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enzymes (10) Show 10 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:03 UTC

HMDB ID

HMDB0015618

Secondary Accession Numbers

HMDB15618

Metabolite Identification

Common Name

Sertindole

Description

Sertindole, a neuroleptic, is one of the newer antipsychotic medications available. Serdolect is developed by the Danish pharmaceutical company H. Lundbeck. Like the other atypical antipsychotics, it has activity at dopamine and serotonin receptors in the brain. It is used in the treatment of schizophrenia. It is classified chemically as a phenylindole derivative. It was first marketed in 1996 in several European countries before being withdrawn two years later because of numerous cardiac adverse effects. It has once again been approved and should soon be available on the French and Australian market.

Structure

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


  Mrv0541 02231218142D          

 31 35  0  0  0  0            999 V2000
    1.6500   -0.3414    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.5992   -4.9670    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.1145    3.3560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3430    1.8501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5741   -1.8304    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6628    3.5885    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4493    4.6672    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8304    0.2817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2794    0.8957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6377    0.4518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5357    1.6799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8939    1.2360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5741   -0.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5992    2.6343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.7539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4066    2.8044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0556   -1.1664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.5789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1791    4.2569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.3414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6652    4.9235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.9914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8304   -2.6145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4479    3.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.7539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.5789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6377   -2.7846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2794   -3.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8939   -3.5688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5357   -4.0128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3430   -4.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 25  1  0  0  0  0
  2 31  1  0  0  0  0
  3 24  2  0  0  0  0
  4 11  1  0  0  0  0
  4 12  1  0  0  0  0
  4 14  1  0  0  0  0
  5 17  1  0  0  0  0
  5 18  1  0  0  0  0
  5 23  1  0  0  0  0
  6 16  1  0  0  0  0
  6 19  1  0  0  0  0
  6 24  1  0  0  0  0
  7 21  1  0  0  0  0
  7 24  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 13  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 13 15  1  0  0  0  0
 13 17  2  0  0  0  0
 14 16  1  0  0  0  0
 15 18  2  0  0  0  0
 15 20  1  0  0  0  0
 18 22  1  0  0  0  0
 19 21  1  0  0  0  0
 20 25  2  0  0  0  0
 22 26  2  0  0  0  0
 23 27  2  0  0  0  0
 23 28  1  0  0  0  0
 25 26  1  0  0  0  0
 27 29  1  0  0  0  0
 28 30  2  0  0  0  0
 29 31  2  0  0  0  0
 30 31  1  0  0  0  0
M  END

HMDB0015618
     RDKit          3D
Sertindole
 57 61  0  0  0  0  0  0  0  0999 V2000
    4.9017    1.6587   -2.5190 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4218    0.9733   -1.6062 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1880   -0.2272   -1.8697 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0979   -0.3655   -0.7369 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6022    0.5610    0.3225 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3804    1.1945   -0.2430 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4087    1.8818    0.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3648    0.7763    0.9207 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6915    0.5230   -0.3576 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2688   -0.8384   -0.5240 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8474   -0.7785   -1.1239 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0004   -0.6448    0.1302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4511   -0.6406   -0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3580    0.3106   -0.4683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6232   -0.0734   -0.2325 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8399    0.6422   -0.3890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4719    1.1568    0.7573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6494    1.9014    0.6782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2476    2.1638   -0.5301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3760    2.8984   -0.6108 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6197    1.6594   -1.6430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4521    0.9199   -1.5866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5456   -1.3012    0.3356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5262   -2.2180    0.7301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1988   -3.4755    1.2372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8586   -3.7848    1.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4056   -5.3605    1.9489 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.8682   -2.9082    0.9566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2566   -1.6588    0.4552 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4344    0.7791    0.6487 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4642    1.3699   -0.2294 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1279   -0.8703   -2.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1535   -1.4012   -0.3518 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0921   -0.0439   -1.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3612    1.3721    0.4957 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2997    0.0837    1.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9861    2.7027    0.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8725    2.2813    1.5181 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8977   -0.1108    1.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6793    1.1245    1.7098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1869   -1.3844    0.4267 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8873   -1.4298   -1.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5918   -1.8222   -1.5216 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6760    0.0047   -1.8161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3483   -1.3778    0.8584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1089    1.2632   -0.9336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0224    0.9537    1.7017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1241    2.2762    1.6024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1047    1.8692   -2.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0054    0.5386   -2.5155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5581   -1.9277    0.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9621   -4.1540    1.5258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8559   -3.2050    1.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4629    1.4570    0.5884 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7245    0.6896    1.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1501    1.7187   -1.2102 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8464    2.2972    0.2976 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  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 15 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  2  0
 12 30  1  0
 30 31  1  0
  6  2  1  0
 31  9  1  0
 29 13  1  0
 22 16  1  0
 29 23  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  7 37  1  0
  7 38  1  0
  8 39  1  0
  8 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 14 46  1  0
 17 47  1  0
 18 48  1  0
 21 49  1  0
 22 50  1  0
 24 51  1  0
 25 52  1  0
 28 53  1  0
 30 54  1  0
 30 55  1  0
 31 56  1  0
 31 57  1  0
M  END


