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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-10-17 09:02:18 UTC

Update Date

2022-03-07 02:49:25 UTC

HMDB ID

HMDB0005021

Secondary Accession Numbers

HMDB05021

Metabolite Identification

Common Name

Quetiapine

Description

The most common side effect is sedation, and is prescribed specifically for this effect in patients with sleep disorders. Seroquel will put the patient into a drowsy state, and will help the patient fall asleep. It is one of the most sedating of all anti psychotic drugs, rivaling even the most sedating older antipsychotics. Many prescriptions call for the entire dose to be taken before bedtime because of its sedative effects. Although quetiapine is approved by the FDA for the treatment of schizophrenia and bipolar disorder, it is frequently prescribed for off-label purposes including insomnia or the treatment of anxiety disorders. Due to its sedative side effects, reports of quetiapine abuse (sometimes by insufflating crushed tablets) have emerged in medical literature; Quetiapine belongs to a series of neuroleptics known as "atypical antipsychotics", which have become increasingly popular alternatives to "typical antipsychotics" such as haloperidol. Quetiapine HAS approvals for the treatment of schizophrenia and acute mania in bipolar disorder. It is also used off-label to treat other disorders, such as post-traumatic stress disorder, alcoholism, obsessive compulsive disorder, anxiety disorders, hallucinations in Parkinson's disease patients using ropinirole, and as a sedative for those with sleep disorders. The most common side effect is sedation, and is prescribed specifically for this effect in patients with sleep disorders. Seroquel will put the patient into a drowsy state, and will help the patient fall asleep. It is one of the most sedating of all anti psychotic drugs, rivaling even the most sedating older antipsychotics. Many prescriptions call for the entire dose to be taken before bedtime because of its sedative effects. Although quetiapine is approved by the FDA for the treatment of schizophrenia and bipolar disorder, it is frequently prescribed for off-label purposes including insomnia or the treatment of anxiety disorders. Due to its sedative side effects, reports of quetiapine abuse (sometimes by insufflating crushed tablets) have emerged in medical literature; for the same reason, abuse of other antipsychotics, such as chlorpromazine (Thorazine), may occur as well, but research related to the abuse of typical antipsychotics is limited. for the same reason, abuse of other antipsychotics, such as chlorpromazine (Thorazine), may occur as well, but research related to the abuse of typical antipsychotics is limited.

Structure

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

1224
  Mrv0541 02231215202D          

 27 30  0  0  0  0            999 V2000
    4.0279   -4.2678    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.2907    1.9368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8621    4.0431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5418   -0.2312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2576   -1.7175    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4403   -2.4607    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0772   -0.9126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3643   -0.2928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4349   -1.6558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7223   -1.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1839    0.5120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6154   -2.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6485    1.1936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1012   -3.1056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2847   -3.9098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2841   -2.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9547   -3.1056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7711   -3.9099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6639   -4.5038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7554    2.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6497   -3.4193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8410   -4.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7717   -2.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3918   -4.5038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3974    3.3615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4060   -3.4193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2148   -4.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 15  1  0  0  0  0
  1 18  1  0  0  0  0
  2 13  1  0  0  0  0
  2 20  1  0  0  0  0
  3 25  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  4 11  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 12  1  0  0  0  0
  6 12  2  0  0  0  0
  6 17  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 15 19  2  0  0  0  0
 16 21  1  0  0  0  0
 17 18  1  0  0  0  0
 17 23  2  0  0  0  0
 18 24  2  0  0  0  0
 19 22  1  0  0  0  0
 20 25  1  0  0  0  0
 21 22  2  0  0  0  0
 23 26  1  0  0  0  0
 24 27  1  0  0  0  0
 26 27  2  0  0  0  0
M  END

