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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (10)transporters (2) Show 12 proteins XML

enzymes (10)transporters (2) Show 12 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:44 UTC

HMDB ID

HMDB0014794

Secondary Accession Numbers

HMDB14794

Metabolite Identification

Common Name

Trazodone

Description

A serotonin uptake inhibitor that is used as an antidepressive agent. It has been shown to be effective in patients with major depressive disorders and other subsets of depressive disorders. It is generally more useful in depressive disorders associated with insomnia and anxiety. This drug does not aggravate psychotic symptoms in patients with schizophrenia or schizoaffective disorders. (From AMA Drug Evaluations Annual, 1994, p309)

Structure

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

656
  Mrv0541 02231214522D          

 26 29  0  0  0  0            999 V2000
    7.6412   -3.5820    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.1159    3.5820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8162    0.7049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6412   -0.7240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3412    2.1339    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    2.5464    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597    1.4699    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4037   -0.0096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6412    0.7049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8162   -0.7240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0537   -0.0096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4037    1.4194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5787    1.4194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1662    2.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0537   -1.4386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6412   -2.1530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8788   -1.4386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597    2.7978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.7214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0537   -2.8675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2913   -2.1530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8788   -2.8675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.5464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.7214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  1  0  0  0  0
  2 18  2  0  0  0  0
  3  8  1  0  0  0  0
  3  9  1  0  0  0  0
  3 12  1  0  0  0  0
  4 10  1  0  0  0  0
  4 11  1  0  0  0  0
  4 15  1  0  0  0  0
  5  7  1  0  0  0  0
  5 14  1  0  0  0  0
  5 18  1  0  0  0  0
  6 18  1  0  0  0  0
  6 19  1  0  0  0  0
  6 23  1  0  0  0  0
  7 19  2  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 14  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 16 20  1  0  0  0  0
 17 21  2  0  0  0  0
 19 24  1  0  0  0  0
 20 22  2  0  0  0  0
 21 22  1  0  0  0  0
 23 25  2  0  0  0  0
 24 26  2  0  0  0  0
 25 26  1  0  0  0  0
M  END

HMDB0014794
     RDKit          3D
Trazodone
 48 51  0  0  0  0  0  0  0  0999 V2000
    4.0001    1.3163   -2.9315 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1299    0.5814   -1.9166 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4218   -0.5302   -1.6602 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3636   -1.1465   -2.4615 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0225   -0.5698   -2.0417 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7450   -0.8281   -0.5845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5358   -0.2808   -0.1948 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7136   -0.4734    1.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0840   -0.0830    1.7055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1151   -0.4669    0.7449 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3972    0.1311    0.7607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3120   -0.0944   -0.2399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5773    0.5095   -0.1861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9010    1.3286    0.8707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9954    1.5664    1.8837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3781    2.5998    3.2363 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.7473    0.9579    1.8109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6858   -1.4959   -0.1748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5542   -0.9100   -0.9896 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8790   -0.9834   -0.5009 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8566   -0.1688   -0.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6228   -0.2404    1.1232 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5705    0.7213    1.3747 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7139    1.7307    0.4352 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9429    1.7732   -0.7021 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0135    0.8186   -0.9356 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5651   -0.8602   -3.5138 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3807   -2.2455   -2.3979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1006    0.5472   -2.1607 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2473   -0.9204   -2.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6761   -1.9392   -0.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5379   -0.3974    0.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0164    0.1814    1.7359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4676   -1.5160    1.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1545    0.9828    1.9054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3046   -0.6335    2.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0554   -0.7335   -1.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2663    0.3052   -0.9938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8786    1.7785    0.8859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0357    1.1333    2.5925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4389   -1.8703   -0.8575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2139   -2.3282    0.4330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9409   -0.1639   -1.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1668   -1.7650   -1.5958 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4770   -1.0464    1.8295 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1785    0.6781    2.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4357    2.5053    0.5785 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0229    2.5445   -1.4611 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  1  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  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 10 18  1  0
 18 19  1  0
  3 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26  2  1  0
 19  7  1  0
 26 21  1  0
 17 11  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 12 37  1  0
 13 38  1  0
 14 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  0
 19 44  1  0
 22 45  1  0
 23 46  1  0
 24 47  1  0
 25 48  1  0
M  END

