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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (30) Show 30 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:36 UTC

HMDB ID

HMDB0014391

Secondary Accession Numbers

HMDB14391

Metabolite Identification

Common Name

Ziprasidone

Description

Ziprasidone (marketed as Geodon, Zeldox) was the fifth atypical antipsychotic to gain FDA approval (February 2001). Ziprasidone is Food and Drug Administration (FDA) approved for the treatment of schizophrenia, and the intramuscular injection form of ziprasidone is approved for acute agitation in schizophrenic patients. Ziprasidone has also received approval for acute treatment of mania associated with bipolar disorder. [Wikipedia ]

Structure

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

246
  Mrv0541 02231214322D          

 28 32  0  0  0  0            999 V2000
    5.8073    3.0921    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.3068    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.0379    2.2671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0928    0.2045    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6638   -0.6205    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2004   -0.6988    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7314    2.9310    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0928   -0.6205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3783    0.6170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3783   -1.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6638    0.2045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8073    0.6170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8073    1.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9494   -1.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5218    1.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8643   -1.8488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9507    1.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2362    1.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9507    2.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5218    2.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7314    1.6031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0570   -2.0189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2362    3.0921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2129    2.2671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4153   -2.4628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8007   -2.8031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1590   -3.2470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3517   -3.4171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  1  0  0  0  0
  2  6  1  0  0  0  0
  2 22  1  0  0  0  0
  3 24  2  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
  4 12  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  1  0  0  0  0
  5 14  1  0  0  0  0
  6 14  2  0  0  0  0
  7 19  1  0  0  0  0
  7 24  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 18  1  0  0  0  0
 15 20  2  0  0  0  0
 16 22  1  0  0  0  0
 16 25  2  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 17 21  1  0  0  0  0
 19 23  2  0  0  0  0
 20 23  1  0  0  0  0
 21 24  1  0  0  0  0
 22 26  2  0  0  0  0
 25 27  1  0  0  0  0
 26 28  1  0  0  0  0
 27 28  2  0  0  0  0
M  END

HMDB0014391
     RDKit          3D
Ziprasidone
 49 53  0  0  0  0  0  0  0  0999 V2000
    8.5536    2.4564   -0.9347 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5043    1.7937   -0.6939 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3460    2.2507    0.0886 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4048    1.1264    0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1445    1.0162    0.6343 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4229   -0.1301    0.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0379   -0.3255    1.0562 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0539   -0.1374   -0.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2995   -0.2835    0.2834 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8547   -1.5237    0.5944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8167   -2.0662   -0.4486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7857   -0.9998   -0.7191 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2137   -1.2625   -0.6299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6353   -2.4104   -1.1786 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2984   -2.3803   -0.9625 S   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4464   -0.8852   -0.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5375   -0.1745    0.3535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3308    1.0523    0.9850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0264    1.4846    1.0555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9711    0.7828    0.5495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1522   -0.4525   -0.0909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2318    0.2646   -1.1148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1901    0.7445   -0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9602   -1.1775   -0.2285 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0387   -2.6713   -0.4159 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.2210   -1.0796   -0.8063 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9376    0.0808   -0.6549 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2381    0.4733   -1.1322 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9225    3.1509   -0.4205 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5807    2.4942    1.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7293    1.8381    1.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9150    0.5441    1.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0355   -1.2825    1.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1927    0.9287   -0.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3691   -0.7294   -0.9561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0885   -2.2943    0.7422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4322   -1.4556    1.5502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2329   -2.1809   -1.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2670   -2.9845   -0.0779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4990   -0.6283    0.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1798    1.5637    1.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8285    2.4437    1.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9776    1.2268    0.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9277    1.0497   -1.3737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6681    0.0409   -2.0817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6095    1.2102    0.7730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5943    1.5318   -0.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6482   -1.8935   -1.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8389   -0.1398   -1.6960 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 12 22  1  0
 22 23  1  0
  6 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 28  2  1  0
 27  4  1  0
 23  9  1  0
 21 13  1  0
 21 16  1  0
  3 29  1  0
  3 30  1  0
  5 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 22 44  1  0
 22 45  1  0
 23 46  1  0
 23 47  1  0
 26 48  1  0
 28 49  1  0
M  END

