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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (11)transporters (3) Show 14 proteins XML

enzymes (11)transporters (3) Show 14 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:55 UTC

HMDB ID

HMDB0015280

Secondary Accession Numbers

HMDB15280

Metabolite Identification

Common Name

Nefazodone

Description

Nefazodone hydrochloride (trade name Serzone) is an antidepressant drug marketed by Bristol-Myers Squibb. Its sale was discontinued in 2003 in some countries, due to the small possibility of hepatic (liver) injury, which could lead to the need for a liver transplant, or even death. The incidence of severe liver damage is approximately 1 in 250,000 to 300,000 patient-years. On May 20, 2004, Bristol-Myers Squibb discontinued the sale of Serzone in the United States. [Wikipedia ]

Structure

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

1149
  Mrv0541 02231215172D          

 33 36  0  0  0  0            999 V2000
    1.6500   -5.0560    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.9811    2.9167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8929    4.1298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.9309    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.5809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.5442    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4012    2.5362    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2616    1.2086    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.3434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.3434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.1058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.3067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -3.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5942    2.3647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8137    1.8217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.8184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -3.8184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7368    3.2899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6342    1.7355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -4.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -4.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5572    3.3761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -5.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9698    0.9818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7133    4.2161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0489    4.9697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1983    3.5486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8694    5.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0188    3.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3543    4.3885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 23  1  0  0  0  0
  2 17  2  0  0  0  0
  3 25  1  0  0  0  0
  3 28  1  0  0  0  0
  4  9  1  0  0  0  0
  4 10  1  0  0  0  0
  4 13  1  0  0  0  0
  5 11  1  0  0  0  0
  5 12  1  0  0  0  0
  5 16  1  0  0  0  0
  6  8  1  0  0  0  0
  6 15  1  0  0  0  0
  6 17  1  0  0  0  0
  7 17  1  0  0  0  0
  7 18  1  0  0  0  0
  7 21  1  0  0  0  0
  8 18  2  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 19  2  0  0  0  0
 16 20  1  0  0  0  0
 18 22  1  0  0  0  0
 19 23  1  0  0  0  0
 20 24  2  0  0  0  0
 21 25  1  0  0  0  0
 22 27  1  0  0  0  0
 23 26  2  0  0  0  0
 24 26  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 29 31  1  0  0  0  0
 30 32  2  0  0  0  0
 31 33  2  0  0  0  0
 32 33  1  0  0  0  0
M  END

HMDB0015280
     RDKit          3D
Nefazodone
 65 68  0  0  0  0  0  0  0  0999 V2000
    4.8816    0.0370   -3.3510 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5700    0.7747   -2.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2444    0.2807   -1.5728 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0956    0.8914   -1.9678 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0627    0.2560   -1.4556 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3172    0.6124   -1.6614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8372    1.5821   -0.6277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2680    1.8658   -0.9814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0744    0.6767   -1.0043 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4115    0.9819   -1.5282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4881    0.1291   -0.9001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4765    0.2721    0.5555 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5649   -0.0644    1.3643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6095    0.3012    2.6840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6977   -0.0458    3.5009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7513   -0.7662    2.9883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7151   -1.1411    1.6514 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0479   -2.0629    0.9736 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -7.6360   -0.7889    0.8699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2304    0.7829    1.0919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1449    0.0582    0.2712 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5621   -0.7561   -0.7362 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9408   -1.6319   -0.0662 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9326   -0.7480   -0.8036 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8161   -1.7136   -0.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1301   -1.4343    1.2515 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7915   -0.2970    1.5707 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0769    0.0810    1.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4926    1.3606    1.7225 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7685    1.7813    1.4614 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7024    1.0340    0.7857 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2988   -0.2116    0.3578 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0036   -0.6690    0.6093 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9136   -0.1324   -3.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5098    0.6721   -4.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3142   -0.9408   -3.1480 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3876    0.6470   -1.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5273    1.8466   -2.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9953   -0.2658   -1.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4413    1.1000   -2.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7132    1.1560    0.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2267    2.5266   -0.6260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7051    2.6619   -0.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2805    2.2743   -2.0419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3913    0.7427   -2.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6181    2.0514   -1.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3576   -0.9122   -1.1854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4542    0.5191   -1.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8112    0.8710    3.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7108    0.2548    4.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6175   -1.0592    3.5827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5777   -1.0690   -0.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0857    0.6226    2.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1930    1.8535    0.7831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5103   -1.0097    0.1158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2041    0.0790    0.8080 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3203   -2.7103   -0.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7252   -1.7254   -0.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1247   -1.4043    1.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6637   -2.3653    1.6697 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7867    1.9843    2.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1245    2.7734    1.7906 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7009    1.4059    0.6010 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9800   -0.8669   -0.1862 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7152   -1.6689    0.2757 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  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  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 12 20  1  0
 20 21  1  0
  5 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 24  3  1  0
 33 28  1  0
 21  9  1  0
 19 13  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  0
  2 38  1  0
  6 39  1  0
  6 40  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  0
  8 44  1  0
 10 45  1  0
 10 46  1  0
 11 47  1  0
 11 48  1  0
 14 49  1  0
 15 50  1  0
 16 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 21 55  1  0
 21 56  1  0
 25 57  1  0
 25 58  1  0
 26 59  1  0
 26 60  1  0
 29 61  1  0
 30 62  1  0
 31 63  1  0
 32 64  1  0
 33 65  1  0
M  END

