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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (8)transporters (1) Show 9 proteins XML

enzymes (8)transporters (1) Show 9 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

HMDB0015558

Secondary Accession Numbers

HMDB15558

Metabolite Identification

Common Name

Pipotiazine

Description

Pipotiazine has actions similar to those of other phenothiazines. Among the different phenothiazine derivatives, it appears to be less sedating and to have a weak propensity for causing hypotension or potentiating the effects of CNS depressants and anesthetics. However, it produces a high incidence of extra pyramidal reactions. It is used for the maintenance treatment of chronic non-agitated schizophrenic patients. Symptoms of overdose include severe extrapyramidal manifestations, hypotension, lethargy and sedation.

Structure

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

1621
  Mrv0541 02231215362D          

 32 35  0  0  0  0            999 V2000
    5.9361   -3.5410    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.8480   -1.8712    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498    3.0581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4328   -1.1584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2631   -2.5840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073    0.5834    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9361   -1.8912    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5608   -1.4561    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    1.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929    1.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073    1.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929    0.1710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641    1.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216    0.1710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641    2.6456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9361   -1.0664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6504   -2.3037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -2.3037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6504   -3.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -3.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3878   -1.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1352   -2.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4843   -1.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3878   -3.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1352   -3.1457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4843   -3.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7368   -2.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7368   -3.1457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2767   -1.8657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5576   -0.6312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  2  4  2  0  0  0  0
  2  5  2  0  0  0  0
  2  8  1  0  0  0  0
  2 24  1  0  0  0  0
  3 17  1  0  0  0  0
  6 12  1  0  0  0  0
  6 13  1  0  0  0  0
  6 15  1  0  0  0  0
  7 18  1  0  0  0  0
  7 19  1  0  0  0  0
  7 20  1  0  0  0  0
  8 31  1  0  0  0  0
  8 32  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 14  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 14 17  1  0  0  0  0
 15 16  1  0  0  0  0
 16 18  1  0  0  0  0
 19 21  2  0  0  0  0
 19 23  1  0  0  0  0
 20 22  1  0  0  0  0
 20 25  2  0  0  0  0
 21 26  1  0  0  0  0
 22 28  2  0  0  0  0
 23 24  2  0  0  0  0
 24 27  1  0  0  0  0
 25 29  1  0  0  0  0
 26 27  2  0  0  0  0
 28 30  1  0  0  0  0
 29 30  2  0  0  0  0
M  END

HMDB0015558
     RDKit          3D
Pipotiazine
 65 68  0  0  0  0  0  0  0  0999 V2000
   -6.9584    2.2330   -0.6102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8076    3.0347   -0.3402 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3800    3.0020    1.0414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5208    2.7699   -1.4380 S   0  0  0  0  0  6  0  0  0  0  0  0
   -5.0240    3.0174   -2.8333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3650    3.6947   -1.1842 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0173    1.1044   -1.3070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5884    0.1334   -2.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1542   -1.1596   -1.9440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1598   -1.4478   -1.0289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5475   -0.5274   -0.2227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0107    0.7789   -0.3876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5421   -0.8545    0.7185 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9623    0.2702    1.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0039    1.0693    0.6093 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1639    0.1756    0.1470 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0954    0.8802   -0.6617 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8837    1.8790   -0.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0972    1.3283    0.6696 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9497    0.5104   -0.3108 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1622    0.0361    0.4053 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0972   -0.7682   -0.4369 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5226   -1.9225   -0.9078 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0592   -0.5959   -0.7964 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8683    0.0360   -1.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0609   -2.1573    0.9364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0766   -2.3406    1.8922 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4445   -3.6130    2.1638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0077   -4.7248    1.4858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9867   -4.5541    0.5322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4698   -3.3059    0.2938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7157   -3.1692   -0.9596 S   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1587    1.4440    0.1425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8923    1.8545   -1.6454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8458    2.9327   -0.6021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2740    1.9465    1.4059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0163    3.6162    1.7009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3537    3.4350    1.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3558    0.4114   -2.7814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6217   -1.9023   -2.5684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6012    1.5549    0.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8283    0.9348    1.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4158    0.0003    2.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4418    1.4894   -0.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4925    1.8737    1.2128 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7141   -0.2536    1.0079 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7081   -0.6636   -0.4108 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2617    2.5601   -0.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3330    2.5239    0.6739 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8760    0.7098    1.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7369    2.1845    0.9635 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2400    1.2101   -1.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9166   -0.5975    1.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7630    0.8916    0.8318 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9870   -1.0542    0.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4202   -0.1304   -1.3049 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9646   -2.7515   -0.6464 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5525   -1.2229   -1.5742 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7709   -1.2264    0.0541 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2683    0.6409   -2.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1954   -0.7899   -1.8655 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3749   -1.5688    2.4933 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2143   -3.7353    2.9150 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3886   -5.7112    1.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3661   -5.4192   -0.0211 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  2  0
  4  7  1  0
  7  8  2  0
  8  9  1  0
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 24 25  1  0
 13 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 12  7  1  0
 25 17  1  0
 31 26  1  0
 32 10  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  3 36  1  0
  3 37  1  0
  3 38  1  0
  8 39  1  0
  9 40  1  0
 12 41  1  0
 14 42  1  0
 14 43  1  0
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 16 46  1  0
 16 47  1  0
 18 48  1  0
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 19 50  1  0
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 25 60  1  0
 25 61  1  0
 27 62  1  0
 28 63  1  0
 29 64  1  0
 30 65  1  0
M  END