  Mrv0541 02231218142D          

 31 35  0  0  0  0            999 V2000
    1.6500   -0.3414    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.5992   -4.9670    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.1145    3.3560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3430    1.8501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5741   -1.8304    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6628    3.5885    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4493    4.6672    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8304    0.2817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2794    0.8957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6377    0.4518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5357    1.6799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8939    1.2360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5741   -0.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5992    2.6343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.7539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4066    2.8044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0556   -1.1664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.5789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1791    4.2569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.3414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6652    4.9235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.9914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8304   -2.6145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4479    3.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.7539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.5789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6377   -2.7846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2794   -3.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8939   -3.5688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5357   -4.0128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3430   -4.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 25  1  0  0  0  0
  2 31  1  0  0  0  0
  3 24  2  0  0  0  0
  4 11  1  0  0  0  0
  4 12  1  0  0  0  0
  4 14  1  0  0  0  0
  5 17  1  0  0  0  0
  5 18  1  0  0  0  0
  5 23  1  0  0  0  0
  6 16  1  0  0  0  0
  6 19  1  0  0  0  0
  6 24  1  0  0  0  0
  7 21  1  0  0  0  0
  7 24  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 13  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 13 15  1  0  0  0  0
 13 17  2  0  0  0  0
 14 16  1  0  0  0  0
 15 18  2  0  0  0  0
 15 20  1  0  0  0  0
 18 22  1  0  0  0  0
 19 21  1  0  0  0  0
 20 25  2  0  0  0  0
 22 26  2  0  0  0  0
 23 27  2  0  0  0  0
 23 28  1  0  0  0  0
 25 26  1  0  0  0  0
 27 29  1  0  0  0  0
 28 30  2  0  0  0  0
 29 31  2  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015618

> <DATABASE_NAME>
hmdb

> <SMILES>
FC1=CC=C(C=C1)N1C=C(C2CCN(CCN3CCNC3=O)CC2)C2=C1C=CC(Cl)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C24H26ClFN4O/c25-18-1-6-23-21(15-18)22(16-30(23)20-4-2-19(26)3-5-20)17-7-10-28(11-8-17)13-14-29-12-9-27-24(29)31/h1-6,15-17H,7-14H2,(H,27,31)

> <INCHI_KEY>
GZKLJWGUPQBVJQ-UHFFFAOYSA-N

> <FORMULA>
C24H26ClFN4O

> <MOLECULAR_WEIGHT>
440.941

> <EXACT_MASS>
440.177917386

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
47.17150851412664

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(2-{4-[5-chloro-1-(4-fluorophenyl)-1H-indol-3-yl]piperidin-1-yl}ethyl)imidazolidin-2-one

> <ALOGPS_LOGP>
4.29

> <JCHEM_LOGP>
3.7738

> <ALOGPS_LOGS>
-4.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.358150699540666

> <JCHEM_PKA_STRONGEST_BASIC>
8.585054865216964

> <JCHEM_POLAR_SURFACE_AREA>
40.510000000000005

> <JCHEM_REFRACTIVITY>
131.7697

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.63e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sertindole

