10-[3-(4-methylpiperazin-1-yl)propyl]-10H-phenothiazine-2-sulfonamide

Traditional Name

thioproperazine

CAS Registry Number

316-81-4

SMILES

CN(C)S(=O)(=O)C1=CC2=C(SC3=CC=CC=C3N2CCCN2CCN(C)CC2)C=C1

InChI Identifier

InChI=1S/C22H30N4O2S2/c1-23(2)30(27,28)18-9-10-22-20(17-18)26(19-7-4-5-8-21(19)29-22)12-6-11-25-15-13-24(3)14-16-25/h4-5,7-10,17H,6,11-16H2,1-3H3

InChI Key

VZYCZNZBPPHOFY-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-methylpiperazine
N-alkylpiperazine
Para-thiazine
1,4-diazinane
Piperazine
Organosulfonic acid amide
Benzenoid
Aminosulfonyl compound
Sulfonyl
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Thioether
Azacycle
Organic oxygen compound
Amine
Organic nitrogen compound
Organosulfur compound
Organopnictogen compound
Organic oxide
Organonitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenothiazines (CHEBI:59120 )
sulfonamide (CHEBI:59120 )
N-alkylpiperazine (CHEBI:59120 )
N-methylpiperazine (CHEBI:59120 )

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

Extracellular (HMDB: HMDB0015559)
Membrane (HMDB: HMDB0015559)

Source

Exogenous

Exogenous (HMDB: HMDB0015559)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	140 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.057 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.057 g/L	ALOGPS
logP	3.09	ALOGPS
logP	2.83	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Basic)	8.36	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	47.1 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	126.95 m³·mol⁻¹	ChemAxon
Polarizability	49.62 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	205.528	31661259
DarkChem	[M-H]-	203.94	31661259
DeepCCS	[M+H]+	205.306	30932474
DeepCCS	[M-H]-	202.948	30932474
DeepCCS	[M-2H]-	236.867	30932474
DeepCCS	[M+Na]+	212.095	30932474
AllCCS	[M+H]+	204.6	32859911
AllCCS	[M+H-H2O]+	202.6	32859911
AllCCS	[M+NH4]+	206.5	32859911
AllCCS	[M+Na]+	207.1	32859911
AllCCS	[M-H]-	196.9	32859911
AllCCS	[M+Na-2H]-	197.5	32859911
AllCCS	[M+HCOO]-	198.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Thioproperazine	CN(C)S(=O)(=O)C1=CC2=C(SC3=CC=CC=C3N2CCCN2CCN(C)CC2)C=C1	4979.4	Standard polar	33892256
Thioproperazine	CN(C)S(=O)(=O)C1=CC2=C(SC3=CC=CC=C3N2CCCN2CCN(C)CC2)C=C1	3630.3	Standard non polar	33892256
Thioproperazine	CN(C)S(=O)(=O)C1=CC2=C(SC3=CC=CC=C3N2CCCN2CCN(C)CC2)C=C1	3617.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Thioproperazine EI-B (Non-derivatized)	splash10-01vo-9411000000-e918c0715fd27f21a62f	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Thioproperazine EI-B (Non-derivatized)	splash10-0229-6924100000-fcb76747a5faaee6b722	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Thioproperazine CI-B (Non-derivatized)	splash10-0002-1001900000-0b26a1120865f1ac9f3a	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Thioproperazine EI-B (Non-derivatized)	splash10-01vo-9411000000-e918c0715fd27f21a62f	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Thioproperazine EI-B (Non-derivatized)	splash10-0229-6924100000-fcb76747a5faaee6b722	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Thioproperazine CI-B (Non-derivatized)	splash10-0002-1001900000-0b26a1120865f1ac9f3a	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Thioproperazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0gvx-9328400000-24ef973c47f4ee47b0dc	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Thioproperazine 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 - Thioproperazine 10V, Positive-QTOF	splash10-0002-0102900000-334bd86e2d2b0ce2fcea	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thioproperazine 20V, Positive-QTOF	splash10-0udm-2708900000-eac9c8a05ffb9ac75d0a	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thioproperazine 40V, Positive-QTOF	splash10-052e-6943000000-358a8803127596b6f408	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thioproperazine 10V, Negative-QTOF	splash10-0002-0000900000-0e1a845ac579fd515a89	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thioproperazine 20V, Negative-QTOF	splash10-052s-1279700000-cd3d31e00a19a457ed05	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thioproperazine 40V, Negative-QTOF	splash10-0a4l-9821000000-d1365c6703280f1d6229	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thioproperazine 10V, Positive-QTOF	splash10-0002-0000900000-c66fe9c7d316941c87d3	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thioproperazine 20V, Positive-QTOF	splash10-000b-0404900000-a12c077deebce81ff6a5	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thioproperazine 40V, Positive-QTOF	splash10-03dm-5900000000-21abf6d9713a9c1f6438	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thioproperazine 10V, Negative-QTOF	splash10-0002-0000900000-143e43d5f9961b7d7d82	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thioproperazine 20V, Negative-QTOF	splash10-0002-0003900000-697e3a0dbe2fbb4e724d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thioproperazine 40V, Negative-QTOF	splash10-0bti-0179300000-530ddc9f24d2a762b5f7	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
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 DB01622	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01622	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01622

