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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4)transporters (1) Show 5 proteins XML

enzymes (4)transporters (1) Show 5 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:03 UTC

HMDB ID

HMDB0015637

Secondary Accession Numbers

HMDB15637

Metabolite Identification

Common Name

Vilazodone

Description

Vilazodone, also known as SB 659746A or HCL, vilazodone, 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. Vilazodone selectively inhibits serotonin reuptake in the central nervous system as well as acting as a partial agonist of 5HT-1A receptors. Vilazodone is a very strong basic compound (based on its pKa). Vilazodone is a novel compound with combined high affinity and selectivity for the 5-hydroxytryptamine (5-HT) transporter and 5-HT(1A) receptors. Clinical cases of fetal and neonatal exposure to SSRIs and SNRIs have lead to a number of complications including respiratory distress, seizures, and temperature instability. The exact mechanism for how these effects translate to its antidepressant effects are not known, though there is an association between these effects and antidepressive activity. Vilazodone is an antidepressant agent that can used as an alternative for patients who cannot tolerate therapy with other antidepressant classes such as selective serotonin reuptake inhibitors or serotonin norepinephrine reuptake inhibitors. Dosage adjustments are not necessary for patients of different genders or with reduced hepatic and renal function.

Structure

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

[NO NAME]
  Mrv0541 04231207232D          
Created with ChemWriter - http://chemwriter.com
 33 37  0  0  0  0            999 V2000
   11.9391   -1.8446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6581   -0.4662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5860    0.4694    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0150   -0.3557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1267    1.8702    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6581   -1.8951    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6884   -1.9751    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5860   -0.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3005    0.8819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3005   -0.7682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0150    0.4694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8715    0.8819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1570    0.4694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4425    0.8819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7294   -0.7682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7280    0.4694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0135    0.8819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4439   -0.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7294   -1.5932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2646    0.5476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1585   -0.7682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9285    1.6976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1585   -1.5932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4439   -2.0057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7136    1.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9391   -0.5168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0083   -0.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9064    0.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4206   -1.1807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2010   -0.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2456   -1.1807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9447   -1.1909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 23  1  0  0  0  0
  1 29  1  0  0  0  0
  2 32  2  0  0  0  0
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  4 11  1  0  0  0  0
  4 15  1  0  0  0  0
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  5 25  1  0  0  0  0
  6 32  1  0  0  0  0
  7 33  3  0  0  0  0
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 30 31  1  0  0  0  0
 30 33  1  0  0  0  0
M  END

HMDB0015637
     RDKit          3D
Vilazodone
 60 64  0  0  0  0  0  0  0  0999 V2000
   -5.0292    4.2772   -2.9365 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3880    3.5232   -2.1377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8395    2.5737   -1.1576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1118    2.7342   -0.6484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5507    1.8294    0.2902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7582    0.7896    0.7200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9316   -0.2218    1.6127 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8398   -0.9901    1.6779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8944   -0.4936    0.8093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5092   -1.0347    0.5450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4598   -1.7725   -0.7462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1461   -2.3823   -1.1141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0013   -1.4256   -1.2707 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3620   -1.6668    0.8216 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0267   -0.5019    0.3086 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4572   -0.4977    0.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1785   -1.5198    0.9645 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5534   -1.4985    1.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2715   -0.4239    0.5696 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5514   -0.1418    0.5197 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7760    1.0207   -0.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0573    1.6709   -0.2702 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2440    1.0232    0.1474 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0847    2.7990   -0.8384 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5214    1.5325   -0.3806 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5629    0.6142    0.0061 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1867    0.5804   -0.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2498   -0.6723   -2.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8075    0.7122   -1.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  3  0
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 31 58  1  0
 31 59  1  0
 33 60  1  0
M  END

[NO NAME]
  Mrv0541 04231207232D          
Created with ChemWriter - http://chemwriter.com
 33 37  0  0  0  0            999 V2000
   11.9391   -1.8446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6581   -0.4662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5860    0.4694    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0150   -0.3557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1267    1.8702    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6581   -1.8951    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6884   -1.9751    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5860   -0.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3005    0.8819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3005   -0.7682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0150    0.4694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8715    0.8819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.7294   -0.7682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.4439   -0.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7294   -1.5932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.1585   -0.7682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9285    1.6976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1585   -1.5932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.4206   -1.1807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6500    0.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2456   -1.1807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9447   -1.1909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1 29  1  0  0  0  0
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  3  8  1  0  0  0  0
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 27 30  2  0  0  0  0
 28 31  2  0  0  0  0
 29 32  1  0  0  0  0
 30 31  1  0  0  0  0
 30 33  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015637

> <DATABASE_NAME>
hmdb

> <SMILES>
NC(=O)C1=CC2=C(O1)C=CC(=C2)N1CCN(CCCCC2=CNC3=C2C=C(C=C3)C#N)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C26H27N5O2/c27-16-18-4-6-23-22(13-18)19(17-29-23)3-1-2-8-30-9-11-31(12-10-30)21-5-7-24-20(14-21)15-25(33-24)26(28)32/h4-7,13-15,17,29H,1-3,8-12H2,(H2,28,32)