246
  Mrv0541 02231214322D          

 28 32  0  0  0  0            999 V2000
    5.8073    3.0921    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.3068    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.0379    2.2671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0928    0.2045    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6638   -0.6205    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2004   -0.6988    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7314    2.9310    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0928   -0.6205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3783    0.6170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3783   -1.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6638    0.2045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8073    0.6170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8073    1.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9494   -1.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5218    1.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8643   -1.8488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9507    1.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2362    1.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9507    2.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5218    2.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7314    1.6031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0570   -2.0189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2362    3.0921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2129    2.2671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4153   -2.4628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8007   -2.8031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1590   -3.2470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3517   -3.4171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  1  0  0  0  0
  2  6  1  0  0  0  0
  2 22  1  0  0  0  0
  3 24  2  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
  4 12  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  1  0  0  0  0
  5 14  1  0  0  0  0
  6 14  2  0  0  0  0
  7 19  1  0  0  0  0
  7 24  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 18  1  0  0  0  0
 15 20  2  0  0  0  0
 16 22  1  0  0  0  0
 16 25  2  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 17 21  1  0  0  0  0
 19 23  2  0  0  0  0
 20 23  1  0  0  0  0
 21 24  1  0  0  0  0
 22 26  2  0  0  0  0
 25 27  1  0  0  0  0
 26 28  1  0  0  0  0
 27 28  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014391

> <DATABASE_NAME>
hmdb

> <SMILES>
ClC1=C(CCN2CCN(CC2)C2=NSC3=CC=CC=C23)C=C2CC(=O)NC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H21ClN4OS/c22-17-13-18-15(12-20(27)23-18)11-14(17)5-6-25-7-9-26(10-8-25)21-16-3-1-2-4-19(16)28-24-21/h1-4,11,13H,5-10,12H2,(H,23,27)

> <INCHI_KEY>
MVWVFYHBGMAFLY-UHFFFAOYSA-N

> <FORMULA>
C21H21ClN4OS

> <MOLECULAR_WEIGHT>
412.936

> <EXACT_MASS>
412.112459711

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
44.95709596112768

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-{2-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]ethyl}-6-chloro-2,3-dihydro-1H-indol-2-one

> <ALOGPS_LOGP>
4.64

> <JCHEM_LOGP>
4.304046458666667

> <ALOGPS_LOGS>
-4.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.886130352471191