1149
  Mrv0541 02231215172D          

 33 36  0  0  0  0            999 V2000
    1.6500   -5.0560    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.9811    2.9167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8929    4.1298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.9309    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.5809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.5442    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4012    2.5362    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2616    1.2086    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.3434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.3434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.1058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.3067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -3.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5942    2.3647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8137    1.8217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.8184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -3.8184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7368    3.2899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6342    1.7355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -4.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -4.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5572    3.3761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -5.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9698    0.9818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7133    4.2161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0489    4.9697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1983    3.5486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8694    5.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0188    3.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3543    4.3885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 23  1  0  0  0  0
  2 17  2  0  0  0  0
  3 25  1  0  0  0  0
  3 28  1  0  0  0  0
  4  9  1  0  0  0  0
  4 10  1  0  0  0  0
  4 13  1  0  0  0  0
  5 11  1  0  0  0  0
  5 12  1  0  0  0  0
  5 16  1  0  0  0  0
  6  8  1  0  0  0  0
  6 15  1  0  0  0  0
  6 17  1  0  0  0  0
  7 17  1  0  0  0  0
  7 18  1  0  0  0  0
  7 21  1  0  0  0  0
  8 18  2  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 19  2  0  0  0  0
 16 20  1  0  0  0  0
 18 22  1  0  0  0  0
 19 23  1  0  0  0  0
 20 24  2  0  0  0  0
 21 25  1  0  0  0  0
 22 27  1  0  0  0  0
 23 26  2  0  0  0  0
 24 26  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 29 31  1  0  0  0  0
 30 32  2  0  0  0  0
 31 33  2  0  0  0  0
 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015280

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC1=NN(CCCN2CCN(CC2)C2=CC(Cl)=CC=C2)C(=O)N1CCOC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H32ClN5O2/c1-2-24-27-31(25(32)30(24)18-19-33-23-10-4-3-5-11-23)13-7-12-28-14-16-29(17-15-28)22-9-6-8-21(26)20-22/h3-6,8-11,20H,2,7,12-19H2,1H3

> <INCHI_KEY>
VRBKIVRKKCLPHA-UHFFFAOYSA-N

> <FORMULA>
C25H32ClN5O2

> <MOLECULAR_WEIGHT>
470.007

> <EXACT_MASS>
469.224453

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
51.848439212139965

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-{3-[4-(3-chlorophenyl)piperazin-1-yl]propyl}-3-ethyl-4-(2-phenoxyethyl)-4,5-dihydro-1H-1,2,4-triazol-5-one