> <INCHI_KEY>
SGEGOXDYSFKCPT-UHFFFAOYSA-N

> <FORMULA>
C26H27N5O2

> <MOLECULAR_WEIGHT>
441.5249

> <EXACT_MASS>
441.216475133

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
50.024221394025105

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-{4-[4-(5-cyano-1H-indol-3-yl)butyl]piperazin-1-yl}-1-benzofuran-2-carboxamide

> <ALOGPS_LOGP>
4.21

> <JCHEM_LOGP>
3.715303905999999

> <ALOGPS_LOGS>
-3.56

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
17.006896668546844

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.192647847280742

> <JCHEM_PKA_STRONGEST_BASIC>
8.604416954748784

> <JCHEM_POLAR_SURFACE_AREA>
102.28999999999999

> <JCHEM_REFRACTIVITY>
129.71140000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.23e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
vilazodone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015637
     RDKit          3D
Vilazodone
 60 64  0  0  0  0  0  0  0  0999 V2000
   -5.0292    4.2772   -2.9365 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3880    3.5232   -2.1377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8395    2.5737   -1.1576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1118    2.7342   -0.6484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5507    1.8294    0.2902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7582    0.7896    0.7200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9316   -0.2218    1.6127 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8398   -0.9901    1.6779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8944   -0.4936    0.8093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5092   -1.0347    0.5450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4598   -1.7725   -0.7462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1461   -2.3823   -1.1141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0013   -1.4256   -1.2707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6568   -0.6801   -0.1147 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0934   -1.3943    0.9744 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3620   -1.6668    0.8216 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0267   -0.5019    0.3086 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4572   -0.4977    0.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1785   -1.5198    0.9645 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5534   -1.4985    1.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2715   -0.4239    0.5696 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5514   -0.1418    0.5197 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7760    1.0207   -0.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0573    1.6709   -0.2702 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2440    1.0232    0.1474 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0847    2.7990   -0.8384 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5214    1.5325   -0.3806 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5629    0.6142    0.0061 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1867    0.5804   -0.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4066    0.6410   -0.2857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0700    0.6017   -0.3636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4738    0.6083    0.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0537    1.5278   -0.7195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7288    3.5545   -0.9913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5417    1.9450    0.6943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8073   -0.3838    2.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7210   -1.8582    2.3093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7885   -0.1642    0.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2233   -1.6666    1.3828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6961   -1.0343   -1.5735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2969   -2.5150   -0.8327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3014   -2.8239   -2.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8461   -3.2024   -0.4154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1523   -2.0017   -1.7037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2498   -0.6723   -2.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2728   -0.8296    1.9155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6868   -2.3374    1.0964 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7488   -1.8930    1.8606 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5194   -2.5584    0.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6578   -2.3910    1.3601 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0566   -2.3330    1.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7930    1.4958    0.9226 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5751    0.1346   -0.2696 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3128    2.4804   -0.8636 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6537    1.3973   -0.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8075    0.7122   -1.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7687    1.5587    0.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4818    0.9762   -1.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4838    1.3160    0.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0482    1.3926   -1.1156 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 23 27  2  0
 27 28  1  0
 28 29  2  0
 17 30  1  0
 30 31  1  0
  9 32  1  0
 32 33  2  0
 33  3  1  0
 32  6  1  0
 31 14  1  0
 29 18  1  0
 28 21  1  0
  4 34  1  0
  5 35  1  0
  7 36  1  0
  8 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 19 50  1  0
 20 51  1  0
 25 52  1  0
 25 53  1  0
 27 54  1  0
 29 55  1  0
 30 56  1  0
 30 57  1  0
 31 58  1  0
 31 59  1  0
 33 60  1  0
M  END

HEADER    PROTEIN                                 23-APR-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: [NO NAME]                                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-12         0                                  
HETATM    1  O   UNK     0      22.286  -3.443   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      25.495  -0.870   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      14.160   0.876   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      16.828  -0.664   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       5.837   3.491   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      25.495  -3.538   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       3.152  -3.687   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      14.160  -0.664   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.494   1.646   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.494  -1.434   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.828   0.876   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.827   1.646   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.493   0.876   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.159   1.646   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      18.162  -1.434   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.826   0.876   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.492   1.646   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      19.495  -0.664   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.162  -2.974   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.094   1.022   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      20.829  -1.434   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.333   3.169   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      20.829  -2.974   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      19.495  -3.744   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.065   2.169   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      22.286  -0.965   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.616  -0.442   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.559   1.851   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      23.185  -2.204   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.109  -0.759   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.080   0.387   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      24.725  -2.204   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.630  -2.223   0.000  0.00  0.00           C+0
CONECT    1   23   29                                                       
CONECT    2   32                                                            
CONECT    3    8    9   12                                                  
CONECT    4   10   11   15                                                  
CONECT    5   22   25                                                       
CONECT    6   32                                                            
CONECT    7   33                                                            
CONECT    8    3   10                                                       
CONECT    9    3   11                                                       
CONECT   10    4    8                                                       
CONECT   11    4    9                                                       
CONECT   12    3   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   16                                                       
CONECT   15    4   18   19                                                  
CONECT   16   14   17                                                       
CONECT   17   16   20   22                                                  
CONECT   18   15   21                                                       
CONECT   19   15   24                                                       
CONECT   20   17   25   27                                                  
CONECT   21   18   23   26                                                  
CONECT   22    5   17                                                       
CONECT   23    1   21   24                                                  
CONECT   24   19   23                                                       
CONECT   25    5   20   28                                                  
CONECT   26   21   29                                                       
CONECT   27   20   30                                                       
CONECT   28   25   31                                                       
CONECT   29    1   26   32                                                  
CONECT   30   27   31   33                                                  
CONECT   31   28   30                                                       
CONECT   32    2    6   29                                                  
CONECT   33    7   30                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

COMPND    HMDB0015637
HETATM    1  N1  UNL     1      -5.029   4.277  -2.936  1.00  0.00           N  
HETATM    2  C1  UNL     1      -5.388   3.523  -2.138  1.00  0.00           C  
HETATM    3  C2  UNL     1      -5.839   2.574  -1.158  1.00  0.00           C  
HETATM    4  C3  UNL     1      -7.112   2.734  -0.648  1.00  0.00           C  
HETATM    5  C4  UNL     1      -7.551   1.829   0.290  1.00  0.00           C  
HETATM    6  C5  UNL     1      -6.758   0.790   0.720  1.00  0.00           C  
HETATM    7  N2  UNL     1      -6.932  -0.222   1.613  1.00  0.00           N  
HETATM    8  C6  UNL     1      -5.840  -0.990   1.678  1.00  0.00           C  
HETATM    9  C7  UNL     1      -4.894  -0.494   0.809  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.509  -1.035   0.545  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.460  -1.773  -0.746  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.146  -2.382  -1.114  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.001  -1.426  -1.271  1.00  0.00           C  
HETATM   14  N3  UNL     1      -0.657  -0.680  -0.115  1.00  0.00           N  
HETATM   15  C12 UNL     1      -0.093  -1.394   0.974  1.00  0.00           C  
HETATM   16  C13 UNL     1       1.362  -1.667   0.822  1.00  0.00           C  
HETATM   17  N4  UNL     1       2.027  -0.502   0.309  1.00  0.00           N  
HETATM   18  C14 UNL     1       3.457  -0.498   0.408  1.00  0.00           C  
HETATM   19  C15 UNL     1       4.179  -1.520   0.964  1.00  0.00           C  
HETATM   20  C16 UNL     1       5.553  -1.498   1.051  1.00  0.00           C  
HETATM   21  C17 UNL     1       6.271  -0.424   0.570  1.00  0.00           C  
HETATM   22  O1  UNL     1       7.551  -0.142   0.520  1.00  0.00           O  
HETATM   23  C18 UNL     1       7.776   1.021  -0.039  1.00  0.00           C  
HETATM   24  C19 UNL     1       9.057   1.671  -0.270  1.00  0.00           C  
HETATM   25  N5  UNL     1      10.244   1.023   0.147  1.00  0.00           N  
HETATM   26  O2  UNL     1       9.085   2.799  -0.838  1.00  0.00           O  
HETATM   27  C20 UNL     1       6.521   1.532  -0.381  1.00  0.00           C  
HETATM   28  C21 UNL     1       5.563   0.614   0.006  1.00  0.00           C  
HETATM   29  C22 UNL     1       4.187   0.580  -0.074  1.00  0.00           C  
HETATM   30  C23 UNL     1       1.407   0.641  -0.286  1.00  0.00           C  
HETATM   31  C24 UNL     1      -0.070   0.602  -0.364  1.00  0.00           C  
HETATM   32  C25 UNL     1      -5.474   0.608   0.222  1.00  0.00           C  
HETATM   33  C26 UNL     1      -5.054   1.528  -0.719  1.00  0.00           C  
HETATM   34  H1  UNL     1      -7.729   3.555  -0.991  1.00  0.00           H  
HETATM   35  H2  UNL     1      -8.542   1.945   0.694  1.00  0.00           H  
HETATM   36  H3  UNL     1      -7.807  -0.384   2.181  1.00  0.00           H  
HETATM   37  H4  UNL     1      -5.721  -1.858   2.309  1.00  0.00           H  
HETATM   38  H5  UNL     1      -2.789  -0.164   0.531  1.00  0.00           H  
HETATM   39  H6  UNL     1      -3.223  -1.667   1.383  1.00  0.00           H  
HETATM   40  H7  UNL     1      -3.696  -1.034  -1.574  1.00  0.00           H  
HETATM   41  H8  UNL     1      -4.297  -2.515  -0.833  1.00  0.00           H  
HETATM   42  H9  UNL     1      -2.301  -2.824  -2.149  1.00  0.00           H  
HETATM   43  H10 UNL     1      -1.846  -3.202  -0.415  1.00  0.00           H  
HETATM   44  H11 UNL     1      -0.152  -2.002  -1.704  1.00  0.00           H  
HETATM   45  H12 UNL     1      -1.250  -0.672  -2.080  1.00  0.00           H  
HETATM   46  H13 UNL     1      -0.273  -0.830   1.915  1.00  0.00           H  
HETATM   47  H14 UNL     1      -0.687  -2.337   1.096  1.00  0.00           H  
HETATM   48  H15 UNL     1       1.749  -1.893   1.861  1.00  0.00           H  
HETATM   49  H16 UNL     1       1.519  -2.558   0.177  1.00  0.00           H  
HETATM   50  H17 UNL     1       3.658  -2.391   1.360  1.00  0.00           H  
HETATM   51  H18 UNL     1       6.057  -2.333   1.498  1.00  0.00           H  
HETATM   52  H19 UNL     1      10.793   1.496   0.923  1.00  0.00           H  
HETATM   53  H20 UNL     1      10.575   0.135  -0.270  1.00  0.00           H  
HETATM   54  H21 UNL     1       6.313   2.480  -0.864  1.00  0.00           H  
HETATM   55  H22 UNL     1       3.654   1.397  -0.515  1.00  0.00           H  
HETATM   56  H23 UNL     1       1.807   0.712  -1.335  1.00  0.00           H  
HETATM   57  H24 UNL     1       1.769   1.559   0.254  1.00  0.00           H  
HETATM   58  H25 UNL     1      -0.482   0.976  -1.344  1.00  0.00           H  
HETATM   59  H26 UNL     1      -0.484   1.316   0.404  1.00  0.00           H  
HETATM   60  H27 UNL     1      -4.048   1.393  -1.116  1.00  0.00           H  
CONECT    1    2    2    2
CONECT    2    3
CONECT    3    4    4   33
CONECT    4    5   34
CONECT    5    6    6   35
CONECT    6    7   32
CONECT    7    8   36
CONECT    8    9    9   37
CONECT    9   10   32
CONECT   10   11   38   39
CONECT   11   12   40   41
CONECT   12   13   42   43
CONECT   13   14   44   45
CONECT   14   15   31
CONECT   15   16   46   47
CONECT   16   17   48   49
CONECT   17   18   30
CONECT   18   19   19   29
CONECT   19   20   50
CONECT   20   21   21   51
CONECT   21   22   28
CONECT   22   23
CONECT   23   24   27   27
CONECT   24   25   26   26
CONECT   25   52   53
CONECT   27   28   54
CONECT   28   29   29
CONECT   29   55
CONECT   30   31   56   57
CONECT   31   58   59
CONECT   32   33   33
CONECT   33   60
END

HMDB0015637
     RDKit          3D
Vilazodone
 60 64  0  0  0  0  0  0  0  0999 V2000
   -5.0292    4.2772   -2.9365 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3880    3.5232   -2.1377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8395    2.5737   -1.1576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1118    2.7342   -0.6484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5507    1.8294    0.2902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7582    0.7896    0.7200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9316   -0.2218    1.6127 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8398   -0.9901    1.6779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8944   -0.4936    0.8093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5092   -1.0347    0.5450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4598   -1.7725   -0.7462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1461   -2.3823   -1.1141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0013   -1.4256   -1.2707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6568   -0.6801   -0.1147 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0934   -1.3943    0.9744 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3620   -1.6668    0.8216 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0267   -0.5019    0.3086 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4572   -0.4977    0.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1785   -1.5198    0.9645 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5534   -1.4985    1.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2715   -0.4239    0.5696 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5514   -0.1418    0.5197 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7760    1.0207   -0.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0573    1.6709   -0.2702 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2440    1.0232    0.1474 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0847    2.7990   -0.8384 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5214    1.5325   -0.3806 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5629    0.6142    0.0061 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1867    0.5804   -0.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4066    0.6410   -0.2857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0700    0.6017   -0.3636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4738    0.6083    0.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0537    1.5278   -0.7195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7288    3.5545   -0.9913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5417    1.9450    0.6943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8073   -0.3838    2.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7210   -1.8582    2.3093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7885   -0.1642    0.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2233   -1.6666    1.3828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6961   -1.0343   -1.5735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2969   -2.5150   -0.8327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3014   -2.8239   -2.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8461   -3.2024   -0.4154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1523   -2.0017   -1.7037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2498   -0.6723   -2.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2728   -0.8296    1.9155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6868   -2.3374    1.0964 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7488   -1.8930    1.8606 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5194   -2.5584    0.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6578   -2.3910    1.3601 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0566   -2.3330    1.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7930    1.4958    0.9226 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5751    0.1346   -0.2696 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3128    2.4804   -0.8636 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6537    1.3973   -0.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8075    0.7122   -1.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7687    1.5587    0.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4818    0.9762   -1.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4838    1.3160    0.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0482    1.3926   -1.1156 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 23 27  2  0
 27 28  1  0
 28 29  2  0
 17 30  1  0
 30 31  1  0
  9 32  1  0
 32 33  2  0
 33  3  1  0
 32  6  1  0
 31 14  1  0
 29 18  1  0
 28 21  1  0
  4 34  1  0
  5 35  1  0
  7 36  1  0
  8 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 19 50  1  0
 20 51  1  0
 25 52  1  0
 25 53  1  0
 27 54  1  0
 29 55  1  0
 30 56  1  0
 30 57  1  0
 31 58  1  0
 31 59  1  0
 33 60  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Vilazodona	ChEBI
Vilazodonum	ChEBI
SB 659746a	HMDB
HCL, Vilazodone	HMDB
Hydrochloride, vilazodone	HMDB
2-Benzofurancarboxamide, 5-(4-(4-(5-cyano-1H-indol-3-yl)butyl)-1-piperazinyl)-, hydrochloride (1:1)	HMDB
Viibryd	HMDB
Vilazodone HCL	HMDB
Vilazodone hydrochloride	HMDB
5-(4-(4-(5-Cyano-3-indolyl)butyl)-1-piperazinyl)benzofuran-2-carboxamide	HMDB

Chemical Formula

C₂₆H₂₇N₅O₂

Average Molecular Weight

441.5249

Monoisotopic Molecular Weight

441.216475133

IUPAC Name

5-{4-[4-(5-cyano-1H-indol-3-yl)butyl]piperazin-1-yl}-1-benzofuran-2-carboxamide

Traditional Name

vilazodone

CAS Registry Number

163521-12-8

SMILES

NC(=O)C1=CC2=C(O1)C=CC(=C2)N1CCN(CCCCC2=CNC3=C2C=C(C=C3)C#N)CC1

InChI Identifier

InChI=1S/C26H27N5O2/c27-16-18-4-6-23-22(13-18)19(17-29-23)3-1-2-8-30-9-11-31(12-10-30)21-5-7-24-20(14-21)15-25(33-24)26(28)32/h4-7,13-15,17,29H,1-3,8-12H2,(H2,28,32)

InChI Key

SGEGOXDYSFKCPT-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
3-alkylindole
Benzofuran
Indole
Indole or derivatives
2-heteroaryl carboxamide
Furoic acid or derivatives
Tertiary aliphatic/aromatic amine
Dialkylarylamine
Aralkylamine
N-alkylpiperazine
Substituted pyrrole
Benzenoid
Furan
Pyrrole
Heteroaromatic compound
Amino acid or derivatives
Carboxamide group
Primary carboxylic acid amide
Tertiary amine
Tertiary aliphatic amine
Nitrile
Carbonitrile
Carboxylic acid derivative
Oxacycle
Azacycle
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

N-arylpiperazine (CHEBI:70707 )
monocarboxylic acid amide (CHEBI:70707 )
1-benzofurans (CHEBI:70707 )
indoles (CHEBI:70707 )
nitrile (CHEBI:70707 )
N-alkylpiperazine (CHEBI:70707 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015637)

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	0.12 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
logP	4.21	ALOGPS
logP	3.72	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	14.19	ChemAxon
pKa (Strongest Basic)	8.6	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	102.29 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	129.71 m³·mol⁻¹	ChemAxon
Polarizability	50.02 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	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	201.95	31661259
DarkChem	[M-H]-	201.183	31661259
DeepCCS	[M+H]+	205.025	30932474
DeepCCS	[M-H]-	202.667	30932474
DeepCCS	[M-2H]-	235.813	30932474
DeepCCS	[M+Na]+	211.118	30932474
AllCCS	[M+H]+	207.2	32859911
AllCCS	[M+H-H2O]+	205.1	32859911
AllCCS	[M+NH4]+	209.1	32859911
AllCCS	[M+Na]+	209.7	32859911
AllCCS	[M-H]-	203.4	32859911
AllCCS	[M+Na-2H]-	204.0	32859911
AllCCS	[M+HCOO]-	204.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Vilazodone	NC(=O)C1=CC2=C(O1)C=CC(=C2)N1CCN(CCCCC2=CNC3=C2C=C(C=C3)C#N)CC1	4425.5	Standard polar	33892256
Vilazodone	NC(=O)C1=CC2=C(O1)C=CC(=C2)N1CCN(CCCCC2=CNC3=C2C=C(C=C3)C#N)CC1	4243.9	Standard non polar	33892256
Vilazodone	NC(=O)C1=CC2=C(O1)C=CC(=C2)N1CCN(CCCCC2=CNC3=C2C=C(C=C3)C#N)CC1	4909.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Vilazodone,1TMS,isomer #1	C[Si](C)(C)NC(=O)C1=CC2=CC(N3CCN(CCCCC4=C[NH]C5=CC=C(C#N)C=C45)CC3)=CC=C2O1	4411.5	Semi standard non polar	33892256
Vilazodone,1TMS,isomer #1	C[Si](C)(C)NC(=O)C1=CC2=CC(N3CCN(CCCCC4=C[NH]C5=CC=C(C#N)C=C45)CC3)=CC=C2O1	4406.5	Standard non polar	33892256
Vilazodone,1TMS,isomer #1	C[Si](C)(C)NC(=O)C1=CC2=CC(N3CCN(CCCCC4=C[NH]C5=CC=C(C#N)C=C45)CC3)=CC=C2O1	5883.0	Standard polar	33892256
Vilazodone,1TMS,isomer #2	C[Si](C)(C)N1C=C(CCCCN2CCN(C3=CC=C4OC(C(N)=O)=CC4=C3)CC2)C2=CC(C#N)=CC=C21	4402.9	Semi standard non polar	33892256
Vilazodone,1TMS,isomer #2	C[Si](C)(C)N1C=C(CCCCN2CCN(C3=CC=C4OC(C(N)=O)=CC4=C3)CC2)C2=CC(C#N)=CC=C21	4222.8	Standard non polar	33892256
Vilazodone,1TMS,isomer #2	C[Si](C)(C)N1C=C(CCCCN2CCN(C3=CC=C4OC(C(N)=O)=CC4=C3)CC2)C2=CC(C#N)=CC=C21	6132.2	Standard polar	33892256
Vilazodone,2TMS,isomer #1	C[Si](C)(C)N(C(=O)C1=CC2=CC(N3CCN(CCCCC4=C[NH]C5=CC=C(C#N)C=C45)CC3)=CC=C2O1)[Si](C)(C)C	4428.0	Semi standard non polar	33892256
Vilazodone,2TMS,isomer #1	C[Si](C)(C)N(C(=O)C1=CC2=CC(N3CCN(CCCCC4=C[NH]C5=CC=C(C#N)C=C45)CC3)=CC=C2O1)[Si](C)(C)C	4433.6	Standard non polar	33892256
Vilazodone,2TMS,isomer #1	C[Si](C)(C)N(C(=O)C1=CC2=CC(N3CCN(CCCCC4=C[NH]C5=CC=C(C#N)C=C45)CC3)=CC=C2O1)[Si](C)(C)C	5667.6	Standard polar	33892256
Vilazodone,2TMS,isomer #2	C[Si](C)(C)NC(=O)C1=CC2=CC(N3CCN(CCCCC4=CN([Si](C)(C)C)C5=CC=C(C#N)C=C45)CC3)=CC=C2O1	4410.9	Semi standard non polar	33892256
Vilazodone,2TMS,isomer #2	C[Si](C)(C)NC(=O)C1=CC2=CC(N3CCN(CCCCC4=CN([Si](C)(C)C)C5=CC=C(C#N)C=C45)CC3)=CC=C2O1	4368.5	Standard non polar	33892256
Vilazodone,2TMS,isomer #2	C[Si](C)(C)NC(=O)C1=CC2=CC(N3CCN(CCCCC4=CN([Si](C)(C)C)C5=CC=C(C#N)C=C45)CC3)=CC=C2O1	5633.1	Standard polar	33892256
Vilazodone,3TMS,isomer #1	C[Si](C)(C)N(C(=O)C1=CC2=CC(N3CCN(CCCCC4=CN([Si](C)(C)C)C5=CC=C(C#N)C=C45)CC3)=CC=C2O1)[Si](C)(C)C	4431.5	Semi standard non polar	33892256
Vilazodone,3TMS,isomer #1	C[Si](C)(C)N(C(=O)C1=CC2=CC(N3CCN(CCCCC4=CN([Si](C)(C)C)C5=CC=C(C#N)C=C45)CC3)=CC=C2O1)[Si](C)(C)C	4361.7	Standard non polar	33892256
Vilazodone,3TMS,isomer #1	C[Si](C)(C)N(C(=O)C1=CC2=CC(N3CCN(CCCCC4=CN([Si](C)(C)C)C5=CC=C(C#N)C=C45)CC3)=CC=C2O1)[Si](C)(C)C	5385.8	Standard polar	33892256
Vilazodone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)C1=CC2=CC(N3CCN(CCCCC4=C[NH]C5=CC=C(C#N)C=C45)CC3)=CC=C2O1	4647.1	Semi standard non polar	33892256
Vilazodone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)C1=CC2=CC(N3CCN(CCCCC4=C[NH]C5=CC=C(C#N)C=C45)CC3)=CC=C2O1	4611.9	Standard non polar	33892256
Vilazodone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)C1=CC2=CC(N3CCN(CCCCC4=C[NH]C5=CC=C(C#N)C=C45)CC3)=CC=C2O1	5863.3	Standard polar	33892256
Vilazodone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=C(CCCCN2CCN(C3=CC=C4OC(C(N)=O)=CC4=C3)CC2)C2=CC(C#N)=CC=C21	4598.8	Semi standard non polar	33892256
Vilazodone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=C(CCCCN2CCN(C3=CC=C4OC(C(N)=O)=CC4=C3)CC2)C2=CC(C#N)=CC=C21	4428.3	Standard non polar	33892256
Vilazodone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=C(CCCCN2CCN(C3=CC=C4OC(C(N)=O)=CC4=C3)CC2)C2=CC(C#N)=CC=C21	6112.0	Standard polar	33892256
Vilazodone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)C1=CC2=CC(N3CCN(CCCCC4=C[NH]C5=CC=C(C#N)C=C45)CC3)=CC=C2O1)[Si](C)(C)C(C)(C)C	4862.0	Semi standard non polar	33892256
Vilazodone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)C1=CC2=CC(N3CCN(CCCCC4=C[NH]C5=CC=C(C#N)C=C45)CC3)=CC=C2O1)[Si](C)(C)C(C)(C)C	4833.0	Standard non polar	33892256
Vilazodone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)C1=CC2=CC(N3CCN(CCCCC4=C[NH]C5=CC=C(C#N)C=C45)CC3)=CC=C2O1)[Si](C)(C)C(C)(C)C	5612.4	Standard polar	33892256
Vilazodone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)C1=CC2=CC(N3CCN(CCCCC4=CN([Si](C)(C)C(C)(C)C)C5=CC=C(C#N)C=C45)CC3)=CC=C2O1	4839.2	Semi standard non polar	33892256
Vilazodone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)C1=CC2=CC(N3CCN(CCCCC4=CN([Si](C)(C)C(C)(C)C)C5=CC=C(C#N)C=C45)CC3)=CC=C2O1	4769.7	Standard non polar	33892256
Vilazodone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)C1=CC2=CC(N3CCN(CCCCC4=CN([Si](C)(C)C(C)(C)C)C5=CC=C(C#N)C=C45)CC3)=CC=C2O1	5611.5	Standard polar	33892256
Vilazodone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)C1=CC2=CC(N3CCN(CCCCC4=CN([Si](C)(C)C(C)(C)C)C5=CC=C(C#N)C=C45)CC3)=CC=C2O1)[Si](C)(C)C(C)(C)C	5006.0	Semi standard non polar	33892256
Vilazodone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)C1=CC2=CC(N3CCN(CCCCC4=CN([Si](C)(C)C(C)(C)C)C5=CC=C(C#N)C=C45)CC3)=CC=C2O1)[Si](C)(C)C(C)(C)C	4916.3	Standard non polar	33892256
Vilazodone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)C1=CC2=CC(N3CCN(CCCCC4=CN([Si](C)(C)C(C)(C)C)C5=CC=C(C#N)C=C45)CC3)=CC=C2O1)[Si](C)(C)C(C)(C)C	5365.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Vilazodone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0pb9-1892200000-e80db0623de8c5d5253b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vilazodone 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 - Vilazodone 10V, Positive-QTOF	splash10-004l-0100900000-419df74d78f3394907e4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vilazodone 20V, Positive-QTOF	splash10-0a6r-0211900000-fc5409d02ddc3a074e29	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vilazodone 40V, Positive-QTOF	splash10-0ard-0930000000-ca1734ab642c796bbcaf	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vilazodone 10V, Negative-QTOF	splash10-0006-0000900000-709b81c1b5cb6d2d8c1b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vilazodone 20V, Negative-QTOF	splash10-0005-1009600000-913d3342fc1dba5181ae	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vilazodone 40V, Negative-QTOF	splash10-0006-9341100000-d9863664c2546f78ac6b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vilazodone 10V, Positive-QTOF	splash10-0006-0000900000-fb0afc1a6de498c1d581	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vilazodone 20V, Positive-QTOF	splash10-002g-0201900000-7049e2907cdc39ce7fa8	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vilazodone 40V, Positive-QTOF	splash10-0pba-0931100000-c3a86c8646e2eb2feac2	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vilazodone 10V, Negative-QTOF	splash10-0006-0004900000-f0610bc45efeb8e8cd19	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vilazodone 20V, Negative-QTOF	splash10-0006-5006900000-70aadc301ad860239f5b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vilazodone 40V, Negative-QTOF	splash10-00kf-5598400000-9ca429b67adcdbb9ca8b	2021-10-12	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 DB06684	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB06684	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB06684

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5293518

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Vilazodone

METLIN ID

Not Available

PubChem Compound

6918314

PDB ID

Not Available

ChEBI ID

70707

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

Page ME, Cryan JF, Sullivan A, Dalvi A, Saucy B, Manning DR, Lucki I: Behavioral and neurochemical effects of 5-(4-[4-(5-Cyano-3-indolyl)-butyl)-butyl]-1-piperazinyl)-benzofuran-2-carboxamide (EMD 68843): a combined selective inhibitor of serotonin reuptake and 5-hydroxytryptamine(1A) receptor partial agonist. J Pharmacol Exp Ther. 2002 Sep;302(3):1220-7. [PubMed:12183683 ]
de Paulis T: Drug evaluation: Vilazodone--a combined SSRI and 5-HT1A partial agonist for the treatment of depression. IDrugs. 2007 Mar;10(3):193-201. [PubMed:17351874 ]
Dawson LA, Watson JM: Vilazodone: a 5-HT1A receptor agonist/serotonin transporter inhibitor for the treatment of affective disorders. CNS Neurosci Ther. 2009 Summer;15(2):107-17. [PubMed:19499624 ]
Howland RH: Vilazodone: another novel atypical antidepressant drug. J Psychosoc Nurs Ment Health Serv. 2011 Mar;49(3):19-22. doi: 10.3928/02793695-20110203-98. Epub 2011 Feb 16. [PubMed:21323263 ]
Traynor K: Vilazodone approved for major depression. Am J Health Syst Pharm. 2011 Mar 1;68(5):366. doi: 10.2146/news110009. [PubMed:21330672 ]
Khan A, Cutler AJ, Kajdasz DK, Gallipoli S, Athanasiou M, Robinson DS, Whalen H, Reed CR: A randomized, double-blind, placebo-controlled, 8-week study of vilazodone, a serotonergic agent for the treatment of major depressive disorder. J Clin Psychiatry. 2011 Apr;72(4):441-7. doi: 10.4088/JCP.10m06596. [PubMed:21527122 ]
Dopheide JA: Vilazodone's comparative merits yet to be demonstrated. Am J Health Syst Pharm. 2012 Sep 15;69(18):1549. doi: 10.2146/ajhp110570. [PubMed:22935936 ]
Wang SM, Han C, Lee SJ, Patkar AA, Masand PS, Pae CU: A review of current evidence for vilazodone in major depressive disorder. Int J Psychiatry Clin Pract. 2013 Aug;17(3):160-9. doi: 10.3109/13651501.2013.794245. Epub 2013 May 29. [PubMed:23578403 ]

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

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

Enzyme Details

3. Cytochrome P450 2C18

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP2C18
Uniprot ID:: P33260
Molecular weight:: 55710.075

Enzyme Details

4. 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

Page ME, Cryan JF, Sullivan A, Dalvi A, Saucy B, Manning DR, Lucki I: Behavioral and neurochemical effects of 5-(4-[4-(5-Cyano-3-indolyl)-butyl)-butyl]-1-piperazinyl)-benzofuran-2-carboxamide (EMD 68843): a combined selective inhibitor of serotonin reuptake and 5-hydroxytryptamine(1A) receptor partial agonist. J Pharmacol Exp Ther. 2002 Sep;302(3):1220-7. [PubMed:12183683 ]
Adamec R, Bartoszyk GD, Burton P: Effects of systemic injections of vilazodone, a selective serotonin reuptake inhibitor and serotonin 1A receptor agonist, on anxiety induced by predator stress in rats. Eur J Pharmacol. 2004 Nov 3;504(1-2):65-77. [PubMed:15507223 ]

Transporters

Enzyme Details

1. Sodium-dependent serotonin transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into the pre-synaptic terminal for re-utilization. Plays a key role in mediating regulation of the availability of serotonin to other receptors of serotonergic systems. Terminates the action of serotonin and recycles it in a sodium-dependent manner.
Gene Name:: SLC6A4
Uniprot ID:: P31645
Molecular weight:: 70324.165

References

Page ME, Cryan JF, Sullivan A, Dalvi A, Saucy B, Manning DR, Lucki I: Behavioral and neurochemical effects of 5-(4-[4-(5-Cyano-3-indolyl)-butyl)-butyl]-1-piperazinyl)-benzofuran-2-carboxamide (EMD 68843): a combined selective inhibitor of serotonin reuptake and 5-hydroxytryptamine(1A) receptor partial agonist. J Pharmacol Exp Ther. 2002 Sep;302(3):1220-7. [PubMed:12183683 ]
Adamec R, Bartoszyk GD, Burton P: Effects of systemic injections of vilazodone, a selective serotonin reuptake inhibitor and serotonin 1A receptor agonist, on anxiety induced by predator stress in rats. Eur J Pharmacol. 2004 Nov 3;504(1-2):65-77. [PubMed:15507223 ]

Showing metabocard for Vilazodone (HMDB0015637)

MOL for HMDB0015637 (Vilazodone)

3D MOL for HMDB0015637 (Vilazodone)

3D SDF for HMDB0015637 (Vilazodone)

3D-SDF for HMDB0015637 (Vilazodone)

PDB for HMDB0015637 (Vilazodone)

3D PDB for HMDB0015637 (Vilazodone)

SMILES for HMDB0015637 (Vilazodone)

INCHI for HMDB0015637 (Vilazodone)

Structure for HMDB0015637 (Vilazodone)

3D Structure for HMDB0015637 (Vilazodone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

Transporters

References