656
  Mrv0541 02231214522D          

 26 29  0  0  0  0            999 V2000
    7.6412   -3.5820    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.1159    3.5820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8162    0.7049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6412   -0.7240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3412    2.1339    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    2.5464    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597    1.4699    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4037   -0.0096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6412    0.7049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8162   -0.7240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0537   -0.0096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4037    1.4194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5787    1.4194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1662    2.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0537   -1.4386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6412   -2.1530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8788   -1.4386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597    2.7978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.7214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0537   -2.8675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2913   -2.1530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8788   -2.8675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.5464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.7214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  1  0  0  0  0
  2 18  2  0  0  0  0
  3  8  1  0  0  0  0
  3  9  1  0  0  0  0
  3 12  1  0  0  0  0
  4 10  1  0  0  0  0
  4 11  1  0  0  0  0
  4 15  1  0  0  0  0
  5  7  1  0  0  0  0
  5 14  1  0  0  0  0
  5 18  1  0  0  0  0
  6 18  1  0  0  0  0
  6 19  1  0  0  0  0
  6 23  1  0  0  0  0
  7 19  2  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 14  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 16 20  1  0  0  0  0
 17 21  2  0  0  0  0
 19 24  1  0  0  0  0
 20 22  2  0  0  0  0
 21 22  1  0  0  0  0
 23 25  2  0  0  0  0
 24 26  2  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014794

> <DATABASE_NAME>
hmdb

> <SMILES>
ClC1=CC=CC(=C1)N1CCN(CCCN2N=C3C=CC=CN3C2=O)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C19H22ClN5O/c20-16-5-3-6-17(15-16)23-13-11-22(12-14-23)8-4-10-25-19(26)24-9-2-1-7-18(24)21-25/h1-3,5-7,9,15H,4,8,10-14H2

> <INCHI_KEY>
PHLBKPHSAVXXEF-UHFFFAOYSA-N

> <FORMULA>
C19H22ClN5O

> <MOLECULAR_WEIGHT>
371.864

> <EXACT_MASS>
371.151288058

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
40.12286773059634

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{3-[4-(3-chlorophenyl)piperazin-1-yl]propyl}-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one

> <ALOGPS_LOGP>
2.68

> <JCHEM_LOGP>
3.1318566039999984

> <ALOGPS_LOGS>
-3.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.088044246802013

> <JCHEM_POLAR_SURFACE_AREA>
42.39000000000001

> <JCHEM_REFRACTIVITY>
105.87960000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.90e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trazodone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014794
     RDKit          3D
Trazodone
 48 51  0  0  0  0  0  0  0  0999 V2000
    4.0001    1.3163   -2.9315 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1299    0.5814   -1.9166 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4218   -0.5302   -1.6602 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3636   -1.1465   -2.4615 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0225   -0.5698   -2.0417 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7450   -0.8281   -0.5845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5358   -0.2808   -0.1948 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7136   -0.4734    1.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0840   -0.0830    1.7055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1151   -0.4669    0.7449 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3972    0.1311    0.7607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3120   -0.0944   -0.2399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5773    0.5095   -0.1861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9010    1.3286    0.8707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9954    1.5664    1.8837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3781    2.5998    3.2363 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.7473    0.9579    1.8109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6858   -1.4959   -0.1748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5542   -0.9100   -0.9896 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8790   -0.9834   -0.5009 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8566   -0.1688   -0.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6228   -0.2404    1.1232 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5705    0.7213    1.3747 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7139    1.7307    0.4352 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9429    1.7732   -0.7021 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0135    0.8186   -0.9356 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5651   -0.8602   -3.5138 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3807   -2.2455   -2.3979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1006    0.5472   -2.1607 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2473   -0.9204   -2.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6761   -1.9392   -0.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5379   -0.3974    0.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0164    0.1814    1.7359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4676   -1.5160    1.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1545    0.9828    1.9054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3046   -0.6335    2.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0554   -0.7335   -1.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2663    0.3052   -0.9938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8786    1.7785    0.8859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0357    1.1333    2.5925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4389   -1.8703   -0.8575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2139   -2.3282    0.4330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9409   -0.1639   -1.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1668   -1.7650   -1.5958 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4770   -1.0464    1.8295 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1785    0.6781    2.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4357    2.5053    0.5785 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0229    2.5445   -1.4611 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  1  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  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 10 18  1  0
 18 19  1  0
  3 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26  2  1  0
 19  7  1  0
 26 21  1  0
 17 11  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 12 37  1  0
 13 38  1  0
 14 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  0
 19 44  1  0
 22 45  1  0
 23 46  1  0
 24 47  1  0
 25 48  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 656                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0      14.264  -6.686   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0       7.683   6.686   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      12.724   1.316   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      14.264  -1.351   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       8.104   3.983   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       5.748   4.753   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       7.205   2.744   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      11.954  -0.018   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.264   1.316   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.724  -1.351   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.034  -0.018   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.954   2.650   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.414   2.650   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.644   3.983   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.034  -2.685   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.264  -4.019   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.574  -2.685   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.205   5.223   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.748   3.213   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.034  -5.353   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      17.344  -4.019   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.574  -5.353   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.414   5.523   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.414   2.443   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.080   4.753   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.080   3.213   0.000  0.00  0.00           C+0
CONECT    1   20                                                            
CONECT    2   18                                                            
CONECT    3    8    9   12                                                  
CONECT    4   10   11   15                                                  
CONECT    5    7   14   18                                                  
CONECT    6   18   19   23                                                  
CONECT    7    5   19                                                       
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    5   13                                                       
CONECT   15    4   16   17                                                  
CONECT   16   15   20                                                       
CONECT   17   15   21                                                       
CONECT   18    2    5    6                                                  
CONECT   19    6    7   24                                                  
CONECT   20    1   16   22                                                  
CONECT   21   17   22                                                       
CONECT   22   20   21                                                       
CONECT   23    6   25                                                       
CONECT   24   19   26                                                       
CONECT   25   23   26                                                       
CONECT   26   24   25                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