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.181677746261201

> <JCHEM_PKA_STRONGEST_BASIC>
7.0878561845648225

> <JCHEM_POLAR_SURFACE_AREA>
48.470000000000006

> <JCHEM_REFRACTIVITY>
116.72480000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.18e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ziprasidone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014391
     RDKit          3D
Ziprasidone
 49 53  0  0  0  0  0  0  0  0999 V2000
    8.5536    2.4564   -0.9347 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5043    1.7937   -0.6939 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3460    2.2507    0.0886 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4048    1.1264    0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1445    1.0162    0.6343 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4229   -0.1301    0.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0379   -0.3255    1.0562 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0539   -0.1374   -0.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2995   -0.2835    0.2834 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8547   -1.5237    0.5944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8167   -2.0662   -0.4486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7857   -0.9998   -0.7191 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2137   -1.2625   -0.6299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6353   -2.4104   -1.1786 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2984   -2.3803   -0.9625 S   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4464   -0.8852   -0.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5375   -0.1745    0.3535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3308    1.0523    0.9850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0264    1.4846    1.0555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9711    0.7828    0.5495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1522   -0.4525   -0.0909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2318    0.2646   -1.1148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1901    0.7445   -0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9602   -1.1775   -0.2285 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0387   -2.6713   -0.4159 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.2210   -1.0796   -0.8063 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9376    0.0808   -0.6549 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2381    0.4733   -1.1322 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9225    3.1509   -0.4205 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5807    2.4942    1.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7293    1.8381    1.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9150    0.5441    1.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0355   -1.2825    1.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1927    0.9287   -0.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3691   -0.7294   -0.9561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0885   -2.2943    0.7422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4322   -1.4556    1.5502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2329   -2.1809   -1.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2670   -2.9845   -0.0779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4990   -0.6283    0.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1798    1.5637    1.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8285    2.4437    1.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9776    1.2268    0.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9277    1.0497   -1.3737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6681    0.0409   -2.0817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6095    1.2102    0.7730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5943    1.5318   -0.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6482   -1.8935   -1.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8389   -0.1398   -1.6960 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 12 22  1  0
 22 23  1  0
  6 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 28  2  1  0
 27  4  1  0
 23  9  1  0
 21 13  1  0
 21 16  1  0
  3 29  1  0
  3 30  1  0
  5 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 22 44  1  0
 22 45  1  0
 23 46  1  0
 23 47  1  0
 26 48  1  0
 28 49  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 246                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0      10.840   5.772   0.000  0.00  0.00          Cl+0
HETATM    2  S   UNK     0       3.080  -2.439   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0      18.737   4.232   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       9.507   0.382   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       6.839  -1.158   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       4.107  -1.304   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      16.299   5.471   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       9.507  -1.158   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.173   1.152   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.173  -1.928   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.839   0.382   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.840   1.152   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.840   2.692   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.506  -1.928   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.174   3.462   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.347  -3.451   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.841   3.462   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.508   2.692   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.841   5.002   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.174   5.002   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.299   2.992   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.840  -3.769   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.508   5.772   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.197   4.232   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.375  -4.597   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.361  -5.232   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.897  -6.061   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.390  -6.379   0.000  0.00  0.00           C+0
CONECT    1   20                                                            
CONECT    2    6   22                                                       
CONECT    3   24                                                            
CONECT    4    8    9   12                                                  
CONECT    5   10   11   14                                                  
CONECT    6    2   14                                                       
CONECT    7   19   24                                                       
CONECT    8    4   10                                                       
CONECT    9    4   11                                                       
CONECT   10    5    8                                                       
CONECT   11    5    9                                                       
CONECT   12    4   13                                                       
CONECT   13   12   15                                                       
CONECT   14    5    6   16                                                  
CONECT   15   13   18   20                                                  
CONECT   16   14   22   25                                                  
CONECT   17   18   19   21                                                  
CONECT   18   15   17                                                       
CONECT   19    7   17   23                                                  
CONECT   20    1   15   23                                                  
CONECT   21   17   24                                                       
CONECT   22    2   16   26                                                  
CONECT   23   19   20                                                       
CONECT   24    3    7   21                                                  
CONECT   25   16   27                                                       
CONECT   26   22   28                                                       
CONECT   27   25   28                                                       
CONECT   28   26   27                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   64    0
END