HMDB0005021
     RDKit          3D
Quetiapine
 52 55  0  0  0  0  0  0  0  0999 V2000
    6.0550   -0.6919   -1.2374 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8296   -0.2021   -0.1967 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5379    1.2057    0.1991 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3935    1.5695    0.6614 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1855    1.3946    0.2101 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4759    0.0810    0.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1566    0.1610   -0.2644 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3302    1.0242    0.5123 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1005    0.2885    1.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6072   -0.2817   -0.0563 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0309   -0.1689   -0.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5043    1.0026   -0.2526 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8116    1.5074   -0.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9100    2.8648   -0.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0906    3.5476   -0.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2341    2.8768   -0.4459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1567    1.5410   -0.7733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9489    0.8680   -0.7256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2119   -0.8319   -1.2043 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9624   -1.8559   -0.4368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4459   -3.1325   -0.2844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6246   -4.0973    0.2943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3556   -3.7075    0.6850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8939   -2.4118    0.5185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7132   -1.4526   -0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1825   -0.9461   -1.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5827   -1.1266   -0.4958 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9862    0.0596   -1.9065 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6627   -0.8412    0.7228 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8933   -0.2918   -0.5288 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3780    1.4810    0.9617 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8673    1.8761   -0.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0951    1.6231   -0.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5096    2.2301    0.6271 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0320   -0.7872    0.1015 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2173   -0.0132    1.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8285    1.4949    1.3839 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9386    1.8278   -0.1268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4920    1.0601    1.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4023   -0.4511    1.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9829    3.3507    0.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1609    4.6163    0.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1625    3.4327   -0.4748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0880    1.0352   -1.0721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4431   -3.4264   -0.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9690   -5.1135    0.4343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7309   -4.4725    1.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8904   -2.1896    0.8488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2481   -1.8928   -1.4320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2902   -0.2157   -1.9242 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1669   -1.7463   -1.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5717   -1.6724    0.4656 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 10 26  1  0
 26 27  1  0
 27  7  1  0
 25 11  1  0
 18 13  1  0
 25 20  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 14 41  1  0
 15 42  1  0
 16 43  1  0
 17 44  1  0
 21 45  1  0
 22 46  1  0
 23 47  1  0
 24 48  1  0
 26 49  1  0
 26 50  1  0
 27 51  1  0
 27 52  1  0
M  END

1224
  Mrv0541 02231215202D          

 27 30  0  0  0  0            999 V2000
    4.0279   -4.2678    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.2907    1.9368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8621    4.0431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5418   -0.2312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2576   -1.7175    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4403   -2.4607    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0772   -0.9126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3643   -0.2928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4349   -1.6558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7223   -1.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1839    0.5120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6154   -2.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6485    1.1936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1012   -3.1056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2847   -3.9098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2841   -2.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9547   -3.1056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7711   -3.9099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6639   -4.5038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7554    2.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6497   -3.4193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8410   -4.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7717   -2.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3918   -4.5038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3974    3.3615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4060   -3.4193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2148   -4.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 15  1  0  0  0  0
  1 18  1  0  0  0  0
  2 13  1  0  0  0  0
  2 20  1  0  0  0  0
  3 25  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  4 11  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 12  1  0  0  0  0
  6 12  2  0  0  0  0
  6 17  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 15 19  2  0  0  0  0
 16 21  1  0  0  0  0
 17 18  1  0  0  0  0
 17 23  2  0  0  0  0
 18 24  2  0  0  0  0
 19 22  1  0  0  0  0
 20 25  1  0  0  0  0
 21 22  2  0  0  0  0
 23 26  1  0  0  0  0
 24 27  1  0  0  0  0
 26 27  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005021

> <DATABASE_NAME>
hmdb

> <SMILES>
OCCOCCN1CCN(CC1)C1=NC2=CC=CC=C2SC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C21H25N3O2S/c25-14-16-26-15-13-23-9-11-24(12-10-23)21-17-5-1-3-7-19(17)27-20-8-4-2-6-18(20)22-21/h1-8,25H,9-16H2