COMPND    HMDB0014794
HETATM    1  O1  UNL     1       4.000   1.316  -2.932  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.130   0.581  -1.917  1.00  0.00           C  
HETATM    3  N1  UNL     1       3.422  -0.530  -1.660  1.00  0.00           N  
HETATM    4  C2  UNL     1       2.364  -1.147  -2.461  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.023  -0.570  -2.042  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.745  -0.828  -0.585  1.00  0.00           C  
HETATM    7  N2  UNL     1      -0.536  -0.281  -0.195  1.00  0.00           N  
HETATM    8  C5  UNL     1      -0.714  -0.473   1.222  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.084  -0.083   1.705  1.00  0.00           C  
HETATM   10  N3  UNL     1      -3.115  -0.467   0.745  1.00  0.00           N  
HETATM   11  C7  UNL     1      -4.397   0.131   0.761  1.00  0.00           C  
HETATM   12  C8  UNL     1      -5.312  -0.094  -0.240  1.00  0.00           C  
HETATM   13  C9  UNL     1      -6.577   0.510  -0.186  1.00  0.00           C  
HETATM   14  C10 UNL     1      -6.901   1.329   0.871  1.00  0.00           C  
HETATM   15  C11 UNL     1      -5.995   1.566   1.884  1.00  0.00           C  
HETATM   16 CL1  UNL     1      -6.378   2.600   3.236  1.00  0.00          CL  
HETATM   17  C12 UNL     1      -4.747   0.958   1.811  1.00  0.00           C  
HETATM   18  C13 UNL     1      -2.686  -1.496  -0.175  1.00  0.00           C  
HETATM   19  C14 UNL     1      -1.554  -0.910  -0.990  1.00  0.00           C  
HETATM   20  N4  UNL     1       3.879  -0.983  -0.501  1.00  0.00           N  
HETATM   21  C15 UNL     1       4.857  -0.169  -0.041  1.00  0.00           C  
HETATM   22  C16 UNL     1       5.623  -0.240   1.123  1.00  0.00           C  
HETATM   23  C17 UNL     1       6.571   0.721   1.375  1.00  0.00           C  
HETATM   24  C18 UNL     1       6.714   1.731   0.435  1.00  0.00           C  
HETATM   25  C19 UNL     1       5.943   1.773  -0.702  1.00  0.00           C  
HETATM   26  N5  UNL     1       5.014   0.819  -0.936  1.00  0.00           N  
HETATM   27  H1  UNL     1       2.565  -0.860  -3.514  1.00  0.00           H  
HETATM   28  H2  UNL     1       2.381  -2.245  -2.398  1.00  0.00           H  
HETATM   29  H3  UNL     1       1.101   0.547  -2.161  1.00  0.00           H  
HETATM   30  H4  UNL     1       0.247  -0.920  -2.718  1.00  0.00           H  
HETATM   31  H5  UNL     1       0.676  -1.939  -0.424  1.00  0.00           H  
HETATM   32  H6  UNL     1       1.538  -0.397   0.056  1.00  0.00           H  
HETATM   33  H7  UNL     1       0.016   0.181   1.736  1.00  0.00           H  
HETATM   34  H8  UNL     1      -0.468  -1.516   1.482  1.00  0.00           H  
HETATM   35  H9  UNL     1      -2.154   0.983   1.905  1.00  0.00           H  
HETATM   36  H10 UNL     1      -2.305  -0.634   2.638  1.00  0.00           H  
HETATM   37  H11 UNL     1      -5.055  -0.733  -1.065  1.00  0.00           H  
HETATM   38  H12 UNL     1      -7.266   0.305  -0.994  1.00  0.00           H  
HETATM   39  H13 UNL     1      -7.879   1.779   0.886  1.00  0.00           H  
HETATM   40  H14 UNL     1      -4.036   1.133   2.592  1.00  0.00           H  
HETATM   41  H15 UNL     1      -3.439  -1.870  -0.857  1.00  0.00           H  
HETATM   42  H16 UNL     1      -2.214  -2.328   0.433  1.00  0.00           H  
HETATM   43  H17 UNL     1      -1.941  -0.164  -1.708  1.00  0.00           H  
HETATM   44  H18 UNL     1      -1.167  -1.765  -1.596  1.00  0.00           H  
HETATM   45  H19 UNL     1       5.477  -1.046   1.830  1.00  0.00           H  
HETATM   46  H20 UNL     1       7.178   0.678   2.284  1.00  0.00           H  
HETATM   47  H21 UNL     1       7.436   2.505   0.579  1.00  0.00           H  
HETATM   48  H22 UNL     1       6.023   2.544  -1.461  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   26
CONECT    3    4   20
CONECT    4    5   27   28
CONECT    5    6   29   30
CONECT    6    7   31   32
CONECT    7    8   19
CONECT    8    9   33   34
CONECT    9   10   35   36
CONECT   10   11   18
CONECT   11   12   12   17
CONECT   12   13   37
CONECT   13   14   14   38
CONECT   14   15   39
CONECT   15   16   17   17
CONECT   17   40
CONECT   18   19   41   42
CONECT   19   43   44
CONECT   20   21   21
CONECT   21   22   26
CONECT   22   23   23   45
CONECT   23   24   46
CONECT   24   25   25   47
CONECT   25   26   48
END