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015618
     RDKit          3D
Sertindole
 57 61  0  0  0  0  0  0  0  0999 V2000
    4.9017    1.6587   -2.5190 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4218    0.9733   -1.6062 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1880   -0.2272   -1.8697 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0979   -0.3655   -0.7369 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6022    0.5610    0.3225 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3804    1.1945   -0.2430 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4087    1.8818    0.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3648    0.7763    0.9207 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6915    0.5230   -0.3576 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2688   -0.8384   -0.5240 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8474   -0.7785   -1.1239 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0004   -0.6448    0.1302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4511   -0.6406   -0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3580    0.3106   -0.4683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6232   -0.0734   -0.2325 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8399    0.6422   -0.3890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4719    1.1568    0.7573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6494    1.9014    0.6782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2476    2.1638   -0.5301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3760    2.8984   -0.6108 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6197    1.6594   -1.6430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4521    0.9199   -1.5866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5456   -1.3012    0.3356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5262   -2.2180    0.7301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1988   -3.4755    1.2372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8586   -3.7848    1.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4056   -5.3605    1.9489 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.8682   -2.9082    0.9566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2566   -1.6588    0.4552 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4344    0.7791    0.6487 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4642    1.3699   -0.2294 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1279   -0.8703   -2.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1535   -1.4012   -0.3518 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0921   -0.0439   -1.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3612    1.3721    0.4957 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2997    0.0837    1.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9861    2.7027    0.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8725    2.2813    1.5181 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8977   -0.1108    1.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6793    1.1245    1.7098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1869   -1.3844    0.4267 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8873   -1.4298   -1.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5918   -1.8222   -1.5216 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6760    0.0047   -1.8161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3483   -1.3778    0.8584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1089    1.2632   -0.9336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0224    0.9537    1.7017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1241    2.2762    1.6024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1047    1.8692   -2.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0054    0.5386   -2.5155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5581   -1.9277    0.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9621   -4.1540    1.5258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8559   -3.2050    1.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4629    1.4570    0.5884 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7245    0.6896    1.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1501    1.7187   -1.2102 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8464    2.2972    0.2976 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  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 15 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  2  0
 12 30  1  0
 30 31  1  0
  6  2  1  0
 31  9  1  0
 29 13  1  0
 22 16  1  0
 29 23  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  7 37  1  0
  7 38  1  0
  8 39  1  0
  8 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 14 46  1  0
 17 47  1  0
 18 48  1  0
 21 49  1  0
 22 50  1  0
 24 51  1  0
 25 52  1  0
 28 53  1  0
 30 54  1  0
 30 55  1  0
 31 56  1  0
 31 57  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       3.080  -0.637   0.000  0.00  0.00          Cl+0
HETATM    2  F   UNK     0      10.452  -9.272   0.000  0.00  0.00           F+0
HETATM    3  O   UNK     0      15.147   6.265   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       9.974   3.454   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       8.538  -3.417   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      12.437   6.699   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      13.905   8.712   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       9.017   0.526   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.988   1.672   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.524   0.843   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.467   3.136   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.002   2.307   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.538  -0.938   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.452   4.917   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081  -1.407   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.959   5.235   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.437  -2.177   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.081  -2.947   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.534   7.946   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.747  -0.637   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.442   9.191   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.747  -3.717   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.017  -4.880   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.903   7.172   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.414  -1.407   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.414  -2.947   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.524  -5.198   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.988  -6.027   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.002  -6.662   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.467  -7.491   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.974  -7.808   0.000  0.00  0.00           C+0
CONECT    1   25                                                            
CONECT    2   31                                                            
CONECT    3   24                                                            
CONECT    4   11   12   14                                                  
CONECT    5   17   18   23                                                  
CONECT    6   16   19   24                                                  
CONECT    7   21   24                                                       
CONECT    8    9   10   13                                                  
CONECT    9    8   11                                                       
CONECT   10    8   12                                                       
CONECT   11    4    9                                                       
CONECT   12    4   10                                                       
CONECT   13    8   15   17                                                  
CONECT   14    4   16                                                       
CONECT   15   13   18   20                                                  
CONECT   16    6   14                                                       
CONECT   17    5   13                                                       
CONECT   18    5   15   22                                                  
CONECT   19    6   21                                                       
CONECT   20   15   25                                                       
CONECT   21    7   19                                                       
CONECT   22   18   26                                                       
CONECT   23    5   27   28                                                  
CONECT   24    3    6    7                                                  
CONECT   25    1   20   26                                                  
CONECT   26   22   25                                                       
CONECT   27   23   29                                                       
CONECT   28   23   30                                                       
CONECT   29   27   31                                                       
CONECT   30   28   31                                                       
CONECT   31    2   29   30                                                  
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