> <INCHI_KEY>
URKOMYMAXPYINW-UHFFFAOYSA-N

> <FORMULA>
C21H25N3O2S

> <MOLECULAR_WEIGHT>
383.507

> <EXACT_MASS>
383.166747749

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
42.78085656642276

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[2-(4-{2-thia-9-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,9,11,13-heptaen-10-yl}piperazin-1-yl)ethoxy]ethan-1-ol

> <ALOGPS_LOGP>
2.93

> <JCHEM_LOGP>
2.8079425159999998

> <ALOGPS_LOGS>
-3.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.121227695042847

> <JCHEM_PKA_STRONGEST_BASIC>
7.064644323860867

> <JCHEM_POLAR_SURFACE_AREA>
48.300000000000004

> <JCHEM_REFRACTIVITY>
114.08540000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.03e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
quetiapine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0005021
     RDKit          3D
Quetiapine
 52 55  0  0  0  0  0  0  0  0999 V2000
    6.0550   -0.6919   -1.2374 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8296   -0.2021   -0.1967 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5379    1.2057    0.1991 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3935    1.5695    0.6614 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1855    1.3946    0.2101 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4759    0.0810    0.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1566    0.1610   -0.2644 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3302    1.0242    0.5123 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1005    0.2885    1.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6072   -0.2817   -0.0563 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0309   -0.1689   -0.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5043    1.0026   -0.2526 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8116    1.5074   -0.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9100    2.8648   -0.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0906    3.5476   -0.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2341    2.8768   -0.4459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1567    1.5410   -0.7733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9489    0.8680   -0.7256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2119   -0.8319   -1.2043 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9624   -1.8559   -0.4368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4459   -3.1325   -0.2844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6246   -4.0973    0.2943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3556   -3.7075    0.6850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8939   -2.4118    0.5185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7132   -1.4526   -0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1825   -0.9461   -1.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5827   -1.1266   -0.4958 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9862    0.0596   -1.9065 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6627   -0.8412    0.7228 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8933   -0.2918   -0.5288 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3780    1.4810    0.9617 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8673    1.8761   -0.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0951    1.6231   -0.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5096    2.2301    0.6271 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0320   -0.7872    0.1015 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2173   -0.0132    1.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8285    1.4949    1.3839 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9386    1.8278   -0.1268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4920    1.0601    1.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4023   -0.4511    1.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9829    3.3507    0.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1609    4.6163    0.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1625    3.4327   -0.4748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0880    1.0352   -1.0721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4431   -3.4264   -0.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9690   -5.1135    0.4343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7309   -4.4725    1.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8904   -2.1896    0.8488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2481   -1.8928   -1.4320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2902   -0.2157   -1.9242 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1669   -1.7463   -1.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5717   -1.6724    0.4656 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 10 26  1  0
 26 27  1  0
 27  7  1  0
 25 11  1  0
 18 13  1  0
 25 20  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 14 41  1  0
 15 42  1  0
 16 43  1  0
 17 44  1  0
 21 45  1  0
 22 46  1  0
 23 47  1  0
 24 48  1  0
 26 49  1  0
 26 50  1  0
 27 51  1  0
 27 52  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1224                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       7.519  -7.966   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       4.276   3.615   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       5.343   7.547   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       4.745  -0.432   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       6.081  -3.206   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       8.289  -4.593   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       3.877  -1.704   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.280  -0.547   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.545  -3.091   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.948  -1.934   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.077   0.956   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.749  -4.593   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.944   2.228   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.789  -5.797   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.131  -7.298   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.264  -5.301   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.249  -5.797   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.906  -7.298   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.973  -8.407   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.143   4.888   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.079  -6.383   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.437  -7.946   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.774  -5.301   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.065  -8.407   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.475   6.275   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.958  -6.383   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.601  -7.946   0.000  0.00  0.00           C+0
CONECT    1   15   18                                                       
CONECT    2   13   20                                                       
CONECT    3   25                                                            
CONECT    4    7    8   11                                                  
CONECT    5    9   10   12                                                  
CONECT    6   12   17                                                       
CONECT    7    4    9                                                       
CONECT    8    4   10                                                       
CONECT    9    5    7                                                       
CONECT   10    5    8                                                       
CONECT   11    4   13                                                       
CONECT   12    5    6   14                                                  
CONECT   13    2   11                                                       
CONECT   14   12   15   16                                                  
CONECT   15    1   14   19                                                  
CONECT   16   14   21                                                       
CONECT   17    6   18   23                                                  
CONECT   18    1   17   24                                                  
CONECT   19   15   22                                                       
CONECT   20    2   25                                                       
CONECT   21   16   22                                                       
CONECT   22   19   21                                                       
CONECT   23   17   26                                                       
CONECT   24   18   27                                                       
CONECT   25    3   20                                                       
CONECT   26   23   27                                                       
CONECT   27   24   26                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