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9058

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Thioproperazine

METLIN ID

Not Available

PubChem Compound

9429

PDB ID

Not Available

ChEBI ID

59120

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

Oades RD, Rao ML, Bender S, Sartory G, Muller BW: Neuropsychological and conditioned blocking performance in patients with schizophrenia: assessment of the contribution of neuroleptic dose, serum levels and dopamine D2-receptor occupancy. Behav Pharmacol. 2000 Jun;11(3-4):317-30. [PubMed:11103886 ]
Seeman P: Atypical antipsychotics: mechanism of action. Can J Psychiatry. 2002 Feb;47(1):27-38. [PubMed:11873706 ]
Wu S, Xing Q, Gao R, Li X, Gu N, Feng G, He L: Response to chlorpromazine treatment may be associated with polymorphisms of the DRD2 gene in Chinese schizophrenic patients. Neurosci Lett. 2005 Mar 7;376(1):1-4. Epub 2004 Dec 2. [PubMed:15694263 ]
Wu SN, Gao R, Xing QH, Li HF, Shen YF, Gu NF, Feng GY, He L: Association of DRD2 polymorphisms and chlorpromazine-induced extrapyramidal syndrome in Chinese schizophrenic patients. Acta Pharmacol Sin. 2006 Aug;27(8):966-70. [PubMed:16867246 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Seeman P: Dopamine D2 receptors as treatment targets in schizophrenia. Clin Schizophr Relat Psychoses. 2010 Apr;4(1):56-73. doi: 10.3371/CSRP.4.1.5. [PubMed:20643630 ]

Enzyme Details

2. 5-hydroxytryptamine receptor 1A

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:: HTR1A
Uniprot ID:: P08908
Molecular weight:: 46106.3

References

Cosi C, Koek W: Agonist, antagonist, and inverse agonist properties of antipsychotics at human recombinant 5-HT(1A) receptors expressed in HeLa cells. Eur J Pharmacol. 2001 Dec 14;433(1):55-62. [PubMed:11755134 ]
Newman-Tancredi A, Gavaudan S, Conte C, Chaput C, Touzard M, Verriele L, Audinot V, Millan MJ: Agonist and antagonist actions of antipsychotic agents at 5-HT1A receptors: a [35S]GTPgammaS binding study. Eur J Pharmacol. 1998 Aug 21;355(2-3):245-56. [PubMed:9760039 ]

Enzyme Details

3. 5-hydroxytryptamine receptor 2A

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production
Gene Name:: HTR2A
Uniprot ID:: P28223
Molecular weight:: 52602.6

References

Kusumi I, Takahashi Y, Suzuki K, Kameda K, Koyama T: Differential effects of subchronic treatments with atypical antipsychotic drugs on dopamine D2 and serotonin 5-HT2A receptors in the rat brain. J Neural Transm (Vienna). 2000;107(3):295-302. [PubMed:10821438 ]
Yamada J, Sugimoto Y, Horisaka K: Serotonin2 (5-HT2) receptor agonist 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) inhibits chlorpromazine- and haloperidol-induced hypothermia in mice. Biol Pharm Bull. 1995 Nov;18(11):1580-3. [PubMed:8593484 ]

Enzyme Details

4. Alpha-1A adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins
Gene Name:: ADRA1A
Uniprot ID:: P35348
Molecular weight:: 51486.0

References

Cahir M, King DJ: Antipsychotics lack alpha 1A/B adrenoceptor subtype selectivity in the rat. Eur Neuropsychopharmacol. 2005 Mar;15(2):231-4. [PubMed:15695070 ]

Enzyme Details

5. Alpha-1B adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system
Gene Name:: ADRA1B
Uniprot ID:: P35368
Molecular weight:: 56835.4

References

Cahir M, King DJ: Antipsychotics lack alpha 1A/B adrenoceptor subtype selectivity in the rat. Eur Neuropsychopharmacol. 2005 Mar;15(2):231-4. [PubMed:15695070 ]

Enzyme Details

6. 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

Kanba S, Suzuki E, Nomura S, Nakaki T, Yagi G, Asai M, Richelson E: Affinity of neuroleptics for D1 receptor of human brain striatum. J Psychiatry Neurosci. 1994 Jul;19(4):265-9. [PubMed:7918347 ]

Transporters

Enzyme Details

1. Solute carrier family 22 member 1

General function:: Involved in ion transmembrane transporter activity
Specific function:: Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)- N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin- dependent kinase II and LCK tyrosine kinase
Gene Name:: SLC22A1
Uniprot ID:: O15245
Molecular weight:: 61187.4

References

Bednarczyk D, Ekins S, Wikel JH, Wright SH: Influence of molecular structure on substrate binding to the human organic cation transporter, hOCT1. Mol Pharmacol. 2003 Mar;63(3):489-98. [PubMed:12606755 ]

Showing metabocard for Thioproperazine (HMDB0015559)

MOL for HMDB0015559 (Thioproperazine)

3D MOL for HMDB0015559 (Thioproperazine)

3D SDF for HMDB0015559 (Thioproperazine)

3D-SDF for HMDB0015559 (Thioproperazine)

PDB for HMDB0015559 (Thioproperazine)

3D PDB for HMDB0015559 (Thioproperazine)

SMILES for HMDB0015559 (Thioproperazine)

INCHI for HMDB0015559 (Thioproperazine)

Structure for HMDB0015559 (Thioproperazine)

3D Structure for HMDB0015559 (Thioproperazine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

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Transporters

References