COMPND    HMDB0015618
HETATM    1  O1  UNL     1       4.902   1.659  -2.519  1.00  0.00           O  
HETATM    2  C1  UNL     1       5.422   0.973  -1.606  1.00  0.00           C  
HETATM    3  N1  UNL     1       6.188  -0.227  -1.870  1.00  0.00           N  
HETATM    4  C2  UNL     1       7.098  -0.366  -0.737  1.00  0.00           C  
HETATM    5  C3  UNL     1       6.602   0.561   0.323  1.00  0.00           C  
HETATM    6  N2  UNL     1       5.380   1.194  -0.243  1.00  0.00           N  
HETATM    7  C4  UNL     1       4.409   1.882   0.620  1.00  0.00           C  
HETATM    8  C5  UNL     1       3.365   0.776   0.921  1.00  0.00           C  
HETATM    9  N3  UNL     1       2.691   0.523  -0.358  1.00  0.00           N  
HETATM   10  C6  UNL     1       2.269  -0.838  -0.524  1.00  0.00           C  
HETATM   11  C7  UNL     1       0.847  -0.779  -1.124  1.00  0.00           C  
HETATM   12  C8  UNL     1       0.000  -0.645   0.130  1.00  0.00           C  
HETATM   13  C9  UNL     1      -1.451  -0.641  -0.051  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.358   0.311  -0.468  1.00  0.00           C  
HETATM   15  N4  UNL     1      -3.623  -0.073  -0.232  1.00  0.00           N  
HETATM   16  C11 UNL     1      -4.840   0.642  -0.389  1.00  0.00           C  
HETATM   17  C12 UNL     1      -5.472   1.157   0.757  1.00  0.00           C  
HETATM   18  C13 UNL     1      -6.649   1.901   0.678  1.00  0.00           C  
HETATM   19  C14 UNL     1      -7.248   2.164  -0.530  1.00  0.00           C  
HETATM   20  F1  UNL     1      -8.376   2.898  -0.611  1.00  0.00           F  
HETATM   21  C15 UNL     1      -6.620   1.659  -1.643  1.00  0.00           C  
HETATM   22  C16 UNL     1      -5.452   0.920  -1.587  1.00  0.00           C  
HETATM   23  C17 UNL     1      -3.546  -1.301   0.336  1.00  0.00           C  
HETATM   24  C18 UNL     1      -4.526  -2.218   0.730  1.00  0.00           C  
HETATM   25  C19 UNL     1      -4.199  -3.475   1.237  1.00  0.00           C  
HETATM   26  C20 UNL     1      -2.859  -3.785   1.334  1.00  0.00           C  
HETATM   27 CL1  UNL     1      -2.406  -5.361   1.949  1.00  0.00          CL  
HETATM   28  C21 UNL     1      -1.868  -2.908   0.957  1.00  0.00           C  
HETATM   29  C22 UNL     1      -2.257  -1.659   0.455  1.00  0.00           C  
HETATM   30  C23 UNL     1       0.434   0.779   0.649  1.00  0.00           C  
HETATM   31  C24 UNL     1       1.464   1.370  -0.229  1.00  0.00           C  
HETATM   32  H1  UNL     1       6.128  -0.870  -2.667  1.00  0.00           H  
HETATM   33  H2  UNL     1       7.154  -1.401  -0.352  1.00  0.00           H  
HETATM   34  H3  UNL     1       8.092  -0.044  -1.105  1.00  0.00           H  
HETATM   35  H4  UNL     1       7.361   1.372   0.496  1.00  0.00           H  
HETATM   36  H5  UNL     1       6.300   0.084   1.281  1.00  0.00           H  
HETATM   37  H6  UNL     1       3.986   2.703   0.050  1.00  0.00           H  
HETATM   38  H7  UNL     1       4.873   2.281   1.518  1.00  0.00           H  
HETATM   39  H8  UNL     1       3.898  -0.111   1.287  1.00  0.00           H  
HETATM   40  H9  UNL     1       2.679   1.125   1.710  1.00  0.00           H  
HETATM   41  H10 UNL     1       2.187  -1.384   0.427  1.00  0.00           H  
HETATM   42  H11 UNL     1       2.887  -1.430  -1.194  1.00  0.00           H  
HETATM   43  H12 UNL     1       0.592  -1.822  -1.522  1.00  0.00           H  
HETATM   44  H13 UNL     1       0.676   0.005  -1.816  1.00  0.00           H  
HETATM   45  H14 UNL     1       0.348  -1.378   0.858  1.00  0.00           H  
HETATM   46  H15 UNL     1      -2.109   1.263  -0.934  1.00  0.00           H  
HETATM   47  H16 UNL     1      -5.022   0.954   1.702  1.00  0.00           H  
HETATM   48  H17 UNL     1      -7.124   2.276   1.602  1.00  0.00           H  
HETATM   49  H18 UNL     1      -7.105   1.869  -2.609  1.00  0.00           H  
HETATM   50  H19 UNL     1      -5.005   0.539  -2.516  1.00  0.00           H  
HETATM   51  H20 UNL     1      -5.558  -1.928   0.639  1.00  0.00           H  
HETATM   52  H21 UNL     1      -4.962  -4.154   1.526  1.00  0.00           H  
HETATM   53  H22 UNL     1      -0.856  -3.205   1.043  1.00  0.00           H  
HETATM   54  H23 UNL     1      -0.463   1.457   0.588  1.00  0.00           H  
HETATM   55  H24 UNL     1       0.724   0.690   1.675  1.00  0.00           H  
HETATM   56  H25 UNL     1       1.150   1.719  -1.210  1.00  0.00           H  
HETATM   57  H26 UNL     1       1.846   2.297   0.298  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    6
CONECT    3    4   32
CONECT    4    5   33   34
CONECT    5    6   35   36
CONECT    6    7
CONECT    7    8   37   38
CONECT    8    9   39   40
CONECT    9   10   31
CONECT   10   11   41   42
CONECT   11   12   43   44
CONECT   12   13   30   45
CONECT   13   14   14   29
CONECT   14   15   46
CONECT   15   16   23
CONECT   16   17   17   22
CONECT   17   18   47
CONECT   18   19   19   48
CONECT   19   20   21
CONECT   21   22   22   49
CONECT   22   50
CONECT   23   24   24   29
CONECT   24   25   51
CONECT   25   26   26   52
CONECT   26   27   28
CONECT   28   29   29   53
CONECT   30   31   54   55
CONECT   31   56   57
END