COMPND    HMDB0005021
HETATM    1  O1  UNL     1       6.055  -0.692  -1.237  1.00  0.00           O  
HETATM    2  C1  UNL     1       6.830  -0.202  -0.197  1.00  0.00           C  
HETATM    3  C2  UNL     1       6.538   1.206   0.199  1.00  0.00           C  
HETATM    4  O2  UNL     1       5.394   1.569   0.661  1.00  0.00           O  
HETATM    5  C3  UNL     1       4.186   1.395   0.210  1.00  0.00           C  
HETATM    6  C4  UNL     1       3.476   0.081   0.351  1.00  0.00           C  
HETATM    7  N1  UNL     1       2.157   0.161  -0.264  1.00  0.00           N  
HETATM    8  C5  UNL     1       1.330   1.024   0.512  1.00  0.00           C  
HETATM    9  C6  UNL     1       0.101   0.289   1.068  1.00  0.00           C  
HETATM   10  N2  UNL     1      -0.607  -0.282  -0.056  1.00  0.00           N  
HETATM   11  C7  UNL     1      -2.031  -0.169  -0.132  1.00  0.00           C  
HETATM   12  N3  UNL     1      -2.504   1.003  -0.253  1.00  0.00           N  
HETATM   13  C8  UNL     1      -3.812   1.507  -0.356  1.00  0.00           C  
HETATM   14  C9  UNL     1      -3.910   2.865  -0.027  1.00  0.00           C  
HETATM   15  C10 UNL     1      -5.091   3.548  -0.067  1.00  0.00           C  
HETATM   16  C11 UNL     1      -6.234   2.877  -0.446  1.00  0.00           C  
HETATM   17  C12 UNL     1      -6.157   1.541  -0.773  1.00  0.00           C  
HETATM   18  C13 UNL     1      -4.949   0.868  -0.726  1.00  0.00           C  
HETATM   19  S1  UNL     1      -5.212  -0.832  -1.204  1.00  0.00           S  
HETATM   20  C14 UNL     1      -3.962  -1.856  -0.437  1.00  0.00           C  
HETATM   21  C15 UNL     1      -4.446  -3.132  -0.284  1.00  0.00           C  
HETATM   22  C16 UNL     1      -3.625  -4.097   0.294  1.00  0.00           C  
HETATM   23  C17 UNL     1      -2.356  -3.707   0.685  1.00  0.00           C  
HETATM   24  C18 UNL     1      -1.894  -2.412   0.518  1.00  0.00           C  
HETATM   25  C19 UNL     1      -2.713  -1.453  -0.057  1.00  0.00           C  
HETATM   26  C20 UNL     1       0.183  -0.946  -1.070  1.00  0.00           C  
HETATM   27  C21 UNL     1       1.583  -1.127  -0.496  1.00  0.00           C  
HETATM   28  H1  UNL     1       5.986   0.060  -1.906  1.00  0.00           H  
HETATM   29  H2  UNL     1       6.663  -0.841   0.723  1.00  0.00           H  
HETATM   30  H3  UNL     1       7.893  -0.292  -0.529  1.00  0.00           H  
HETATM   31  H4  UNL     1       7.378   1.481   0.962  1.00  0.00           H  
HETATM   32  H5  UNL     1       6.867   1.876  -0.714  1.00  0.00           H  
HETATM   33  H6  UNL     1       4.095   1.623  -0.929  1.00  0.00           H  
HETATM   34  H7  UNL     1       3.510   2.230   0.627  1.00  0.00           H  
HETATM   35  H8  UNL     1       4.032  -0.787   0.102  1.00  0.00           H  
HETATM   36  H9  UNL     1       3.217  -0.013   1.465  1.00  0.00           H  
HETATM   37  H10 UNL     1       1.829   1.495   1.384  1.00  0.00           H  
HETATM   38  H11 UNL     1       0.939   1.828  -0.127  1.00  0.00           H  
HETATM   39  H12 UNL     1      -0.492   1.060   1.597  1.00  0.00           H  
HETATM   40  H13 UNL     1       0.402  -0.451   1.828  1.00  0.00           H  
HETATM   41  H14 UNL     1      -2.983   3.351   0.263  1.00  0.00           H  
HETATM   42  H15 UNL     1      -5.161   4.616   0.191  1.00  0.00           H  
HETATM   43  H16 UNL     1      -7.162   3.433  -0.475  1.00  0.00           H  
HETATM   44  H17 UNL     1      -7.088   1.035  -1.072  1.00  0.00           H  
HETATM   45  H18 UNL     1      -5.443  -3.426  -0.596  1.00  0.00           H  
HETATM   46  H19 UNL     1      -3.969  -5.113   0.434  1.00  0.00           H  
HETATM   47  H20 UNL     1      -1.731  -4.473   1.135  1.00  0.00           H  
HETATM   48  H21 UNL     1      -0.890  -2.190   0.849  1.00  0.00           H  
HETATM   49  H22 UNL     1      -0.248  -1.893  -1.432  1.00  0.00           H  
HETATM   50  H23 UNL     1       0.290  -0.216  -1.924  1.00  0.00           H  
HETATM   51  H24 UNL     1       2.167  -1.746  -1.207  1.00  0.00           H  
HETATM   52  H25 UNL     1       1.572  -1.672   0.466  1.00  0.00           H  
CONECT    1    2   28
CONECT    2    3   29   30
CONECT    3    4   31   32
CONECT    4    5
CONECT    5    6   33   34
CONECT    6    7   35   36
CONECT    7    8   27
CONECT    8    9   37   38
CONECT    9   10   39   40
CONECT   10   11   26
CONECT   11   12   12   25
CONECT   12   13
CONECT   13   14   14   18
CONECT   14   15   41
CONECT   15   16   16   42
CONECT   16   17   43
CONECT   17   18   18   44
CONECT   18   19
CONECT   19   20
CONECT   20   21   21   25
CONECT   21   22   45
CONECT   22   23   23   46
CONECT   23   24   47
CONECT   24   25   25   48
CONECT   26   27   49   50
CONECT   27   51   52
END