> <ALOGPS_LOGP>
3.71

> <JCHEM_LOGP>
4.652967894333333

> <ALOGPS_LOGS>
-3.83

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.088044376629501

> <JCHEM_POLAR_SURFACE_AREA>
51.620000000000005

> <JCHEM_REFRACTIVITY>
132.376

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.98e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nefazodone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015280
     RDKit          3D
Nefazodone
 65 68  0  0  0  0  0  0  0  0999 V2000
    4.8816    0.0370   -3.3510 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5700    0.7747   -2.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2444    0.2807   -1.5728 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0956    0.8914   -1.9678 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0627    0.2560   -1.4556 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3172    0.6124   -1.6614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8372    1.5821   -0.6277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2680    1.8658   -0.9814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0744    0.6767   -1.0043 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4115    0.9819   -1.5282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4881    0.1291   -0.9001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4765    0.2721    0.5555 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5649   -0.0644    1.3643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6095    0.3012    2.6840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6977   -0.0458    3.5009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7513   -0.7662    2.9883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7151   -1.1411    1.6514 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0479   -2.0629    0.9736 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -7.6360   -0.7889    0.8699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2304    0.7829    1.0919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1449    0.0582    0.2712 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5621   -0.7561   -0.7362 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9408   -1.6319   -0.0662 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9326   -0.7480   -0.8036 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8161   -1.7136   -0.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1301   -1.4343    1.2515 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7915   -0.2970    1.5707 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0769    0.0810    1.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4926    1.3606    1.7225 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7685    1.7813    1.4614 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7024    1.0340    0.7857 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2988   -0.2116    0.3578 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0036   -0.6690    0.6093 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9136   -0.1324   -3.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5098    0.6721   -4.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3142   -0.9408   -3.1480 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3876    0.6470   -1.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5273    1.8466   -2.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9953   -0.2658   -1.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4413    1.1000   -2.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7132    1.1560    0.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2267    2.5266   -0.6260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7051    2.6619   -0.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2805    2.2743   -2.0419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3913    0.7427   -2.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6181    2.0514   -1.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3576   -0.9122   -1.1854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4542    0.5191   -1.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8112    0.8710    3.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7108    0.2548    4.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6175   -1.0592    3.5827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5777   -1.0690   -0.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0857    0.6226    2.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1930    1.8535    0.7831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5103   -1.0097    0.1158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2041    0.0790    0.8080 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3203   -2.7103   -0.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7252   -1.7254   -0.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1247   -1.4043    1.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6637   -2.3653    1.6697 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7867    1.9843    2.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1245    2.7734    1.7906 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7009    1.4059    0.6010 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9800   -0.8669   -0.1862 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7152   -1.6689    0.2757 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  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  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 12 20  1  0
 20 21  1  0
  5 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 24  3  1  0
 33 28  1  0
 21  9  1  0
 19 13  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  0
  2 38  1  0
  6 39  1  0
  6 40  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  0
  8 44  1  0
 10 45  1  0
 10 46  1  0
 11 47  1  0
 11 48  1  0
 14 49  1  0
 15 50  1  0
 16 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 21 55  1  0
 21 56  1  0
 25 57  1  0
 25 58  1  0
 26 59  1  0
 26 60  1  0
 29 61  1  0
 30 62  1  0
 31 63  1  0
 32 64  1  0
 33 65  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1149                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       3.080  -9.438   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0       7.431   5.445   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      12.867   7.709   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       5.748  -1.738   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       5.748  -4.818   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       8.415   2.883   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      10.082   4.734   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       9.822   2.256   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       4.414  -2.508   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.081  -2.508   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414  -4.048   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.081  -4.048   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.748  -0.197   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.081   0.573   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081   2.113   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.748  -6.358   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.576   4.414   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.852   3.401   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.414  -7.128   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.081  -7.128   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.709   6.141   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.384   3.240   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.414  -8.668   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.081  -8.668   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.240   6.302   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.748  -9.438   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.010   1.833   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.398   7.870   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      15.025   9.277   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      15.303   6.624   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      16.556   9.438   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      16.835   6.785   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      17.461   8.192   0.000  0.00  0.00           C+0
CONECT    1   23                                                            
CONECT    2   17                                                            
CONECT    3   25   28                                                       
CONECT    4    9   10   13                                                  
CONECT    5   11   12   16                                                  
CONECT    6    8   15   17                                                  
CONECT    7   17   18   21                                                  
CONECT    8    6   18                                                       
CONECT    9    4   11                                                       
CONECT   10    4   12                                                       
CONECT   11    5    9                                                       
CONECT   12    5   10                                                       
CONECT   13    4   14                                                       
CONECT   14   13   15                                                       
CONECT   15    6   14                                                       
CONECT   16    5   19   20                                                  
CONECT   17    2    6    7                                                  
CONECT   18    7    8   22                                                  
CONECT   19   16   23                                                       
CONECT   20   16   24                                                       
CONECT   21    7   25                                                       
CONECT   22   18   27                                                       
CONECT   23    1   19   26                                                  
CONECT   24   20   26                                                       
CONECT   25    3   21                                                       
CONECT   26   23   24                                                       
CONECT   27   22                                                            
CONECT   28    3   29   30                                                  
CONECT   29   28   31                                                       
CONECT   30   28   32                                                       
CONECT   31   29   33                                                       
CONECT   32   30   33                                                       
CONECT   33   31   32                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