HMDB0015618
     RDKit          3D
Sertindole
 57 61  0  0  0  0  0  0  0  0999 V2000
    4.9017    1.6587   -2.5190 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4218    0.9733   -1.6062 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1880   -0.2272   -1.8697 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0979   -0.3655   -0.7369 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6022    0.5610    0.3225 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3804    1.1945   -0.2430 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4087    1.8818    0.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3648    0.7763    0.9207 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6915    0.5230   -0.3576 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2688   -0.8384   -0.5240 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8474   -0.7785   -1.1239 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0004   -0.6448    0.1302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4511   -0.6406   -0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3580    0.3106   -0.4683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6232   -0.0734   -0.2325 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8399    0.6422   -0.3890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4719    1.1568    0.7573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6494    1.9014    0.6782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2476    2.1638   -0.5301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3760    2.8984   -0.6108 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6197    1.6594   -1.6430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4521    0.9199   -1.5866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5456   -1.3012    0.3356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5262   -2.2180    0.7301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1988   -3.4755    1.2372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8586   -3.7848    1.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4056   -5.3605    1.9489 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.8682   -2.9082    0.9566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2566   -1.6588    0.4552 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4344    0.7791    0.6487 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4642    1.3699   -0.2294 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1279   -0.8703   -2.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1535   -1.4012   -0.3518 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0921   -0.0439   -1.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3612    1.3721    0.4957 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2997    0.0837    1.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9861    2.7027    0.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8725    2.2813    1.5181 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8977   -0.1108    1.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6793    1.1245    1.7098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1869   -1.3844    0.4267 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8873   -1.4298   -1.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5918   -1.8222   -1.5216 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6760    0.0047   -1.8161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3483   -1.3778    0.8584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1089    1.2632   -0.9336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0224    0.9537    1.7017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1241    2.2762    1.6024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1047    1.8692   -2.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0054    0.5386   -2.5155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5581   -1.9277    0.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9621   -4.1540    1.5258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8559   -3.2050    1.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4629    1.4570    0.5884 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7245    0.6896    1.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1501    1.7187   -1.2102 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8464    2.2972    0.2976 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  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 15 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  2  0
 12 30  1  0
 30 31  1  0
  6  2  1  0
 31  9  1  0
 29 13  1  0
 22 16  1  0
 29 23  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  7 37  1  0
  7 38  1  0
  8 39  1  0
  8 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 14 46  1  0
 17 47  1  0
 18 48  1  0
 21 49  1  0
 22 50  1  0
 24 51  1  0
 25 52  1  0
 28 53  1  0
 30 54  1  0
 30 55  1  0
 31 56  1  0
 31 57  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-[2-[4-[5-Chloro-1-(4-fluorophenyl)-indol-3-yl]-1-piperidyl]ethyl]imidazolidin-2-one	ChEBI
Serdolect	ChEBI
SerLect	ChEBI
Sertindol	ChEBI
Sertindolum	ChEBI
Sertindole hydrochloride	HMDB
1-(2-(4-(5-Chloro-1-(4-fluorophenyl)-1H-indol-3-yl)-1-piperidinyl)ethyl)-2-imidazolidinone	HMDB

Chemical Formula

C₂₄H₂₆ClFN₄O

Average Molecular Weight

440.941

Monoisotopic Molecular Weight

440.177917386

IUPAC Name

1-(2-{4-[5-chloro-1-(4-fluorophenyl)-1H-indol-3-yl]piperidin-1-yl}ethyl)imidazolidin-2-one

Traditional Name

sertindole

CAS Registry Number

106516-24-9

SMILES

FC1=CC=C(C=C1)N1C=C(C2CCN(CCN3CCNC3=O)CC2)C2=C1C=CC(Cl)=C2

InChI Identifier

InChI=1S/C24H26ClFN4O/c25-18-1-6-23-21(15-18)22(16-30(23)20-4-2-19(26)3-5-20)17-7-10-28(11-8-17)13-14-29-12-9-27-24(29)31/h1-6,15-17H,7-14H2,(H,27,31)