HMDB0014794
     RDKit          3D
Trazodone
 48 51  0  0  0  0  0  0  0  0999 V2000
    4.0001    1.3163   -2.9315 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1299    0.5814   -1.9166 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4218   -0.5302   -1.6602 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3636   -1.1465   -2.4615 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0225   -0.5698   -2.0417 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7450   -0.8281   -0.5845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5358   -0.2808   -0.1948 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7136   -0.4734    1.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0840   -0.0830    1.7055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1151   -0.4669    0.7449 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3972    0.1311    0.7607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3120   -0.0944   -0.2399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5773    0.5095   -0.1861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9010    1.3286    0.8707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9954    1.5664    1.8837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3781    2.5998    3.2363 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.7473    0.9579    1.8109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6858   -1.4959   -0.1748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5542   -0.9100   -0.9896 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8790   -0.9834   -0.5009 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8566   -0.1688   -0.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6228   -0.2404    1.1232 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5705    0.7213    1.3747 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7139    1.7307    0.4352 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9429    1.7732   -0.7021 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0135    0.8186   -0.9356 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5651   -0.8602   -3.5138 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3807   -2.2455   -2.3979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1006    0.5472   -2.1607 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2473   -0.9204   -2.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6761   -1.9392   -0.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5379   -0.3974    0.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0164    0.1814    1.7359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4676   -1.5160    1.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1545    0.9828    1.9054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3046   -0.6335    2.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0554   -0.7335   -1.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2663    0.3052   -0.9938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8786    1.7785    0.8859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0357    1.1333    2.5925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4389   -1.8703   -0.8575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2139   -2.3282    0.4330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9409   -0.1639   -1.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1668   -1.7650   -1.5958 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4770   -1.0464    1.8295 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1785    0.6781    2.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4357    2.5053    0.5785 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0229    2.5445   -1.4611 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  1  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  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 10 18  1  0
 18 19  1  0
  3 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26  2  1  0
 19  7  1  0
 26 21  1  0
 17 11  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 12 37  1  0
 13 38  1  0
 14 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  0
 19 44  1  0
 22 45  1  0
 23 46  1  0
 24 47  1  0
 25 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(3-[4-(3-Chlorophenyl)-1-piperazinyl]propyl)[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one	ChEBI
Trazodona	ChEBI
Trazodonum	ChEBI
Trittico	Kegg
Aventis brand OF trazodone hydrochloride	HMDB
Desyrel	HMDB
Farma lepori brand OF trazodone hydrochloride	HMDB
Gen-trazodone	HMDB
Genpharm brand OF trazodone hydrochloride	HMDB
Novopharm brand OF trazodone hydrochloride	HMDB
Nu pharm brand OF trazodone hydrochloride	HMDB
Ratiopharm brand OF trazodone hydrochloride	HMDB
Searle brand OF trazodone hydrochloride	HMDB
Trazodon-neuraxpharm	HMDB
Apo-trazodone	HMDB
Apotex brand OF trazodone hydrochloride	HMDB
Boehringer ingelheim brand OF trazodone hydrochloride	HMDB
Bristol myers squibb brand OF trazodone hydrochloride	HMDB
Bristol-myers squibb brand OF trazodone hydrochloride	HMDB
Gen trazodone	HMDB
Molipaxin	HMDB
Sidmark brand OF trazodone hydrochloride	HMDB
Tradozone	HMDB
Trazodon hexal	HMDB
Trazodone hydrochloride	HMDB
Ratio trazodone	HMDB
Apo trazodone	HMDB
Deprax	HMDB
Novo-trazodone	HMDB
Nu trazodone	HMDB
Nu-trazodone	HMDB
Pharmascience brand OF trazodone hydrochloride	HMDB
Thombran	HMDB
Neuraxpharm brand OF trazodone hydrochloride	HMDB
Apothecon brand OF trazodone hydrochloride	HMDB
Aventis pharma brand OF trazodone hydrochloride	HMDB
Hexal brand OF trazodone hydrochloride	HMDB
Novo trazodone	HMDB
Nu-pharm brand OF trazodone hydrochloride	HMDB
PMS Trazodone	HMDB
PMS-Trazodone	HMDB
Trazodon neuraxpharm	HMDB
Trazon	HMDB
Ratio-trazodone	HMDB
RatioTrazodone	HMDB
TrazodonNeuraxpharm	HMDB