COMPND    HMDB0014391
HETATM    1  O1  UNL     1       8.554   2.456  -0.935  1.00  0.00           O  
HETATM    2  C1  UNL     1       7.504   1.794  -0.694  1.00  0.00           C  
HETATM    3  C2  UNL     1       6.346   2.251   0.089  1.00  0.00           C  
HETATM    4  C3  UNL     1       5.405   1.126   0.062  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.144   1.016   0.634  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.423  -0.130   0.490  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.038  -0.325   1.056  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.054  -0.137  -0.039  1.00  0.00           C  
HETATM    9  N1  UNL     1      -0.299  -0.284   0.283  1.00  0.00           N  
HETATM   10  C8  UNL     1      -0.855  -1.524   0.594  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.817  -2.066  -0.449  1.00  0.00           C  
HETATM   12  N2  UNL     1      -2.786  -1.000  -0.719  1.00  0.00           N  
HETATM   13  C10 UNL     1      -4.214  -1.263  -0.630  1.00  0.00           C  
HETATM   14  N3  UNL     1      -4.635  -2.410  -1.179  1.00  0.00           N  
HETATM   15  S1  UNL     1      -6.298  -2.380  -0.962  1.00  0.00           S  
HETATM   16  C11 UNL     1      -6.446  -0.885  -0.162  1.00  0.00           C  
HETATM   17  C12 UNL     1      -7.538  -0.175   0.354  1.00  0.00           C  
HETATM   18  C13 UNL     1      -7.331   1.052   0.985  1.00  0.00           C  
HETATM   19  C14 UNL     1      -6.026   1.485   1.056  1.00  0.00           C  
HETATM   20  C15 UNL     1      -4.971   0.783   0.549  1.00  0.00           C  
HETATM   21  C16 UNL     1      -5.152  -0.452  -0.091  1.00  0.00           C  
HETATM   22  C17 UNL     1      -2.232   0.265  -1.115  1.00  0.00           C  
HETATM   23  C18 UNL     1      -1.190   0.744  -0.138  1.00  0.00           C  
HETATM   24  C19 UNL     1       3.960  -1.178  -0.229  1.00  0.00           C  
HETATM   25 CL1  UNL     1       3.039  -2.671  -0.416  1.00  0.00          CL  
HETATM   26  C20 UNL     1       5.221  -1.080  -0.806  1.00  0.00           C  
HETATM   27  C21 UNL     1       5.938   0.081  -0.655  1.00  0.00           C  
HETATM   28  N4  UNL     1       7.238   0.473  -1.132  1.00  0.00           N  
HETATM   29  H1  UNL     1       5.923   3.151  -0.420  1.00  0.00           H  
HETATM   30  H2  UNL     1       6.581   2.494   1.141  1.00  0.00           H  
HETATM   31  H3  UNL     1       3.729   1.838   1.196  1.00  0.00           H  
HETATM   32  H4  UNL     1       1.915   0.544   1.763  1.00  0.00           H  
HETATM   33  H5  UNL     1       2.035  -1.283   1.565  1.00  0.00           H  
HETATM   34  H6  UNL     1       1.193   0.929  -0.401  1.00  0.00           H  
HETATM   35  H7  UNL     1       1.369  -0.729  -0.956  1.00  0.00           H  
HETATM   36  H8  UNL     1      -0.089  -2.294   0.742  1.00  0.00           H  
HETATM   37  H9  UNL     1      -1.432  -1.456   1.550  1.00  0.00           H  
HETATM   38  H10 UNL     1      -1.233  -2.181  -1.402  1.00  0.00           H  
HETATM   39  H11 UNL     1      -2.267  -2.985  -0.078  1.00  0.00           H  
HETATM   40  H12 UNL     1      -8.499  -0.628   0.230  1.00  0.00           H  
HETATM   41  H13 UNL     1      -8.180   1.564   1.363  1.00  0.00           H  
HETATM   42  H14 UNL     1      -5.828   2.444   1.545  1.00  0.00           H  
HETATM   43  H15 UNL     1      -3.978   1.227   0.680  1.00  0.00           H  
HETATM   44  H16 UNL     1      -2.928   1.050  -1.374  1.00  0.00           H  
HETATM   45  H17 UNL     1      -1.668   0.041  -2.082  1.00  0.00           H  
HETATM   46  H18 UNL     1      -1.610   1.210   0.773  1.00  0.00           H  
HETATM   47  H19 UNL     1      -0.594   1.532  -0.644  1.00  0.00           H  
HETATM   48  H20 UNL     1       5.648  -1.893  -1.371  1.00  0.00           H  
HETATM   49  H21 UNL     1       7.839  -0.140  -1.696  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   28
CONECT    3    4   29   30
CONECT    4    5    5   27
CONECT    5    6   31
CONECT    6    7   24   24
CONECT    7    8   32   33
CONECT    8    9   34   35
CONECT    9   10   23
CONECT   10   11   36   37
CONECT   11   12   38   39
CONECT   12   13   22
CONECT   13   14   14   21
CONECT   14   15
CONECT   15   16
CONECT   16   17   17   21
CONECT   17   18   40
CONECT   18   19   19   41
CONECT   19   20   42
CONECT   20   21   21   43
CONECT   22   23   44   45
CONECT   23   46   47
CONECT   24   25   26
CONECT   26   27   27   48
CONECT   27   28
CONECT   28   49
END