InChI Key

GZKLJWGUPQBVJQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpyrroles. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrole ring through a CC or CN bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrroles

Sub Class

Substituted pyrroles

Direct Parent

Phenylpyrroles

Alternative Parents

Substituents

1-phenylpyrrole
3-alkylindole
Indole
Indole or derivatives
Fluorobenzene
Halobenzene
Aralkylamine
Aryl chloride
Aryl fluoride
Aryl halide
Monocyclic benzene moiety
Imidazolidinone
Piperidine
Benzenoid
Heteroaromatic compound
Imidazolidine
Urea
Tertiary aliphatic amine
Tertiary amine
Carbonic acid derivative
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Amine
Organohalogen compound
Organic oxygen compound
Organic nitrogen compound
Organochloride
Organofluoride
Organonitrogen compound
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organofluorine compound (CHEBI:9122 )
organochlorine compound (CHEBI:9122 )
imidazolidinone (CHEBI:9122 )
heteroarylpiperidine (CHEBI:9122 )
phenylindole (CHEBI:9122 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015618)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0096 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0096 g/L	ALOGPS
logP	4.29	ALOGPS
logP	3.77	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	14.36	ChemAxon
pKa (Strongest Basic)	8.59	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	40.51 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	131.77 m³·mol⁻¹	ChemAxon
Polarizability	47.17 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	202.755	30932474
DeepCCS	[M-H]-	200.397	30932474
DeepCCS	[M-2H]-	234.645	30932474
DeepCCS	[M+Na]+	209.873	30932474
AllCCS	[M+H]+	203.0	32859911
AllCCS	[M+H-H2O]+	200.8	32859911
AllCCS	[M+NH4]+	205.0	32859911
AllCCS	[M+Na]+	205.6	32859911
AllCCS	[M-H]-	200.5	32859911
AllCCS	[M+Na-2H]-	200.7	32859911
AllCCS	[M+HCOO]-	201.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sertindole	FC1=CC=C(C=C1)N1C=C(C2CCN(CCN3CCNC3=O)CC2)C2=C1C=CC(Cl)=C2	4908.7	Standard polar	33892256
Sertindole	FC1=CC=C(C=C1)N1C=C(C2CCN(CCN3CCNC3=O)CC2)C2=C1C=CC(Cl)=C2	3882.9	Standard non polar	33892256
Sertindole	FC1=CC=C(C=C1)N1C=C(C2CCN(CCN3CCNC3=O)CC2)C2=C1C=CC(Cl)=C2	4088.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Sertindole,1TMS,isomer #1	C[Si](C)(C)N1CCN(CCN2CCC(C3=CN(C4=CC=C(F)C=C4)C4=CC=C(Cl)C=C34)CC2)C1=O	3747.3	Semi standard non polar	33892256
Sertindole,1TMS,isomer #1	C[Si](C)(C)N1CCN(CCN2CCC(C3=CN(C4=CC=C(F)C=C4)C4=CC=C(Cl)C=C34)CC2)C1=O	3670.5	Standard non polar	33892256
Sertindole,1TMS,isomer #1	C[Si](C)(C)N1CCN(CCN2CCC(C3=CN(C4=CC=C(F)C=C4)C4=CC=C(Cl)C=C34)CC2)C1=O	4787.5	Standard polar	33892256
Sertindole,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN(CCN2CCC(C3=CN(C4=CC=C(F)C=C4)C4=CC=C(Cl)C=C34)CC2)C1=O	3951.6	Semi standard non polar	33892256
Sertindole,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN(CCN2CCC(C3=CN(C4=CC=C(F)C=C4)C4=CC=C(Cl)C=C34)CC2)C1=O	3857.6	Standard non polar	33892256
Sertindole,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN(CCN2CCC(C3=CN(C4=CC=C(F)C=C4)C4=CC=C(Cl)C=C34)CC2)C1=O	4840.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Sertindole GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9316000000-4bb52e2e5e8e2a9184d6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sertindole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sertindole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sertindole 10V, Positive-QTOF	splash10-0006-1102900000-e335eb6b5c8c8eef4ad5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sertindole 20V, Positive-QTOF	splash10-0bt9-9608100000-46bf4f0a0cb438e48d2d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sertindole 40V, Positive-QTOF	splash10-05n3-9102000000-c2f828835f177b419d84	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sertindole 10V, Negative-QTOF	splash10-000i-2002900000-d0dc328638ffb9d02e6e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sertindole 20V, Negative-QTOF	splash10-000f-9006500000-81edac274ee530e66a04	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sertindole 40V, Negative-QTOF	splash10-0006-9000000000-f6bff0a5529034a8c762	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sertindole 10V, Positive-QTOF	splash10-0006-0000900000-b94ed5b6a2bb56ffd763	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sertindole 20V, Positive-QTOF	splash10-0006-0306900000-ea94866f94a9c7569ff8	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sertindole 40V, Positive-QTOF	splash10-074r-9417200000-c67920dfb0cb81309e4a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sertindole 10V, Negative-QTOF	splash10-000i-0000900000-1eb0a7d6abf1ae0f18be	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sertindole 20V, Negative-QTOF	splash10-0019-8006900000-ac9fbc1ceebafe4be96e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sertindole 40V, Negative-QTOF	splash10-001i-9002000000-7ad68bf9c03599f52b43	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 DB06144	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB06144	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB06144