COMPND    HMDB0015280
HETATM    1  C1  UNL     1       4.882   0.037  -3.351  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.570   0.775  -2.037  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.244   0.281  -1.573  1.00  0.00           C  
HETATM    4  N1  UNL     1       2.096   0.891  -1.968  1.00  0.00           N  
HETATM    5  N2  UNL     1       1.063   0.256  -1.456  1.00  0.00           N  
HETATM    6  C4  UNL     1      -0.317   0.612  -1.661  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.837   1.582  -0.628  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.268   1.866  -0.981  1.00  0.00           C  
HETATM    9  N3  UNL     1      -3.074   0.677  -1.004  1.00  0.00           N  
HETATM   10  C7  UNL     1      -4.411   0.982  -1.528  1.00  0.00           C  
HETATM   11  C8  UNL     1      -5.488   0.129  -0.900  1.00  0.00           C  
HETATM   12  N4  UNL     1      -5.476   0.272   0.556  1.00  0.00           N  
HETATM   13  C9  UNL     1      -6.565  -0.064   1.364  1.00  0.00           C  
HETATM   14  C10 UNL     1      -6.609   0.301   2.684  1.00  0.00           C  
HETATM   15  C11 UNL     1      -7.698  -0.046   3.501  1.00  0.00           C  
HETATM   16  C12 UNL     1      -8.751  -0.766   2.988  1.00  0.00           C  
HETATM   17  C13 UNL     1      -8.715  -1.141   1.651  1.00  0.00           C  
HETATM   18 CL1  UNL     1     -10.048  -2.063   0.974  1.00  0.00          CL  
HETATM   19  C14 UNL     1      -7.636  -0.789   0.870  1.00  0.00           C  
HETATM   20  C15 UNL     1      -4.230   0.783   1.092  1.00  0.00           C  
HETATM   21  C16 UNL     1      -3.145   0.058   0.271  1.00  0.00           C  
HETATM   22  C17 UNL     1       1.562  -0.756  -0.736  1.00  0.00           C  
HETATM   23  O1  UNL     1       0.941  -1.632  -0.066  1.00  0.00           O  
HETATM   24  N5  UNL     1       2.933  -0.748  -0.804  1.00  0.00           N  
HETATM   25  C18 UNL     1       3.816  -1.714  -0.186  1.00  0.00           C  
HETATM   26  C19 UNL     1       4.130  -1.434   1.252  1.00  0.00           C  
HETATM   27  O2  UNL     1       4.791  -0.297   1.571  1.00  0.00           O  
HETATM   28  C20 UNL     1       6.077   0.081   1.283  1.00  0.00           C  
HETATM   29  C21 UNL     1       6.493   1.361   1.723  1.00  0.00           C  
HETATM   30  C22 UNL     1       7.769   1.781   1.461  1.00  0.00           C  
HETATM   31  C23 UNL     1       8.702   1.034   0.786  1.00  0.00           C  
HETATM   32  C24 UNL     1       8.299  -0.212   0.358  1.00  0.00           C  
HETATM   33  C25 UNL     1       7.004  -0.669   0.609  1.00  0.00           C  
HETATM   34  H1  UNL     1       3.914  -0.132  -3.888  1.00  0.00           H  
HETATM   35  H2  UNL     1       5.510   0.672  -4.012  1.00  0.00           H  
HETATM   36  H3  UNL     1       5.314  -0.941  -3.148  1.00  0.00           H  
HETATM   37  H4  UNL     1       5.388   0.647  -1.357  1.00  0.00           H  
HETATM   38  H5  UNL     1       4.527   1.847  -2.324  1.00  0.00           H  
HETATM   39  H6  UNL     1      -0.995  -0.266  -1.652  1.00  0.00           H  
HETATM   40  H7  UNL     1      -0.441   1.100  -2.655  1.00  0.00           H  
HETATM   41  H8  UNL     1      -0.713   1.156   0.366  1.00  0.00           H  
HETATM   42  H9  UNL     1      -0.227   2.527  -0.626  1.00  0.00           H  
HETATM   43  H10 UNL     1      -2.705   2.662  -0.333  1.00  0.00           H  
HETATM   44  H11 UNL     1      -2.280   2.274  -2.042  1.00  0.00           H  
HETATM   45  H12 UNL     1      -4.391   0.743  -2.611  1.00  0.00           H  
HETATM   46  H13 UNL     1      -4.618   2.051  -1.400  1.00  0.00           H  
HETATM   47  H14 UNL     1      -5.358  -0.912  -1.185  1.00  0.00           H  
HETATM   48  H15 UNL     1      -6.454   0.519  -1.283  1.00  0.00           H  
HETATM   49  H16 UNL     1      -5.811   0.871   3.137  1.00  0.00           H  
HETATM   50  H17 UNL     1      -7.711   0.255   4.543  1.00  0.00           H  
HETATM   51  H18 UNL     1      -9.617  -1.059   3.583  1.00  0.00           H  
HETATM   52  H19 UNL     1      -7.578  -1.069  -0.185  1.00  0.00           H  
HETATM   53  H20 UNL     1      -4.086   0.623   2.157  1.00  0.00           H  
HETATM   54  H21 UNL     1      -4.193   1.854   0.783  1.00  0.00           H  
HETATM   55  H22 UNL     1      -3.510  -1.010   0.116  1.00  0.00           H  
HETATM   56  H23 UNL     1      -2.204   0.079   0.808  1.00  0.00           H  
HETATM   57  H24 UNL     1       3.320  -2.710  -0.314  1.00  0.00           H  
HETATM   58  H25 UNL     1       4.725  -1.725  -0.812  1.00  0.00           H  
HETATM   59  H26 UNL     1       3.125  -1.404   1.808  1.00  0.00           H  
HETATM   60  H27 UNL     1       4.664  -2.365   1.670  1.00  0.00           H  
HETATM   61  H28 UNL     1       5.787   1.984   2.261  1.00  0.00           H  
HETATM   62  H29 UNL     1       8.125   2.773   1.791  1.00  0.00           H  
HETATM   63  H30 UNL     1       9.701   1.406   0.601  1.00  0.00           H  
HETATM   64  H31 UNL     1       8.980  -0.867  -0.186  1.00  0.00           H  
HETATM   65  H32 UNL     1       6.715  -1.669   0.276  1.00  0.00           H  
CONECT    1    2   34   35   36
CONECT    2    3   37   38
CONECT    3    4    4   24
CONECT    4    5
CONECT    5    6   22
CONECT    6    7   39   40
CONECT    7    8   41   42
CONECT    8    9   43   44
CONECT    9   10   21
CONECT   10   11   45   46
CONECT   11   12   47   48
CONECT   12   13   20
CONECT   13   14   14   19
CONECT   14   15   49
CONECT   15   16   16   50
CONECT   16   17   51
CONECT   17   18   19   19
CONECT   19   52
CONECT   20   21   53   54
CONECT   21   55   56
CONECT   22   23   23   24
CONECT   24   25
CONECT   25   26   57   58
CONECT   26   27   59   60
CONECT   27   28
CONECT   28   29   29   33
CONECT   29   30   61
CONECT   30   31   31   62
CONECT   31   32   63
CONECT   32   33   33   64
CONECT   33   65
END