1621
  Mrv0541 02231215362D          

 32 35  0  0  0  0            999 V2000
    5.9361   -3.5410    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.8480   -1.8712    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498    3.0581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4328   -1.1584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2631   -2.5840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073    0.5834    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9361   -1.8912    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5608   -1.4561    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    1.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929    1.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073    1.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3641    1.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216    0.1710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641    2.6456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9361   -1.0664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6504   -2.3037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -2.3037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6504   -3.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -3.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3878   -1.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1352   -2.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4843   -1.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3878   -3.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1352   -3.1457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4843   -3.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7368   -2.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7368   -3.1457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2767   -1.8657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5576   -0.6312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  2  4  2  0  0  0  0
  2  5  2  0  0  0  0
  2  8  1  0  0  0  0
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 10 12  1  0  0  0  0
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 19 23  1  0  0  0  0
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 21 26  1  0  0  0  0
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 24 27  1  0  0  0  0
 25 29  1  0  0  0  0
 26 27  2  0  0  0  0
 28 30  1  0  0  0  0
 29 30  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015558

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)S(=O)(=O)C1=CC2=C(SC3=CC=CC=C3N2CCCN2CCC(CCO)CC2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H33N3O3S2/c1-25(2)32(29,30)20-8-9-24-22(18-20)27(21-6-3-4-7-23(21)31-24)14-5-13-26-15-10-19(11-16-26)12-17-28/h3-4,6-9,18-19,28H,5,10-17H2,1-2H3