Chemical Formula

C₁₉H₂₂ClN₅O

Average Molecular Weight

371.864

Monoisotopic Molecular Weight

371.151288058

IUPAC Name

2-{3-[4-(3-chlorophenyl)piperazin-1-yl]propyl}-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one

Traditional Name

trazodone

CAS Registry Number

19794-93-5

SMILES

ClC1=CC=CC(=C1)N1CCN(CCCN2N=C3C=CC=CN3C2=O)CC1

InChI Identifier

InChI=1S/C19H22ClN5O/c20-16-5-3-6-17(15-16)23-13-11-22(12-14-23)8-4-10-25-19(26)24-9-2-1-7-18(24)21-25/h1-3,5-7,9,15H,4,8,10-14H2

InChI Key

PHLBKPHSAVXXEF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpiperazines. Phenylpiperazines are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazinanes

Sub Class

Piperazines

Direct Parent

Phenylpiperazines

Alternative Parents

Substituents

Phenylpiperazine
N-arylpiperazine
Aryl 1,2,4-triazol-3-one
Triazolopyridine
Tertiary aliphatic/aromatic amine
Aniline or substituted anilines
Dialkylarylamine
Pyridinone
Chlorobenzene
N-alkylpiperazine
Halobenzene
Aryl chloride
Aryl halide
Pyridine
Monocyclic benzene moiety
Benzenoid
1,2,4-triazole
Azole
Heteroaromatic compound
Triazole
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