HMDB0015280
     RDKit          3D
Nefazodone
 65 68  0  0  0  0  0  0  0  0999 V2000
    4.8816    0.0370   -3.3510 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5700    0.7747   -2.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2444    0.2807   -1.5728 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0956    0.8914   -1.9678 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0627    0.2560   -1.4556 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3172    0.6124   -1.6614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8372    1.5821   -0.6277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2680    1.8658   -0.9814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0744    0.6767   -1.0043 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4115    0.9819   -1.5282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4881    0.1291   -0.9001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4765    0.2721    0.5555 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5649   -0.0644    1.3643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6095    0.3012    2.6840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6977   -0.0458    3.5009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7513   -0.7662    2.9883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7151   -1.1411    1.6514 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0479   -2.0629    0.9736 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -7.6360   -0.7889    0.8699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2304    0.7829    1.0919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1449    0.0582    0.2712 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5621   -0.7561   -0.7362 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9408   -1.6319   -0.0662 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9326   -0.7480   -0.8036 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8161   -1.7136   -0.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1301   -1.4343    1.2515 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7915   -0.2970    1.5707 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0769    0.0810    1.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4926    1.3606    1.7225 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7685    1.7813    1.4614 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7024    1.0340    0.7857 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2988   -0.2116    0.3578 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0036   -0.6690    0.6093 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9136   -0.1324   -3.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5098    0.6721   -4.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3142   -0.9408   -3.1480 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3876    0.6470   -1.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5273    1.8466   -2.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9953   -0.2658   -1.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4413    1.1000   -2.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7132    1.1560    0.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2267    2.5266   -0.6260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7051    2.6619   -0.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2805    2.2743   -2.0419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3913    0.7427   -2.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6181    2.0514   -1.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3576   -0.9122   -1.1854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4542    0.5191   -1.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8112    0.8710    3.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7108    0.2548    4.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6175   -1.0592    3.5827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5777   -1.0690   -0.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0857    0.6226    2.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1930    1.8535    0.7831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5103   -1.0097    0.1158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2041    0.0790    0.8080 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3203   -2.7103   -0.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7252   -1.7254   -0.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1247   -1.4043    1.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6637   -2.3653    1.6697 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7867    1.9843    2.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1245    2.7734    1.7906 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7009    1.4059    0.6010 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9800   -0.8669   -0.1862 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7152   -1.6689    0.2757 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  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  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 12 20  1  0
 20 21  1  0
  5 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 24  3  1  0
 33 28  1  0
 21  9  1  0
 19 13  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  0
  2 38  1  0
  6 39  1  0
  6 40  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  0
  8 44  1  0
 10 45  1  0
 10 46  1  0
 11 47  1  0
 11 48  1  0
 14 49  1  0
 15 50  1  0
 16 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 21 55  1  0
 21 56  1  0
 25 57  1  0
 25 58  1  0
 26 59  1  0
 26 60  1  0
 29 61  1  0
 30 62  1  0
 31 63  1  0
 32 64  1  0
 33 65  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(3-(4-(m-Chlorophenyl)-1-piperazinyl)propyl)-3-ethyl-4-(2-phenoxyethyl)-delta2-1,2,4-triazolin-5-one	ChEBI
Nefazodona	ChEBI
Nefazodonum	ChEBI
1-(3-(4-(m-Chlorophenyl)-1-piperazinyl)propyl)-3-ethyl-4-(2-phenoxyethyl)-δ2-1,2,4-triazolin-5-one	Generator
Bristol-myers squibb brand OF nefazodone hydrochloride	HMDB
Dutonin	HMDB
Rulivan	HMDB
Apo-nefazodone	HMDB
Apotex brand OF nefazodone hydrochloride	HMDB
Hormosan brand OF nefazodone hydrochloride	HMDB
Linson pharma brand OF nefazodone hydrochloride	HMDB
Nefadar	HMDB
Lin-nefazodone	HMDB
Serzone	HMDB
Bristol-myers brand OF nefazodone hydrochloride	HMDB
Europharma brand OF nefazodone hydrochloride	HMDB
Menarini brand OF nefazodone hydrochloride	HMDB
Menfazona	HMDB
Nefazodone hydrochloride	HMDB

Chemical Formula

C₂₅H₃₂ClN₅O₂

Average Molecular Weight

470.007

Monoisotopic Molecular Weight

469.224453

IUPAC Name

1-{3-[4-(3-chlorophenyl)piperazin-1-yl]propyl}-3-ethyl-4-(2-phenoxyethyl)-4,5-dihydro-1H-1,2,4-triazol-5-one

Traditional Name

nefazodone

CAS Registry Number

83366-66-9

SMILES

CCC1=NN(CCCN2CCN(CC2)C2=CC(Cl)=CC=C2)C(=O)N1CCOC1=CC=CC=C1

InChI Identifier

InChI=1S/C25H32ClN5O2/c1-2-24-27-31(25(32)30(24)18-19-33-23-10-4-3-5-11-23)13-7-12-28-14-16-29(17-15-28)22-9-6-8-21(26)20-22/h3-6,8-11,20H,2,7,12-19H2,1H3

InChI Key

VRBKIVRKKCLPHA-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
Phenol ether
Tertiary aliphatic/aromatic amine
Phenoxy compound
Dialkylarylamine
Aniline or substituted anilines
Chlorobenzene
N-alkylpiperazine
Halobenzene
Alkyl aryl ether
Monocyclic benzene moiety
Aryl halide
Aryl chloride
Benzenoid
Heteroaromatic compound
Azole
1,2,4-triazole
Tertiary aliphatic amine
Tertiary amine
Ether
Azacycle
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

aromatic ether (CHEBI:7494 )
N-arylpiperazine (CHEBI:7494 )
monochlorobenzenes (CHEBI:7494 )
N-alkylpiperazine (CHEBI:7494 )
triazoles (CHEBI:7494 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015280)

Process

Not Available

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	83 - 84 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.07 g/L	Not Available
LogP	4.7	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	211.7	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.07 g/L	ALOGPS
logP	3.71	ALOGPS
logP	4.65	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Basic)	7.09	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	51.62 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	132.38 m³·mol⁻¹	ChemAxon
Polarizability	51.85 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	204.244	30932474
DeepCCS	[M-H]-	201.886	30932474
DeepCCS	[M-2H]-	235.403	30932474
DeepCCS	[M+Na]+	210.632	30932474
AllCCS	[M+H]+	212.3	32859911
AllCCS	[M+H-H2O]+	210.4	32859911
AllCCS	[M+NH4]+	213.9	32859911
AllCCS	[M+Na]+	214.4	32859911
AllCCS	[M-H]-	203.0	32859911
AllCCS	[M+Na-2H]-	203.6	32859911
AllCCS	[M+HCOO]-	204.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nefazodone	CCC1=NN(CCCN2CCN(CC2)C2=CC(Cl)=CC=C2)C(=O)N1CCOC1=CC=CC=C1	4478.7	Standard polar	33892256
Nefazodone	CCC1=NN(CCCN2CCN(CC2)C2=CC(Cl)=CC=C2)C(=O)N1CCOC1=CC=CC=C1	3738.9	Standard non polar	33892256
Nefazodone	CCC1=NN(CCCN2CCN(CC2)C2=CC(Cl)=CC=C2)C(=O)N1CCOC1=CC=CC=C1	4056.7	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 - Nefazodone GC-MS (Non-derivatized) - 70eV, Positive	splash10-08fv-6496100000-3f42082c30f022624e00	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nefazodone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0uk9-9846000000-49cb6e97c09a9e806dd5	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 - Nefazodone , positive-QTOF	splash10-00di-0260900000-3ebf8f0b9eda5fea1378	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nefazodone , positive-QTOF	splash10-00di-3790200000-9f64b1295a633dcdd772	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nefazodone 35V, Positive-QTOF	splash10-00di-0190600000-e660a26f2b5417360e81	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nefazodone 10V, Positive-QTOF	splash10-00di-0152900000-340890a453c0a56c76b3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nefazodone 20V, Positive-QTOF	splash10-0fbl-4695100000-93bef331c390dbfee2d6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nefazodone 40V, Positive-QTOF	splash10-01pd-7940000000-d9eeb95454a6d048ce65	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nefazodone 10V, Negative-QTOF	splash10-016r-3931500000-a506620891ae02e35e82	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nefazodone 20V, Negative-QTOF	splash10-002f-9730100000-83a513c505af8bed8b82	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nefazodone 40V, Negative-QTOF	splash10-0006-9200000000-522fe62ba68195d5d1b2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nefazodone 10V, Positive-QTOF	splash10-00di-1200900000-c3db8beb65c2741f9ab9	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nefazodone 20V, Positive-QTOF	splash10-00dr-2359600000-4969e962cd4b5264e810	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nefazodone 40V, Positive-QTOF	splash10-002s-1981100000-c2114e4725584e3d862a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nefazodone 10V, Negative-QTOF	splash10-0007-6805900000-806a5c4806b242b95249	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nefazodone 20V, Negative-QTOF	splash10-0006-9014200000-f95736b782384e65b6cf	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nefazodone 40V, Negative-QTOF	splash10-0006-9000000000-37e7f69fd131b8f395dd	2021-10-11	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 DB01149	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01149	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

DB01149

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4294

KEGG Compound ID

C07256

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nefazodone

METLIN ID

Not Available

PubChem Compound

4449

PDB ID

Not Available

ChEBI ID

7494

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

Davis R, Whittington R, Bryson HM: Nefazodone. A review of its pharmacology and clinical efficacy in the management of major depression. Drugs. 1997 Apr;53(4):608-36. [PubMed:9098663 ]

Only showing the first 10 proteins. There are 14 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

Davis R, Whittington R, Bryson HM: Nefazodone. A review of its pharmacology and clinical efficacy in the management of major depression. Drugs. 1997 Apr;53(4):608-36. [PubMed:9098663 ]
DeVane CL, Donovan JL, Liston HL, Markowitz JS, Cheng KT, Risch SC, Willard L: Comparative CYP3A4 inhibitory effects of venlafaxine, fluoxetine, sertraline, and nefazodone in healthy volunteers. J Clin Psychopharmacol. 2004 Feb;24(1):4-10. [PubMed:14709940 ]
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 ]
von Moltke LL, Greenblatt DJ, Granda BW, Grassi JM, Schmider J, Harmatz JS, Shader RI: Nefazodone, meta-chlorophenylpiperazine, and their metabolites in vitro: cytochromes mediating transformation, and P450-3A4 inhibitory actions. Psychopharmacology (Berl). 1999 Jul;145(1):113-22. [PubMed:10445380 ]

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

von Moltke LL, Greenblatt DJ, Granda BW, Grassi JM, Schmider J, Harmatz JS, Shader RI: Nefazodone, meta-chlorophenylpiperazine, and their metabolites in vitro: cytochromes mediating transformation, and P450-3A4 inhibitory actions. Psychopharmacology (Berl). 1999 Jul;145(1):113-22. [PubMed:10445380 ]
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

References

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

Enzyme Details

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

References

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

Enzyme Details

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 ]

Enzyme Details

6. Sodium-dependent dopamine transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:: SLC6A3
Uniprot ID:: Q01959
Molecular weight:: 68494.255

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 ]

Enzyme Details

7. 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

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 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

Hidalgo R, Hertzberg MA, Mellman T, Petty F, Tucker P, Weisler R, Zisook S, Chen S, Churchill E, Davidson J: Nefazodone in post-traumatic stress disorder: results from six open-label trials. Int Clin Psychopharmacol. 1999 Mar;14(2):61-8. [PubMed:10220119 ]
Meyer JH, Cho R, Kennedy S, Kapur S: The effects of single dose nefazodone and paroxetine upon 5-HT2A binding potential in humans using [18F]-setoperone PET. Psychopharmacology (Berl). 1999 Jun;144(3):279-81. [PubMed:10435395 ]
Horton JC, Trobe JD: Akinetopsia from nefazodone toxicity. Am J Ophthalmol. 1999 Oct;128(4):530-1. [PubMed:10577608 ]
Eckler JR, Rabin RA, Winter JC: Nefazodone in the rat: mimicry and antagonism of [-]-DOM-induced stimulus control. Pharmacol Biochem Behav. 2003 May;75(2):405-10. [PubMed:12873632 ]
Avila A, Cardona X, Martin-Baranera M, Maho P, Sastre F, Bello J: Does nefazodone improve both depression and Parkinson disease? A pilot randomized trial. J Clin Psychopharmacol. 2003 Oct;23(5):509-13. [PubMed:14520130 ]
Taylor DP, Carter RB, Eison AS, Mullins UL, Smith HL, Torrente JR, Wright RN, Yocca FD: Pharmacology and neurochemistry of nefazodone, a novel antidepressant drug. J Clin Psychiatry. 1995;56 Suppl 6:3-11. [PubMed:7649970 ]
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 ]
Davis R, Whittington R, Bryson HM: Nefazodone. A review of its pharmacology and clinical efficacy in the management of major depression. Drugs. 1997 Apr;53(4):608-36. [PubMed:9098663 ]

Enzyme Details

9. 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

Millan MJ: Serotonin 5-HT2C receptors as a target for the treatment of depressive and anxious states: focus on novel therapeutic strategies. Therapie. 2005 Sep-Oct;60(5):441-60. [PubMed:16433010 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

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

Taylor DP, Carter RB, Eison AS, Mullins UL, Smith HL, Torrente JR, Wright RN, Yocca FD: Pharmacology and neurochemistry of nefazodone, a novel antidepressant drug. J Clin Psychiatry. 1995;56 Suppl 6:3-11. [PubMed:7649970 ]
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 noradrenaline transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:: SLC6A2
Uniprot ID:: P23975
Molecular weight:: 69331.42

References

Owens MJ, Ieni JR, Knight DL, Winders K, Nemeroff CB: The serotonergic antidepressant nefazodone inhibits the serotonin transporter: in vivo and ex vivo studies. Life Sci. 1995;57(24):PL373-80. [PubMed:7475971 ]
Owen D, Du L, Bakish D, Lapierre YD, Hrdina PD: Norepinephrine transporter gene polymorphism is not associated with susceptibility to major depression. Psychiatry Res. 1999 Jul 30;87(1):1-5. [PubMed:10512149 ]
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 ]
Taylor DP, Carter RB, Eison AS, Mullins UL, Smith HL, Torrente JR, Wright RN, Yocca FD: Pharmacology and neurochemistry of nefazodone, a novel antidepressant drug. J Clin Psychiatry. 1995;56 Suppl 6:3-11. [PubMed:7649970 ]
Davis R, Whittington R, Bryson HM: Nefazodone. A review of its pharmacology and clinical efficacy in the management of major depression. Drugs. 1997 Apr;53(4):608-36. [PubMed:9098663 ]

Enzyme Details

3. 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

Owens MJ, Ieni JR, Knight DL, Winders K, Nemeroff CB: The serotonergic antidepressant nefazodone inhibits the serotonin transporter: in vivo and ex vivo studies. Life Sci. 1995;57(24):PL373-80. [PubMed:7475971 ]
Narayan M, Anderson G, Cellar J, Mallison RT, Price LH, Nelson JC: Serotonin transporter-blocking properties of nefazodone assessed by measurement of platelet serotonin. J Clin Psychopharmacol. 1998 Feb;18(1):67-71. [PubMed:9472845 ]
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 ]
Taylor DP, Carter RB, Eison AS, Mullins UL, Smith HL, Torrente JR, Wright RN, Yocca FD: Pharmacology and neurochemistry of nefazodone, a novel antidepressant drug. J Clin Psychiatry. 1995;56 Suppl 6:3-11. [PubMed:7649970 ]
Davis R, Whittington R, Bryson HM: Nefazodone. A review of its pharmacology and clinical efficacy in the management of major depression. Drugs. 1997 Apr;53(4):608-36. [PubMed:9098663 ]

Only showing the first 10 proteins. There are 14 proteins in total.

Show all enzymes and transporters

Showing metabocard for Nefazodone (HMDB0015280)

MOL for HMDB0015280 (Nefazodone)

3D MOL for HMDB0015280 (Nefazodone)

3D SDF for HMDB0015280 (Nefazodone)

3D-SDF for HMDB0015280 (Nefazodone)

PDB for HMDB0015280 (Nefazodone)

3D PDB for HMDB0015280 (Nefazodone)

SMILES for HMDB0015280 (Nefazodone)

INCHI for HMDB0015280 (Nefazodone)

Structure for HMDB0015280 (Nefazodone)

3D Structure for HMDB0015280 (Nefazodone)

Experimental Collision Cross Sections

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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