> <INCHI_KEY>
JOMHSQGEWSNUKU-UHFFFAOYSA-N

> <FORMULA>
C24H33N3O3S2

> <MOLECULAR_WEIGHT>
475.667

> <EXACT_MASS>
475.196333317

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
53.17447112792491

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
3.94

> <JCHEM_LOGP>
3.1296137433333326

> <ALOGPS_LOGS>
-4.57

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.086569164709193

> <JCHEM_PKA_STRONGEST_BASIC>
8.857536507071535

> <JCHEM_POLAR_SURFACE_AREA>
64.09

> <JCHEM_REFRACTIVITY>
134.1231

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.27e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pipotiazine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015558
     RDKit          3D
Pipotiazine
 65 68  0  0  0  0  0  0  0  0999 V2000
   -6.9584    2.2330   -0.6102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8076    3.0347   -0.3402 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3800    3.0020    1.0414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5208    2.7699   -1.4380 S   0  0  0  0  0  6  0  0  0  0  0  0
   -5.0240    3.0174   -2.8333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3650    3.6947   -1.1842 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0173    1.1044   -1.3070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5884    0.1334   -2.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1542   -1.1596   -1.9440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1598   -1.4478   -1.0289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5475   -0.5274   -0.2227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0107    0.7789   -0.3876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5421   -0.8545    0.7185 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9623    0.2702    1.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0039    1.0693    0.6093 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1639    0.1756    0.1470 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0954    0.8802   -0.6617 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8837    1.8790   -0.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0972    1.3283    0.6696 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9497    0.5104   -0.3108 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1622    0.0361    0.4053 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0972   -0.7682   -0.4369 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5226   -1.9225   -0.9078 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0592   -0.5959   -0.7964 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8683    0.0360   -1.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0609   -2.1573    0.9364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0766   -2.3406    1.8922 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4445   -3.6130    2.1638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0077   -4.7248    1.4858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9867   -4.5541    0.5322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4698   -3.3059    0.2938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7157   -3.1692   -0.9596 S   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1587    1.4440    0.1425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8923    1.8545   -1.6454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8458    2.9327   -0.6021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2740    1.9465    1.4059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0163    3.6162    1.7009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3537    3.4350    1.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3558    0.4114   -2.7814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6217   -1.9023   -2.5684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6012    1.5549    0.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8283    0.9348    1.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4158    0.0003    2.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4418    1.4894   -0.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4925    1.8737    1.2128 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7141   -0.2536    1.0079 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7081   -0.6636   -0.4108 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2617    2.5601   -0.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3330    2.5239    0.6739 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8760    0.7098    1.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7369    2.1845    0.9635 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2400    1.2101   -1.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9166   -0.5975    1.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7630    0.8916    0.8318 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9870   -1.0542    0.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4202   -0.1304   -1.3049 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9646   -2.7515   -0.6464 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5525   -1.2229   -1.5742 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7709   -1.2264    0.0541 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2683    0.6409   -2.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1954   -0.7899   -1.8655 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3749   -1.5688    2.4933 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2143   -3.7353    2.9150 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3886   -5.7112    1.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3661   -5.4192   -0.0211 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  2  0
  4  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 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
 20 21  1  0
 21 22  1  0
 22 23  1  0
 20 24  1  0
 24 25  1  0
 13 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 12  7  1  0
 25 17  1  0
 31 26  1  0
 32 10  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  3 36  1  0
  3 37  1  0
  3 38  1  0
  8 39  1  0
  9 40  1  0
 12 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 21 53  1  0
 21 54  1  0
 22 55  1  0
 22 56  1  0
 23 57  1  0
 24 58  1  0
 24 59  1  0
 25 60  1  0
 25 61  1  0
 27 62  1  0
 28 63  1  0
 29 64  1  0
 30 65  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1621                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0      11.081  -6.610   0.000  0.00  0.00           S+0
HETATM    2  S   UNK     0      16.516  -3.493   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0       3.080   5.708   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      15.741  -2.162   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      17.291  -4.824   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       8.414   1.089   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      11.081  -3.530   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      17.847  -2.718   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       5.747   2.629   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.080   3.399   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.747   1.089   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.414   2.629   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.080   0.319   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.413   3.399   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.747   0.319   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.747  -1.221   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.413   4.939   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.081  -1.991   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.414  -4.300   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.747  -4.300   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.414  -5.840   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.747  -5.840   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.791  -3.477   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.186  -4.268   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.371  -3.477   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.791  -6.663   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.186  -5.872   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.371  -6.663   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.975  -4.268   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.975  -5.872   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      19.183  -3.483   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      17.841  -1.178   0.000  0.00  0.00           C+0
CONECT    1   21   22                                                       
CONECT    2    4    5    8   24                                             
CONECT    3   17                                                            
CONECT    4    2                                                            
CONECT    5    2                                                            
CONECT    6   12   13   15                                                  
CONECT    7   18   19   20                                                  
CONECT    8    2   31   32                                                  
CONECT    9   10   11   14                                                  
CONECT   10    9   12                                                       
CONECT   11    9   13                                                       
CONECT   12    6   10                                                       
CONECT   13    6   11                                                       
CONECT   14    9   17                                                       
CONECT   15    6   16                                                       
CONECT   16   15   18                                                       
CONECT   17    3   14                                                       
CONECT   18    7   16                                                       
CONECT   19    7   21   23                                                  
CONECT   20    7   22   25                                                  
CONECT   21    1   19   26                                                  
CONECT   22    1   20   28                                                  
CONECT   23   19   24                                                       
CONECT   24    2   23   27                                                  
CONECT   25   20   29                                                       
CONECT   26   21   27                                                       
CONECT   27   24   26                                                       
CONECT   28   22   30                                                       
CONECT   29   25   30                                                       
CONECT   30   28   29                                                       
CONECT   31    8                                                            
CONECT   32    8                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