N-arylpiperazine (CHEBI:9654 )
monochlorobenzenes (CHEBI:9654 )
N-alkylpiperazine (CHEBI:9654 )
triazolopyridine (CHEBI:9654 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0014794)
Membrane (HMDB: HMDB0014794)

Process

Not Available

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	86 - 87 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.29 g/L	Not Available
LogP	2.9	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.29 g/L	ALOGPS
logP	2.68	ALOGPS
logP	3.13	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Basic)	7.09	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	42.39 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	105.88 m³·mol⁻¹	ChemAxon
Polarizability	40.12 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	182.046	30932474
DeepCCS	[M-H]-	179.688	30932474
DeepCCS	[M-2H]-	213.405	30932474
DeepCCS	[M+Na]+	188.632	30932474
AllCCS	[M+H]+	185.9	32859911
AllCCS	[M+H-H2O]+	183.1	32859911
AllCCS	[M+NH4]+	188.4	32859911
AllCCS	[M+Na]+	189.1	32859911
AllCCS	[M-H]-	186.9	32859911
AllCCS	[M+Na-2H]-	186.6	32859911
AllCCS	[M+HCOO]-	186.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Trazodone	ClC1=CC=CC(=C1)N1CCN(CCCN2N=C3C=CC=CN3C2=O)CC1	4032.9	Standard polar	33892256
Trazodone	ClC1=CC=CC(=C1)N1CCN(CCCN2N=C3C=CC=CN3C2=O)CC1	3352.7	Standard non polar	33892256
Trazodone	ClC1=CC=CC(=C1)N1CCN(CCCN2N=C3C=CC=CN3C2=O)CC1	3452.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Trazodone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4j-3940000000-a9996f74a013c4cd5f34	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trazodone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-7980000000-5d2bde624fdd9a946993	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trazodone , positive-QTOF	splash10-00di-0609000000-cee74b5bf3182c2aa324	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trazodone 75V, Positive-QTOF	splash10-0002-6900000000-cad4ab75befff3f2968b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trazodone 90V, Positive-QTOF	splash10-0002-9400000000-c7d8f0dfcdffc01eea38	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trazodone 60V, Positive-QTOF	splash10-0002-1900000000-28ba21055e54b4402211	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trazodone 50V, Positive-QTOF	splash10-0002-0900000000-6fb990f5da8a065e9e2d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trazodone 40V, Positive-QTOF	splash10-004j-0900000000-3e00b6f236166b87e556	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trazodone 15V, Positive-QTOF	splash10-00di-0009000000-389ead4eddc071685054	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trazodone 30V, Positive-QTOF	splash10-00b9-0905000000-7559d512fbf6d562d524	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trazodone 30V, Positive-QTOF	splash10-004i-0902000000-32913e34f1b8199d47e2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trazodone 40V, Positive-QTOF	splash10-004j-0900000000-eba2f098618563ae8d8d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trazodone 20V, Positive-QTOF	splash10-00di-0209000000-df47170d3861120bdd95	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trazodone 10V, Positive-QTOF	splash10-00di-0009000000-bcfc1f78608d8da92b69	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trazodone 90V, Positive-QTOF	splash10-0002-9400000000-e57c89e0b5532e2d9949	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trazodone 35V, Positive-QTOF	splash10-00ba-0904000000-6d3af981b3cc1292370a	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trazodone 10V, Positive-QTOF	splash10-00di-0409000000-aa395fcbb17de632c6bd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trazodone 20V, Positive-QTOF	splash10-009j-3943000000-2a70b3bfe44c6f0cbc7b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trazodone 40V, Positive-QTOF	splash10-0f7d-6910000000-98fd05d57a2cfaca1e18	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trazodone 10V, Negative-QTOF	splash10-00di-1509000000-86e48f5bf6cb797c7455	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trazodone 20V, Negative-QTOF	splash10-001i-4903000000-dbd293226ccdf09ec683	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trazodone 40V, Negative-QTOF	splash10-053r-2900000000-cc4d58e26d8dc2a62148	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trazodone 10V, Positive-QTOF	splash10-00di-0009000000-6eafab677fc7a5bcdc94	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trazodone 20V, Positive-QTOF	splash10-00di-0429000000-7ff66c2ff10e98b15b9b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trazodone 40V, Positive-QTOF	splash10-0f6x-2935000000-39b0f2302534fa91975f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trazodone 10V, Negative-QTOF	splash10-00di-0009000000-46b6e1f93b93a9142b29	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trazodone 20V, Negative-QTOF	splash10-00di-1009000000-fb123f08ae47e01d90aa	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00656	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00656	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00656