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

54229

KEGG Compound ID

C07567

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sertindole

METLIN ID

Not Available

PubChem Compound

60149

PDB ID

Not Available

ChEBI ID

9122

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

Hertel P: Comparing sertindole to other new generation antipsychotics on preferential dopamine output in limbic versus striatal projection regions: mechanism of action. Synapse. 2006 Dec 1;60(7):543-52. [PubMed:16952163 ]
Lindstrom E, Levander S: Sertindole: efficacy and safety in schizophrenia. Expert Opin Pharmacother. 2006 Sep;7(13):1825-34. [PubMed:16925508 ]
Kane JM, Tamminga CA: Sertindole (Serdolect): preclinical and clinical findings of a new atypical antipsychotic. Expert Opin Investig Drugs. 1997 Nov;6(11):1729-41. [PubMed:15989577 ]
Lewis R, Bagnall AM, Leitner M: Sertindole for schizophrenia. Cochrane Database Syst Rev. 2005 Jul 20;(3):CD001715. [PubMed:16034864 ]
Perquin LN: Treatment with the new antipsychotic sertindole for late-occurring undesirable movement effects. Int Clin Psychopharmacol. 2005 Nov;20(6):335-8. [PubMed:16192844 ]
Murdoch D, Keating GM: Sertindole : a review of its use in schizophrenia. CNS Drugs. 2006;20(3):233-55. [PubMed:16529528 ]
Authors unspecified: Sertindole: new drug. Another "atypical" neuroleptic; QT prolongation. Prescrire Int. 2007 Apr;16(88):59-62. [PubMed:17458045 ]

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

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

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. D(2) dopamine receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:: DRD2
Uniprot ID:: P14416
Molecular weight:: 50618.9

References

Lindstrom E, Levander S: Sertindole: efficacy and safety in schizophrenia. Expert Opin Pharmacother. 2006 Sep;7(13):1825-34. [PubMed:16925508 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Mork A, Witten LM, Arnt J: Effect of sertindole on extracellular dopamine, acetylcholine, and glutamate in the medial prefrontal cortex of conscious rats: a comparison with risperidone and exploration of mechanisms involved. Psychopharmacology (Berl). 2009 Sep;206(1):39-49. doi: 10.1007/s00213-009-1578-4. Epub 2009 Jun 9. [PubMed:19506838 ]
Seeman P: Dopamine D2(High) receptors moderately elevated by sertindole. Synapse. 2008 May;62(5):389-93. doi: 10.1002/syn.20498. [PubMed:18293356 ]
Cincotta SL, Rodefer JS: Emerging role of sertindole in the management of schizophrenia. Neuropsychiatr Dis Treat. 2010 Sep 7;6:429-41. [PubMed:20856607 ]

Enzyme Details

4. Potassium voltage-gated channel subfamily H member 2

General function:: Involved in ion channel activity
Specific function:: Pore-forming (alpha) subunit of voltage-gated inwardly rectifying potassium channel. Channel properties are modulated by cAMP and subunit assembly. Mediates the rapidly activating component of the delayed rectifying potassium current in heart (IKr). Isoform 3 has no channel activity by itself, but modulates channel characteristics when associated with isoform 1
Gene Name:: KCNH2
Uniprot ID:: Q12809
Molecular weight:: 126653.5

References

Rampe D, Murawsky MK, Grau J, Lewis EW: The antipsychotic agent sertindole is a high affinity antagonist of the human cardiac potassium channel HERG. J Pharmacol Exp Ther. 1998 Aug;286(2):788-93. [PubMed:9694935 ]
Kang J, Chen XL, Rampe D: The antipsychotic drugs sertindole and pimozide block erg3, a human brain K(+) channel. Biochem Biophys Res Commun. 2001 Aug 24;286(3):499-504. [PubMed:11511086 ]
Tang W, Kang J, Wu X, Rampe D, Wang L, Shen H, Li Z, Dunnington D, Garyantes T: Development and evaluation of high throughput functional assay methods for HERG potassium channel. J Biomol Screen. 2001 Oct;6(5):325-31. [PubMed:11689132 ]