HMDB0014391
     RDKit          3D
Ziprasidone
 49 53  0  0  0  0  0  0  0  0999 V2000
    8.5536    2.4564   -0.9347 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5043    1.7937   -0.6939 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3460    2.2507    0.0886 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4048    1.1264    0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1445    1.0162    0.6343 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4229   -0.1301    0.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0379   -0.3255    1.0562 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0539   -0.1374   -0.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2995   -0.2835    0.2834 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8547   -1.5237    0.5944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8167   -2.0662   -0.4486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7857   -0.9998   -0.7191 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2137   -1.2625   -0.6299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6353   -2.4104   -1.1786 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2984   -2.3803   -0.9625 S   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4464   -0.8852   -0.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5375   -0.1745    0.3535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3308    1.0523    0.9850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0264    1.4846    1.0555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9711    0.7828    0.5495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1522   -0.4525   -0.0909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2318    0.2646   -1.1148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1901    0.7445   -0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9602   -1.1775   -0.2285 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0387   -2.6713   -0.4159 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.2210   -1.0796   -0.8063 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9376    0.0808   -0.6549 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2381    0.4733   -1.1322 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9225    3.1509   -0.4205 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5807    2.4942    1.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7293    1.8381    1.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9150    0.5441    1.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0355   -1.2825    1.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1927    0.9287   -0.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3691   -0.7294   -0.9561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0885   -2.2943    0.7422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4322   -1.4556    1.5502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2329   -2.1809   -1.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2670   -2.9845   -0.0779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4990   -0.6283    0.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1798    1.5637    1.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8285    2.4437    1.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9776    1.2268    0.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9277    1.0497   -1.3737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6681    0.0409   -2.0817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6095    1.2102    0.7730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5943    1.5318   -0.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6482   -1.8935   -1.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8389   -0.1398   -1.6960 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 12 22  1  0
 22 23  1  0
  6 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 28  2  1  0
 27  4  1  0
 23  9  1  0
 21 13  1  0
 21 16  1  0
  3 29  1  0
  3 30  1  0
  5 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 22 44  1  0
 22 45  1  0
 23 46  1  0
 23 47  1  0
 26 48  1  0
 28 49  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Ziprasidona	ChEBI
Ziprasidonum	ChEBI
Zipradon	Kegg
Ziprasidone mesylate trihydrate	HMDB
5-(2-(4-(3-Benzisothiazolyl)piperazinyl)ethyl)-6-chloro-1,3-dihydro-2H-indol-2-one	HMDB
Ziprasidone hydrochloride	HMDB
Ziprazidone	HMDB
Ziprasidone hydrochloride, monohydrate	HMDB
Geodon	HMDB

Chemical Formula

C₂₁H₂₁ClN₄OS

Average Molecular Weight

412.936

Monoisotopic Molecular Weight

412.112459711

IUPAC Name

5-{2-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]ethyl}-6-chloro-2,3-dihydro-1H-indol-2-one

Traditional Name

ziprasidone

CAS Registry Number

146939-27-7

SMILES

ClC1=C(CCN2CCN(CC2)C2=NSC3=CC=CC=C23)C=C2CC(=O)NC2=C1

InChI Identifier

InChI=1S/C21H21ClN4OS/c22-17-13-18-15(12-20(27)23-18)11-14(17)5-6-25-7-9-26(10-8-25)21-16-3-1-2-4-19(16)28-24-21/h1-4,11,13H,5-10,12H2,(H,23,27)

InChI Key

MVWVFYHBGMAFLY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-arylpiperazines. These are organic compounds containing a piperazine ring where the nitrogen ring atom carries an aryl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazinanes

Sub Class

Piperazines

Direct Parent

N-arylpiperazines

Alternative Parents

Substituents

N-arylpiperazine
1,2-benzothiazole
Indole
Indole or derivatives
Phenethylamine
Dialkylarylamine
N-alkylpiperazine
Aralkylamine
Imidolactam
Benzenoid
1,2-thiazolamine
Aryl chloride
Aryl halide
Cyclic carboximidic acid
Heteroaromatic compound
Thiazole
Azole
Tertiary aliphatic amine
Tertiary amine
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Azacycle
Amine
Organohalogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organochloride
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organochlorine compound (CHEBI:10119 )
indolones (CHEBI:10119 )
piperazines (CHEBI:10119 )
1,2-benzisothiazole (CHEBI:10119 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014391)

Source

Exogenous

Exogenous (HMDB: HMDB0014391)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	> 300 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0072 g/L	Not Available
LogP	3.8	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	192.6	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0072 g/L	ALOGPS
logP	4.64	ALOGPS
logP	4.3	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	13.18	ChemAxon
pKa (Strongest Basic)	7.09	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	48.47 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	116.72 m³·mol⁻¹	ChemAxon
Polarizability	44.96 Å³	ChemAxon
Number of Rings	5	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
DeepCCS	[M-2H]-	221.017	30932474
DeepCCS	[M+Na]+	196.422	30932474
AllCCS	[M+H]+	195.7	32859911
AllCCS	[M+H-H2O]+	193.3	32859911
AllCCS	[M+NH4]+	197.8	32859911
AllCCS	[M+Na]+	198.5	32859911
AllCCS	[M-H]-	191.7	32859911
AllCCS	[M+Na-2H]-	191.5	32859911
AllCCS	[M+HCOO]-	191.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.52 minutes	32390414
Predicted by Siyang on May 30, 2022	10.6543 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.15 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	46.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1064.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	199.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	175.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	174.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	78.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	381.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	478.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	453.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	784.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	377.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1540.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	279.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	321.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	313.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	356.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ziprasidone	ClC1=C(CCN2CCN(CC2)C2=NSC3=CC=CC=C23)C=C2CC(=O)NC2=C1	4649.7	Standard polar	33892256
Ziprasidone	ClC1=C(CCN2CCN(CC2)C2=NSC3=CC=CC=C23)C=C2CC(=O)NC2=C1	3628.7	Standard non polar	33892256
Ziprasidone	ClC1=C(CCN2CCN(CC2)C2=NSC3=CC=CC=C23)C=C2CC(=O)NC2=C1	4055.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ziprasidone,1TMS,isomer #1	C[Si](C)(C)N1C(=O)CC2=CC(CCN3CCN(C4=NSC5=CC=CC=C45)CC3)=C(Cl)C=C21	3651.1	Semi standard non polar	33892256
Ziprasidone,1TMS,isomer #1	C[Si](C)(C)N1C(=O)CC2=CC(CCN3CCN(C4=NSC5=CC=CC=C45)CC3)=C(Cl)C=C21	3582.0	Standard non polar	33892256
Ziprasidone,1TMS,isomer #1	C[Si](C)(C)N1C(=O)CC2=CC(CCN3CCN(C4=NSC5=CC=CC=C45)CC3)=C(Cl)C=C21	4792.9	Standard polar	33892256
Ziprasidone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)CC2=CC(CCN3CCN(C4=NSC5=CC=CC=C45)CC3)=C(Cl)C=C21	3820.6	Semi standard non polar	33892256
Ziprasidone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)CC2=CC(CCN3CCN(C4=NSC5=CC=CC=C45)CC3)=C(Cl)C=C21	3807.5	Standard non polar	33892256
Ziprasidone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)CC2=CC(CCN3CCN(C4=NSC5=CC=CC=C45)CC3)=C(Cl)C=C21	4825.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ziprasidone GC-MS (Non-derivatized) - 70eV, Positive	splash10-00lr-2963000000-73cfc43e5f403e3ecc3c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ziprasidone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ziprasidone 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ziprasidone LC-ESI-QFT , positive-QTOF	splash10-01ox-0900400000-0a17dd0e237f50ba91c5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ziprasidone 35V, Positive-QTOF	splash10-01ox-0900400000-f48ae3c72fd303348090	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ziprasidone 40V, Positive-QTOF	splash10-0006-0900000000-af32fe00a14db315cf8b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ziprasidone 30V, Positive-QTOF	splash10-0006-0900200000-4a3f1cc15848e67e20a4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ziprasidone 10V, Positive-QTOF	splash10-03di-0000900000-a6bfb6420e00cb948710	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ziprasidone 20V, Positive-QTOF	splash10-03di-0100900000-c6778b116b9686acf160	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ziprasidone 50V, Positive-QTOF	splash10-05mo-0900000000-7fa49aa5ae170ec5d44d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ziprasidone 20V, Positive-QTOF	splash10-03di-0100900000-729ef7c784ed6b441be2	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ziprasidone 10V, Positive-QTOF	splash10-03di-0102900000-fa5da81fd10bba242977	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ziprasidone 20V, Positive-QTOF	splash10-01po-0977400000-7e1cc88e25385239ddce	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ziprasidone 40V, Positive-QTOF	splash10-01r6-0910000000-cf9cd1eba914ad67bfd4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ziprasidone 10V, Negative-QTOF	splash10-03di-0001900000-6744a80d8f97817dd4d9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ziprasidone 20V, Negative-QTOF	splash10-03xu-1239400000-c4b9e0aa1e6ecda282ad	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ziprasidone 40V, Negative-QTOF	splash10-0006-9771000000-b7a94f6b2c87097c90ab	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ziprasidone 10V, Negative-QTOF	splash10-03di-0000900000-a39ff6e23c7d3ae58642	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ziprasidone 20V, Negative-QTOF	splash10-01q9-9200700000-1c46f9707ae8ff17a567	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ziprasidone 40V, Negative-QTOF	splash10-001i-6923100000-63bd8cda1809361ef1d9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ziprasidone 10V, Positive-QTOF	splash10-03di-0000900000-eee450689fc3c8c5f739	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ziprasidone 20V, Positive-QTOF	splash10-03di-0100900000-9282980f21fd87d87ec4	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ziprasidone 40V, Positive-QTOF	splash10-03di-3925600000-35b0278722002948c536	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00246	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00246	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00246