HMDB0005021
     RDKit          3D
Quetiapine
 52 55  0  0  0  0  0  0  0  0999 V2000
    6.0550   -0.6919   -1.2374 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8296   -0.2021   -0.1967 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5379    1.2057    0.1991 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3935    1.5695    0.6614 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1855    1.3946    0.2101 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4759    0.0810    0.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1566    0.1610   -0.2644 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3302    1.0242    0.5123 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1005    0.2885    1.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6072   -0.2817   -0.0563 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0309   -0.1689   -0.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5043    1.0026   -0.2526 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8116    1.5074   -0.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9100    2.8648   -0.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0906    3.5476   -0.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2341    2.8768   -0.4459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1567    1.5410   -0.7733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9489    0.8680   -0.7256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2119   -0.8319   -1.2043 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9624   -1.8559   -0.4368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4459   -3.1325   -0.2844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6246   -4.0973    0.2943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3556   -3.7075    0.6850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8939   -2.4118    0.5185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7132   -1.4526   -0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1825   -0.9461   -1.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5827   -1.1266   -0.4958 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9862    0.0596   -1.9065 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6627   -0.8412    0.7228 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8933   -0.2918   -0.5288 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3780    1.4810    0.9617 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8673    1.8761   -0.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0951    1.6231   -0.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5096    2.2301    0.6271 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0320   -0.7872    0.1015 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2173   -0.0132    1.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8285    1.4949    1.3839 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9386    1.8278   -0.1268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4920    1.0601    1.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4023   -0.4511    1.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9829    3.3507    0.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1609    4.6163    0.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1625    3.4327   -0.4748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0880    1.0352   -1.0721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4431   -3.4264   -0.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9690   -5.1135    0.4343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7309   -4.4725    1.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8904   -2.1896    0.8488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2481   -1.8928   -1.4320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2902   -0.2157   -1.9242 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1669   -1.7463   -1.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5717   -1.6724    0.4656 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 10 26  1  0
 26 27  1  0
 27  7  1  0
 25 11  1  0
 18 13  1  0
 25 20  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 14 41  1  0
 15 42  1  0
 16 43  1  0
 17 44  1  0
 21 45  1  0
 22 46  1  0
 23 47  1  0
 24 48  1  0
 26 49  1  0
 26 50  1  0
 27 51  1  0
 27 52  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-[2-(4-Dibenzo[b,F][1,4]thiazepin-11-yl-1-piperazinyl)ethoxy]ethanol	ChEBI
Quetiapina	ChEBI
Quetiapinum	ChEBI
Norsic	Kegg
Quetiapine fumarate	HMDB
Seroquel	HMDB
Ethanol, 2-(2-(4-dibenzo(b,F)(1,4)thiazepin-11-yl-1-piperazinyl)ethoxy)-, (e)-2-butenedioate (2:1) (salt)	HMDB
Fumarate, quetiapine	HMDB
2-(2-(4-Dibenzo(b,F)(1,4)thiazepine-11-yl-1-piperazinyl)ethoxy)ethanol	HMDB