Enzyme Details

5. 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

Lindstrom E, Levander S: Sertindole: efficacy and safety in schizophrenia. Expert Opin Pharmacother. 2006 Sep;7(13):1825-34. [PubMed:16925508 ]
Schreiber R, Brocco M, Millan MJ: Blockade of the discriminative stimulus effects of DOI by MDL 100,907 and the 'atypical' antipsychotics, clozapine and risperidone. Eur J Pharmacol. 1994 Oct 13;264(1):99-102. [PubMed:7530204 ]
Hietala J, Kuonnamaki M, Palvimaki EP, Laakso A, Majasuo H, Syvalahti E: Sertindole is a serotonin 5-HT2c inverse agonist and decreases agonist but not antagonist binding to 5-HT2c receptors after chronic treatment. Psychopharmacology (Berl). 2001 Sep;157(2):180-7. [PubMed:11594443 ]

Enzyme Details

6. 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

Lindstrom E, Levander S: Sertindole: efficacy and safety in schizophrenia. Expert Opin Pharmacother. 2006 Sep;7(13):1825-34. [PubMed:16925508 ]
Hietala J, Kuonnamaki M, Palvimaki EP, Laakso A, Majasuo H, Syvalahti E: Sertindole is a serotonin 5-HT2c inverse agonist and decreases agonist but not antagonist binding to 5-HT2c receptors after chronic treatment. Psychopharmacology (Berl). 2001 Sep;157(2):180-7. [PubMed:11594443 ]

Enzyme Details

7. 5-hydroxytryptamine receptor 6

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that stimulate adenylate cyclase. It has a high affinity for tricyclic psychotropic drugs
Gene Name:: HTR6
Uniprot ID:: P50406
Molecular weight:: 46953.6

References

Pouzet B, Didriksen M, Arnt J: Effects of the 5-HT(6) receptor antagonist, SB-271046, in animal models for schizophrenia. Pharmacol Biochem Behav. 2002 Apr;71(4):635-43. [PubMed:11888555 ]
Mork A, Witten LM, Arnt J: Effect of sertindole on extracellular dopamine, acetylcholine, and glutamate in the medial prefrontal cortex of conscious rats: a comparison with risperidone and exploration of mechanisms involved. Psychopharmacology (Berl). 2009 Sep;206(1):39-49. doi: 10.1007/s00213-009-1578-4. Epub 2009 Jun 9. [PubMed:19506838 ]

Enzyme Details

8. 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

Lindstrom E, Levander S: Sertindole: efficacy and safety in schizophrenia. Expert Opin Pharmacother. 2006 Sep;7(13):1825-34. [PubMed:16925508 ]
Hietala J, Kuonnamaki M, Palvimaki EP, Laakso A, Majasuo H, Syvalahti E: Sertindole is a serotonin 5-HT2c inverse agonist and decreases agonist but not antagonist binding to 5-HT2c receptors after chronic treatment. Psychopharmacology (Berl). 2001 Sep;157(2):180-7. [PubMed:11594443 ]

Enzyme Details

9. Alpha-1B 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
Gene Name:: ADRA1B
Uniprot ID:: P35368
Molecular weight:: 56835.4

References

Lindstrom E, Levander S: Sertindole: efficacy and safety in schizophrenia. Expert Opin Pharmacother. 2006 Sep;7(13):1825-34. [PubMed:16925508 ]

Enzyme Details

10. Alpha-1D adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This alpha-adrenergic receptor mediates its effect through the influx of extracellular calcium
Gene Name:: ADRA1D
Uniprot ID:: P25100
Molecular weight:: 60462.2

References

Lindstrom E, Levander S: Sertindole: efficacy and safety in schizophrenia. Expert Opin Pharmacother. 2006 Sep;7(13):1825-34. [PubMed:16925508 ]

Showing metabocard for Sertindole (HMDB0015618)

MOL for HMDB0015618 (Sertindole)

3D MOL for HMDB0015618 (Sertindole)

3D SDF for HMDB0015618 (Sertindole)

3D-SDF for HMDB0015618 (Sertindole)

PDB for HMDB0015618 (Sertindole)

3D PDB for HMDB0015618 (Sertindole)

SMILES for HMDB0015618 (Sertindole)

INCHI for HMDB0015618 (Sertindole)

Structure for HMDB0015618 (Sertindole)

3D Structure for HMDB0015618 (Sertindole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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