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

54841

KEGG Compound ID

C07568

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ziprasidone

METLIN ID

Not Available

PubChem Compound

60854

PDB ID

Not Available

ChEBI ID

10119

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

Stahl SM, Shayegan DK: The psychopharmacology of ziprasidone: receptor-binding properties and real-world psychiatric practice. J Clin Psychiatry. 2003;64 Suppl 19:6-12. [PubMed:14728084 ]

Only showing the first 10 proteins. There are 30 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

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

References

Prakash C, Kamel A, Cui D, Whalen RD, Miceli JJ, Tweedie D: Identification of the major human liver cytochrome P450 isoform(s) responsible for the formation of the primary metabolites of ziprasidone and prediction of possible drug interactions. Br J Clin Pharmacol. 2000;49 Suppl 1:35S-42S. [PubMed:10771452 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Nakamura H, Nakasa H, Ishii I, Ariyoshi N, Igarashi T, Ohmori S, Kitada M: Effects of endogenous steroids on CYP3A4-mediated drug metabolism by human liver microsomes. Drug Metab Dispos. 2002 May;30(5):534-40. [PubMed:11950784 ]

Enzyme Details

2. 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

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Cytochrome P450 3A5

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

Enzyme Details

4. Cytochrome P450 3A7

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

Enzyme Details

5. 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

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

6. Alpha-2A adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:: ADRA2A
Uniprot ID:: P08913
Molecular weight:: 48956.3

References

Nasrallah HA: Atypical antipsychotic-induced metabolic side effects: insights from receptor-binding profiles. Mol Psychiatry. 2008 Jan;13(1):27-35. Epub 2007 Sep 11. [PubMed:17848919 ]