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5332

KEGG Compound ID

C07156

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Trazodone

METLIN ID

Not Available

PubChem Compound

5533

PDB ID

Not Available

ChEBI ID

9654

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

Rotzinger S, Fang J, Baker GB: Trazodone is metabolized to m-chlorophenylpiperazine by CYP3A4 from human sources. Drug Metab Dispos. 1998 Jun;26(6):572-5. [PubMed:9616194 ]
Kalgutkar AS, Henne KR, Lame ME, Vaz AD, Collin C, Soglia JR, Zhao SX, Hop CE: Metabolic activation of the nontricyclic antidepressant trazodone to electrophilic quinone-imine and epoxide intermediates in human liver microsomes and recombinant P4503A4. Chem Biol Interact. 2005 Jun 30;155(1-2):10-20. Epub 2005 Apr 18. [PubMed:15978881 ]
Marek GJ, McDougle CJ, Price LH, Seiden LS: A comparison of trazodone and fluoxetine: implications for a serotonergic mechanism of antidepressant action. Psychopharmacology (Berl). 1992;109(1-2):2-11. [PubMed:1365657 ]
Jauch R, Kopitar Z, Prox A, Zimmer A: [Pharmacokinetics and metabolism of trazodone in man (author's transl)]. Arzneimittelforschung. 1976;26(11):2084-9. [PubMed:1037253 ]
Otani K, Yasui N, Kaneko S, Ishida M, Ohkubo T, Osanai T, Sugawara K, Fukushima Y: Trazodone treatment increases plasma prolactin concentrations in depressed patients. Int Clin Psychopharmacol. 1995 Jun;10(2):115-7. [PubMed:7673654 ]
Saletu-Zyhlarz GM, Abu-Bakr MH, Anderer P, Gruber G, Mandl M, Strobl R, Gollner D, Prause W, Saletu B: Insomnia in depression: differences in objective and subjective sleep and awakening quality to normal controls and acute effects of trazodone. Prog Neuropsychopharmacol Biol Psychiatry. 2002 Feb;26(2):249-60. [PubMed:11817501 ]
Fink HA, MacDonald R, Rutks IR, Wilt TJ: Trazodone for erectile dysfunction: a systematic review and meta-analysis. BJU Int. 2003 Sep;92(4):441-6. [PubMed:12930437 ]

Only showing the first 10 proteins. There are 12 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

Rotzinger S, Fang J, Baker GB: Trazodone is metabolized to m-chlorophenylpiperazine by CYP3A4 from human sources. Drug Metab Dispos. 1998 Jun;26(6):572-5. [PubMed:9616194 ]
Kalgutkar AS, Henne KR, Lame ME, Vaz AD, Collin C, Soglia JR, Zhao SX, Hop CE: Metabolic activation of the nontricyclic antidepressant trazodone to electrophilic quinone-imine and epoxide intermediates in human liver microsomes and recombinant P4503A4. Chem Biol Interact. 2005 Jun 30;155(1-2):10-20. Epub 2005 Apr 18. [PubMed:15978881 ]
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

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

Wen B, Ma L, Rodrigues AD, Zhu M: Detection of novel reactive metabolites of trazodone: evidence for CYP2D6-mediated bioactivation of m-chlorophenylpiperazine. Drug Metab Dispos. 2008 May;36(5):841-50. doi: 10.1124/dmd.107.019471. Epub 2008 Jan 31. [PubMed:18238857 ]
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. 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

Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217 ]
Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Enzyme Details

6. 5-hydroxytryptamine receptor 1A

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

References

Odagaki Y, Toyoshima R, Yamauchi T: Trazodone and its active metabolite m-chlorophenylpiperazine as partial agonists at 5-HT1A receptors assessed by [35S]GTPgammaS binding. J Psychopharmacol. 2005 May;19(3):235-41. [PubMed:15888508 ]
Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217 ]
Subhash MN, Srinivas BN, Vinod KY: Alterations in 5-HT(1A) receptors and adenylyl cyclase response by trazodone in regions of rat brain. Life Sci. 2002 Aug 16;71(13):1559-67. [PubMed:12127910 ]