Chemical Formula

C₂₁H₂₅N₃O₂S

Average Molecular Weight

383.507

Monoisotopic Molecular Weight

383.166747749

IUPAC Name

2-[2-(4-{2-thia-9-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,9,11,13-heptaen-10-yl}piperazin-1-yl)ethoxy]ethan-1-ol

Traditional Name

quetiapine

CAS Registry Number

111974-69-7

SMILES

OCCOCCN1CCN(CC1)C1=NC2=CC=CC=C2SC2=CC=CC=C12

InChI Identifier

InChI=1S/C21H25N3O2S/c25-14-16-26-15-13-23-9-11-24(12-10-23)21-17-5-1-3-7-19(17)27-20-8-4-2-6-18(20)22-21/h1-8,25H,9-16H2

InChI Key

URKOMYMAXPYINW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzothiazepines. Dibenzothiazepines are compounds containing a dibenzothiazepine moiety, which consists of two benzene connected by a thiazepine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiazepines

Sub Class

Dibenzothiazepines

Direct Parent

Dibenzothiazepines

Alternative Parents

Substituents

Dibenzothiazepine
Diarylthioether
Aryl thioether
N-alkylpiperazine
1,4-diazinane
Piperazine
Benzenoid
Imidolactam
Tertiary amine
Tertiary aliphatic amine
Azacycle
Carboxylic acid amidine
Dialkyl ether
Ether
Amidine
Organic 1,3-dipolar compound
Thioether
Propargyl-type 1,3-dipolar organic compound
Organonitrogen compound
Organopnictogen compound
Organooxygen compound
Hydrocarbon derivative
Primary alcohol
Alcohol
Organic nitrogen compound
Organic oxygen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