Enzyme Details

7. Alpha-2B adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol
Gene Name:: ADRA2B
Uniprot ID:: P18089
Molecular weight:: 49953.1

References

Nasrallah HA: Atypical antipsychotic-induced metabolic side effects: insights from receptor-binding profiles. Mol Psychiatry. 2008 Jan;13(1):27-35. Epub 2007 Sep 11. [PubMed:17848919 ]

Enzyme Details

8. 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

Seeman P: Atypical antipsychotics: mechanism of action. Can J Psychiatry. 2002 Feb;47(1):27-38. [PubMed:11873706 ]
Kopecek M, Bares M, Mohr P: Ziprasidone-induced galactorrhea: a case report. Neuro Endocrinol Lett. 2005 Feb;26(1):69-70. [PubMed:15726024 ]
Seeger TF, Seymour PA, Schmidt AW, Zorn SH, Schulz DW, Lebel LA, McLean S, Guanowsky V, Howard HR, Lowe JA 3rd, et al.: Ziprasidone (CP-88,059): a new antipsychotic with combined dopamine and serotonin receptor antagonist activity. J Pharmacol Exp Ther. 1995 Oct;275(1):101-13. [PubMed:7562537 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Stahl SM, Shayegan DK: The psychopharmacology of ziprasidone: receptor-binding properties and real-world psychiatric practice. J Clin Psychiatry. 2003;64 Suppl 19:6-12. [PubMed:14728084 ]
Nasrallah HA: Atypical antipsychotic-induced metabolic side effects: insights from receptor-binding profiles. Mol Psychiatry. 2008 Jan;13(1):27-35. Epub 2007 Sep 11. [PubMed:17848919 ]

Enzyme Details

9. 5-hydroxytryptamine receptor 7

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 stimulate adenylate cyclase
Gene Name:: HTR7
Uniprot ID:: P34969
Molecular weight:: 53554.4

References

Stark AD, Jordan S, Allers KA, Bertekap RL, Chen R, Mistry Kannan T, Molski TF, Yocca FD, Sharp T, Kikuchi T, Burris KD: Interaction of the novel antipsychotic aripiprazole with 5-HT1A and 5-HT 2A receptors: functional receptor-binding and in vivo electrophysiological studies. Psychopharmacology (Berl). 2007 Feb;190(3):373-82. Epub 2006 Nov 25. [PubMed:17242925 ]
Meltzer HY: The role of serotonin in antipsychotic drug action. Neuropsychopharmacology. 1999 Aug;21(2 Suppl):106S-115S. [PubMed:10432496 ]
Meltzer HY: Role of serotonin in the action of atypical antipsychotic drugs. Clin Neurosci. 1995;3(2):64-75. [PubMed:7583621 ]

Enzyme Details

10. 5-hydroxytryptamine receptor 1B

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:: HTR1B
Uniprot ID:: P28222
Molecular weight:: 43567.5

References

Nasrallah HA: Atypical antipsychotic-induced metabolic side effects: insights from receptor-binding profiles. Mol Psychiatry. 2008 Jan;13(1):27-35. Epub 2007 Sep 11. [PubMed:17848919 ]

Only showing the first 10 proteins. There are 30 proteins in total.

Show all enzymes and transporters

Showing metabocard for Ziprasidone (HMDB0014391)

MOL for HMDB0014391 (Ziprasidone)

3D MOL for HMDB0014391 (Ziprasidone)

3D SDF for HMDB0014391 (Ziprasidone)

3D-SDF for HMDB0014391 (Ziprasidone)

PDB for HMDB0014391 (Ziprasidone)

3D PDB for HMDB0014391 (Ziprasidone)

SMILES for HMDB0014391 (Ziprasidone)

INCHI for HMDB0014391 (Ziprasidone)

Structure for HMDB0014391 (Ziprasidone)

3D Structure for HMDB0014391 (Ziprasidone)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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References