Enzyme Details

7. 5-hydroxytryptamine receptor 2A

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

References

Pazzagli M, Giovannini MG, Pepeu G: Trazodone increases extracellular serotonin levels in the frontal cortex of rats. Eur J Pharmacol. 1999 Nov 3;383(3):249-57. [PubMed:10594316 ]
Marcoli M, Rosu C, Bonfanti A, Raiteri M, Maura G: Inhibitory presynaptic 5-hydroxytryptamine(2A) receptors regulate evoked glutamate release from rat cerebellar mossy fibers. J Pharmacol Exp Ther. 2001 Dec;299(3):1106-11. [PubMed:11714900 ]
Marek GJ, McDougle CJ, Price LH, Seiden LS: A comparison of trazodone and fluoxetine: implications for a serotonergic mechanism of antidepressant action. Psychopharmacology (Berl). 1992;109(1-2):2-11. [PubMed:1365657 ]
Luparini MR, Garrone B, Pazzagli M, Pinza M, Pepeu G: A cortical GABA-5HT interaction in the mechanism of action of the antidepressant trazodone. Prog Neuropsychopharmacol Biol Psychiatry. 2004 Nov;28(7):1117-27. [PubMed:15610924 ]
Conn PJ, Sanders-Bush E: Relative efficacies of piperazines at the phosphoinositide hydrolysis-linked serotonergic (5-HT-2 and 5-HT-1c) receptors. J Pharmacol Exp Ther. 1987 Aug;242(2):552-7. [PubMed:3039120 ]
Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217 ]

Enzyme Details

8. 5-hydroxytryptamine receptor 2C

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system
Gene Name:: HTR2C
Uniprot ID:: P28335
Molecular weight:: 51820.7

References

Fiorella D, Rabin RA, Winter JC: The role of the 5-HT2A and 5-HT2C receptors in the stimulus effects of m-chlorophenylpiperazine. Psychopharmacology (Berl). 1995 May;119(2):222-30. [PubMed:7659770 ]
Conn PJ, Sanders-Bush E: Relative efficacies of piperazines at the phosphoinositide hydrolysis-linked serotonergic (5-HT-2 and 5-HT-1c) receptors. J Pharmacol Exp Ther. 1987 Aug;242(2):552-7. [PubMed:3039120 ]

Enzyme Details

9. Histamine H1 receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
Gene Name:: HRH1
Uniprot ID:: P35367
Molecular weight:: 55783.6

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Richelson E, Nelson A: Antagonism by antidepressants of neurotransmitter receptors of normal human brain in vitro. J Pharmacol Exp Ther. 1984 Jul;230(1):94-102. [PubMed:6086881 ]
Noguchi S, Inukai T, Kuno T, Tanaka C: The suppression of olfactory bulbectomy-induced muricide by antidepressants and antihistamines via histamine H1 receptor blocking. Physiol Behav. 1992 Jun;51(6):1123-7. [PubMed:1353628 ]

Enzyme Details

10. Alpha-1A adrenergic receptor

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

References

Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217 ]

Transporters

Enzyme Details

1. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Stormer E, von Moltke LL, Perloff MD, Greenblatt DJ: P-glycoprotein interactions of nefazodone and trazodone in cell culture. J Clin Pharmacol. 2001 Jul;41(7):708-14. [PubMed:11452702 ]

Enzyme Details

2. 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

Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [PubMed:9537821 ]

Only showing the first 10 proteins. There are 12 proteins in total.

Show all enzymes and transporters

Showing metabocard for Trazodone (HMDB0014794)

MOL for HMDB0014794 (Trazodone)

3D MOL for HMDB0014794 (Trazodone)

3D SDF for HMDB0014794 (Trazodone)

3D-SDF for HMDB0014794 (Trazodone)

PDB for HMDB0014794 (Trazodone)

3D PDB for HMDB0014794 (Trazodone)

SMILES for HMDB0014794 (Trazodone)

INCHI for HMDB0014794 (Trazodone)

Structure for HMDB0014794 (Trazodone)

3D Structure for HMDB0014794 (Trazodone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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Transporters

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