N-arylpiperazine (CHEBI:8707 )
N-alkylpiperazine (CHEBI:8707 )
dibenzothiazepine (CHEBI:8707 )

Ontology

Physiological effect

Health effect

Observation

Circulatory system disorder

Vascular disorder

Hypotension (HMDB: HMDB0005021)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 16803670)
Cerebrospinal Fluid (CSF) (PMID: 21148022)
Cerebrospinal fluid (HMDB: HMDB0005021)

Cellular substructure

Membrane (HMDB: HMDB0005021)
Cell membrane (HMDB: HMDB0005021)

Organ

Brain (HMDB: HMDB0005021)
Liver (HMDB: HMDB0005021)

Route of exposure

Parenteral

Dermal (HMDB: HMDB0005021)
Inhalation (HMDB: HMDB0005021)

Enteral

Ingestion (HMDB: HMDB0005021)

Source

Exogenous

Exogenous (HMDB: HMDB0005021)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Quetiapine H1-Antihistamine Action (HMDB: HMDB0005021)
Quetiapine H1-Antihistamine Action (PathBank: SMP0062884)

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	192.9	30932474
[M+H]+	Not Available	191.459	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001038

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.04 g/L	ALOGPS
logP	2.93	ALOGPS
logP	2.81	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	15.12	ChemAxon
pKa (Strongest Basic)	7.06	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	48.3 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	114.09 m³·mol⁻¹	ChemAxon
Polarizability	42.78 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	190.249	31661259
DarkChem	[M-H]-	187.696	31661259
DeepCCS	[M-2H]-	215.118	30932474
DeepCCS	[M+Na]+	190.538	30932474
AllCCS	[M+H]+	190.1	32859911
AllCCS	[M+H-H2O]+	187.6	32859911
AllCCS	[M+NH4]+	192.3	32859911
AllCCS	[M+Na]+	193.0	32859911
AllCCS	[M-H]-	188.0	32859911
AllCCS	[M+Na-2H]-	188.0	32859911
AllCCS	[M+HCOO]-	188.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.02 minutes	32390414
Predicted by Siyang on May 30, 2022	10.1829 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.66 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	96.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1030.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	199.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	148.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	181.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	69.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	305.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	388.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	483.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	725.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	269.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	969.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	225.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	296.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	298.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	418.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	234.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Quetiapine	OCCOCCN1CCN(CC1)C1=NC2=CC=CC=C2SC2=CC=CC=C12	4646.9	Standard polar	33892256
Quetiapine	OCCOCCN1CCN(CC1)C1=NC2=CC=CC=C2SC2=CC=CC=C12	3131.8	Standard non polar	33892256
Quetiapine	OCCOCCN1CCN(CC1)C1=NC2=CC=CC=C2SC2=CC=CC=C12	3154.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Quetiapine,1TMS,isomer #1	C[Si](C)(C)OCCOCCN1CCN(C2=NC3=CC=CC=C3SC3=CC=CC=C23)CC1	3374.0	Semi standard non polar	33892256
Quetiapine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCOCCN1CCN(C2=NC3=CC=CC=C3SC3=CC=CC=C23)CC1	3548.1	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)

Tissue Locations

Brain
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Quetiapine H1-Antihistamine Action		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	20.7 (1.04-198.0) uM	Adult (>18 years old)	Both	Quetiapine poisoning	16803670	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0783 (0.00157-0.146) uM	Adult (>18 years old)	Both	schizophrenia (CYP2D6)	21148022	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0809 (0.00157-0.146) uM	Adult (>18 years old)	Not Specified	schizophrenia (CYP3A4 rs4646437)	21148022	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0626 (0.00157-0.146) uM	Adult (>18 years old)	Not Specified	schizophrenia (CYP3A5)	21148022	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0652 (0.00157-0.146) uM	Adult (>18 years old)	Not Specified	schizophrenia (CYP3A7)	21148022	details