COMPND    HMDB0015558
HETATM    1  C1  UNL     1      -6.958   2.233  -0.610  1.00  0.00           C  
HETATM    2  N1  UNL     1      -5.808   3.035  -0.340  1.00  0.00           N  
HETATM    3  C2  UNL     1      -5.380   3.002   1.041  1.00  0.00           C  
HETATM    4  S1  UNL     1      -4.521   2.770  -1.438  1.00  0.00           S  
HETATM    5  O1  UNL     1      -5.024   3.017  -2.833  1.00  0.00           O  
HETATM    6  O2  UNL     1      -3.365   3.695  -1.184  1.00  0.00           O  
HETATM    7  C3  UNL     1      -4.017   1.104  -1.307  1.00  0.00           C  
HETATM    8  C4  UNL     1      -4.588   0.133  -2.085  1.00  0.00           C  
HETATM    9  C5  UNL     1      -4.154  -1.160  -1.944  1.00  0.00           C  
HETATM   10  C6  UNL     1      -3.160  -1.448  -1.029  1.00  0.00           C  
HETATM   11  C7  UNL     1      -2.547  -0.527  -0.223  1.00  0.00           C  
HETATM   12  C8  UNL     1      -3.011   0.779  -0.388  1.00  0.00           C  
HETATM   13  N2  UNL     1      -1.542  -0.854   0.719  1.00  0.00           N  
HETATM   14  C9  UNL     1      -0.962   0.270   1.460  1.00  0.00           C  
HETATM   15  C10 UNL     1       0.004   1.069   0.609  1.00  0.00           C  
HETATM   16  C11 UNL     1       1.164   0.176   0.147  1.00  0.00           C  
HETATM   17  N3  UNL     1       2.095   0.880  -0.662  1.00  0.00           N  
HETATM   18  C12 UNL     1       2.884   1.879  -0.024  1.00  0.00           C  
HETATM   19  C13 UNL     1       4.097   1.328   0.670  1.00  0.00           C  
HETATM   20  C14 UNL     1       4.950   0.510  -0.311  1.00  0.00           C  
HETATM   21  C15 UNL     1       6.162   0.036   0.405  1.00  0.00           C  
HETATM   22  C16 UNL     1       7.097  -0.768  -0.437  1.00  0.00           C  
HETATM   23  O3  UNL     1       6.523  -1.923  -0.908  1.00  0.00           O  
HETATM   24  C17 UNL     1       4.059  -0.596  -0.796  1.00  0.00           C  
HETATM   25  C18 UNL     1       2.868   0.036  -1.502  1.00  0.00           C  
HETATM   26  C19 UNL     1      -1.061  -2.157   0.936  1.00  0.00           C  
HETATM   27  C20 UNL     1      -0.077  -2.341   1.892  1.00  0.00           C  
HETATM   28  C21 UNL     1       0.445  -3.613   2.164  1.00  0.00           C  
HETATM   29  C22 UNL     1      -0.008  -4.725   1.486  1.00  0.00           C  
HETATM   30  C23 UNL     1      -0.987  -4.554   0.532  1.00  0.00           C  
HETATM   31  C24 UNL     1      -1.470  -3.306   0.294  1.00  0.00           C  
HETATM   32  S2  UNL     1      -2.716  -3.169  -0.960  1.00  0.00           S  
HETATM   33  H1  UNL     1      -7.159   1.444   0.142  1.00  0.00           H  
HETATM   34  H2  UNL     1      -6.892   1.854  -1.645  1.00  0.00           H  
HETATM   35  H3  UNL     1      -7.846   2.933  -0.602  1.00  0.00           H  
HETATM   36  H4  UNL     1      -5.274   1.946   1.406  1.00  0.00           H  
HETATM   37  H5  UNL     1      -6.016   3.616   1.701  1.00  0.00           H  
HETATM   38  H6  UNL     1      -4.354   3.435   1.074  1.00  0.00           H  
HETATM   39  H7  UNL     1      -5.356   0.411  -2.781  1.00  0.00           H  
HETATM   40  H8  UNL     1      -4.622  -1.902  -2.568  1.00  0.00           H  
HETATM   41  H9  UNL     1      -2.601   1.555   0.212  1.00  0.00           H  
HETATM   42  H10 UNL     1      -1.828   0.935   1.760  1.00  0.00           H  
HETATM   43  H11 UNL     1      -0.416   0.000   2.360  1.00  0.00           H  
HETATM   44  H12 UNL     1      -0.442   1.489  -0.291  1.00  0.00           H  
HETATM   45  H13 UNL     1       0.492   1.874   1.213  1.00  0.00           H  
HETATM   46  H14 UNL     1       1.714  -0.254   1.008  1.00  0.00           H  
HETATM   47  H15 UNL     1       0.708  -0.664  -0.411  1.00  0.00           H  
HETATM   48  H16 UNL     1       3.262   2.560  -0.826  1.00  0.00           H  
HETATM   49  H17 UNL     1       2.333   2.524   0.674  1.00  0.00           H  
HETATM   50  H18 UNL     1       3.876   0.710   1.544  1.00  0.00           H  
HETATM   51  H19 UNL     1       4.737   2.185   0.963  1.00  0.00           H  
HETATM   52  H20 UNL     1       5.240   1.210  -1.109  1.00  0.00           H  
HETATM   53  H21 UNL     1       5.917  -0.598   1.296  1.00  0.00           H  
HETATM   54  H22 UNL     1       6.763   0.892   0.832  1.00  0.00           H  
HETATM   55  H23 UNL     1       7.987  -1.054   0.179  1.00  0.00           H  
HETATM   56  H24 UNL     1       7.420  -0.130  -1.305  1.00  0.00           H  
HETATM   57  H25 UNL     1       6.965  -2.752  -0.646  1.00  0.00           H  
HETATM   58  H26 UNL     1       4.553  -1.223  -1.574  1.00  0.00           H  
HETATM   59  H27 UNL     1       3.771  -1.226   0.054  1.00  0.00           H  
HETATM   60  H28 UNL     1       3.268   0.641  -2.337  1.00  0.00           H  
HETATM   61  H29 UNL     1       2.195  -0.790  -1.866  1.00  0.00           H  
HETATM   62  H30 UNL     1       0.375  -1.569   2.493  1.00  0.00           H  
HETATM   63  H31 UNL     1       1.214  -3.735   2.915  1.00  0.00           H  
HETATM   64  H32 UNL     1       0.389  -5.711   1.689  1.00  0.00           H  
HETATM   65  H33 UNL     1      -1.366  -5.419  -0.021  1.00  0.00           H  
CONECT    1    2   33   34   35
CONECT    2    3    4
CONECT    3   36   37   38
CONECT    4    5    5    6    6
CONECT    4    7
CONECT    7    8    8   12
CONECT    8    9   39
CONECT    9   10   10   40
CONECT   10   11   32
CONECT   11   12   12   13
CONECT   12   41
CONECT   13   14   26
CONECT   14   15   42   43
CONECT   15   16   44   45
CONECT   16   17   46   47
CONECT   17   18   25
CONECT   18   19   48   49
CONECT   19   20   50   51
CONECT   20   21   24   52
CONECT   21   22   53   54
CONECT   22   23   55   56
CONECT   23   57
CONECT   24   25   58   59
CONECT   25   60   61
CONECT   26   27   27   31
CONECT   27   28   62
CONECT   28   29   29   63
CONECT   29   30   64
CONECT   30   31   31   65
CONECT   31   32
END

HMDB0015558
     RDKit          3D
Pipotiazine
 65 68  0  0  0  0  0  0  0  0999 V2000
   -6.9584    2.2330   -0.6102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8076    3.0347   -0.3402 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3800    3.0020    1.0414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5208    2.7699   -1.4380 S   0  0  0  0  0  6  0  0  0  0  0  0
   -5.0240    3.0174   -2.8333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3650    3.6947   -1.1842 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0173    1.1044   -1.3070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5884    0.1334   -2.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1542   -1.1596   -1.9440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1598   -1.4478   -1.0289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5475   -0.5274   -0.2227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0107    0.7789   -0.3876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5421   -0.8545    0.7185 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9623    0.2702    1.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0039    1.0693    0.6093 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1639    0.1756    0.1470 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0954    0.8802   -0.6617 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8837    1.8790   -0.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0972    1.3283    0.6696 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9497    0.5104   -0.3108 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1622    0.0361    0.4053 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0972   -0.7682   -0.4369 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5226   -1.9225   -0.9078 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0592   -0.5959   -0.7964 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8683    0.0360   -1.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0609   -2.1573    0.9364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0766   -2.3406    1.8922 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4445   -3.6130    2.1638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0077   -4.7248    1.4858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9867   -4.5541    0.5322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4698   -3.3059    0.2938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7157   -3.1692   -0.9596 S   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1587    1.4440    0.1425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8923    1.8545   -1.6454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8458    2.9327   -0.6021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2740    1.9465    1.4059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0163    3.6162    1.7009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3537    3.4350    1.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3558    0.4114   -2.7814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6217   -1.9023   -2.5684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6012    1.5549    0.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8283    0.9348    1.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4158    0.0003    2.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4418    1.4894   -0.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4925    1.8737    1.2128 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7141   -0.2536    1.0079 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7081   -0.6636   -0.4108 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2617    2.5601   -0.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3330    2.5239    0.6739 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8760    0.7098    1.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7369    2.1845    0.9635 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2400    1.2101   -1.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9166   -0.5975    1.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7630    0.8916    0.8318 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9870   -1.0542    0.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4202   -0.1304   -1.3049 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9646   -2.7515   -0.6464 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5525   -1.2229   -1.5742 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7709   -1.2264    0.0541 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2683    0.6409   -2.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1954   -0.7899   -1.8655 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3749   -1.5688    2.4933 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2143   -3.7353    2.9150 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3886   -5.7112    1.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3661   -5.4192   -0.0211 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  2  0
  4  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 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
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 22 23  1  0
 20 24  1  0
 24 25  1  0
 13 26  1  0
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 27 28  1  0
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 25 17  1  0
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  1 33  1  0
  1 34  1  0
  1 35  1  0
  3 36  1  0
  3 37  1  0
  3 38  1  0
  8 39  1  0
  9 40  1  0
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 24 59  1  0
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 25 61  1  0
 27 62  1  0
 28 63  1  0
 29 64  1  0
 30 65  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Piportil	Kegg
Pipothiazine	HMDB
Pipotiazin	HMDB

Chemical Formula

C₂₄H₃₃N₃O₃S₂

Average Molecular Weight

475.667

Monoisotopic Molecular Weight

475.196333317

IUPAC Name

10-{3-[4-(2-hydroxyethyl)piperidin-1-yl]propyl}-N,N-dimethyl-10H-phenothiazine-2-sulfonamide

Traditional Name

pipotiazine

CAS Registry Number

39860-99-6

SMILES

CN(C)S(=O)(=O)C1=CC2=C(SC3=CC=CC=C3N2CCCN2CCC(CCO)CC2)C=C1

InChI Identifier

InChI=1S/C24H33N3O3S2/c1-25(2)32(29,30)20-8-9-24-22(18-20)27(21-6-3-4-7-23(21)31-24)14-5-13-26-15-10-19(11-16-26)12-17-28/h3-4,6-9,18-19,28H,5,10-17H2,1-2H3

InChI Key

JOMHSQGEWSNUKU-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
Piperidine
Organosulfonic acid amide
Benzenoid
Para-thiazine
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Sulfonyl
Aminosulfonyl compound
Tertiary amine
Tertiary aliphatic amine
Thioether
Azacycle
Hydrocarbon derivative
Amine
Organic oxide
Alcohol
Organic oxygen compound
Primary alcohol
Organopnictogen compound
Organic nitrogen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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: HMDB0015558)
Membrane (HMDB: HMDB0015558)

Source

Exogenous

Exogenous (HMDB: HMDB0015558)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.013 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.013 g/L	ALOGPS
logP	3.94	ALOGPS
logP	3.13	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	17.09	ChemAxon
pKa (Strongest Basic)	8.86	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.09 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	134.12 m³·mol⁻¹	ChemAxon
Polarizability	53.17 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	205.065	31661259
DarkChem	[M-H]-	205.748	31661259
DeepCCS	[M+H]+	208.247	30932474
DeepCCS	[M-H]-	205.889	30932474
DeepCCS	[M-2H]-	239.524	30932474
DeepCCS	[M+Na]+	214.752	30932474
AllCCS	[M+H]+	209.6	32859911
AllCCS	[M+H-H2O]+	207.8	32859911
AllCCS	[M+NH4]+	211.1	32859911
AllCCS	[M+Na]+	211.5	32859911
AllCCS	[M-H]-	197.4	32859911
AllCCS	[M+Na-2H]-	198.6	32859911
AllCCS	[M+HCOO]-	200.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pipotiazine	CN(C)S(=O)(=O)C1=CC2=C(SC3=CC=CC=C3N2CCCN2CCC(CCO)CC2)C=C1	5470.2	Standard polar	33892256
Pipotiazine	CN(C)S(=O)(=O)C1=CC2=C(SC3=CC=CC=C3N2CCCN2CCC(CCO)CC2)C=C1	4002.6	Standard non polar	33892256
Pipotiazine	CN(C)S(=O)(=O)C1=CC2=C(SC3=CC=CC=C3N2CCCN2CCC(CCO)CC2)C=C1	4031.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Pipotiazine,1TMS,isomer #1	CN(C)S(=O)(=O)C1=CC=C2SC3=CC=CC=C3N(CCCN3CCC(CCO[Si](C)(C)C)CC3)C2=C1	3964.6	Semi standard non polar	33892256
Pipotiazine,1TBDMS,isomer #1	CN(C)S(=O)(=O)C1=CC=C2SC3=CC=CC=C3N(CCCN3CCC(CCO[Si](C)(C)C(C)(C)C)CC3)C2=C1	4174.6	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 - Pipotiazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-000x-9426500000-b266b7d1d6c58c4317de	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pipotiazine GC-MS (1 TMS) - 70eV, Positive	splash10-0ffc-9322450000-7343ab0e69605271f6b1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pipotiazine 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 - Pipotiazine 10V, Positive-QTOF	splash10-0a6r-0101900000-108417d385430a8ac69a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pipotiazine 20V, Positive-QTOF	splash10-0n30-0303900000-ff4bba693555abab5b17	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pipotiazine 40V, Positive-QTOF	splash10-0072-1917000000-89166c8954aa79ff8a6e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pipotiazine 10V, Negative-QTOF	splash10-00di-0000900000-fbbc429131b98fcae068	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pipotiazine 20V, Negative-QTOF	splash10-0a4i-0237900000-8ee245c37c26fd622af3	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pipotiazine 40V, Negative-QTOF	splash10-0a4i-6911000000-a32289e3b3bb21f93e85	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pipotiazine 10V, Positive-QTOF	splash10-004i-0000900000-d06e5b509b1411547d45	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pipotiazine 20V, Positive-QTOF	splash10-00or-0608900000-9e675242143c2b793440	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pipotiazine 40V, Positive-QTOF	splash10-0230-5912100000-1201296404fff21e9df0	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pipotiazine 10V, Negative-QTOF	splash10-00di-0000900000-7d7a0aa726269d5fe1ec	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pipotiazine 20V, Negative-QTOF	splash10-00di-0001900000-4140b9e96cc2440693db	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pipotiazine 40V, Negative-QTOF	splash10-08g3-1289400000-dc29750e63b3bfdbeb7a	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 DB01621	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01621	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01621

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

56598

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pipotiazine

METLIN ID

Not Available

PubChem Compound

62867

PDB ID

Not Available

ChEBI ID

521177

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. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Wojcikowski J, Boksa J, Daniel WA: Main contribution of the cytochrome P450 isoenzyme 1A2 (CYP1A2) to N-demethylation and 5-sulfoxidation of the phenothiazine neuroleptic chlorpromazine in human liver--A comparison with other phenothiazines. Biochem Pharmacol. 2010 Oct 15;80(8):1252-9. doi: 10.1016/j.bcp.2010.06.045. Epub 2010 Jul 6. [PubMed:20615392 ]

Enzyme Details

2. Cytochrome P450 2C19

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

References

Wojcikowski J, Boksa J, Daniel WA: Main contribution of the cytochrome P450 isoenzyme 1A2 (CYP1A2) to N-demethylation and 5-sulfoxidation of the phenothiazine neuroleptic chlorpromazine in human liver--A comparison with other phenothiazines. Biochem Pharmacol. 2010 Oct 15;80(8):1252-9. doi: 10.1016/j.bcp.2010.06.045. Epub 2010 Jul 6. [PubMed:20615392 ]

Enzyme Details

3. Cytochrome P450 2D6

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

References

Zhou SF: Polymorphism of human cytochrome P450 2D6 and its clinical significance: part II. Clin Pharmacokinet. 2009;48(12):761-804. doi: 10.2165/11318070-000000000-00000. [PubMed:19902987 ]
Bhoopathy S, Xin B, Unger SE, Karnes HT: A novel incubation direct injection LC/MS/MS technique for in vitro drug metabolism screening studies involving the CYP 2D6 and the CYP 3A4 isozymes. J Pharm Biomed Anal. 2005 Apr 1;37(4):739-49. Epub 2004 Dec 30. [PubMed:15797796 ]

Enzyme Details

4. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Wojcikowski J, Boksa J, Daniel WA: Main contribution of the cytochrome P450 isoenzyme 1A2 (CYP1A2) to N-demethylation and 5-sulfoxidation of the phenothiazine neuroleptic chlorpromazine in human liver--A comparison with other phenothiazines. Biochem Pharmacol. 2010 Oct 15;80(8):1252-9. doi: 10.1016/j.bcp.2010.06.045. Epub 2010 Jul 6. [PubMed:20615392 ]

Enzyme Details

5. 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 ]
Boireau A, Chambry J, Dubedat P, Farges G, Carruette AM, Zundel JL, Blanchard JC: Enhancing effect of dopamine blockers on evoked acetylcholine release in rat striatal slices: a classical D-2 antagonist response? Eur J Pharmacol. 1986 Aug 22;128(1-2):93-8. [PubMed:2875894 ]

Enzyme Details

6. 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

7. 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

8. 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 Pipotiazine (HMDB0015558)

MOL for HMDB0015558 (Pipotiazine)

3D MOL for HMDB0015558 (Pipotiazine)

3D SDF for HMDB0015558 (Pipotiazine)

3D-SDF for HMDB0015558 (Pipotiazine)

PDB for HMDB0015558 (Pipotiazine)

3D PDB for HMDB0015558 (Pipotiazine)

SMILES for HMDB0015558 (Pipotiazine)

INCHI for HMDB0015558 (Pipotiazine)

Structure for HMDB0015558 (Pipotiazine)

3D Structure for HMDB0015558 (Pipotiazine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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Transporters

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