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

Quetiapine poisoning
Flammia DD, Valouch T, Venuti S: Tissue distribution of quetiapine in 20 cases in Virginia. J Anal Toxicol. 2006 May;30(4):287-92. [PubMed:16803670 ]

Associated OMIM IDs

None

External Links

DrugBank ID

DB01224

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023592

KNApSAcK ID

Not Available

Chemspider ID

4827

KEGG Compound ID

C07397

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Quetiapine

METLIN ID

Not Available

PubChem Compound

5002

PDB ID

Not Available

ChEBI ID

8707

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Bozsing, Daniel; Kovanyine, Lax Gyoergyi; Simig, Gyula; Rakoczy, Gyoergyne; Toempe, Peter; Krasznai, Gyoergy; Vereczkeyne, Donath Gyoergyi; Nagy, Kalman. A process for the preparation of quetiapine and its intermediates. 2001, Patent WO2001055125A1 (https://patents.google.com/patent/WO2001055125A1/en)

Material Safety Data Sheet (MSDS)

Not Available

General References

Parker DR, McIntyre IM: Case studies of postmortem quetiapine: therapeutic or toxic concentrations? J Anal Toxicol. 2005 Jul-Aug;29(5):407-12. [PubMed:16105271 ]
Stip E, Fahim C, Mancini-Marie A, Bentaleb LA, Mensour B, Mendrek A, Beauregard M: Restoration of frontal activation during a treatment with quetiapine: an fMRI study of blunted affect in schizophrenia. Prog Neuropsychopharmacol Biol Psychiatry. 2005 Jan;29(1):21-6. Epub 2004 Nov 5. [PubMed:15610941 ]
Langman LJ, Kaliciak HA, Carlyle S: Fatal overdoses associated with quetiapine. J Anal Toxicol. 2004 Sep;28(6):520-5. [PubMed:15516308 ]
Stephan PL, Jaquenoud Sirot E, Mueller B, Eap CB, Baumann P: Adverse drug reactions following nonresponse in a depressed patient with CYP2D6 deficiency and low CYP 3A4/5 activity. Pharmacopsychiatry. 2006 Jul;39(4):150-2. [PubMed:16871470 ]
Fahim C, Stip E, Mancini-Marie A, Gendron A, Mensour B, Beauregard M: Differential hemodynamic brain activity in schizophrenia patients with blunted affect during quetiapine treatment. J Clin Psychopharmacol. 2005 Aug;25(4):367-71. [PubMed:16012281 ]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

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

Enzyme Details

2. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

Enzyme Details

3. 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

Enzyme Details

4. 5-hydroxytryptamine receptor 2B

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:: HTR2B
Uniprot ID:: P41595
Molecular weight:: 54297.4

Enzyme Details

5. 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

Enzyme Details

6. 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

Enzyme Details

7. 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

Enzyme Details

8. Histamine H1 receptor

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

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

Enzyme Details

10. D(1A) 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 activate adenylyl cyclase
Gene Name:: DRD1
Uniprot ID:: P21728
Molecular weight:: 49292.8

Showing metabocard for Quetiapine (HMDB0005021)

MOL for HMDB0005021 (Quetiapine)

3D MOL for HMDB0005021 (Quetiapine)

3D SDF for HMDB0005021 (Quetiapine)

3D-SDF for HMDB0005021 (Quetiapine)

PDB for HMDB0005021 (Quetiapine)

3D PDB for HMDB0005021 (Quetiapine)

SMILES for HMDB0005021 (Quetiapine)

INCHI for HMDB0005021 (Quetiapine)

Structure for HMDB0005021 (Quetiapine)

3D Structure for HMDB0005021 (Quetiapine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes