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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (8)transporters (3) Show 11 proteins XML

enzymes (8)transporters (3) Show 11 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 02:51:58 UTC

HMDB ID

HMDB0015372

Secondary Accession Numbers

HMDB15372

Metabolite Identification

Common Name

Clomipramine

Description

Clomipramine, the 3-chloro analog of imipramine, is a dibenzazepine-derivative tricyclic antidepressant (TCA). TCAs are structurally similar to phenothiazines. They contain a tricyclic ring system with an alkyl amine substituent on the central ring. In non-depressed individuals, clomipramine does not affect mood or arousal, but may cause sedation. In depressed individuals, clomipramine exerts a positive effect on mood. TCAs are potent inhibitors of serotonin and norepinephrine reuptake. Tertiary amine TCAs, such as clomipramine, are more potent inhibitors of serotonin reuptake than secondary amine TCAs, such as nortriptyline and desipramine. TCAs also down-regulate cerebral cortical β-adrenergic receptors and sensitize post-synaptic serotonergic receptors with chronic use. The antidepressant effects of TCAs are thought to be due to an overall increase in serotonergic neurotransmission. TCAs also block histamine-H₁ receptors, α₁-adrenergic receptors and muscarinic receptors, which accounts for their sedative, hypotensive and anticholinergic effects (e.g. blurred vision, dry mouth, constipation, urinary retention), respectively. See toxicity section below for a complete listing of side effects. Clomipramine may be used to treat obsessive-compulsive disorder and disorders with an obsessive-compulsive component (e.g. depression, schizophrenia, Tourette's disorder). Unlabeled indications include panic disorder, chronic pain (e.g. central pain, idiopathic pain disorder, tension headache, diabetic peripheral neuropathy, neuropathic pain), cataplexy and associated narcolepsy, autistic disorder, trichotillomania, onchophagia, stuttering, premature ejaculation, and premenstrual syndrome. Clomipramine is rapidly absorbed from the gastrointestinal tract and demethylated in the liver to its primary active metabolite, desmethylclomipramine.

Structure

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

HMDB0015372
     RDKit          3D
Clomipramine
 45 47  0  0  0  0  0  0  0  0999 V2000
   -3.5792   -1.2314   -0.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6180   -0.0050   -0.7080 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8463    0.2577   -1.4370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9676    1.1466   -0.2422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4880    1.1010   -0.3666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8592   -0.0027    0.4521 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5626   -0.0643    0.4136 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1924   -1.3651    0.3653 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3473   -2.3157    0.8743 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7805   -3.6210    0.8918 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0429   -3.9148    0.3987 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8584   -2.9263   -0.1020 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4557   -1.5852   -0.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5287   -0.7444   -0.6955 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1793    0.6050   -1.1839 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4059    1.4651   -0.2515 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9573    2.7165   -0.0957 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3603    3.6575    0.7468 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1891    3.3155    1.4360 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4175    4.4520    2.4896 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.6201    2.0734    1.2969 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2529    1.1950    0.4559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1287   -2.0498   -0.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2574   -1.2621    1.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6715   -1.6035    0.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8986   -0.4741   -2.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6870    0.0468   -0.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9109    1.2854   -1.8016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2941    2.0026   -0.9348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2906    1.4441    0.8017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9911    2.0670   -0.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3518    0.8391   -1.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2044   -0.8917   -0.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3018   -0.0988    1.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6270   -2.0133    1.2630 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1129   -4.3574    1.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3270   -4.9577    0.4388 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8303   -3.1791   -0.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4279   -0.7273   -0.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8965   -1.3186   -1.6020 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1440    1.1294   -1.3718 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6882    0.5428   -2.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8757    3.0070   -0.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7958    4.6453    0.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2759    1.7144    1.7831 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  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
 22  7  1  0
 13  8  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 17 43  1  0
 18 44  1  0
 21 45  1  0
M  END

1242
  Mrv0541 02231215212D          

 22 24  0  0  0  0            999 V2000
    1.5842    0.1860    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.2627    0.7166    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6347   -1.6596    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2627   -0.0755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5491    1.0603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9763    1.0603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8667    2.4517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6588    2.4517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3729    1.8325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1526    1.8325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9488   -0.4715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9488   -1.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9530    0.4898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5725    0.4898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5884    2.0878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9373    2.0878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1627    0.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3627    0.7269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9792    1.5314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5464    1.5313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6347   -2.4517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3207   -1.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 17  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3 12  1  0  0  0  0
  3 21  1  0  0  0  0
  3 22  1  0  0  0  0
  4 11  1  0  0  0  0
  5  9  2  0  0  0  0
  5 13  1  0  0  0  0
  6 10  1  0  0  0  0
  6 14  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 15  1  0  0  0  0
 10 16  2  0  0  0  0
 11 12  1  0  0  0  0
 13 17  2  0  0  0  0
 14 18  1  0  0  0  0
 15 19  2  0  0  0  0
 16 20  1  0  0  0  0
 17 19  1  0  0  0  0
 18 20  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015372

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)CCCN1C2=CC=CC=C2CCC2=C1C=C(Cl)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C19H23ClN2/c1-21(2)12-5-13-22-18-7-4-3-6-15(18)8-9-16-10-11-17(20)14-19(16)22/h3-4,6-7,10-11,14H,5,8-9,12-13H2,1-2H3

> <INCHI_KEY>
GDLIGKIOYRNHDA-UHFFFAOYSA-N

> <FORMULA>
C19H23ClN2

> <MOLECULAR_WEIGHT>
314.852

> <EXACT_MASS>
314.154976453

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
35.73064379062186

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3-{14-chloro-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaen-2-yl}propyl)dimethylamine

> <ALOGPS_LOGP>
5.04

> <JCHEM_LOGP>
4.882613470666667

> <ALOGPS_LOGS>
-4.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.19697706986717

> <JCHEM_POLAR_SURFACE_AREA>
6.48

> <JCHEM_REFRACTIVITY>
95.41040000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.44e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
clomipramine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015372
     RDKit          3D
Clomipramine
 45 47  0  0  0  0  0  0  0  0999 V2000
   -3.5792   -1.2314   -0.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6180   -0.0050   -0.7080 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8463    0.2577   -1.4370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9676    1.1466   -0.2422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4880    1.1010   -0.3666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8592   -0.0027    0.4521 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5626   -0.0643    0.4136 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1924   -1.3651    0.3653 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3473   -2.3157    0.8743 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7805   -3.6210    0.8918 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0429   -3.9148    0.3987 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8584   -2.9263   -0.1020 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4557   -1.5852   -0.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5287   -0.7444   -0.6955 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1793    0.6050   -1.1839 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4059    1.4651   -0.2515 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9573    2.7165   -0.0957 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3603    3.6575    0.7468 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1891    3.3155    1.4360 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4175    4.4520    2.4896 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.6201    2.0734    1.2969 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2529    1.1950    0.4559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1287   -2.0498   -0.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2574   -1.2621    1.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6715   -1.6035    0.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8986   -0.4741   -2.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6870    0.0468   -0.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9109    1.2854   -1.8016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2941    2.0026   -0.9348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2906    1.4441    0.8017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9911    2.0670   -0.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3518    0.8391   -1.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2044   -0.8917   -0.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3018   -0.0988    1.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6270   -2.0133    1.2630 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1129   -4.3574    1.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3270   -4.9577    0.4388 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8303   -3.1791   -0.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4279   -0.7273   -0.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8965   -1.3186   -1.6020 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1440    1.1294   -1.3718 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6882    0.5428   -2.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8757    3.0070   -0.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7958    4.6453    0.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2759    1.7144    1.7831 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  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
 22  7  1  0
 13  8  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 17 43  1  0
 18 44  1  0
 21 45  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1242                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       2.957   0.347   0.000  0.00  0.00          Cl+0
HETATM    2  N   UNK     0       7.957   1.338   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0      10.518  -3.098   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       7.957  -0.141   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.625   1.979   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.289   1.979   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.218   4.577   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.697   4.577   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.296   3.421   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.618   3.421   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.238  -0.880   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.238  -2.359   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.512   0.914   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.402   0.914   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.832   3.897   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.083   3.897   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.037   1.357   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.877   1.357   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.694   2.859   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.220   2.858   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.518  -4.577   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.799  -2.359   0.000  0.00  0.00           C+0
CONECT    1   17                                                            
CONECT    2    4    5    6                                                  
CONECT    3   12   21   22                                                  
CONECT    4    2   11                                                       
CONECT    5    2    9   13                                                  
CONECT    6    2   10   14                                                  
CONECT    7    8    9                                                       
CONECT    8    7   10                                                       
CONECT    9    5    7   15                                                  
CONECT   10    6    8   16                                                  
CONECT   11    4   12                                                       
CONECT   12    3   11                                                       
CONECT   13    5   17                                                       
CONECT   14    6   18                                                       
CONECT   15    9   19                                                       
CONECT   16   10   20                                                       
CONECT   17    1   13   19                                                  
CONECT   18   14   20                                                       
CONECT   19   15   17                                                       
CONECT   20   16   18                                                       
CONECT   21    3                                                            
CONECT   22    3                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0015372
HETATM    1  C1  UNL     1      -3.579  -1.231  -0.043  1.00  0.00           C  
HETATM    2  N1  UNL     1      -3.618  -0.005  -0.708  1.00  0.00           N  
HETATM    3  C2  UNL     1      -4.846   0.258  -1.437  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.968   1.147  -0.242  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.488   1.101  -0.367  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.859  -0.003   0.452  1.00  0.00           C  
HETATM    7  N2  UNL     1       0.563  -0.064   0.414  1.00  0.00           N  
HETATM    8  C6  UNL     1       1.192  -1.365   0.365  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.347  -2.316   0.874  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.780  -3.621   0.892  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.043  -3.915   0.399  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.858  -2.926  -0.102  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.456  -1.585  -0.138  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.529  -0.744  -0.696  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.179   0.605  -1.184  1.00  0.00           C  
HETATM   16  C14 UNL     1       2.406   1.465  -0.251  1.00  0.00           C  
HETATM   17  C15 UNL     1       2.957   2.717  -0.096  1.00  0.00           C  
HETATM   18  C16 UNL     1       2.360   3.658   0.747  1.00  0.00           C  
HETATM   19  C17 UNL     1       1.189   3.315   1.436  1.00  0.00           C  
HETATM   20 CL1  UNL     1       0.417   4.452   2.490  1.00  0.00          CL  
HETATM   21  C18 UNL     1       0.620   2.073   1.297  1.00  0.00           C  
HETATM   22  C19 UNL     1       1.253   1.195   0.456  1.00  0.00           C  
HETATM   23  H1  UNL     1      -3.129  -2.050  -0.684  1.00  0.00           H  
HETATM   24  H2  UNL     1      -3.257  -1.262   1.003  1.00  0.00           H  
HETATM   25  H3  UNL     1      -4.671  -1.604   0.028  1.00  0.00           H  
HETATM   26  H4  UNL     1      -4.899  -0.474  -2.262  1.00  0.00           H  
HETATM   27  H5  UNL     1      -5.687   0.047  -0.721  1.00  0.00           H  
HETATM   28  H6  UNL     1      -4.911   1.285  -1.802  1.00  0.00           H  
HETATM   29  H7  UNL     1      -3.294   2.003  -0.935  1.00  0.00           H  
HETATM   30  H8  UNL     1      -3.291   1.444   0.802  1.00  0.00           H  
HETATM   31  H9  UNL     1      -0.991   2.067  -0.361  1.00  0.00           H  
HETATM   32  H10 UNL     1      -1.352   0.839  -1.501  1.00  0.00           H  
HETATM   33  H11 UNL     1      -1.204  -0.892  -0.125  1.00  0.00           H  
HETATM   34  H12 UNL     1      -1.302  -0.099   1.453  1.00  0.00           H  
HETATM   35  H13 UNL     1      -0.627  -2.013   1.263  1.00  0.00           H  
HETATM   36  H14 UNL     1       0.113  -4.357   1.291  1.00  0.00           H  
HETATM   37  H15 UNL     1       2.327  -4.958   0.439  1.00  0.00           H  
HETATM   38  H16 UNL     1       3.830  -3.179  -0.477  1.00  0.00           H  
HETATM   39  H17 UNL     1       4.428  -0.727  -0.033  1.00  0.00           H  
HETATM   40  H18 UNL     1       3.897  -1.319  -1.602  1.00  0.00           H  
HETATM   41  H19 UNL     1       4.144   1.129  -1.372  1.00  0.00           H  
HETATM   42  H20 UNL     1       2.688   0.543  -2.183  1.00  0.00           H  
HETATM   43  H21 UNL     1       3.876   3.007  -0.627  1.00  0.00           H  
HETATM   44  H22 UNL     1       2.796   4.645   0.869  1.00  0.00           H  
HETATM   45  H23 UNL     1      -0.276   1.714   1.783  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    4
CONECT    3   26   27   28
CONECT    4    5   29   30
CONECT    5    6   31   32
CONECT    6    7   33   34
CONECT    7    8   22
CONECT    8    9    9   13
CONECT    9   10   35
CONECT   10   11   11   36
CONECT   11   12   37
CONECT   12   13   13   38
CONECT   13   14
CONECT   14   15   39   40
CONECT   15   16   41   42
CONECT   16   17   17   22
CONECT   17   18   43
CONECT   18   19   19   44
CONECT   19   20   21
CONECT   21   22   22   45
END

HMDB0015372
     RDKit          3D
Clomipramine
 45 47  0  0  0  0  0  0  0  0999 V2000
   -3.5792   -1.2314   -0.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6180   -0.0050   -0.7080 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8463    0.2577   -1.4370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9676    1.1466   -0.2422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4880    1.1010   -0.3666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8592   -0.0027    0.4521 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5626   -0.0643    0.4136 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1924   -1.3651    0.3653 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3473   -2.3157    0.8743 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7805   -3.6210    0.8918 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0429   -3.9148    0.3987 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8584   -2.9263   -0.1020 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4557   -1.5852   -0.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5287   -0.7444   -0.6955 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1793    0.6050   -1.1839 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4059    1.4651   -0.2515 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9573    2.7165   -0.0957 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3603    3.6575    0.7468 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1891    3.3155    1.4360 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4175    4.4520    2.4896 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.6201    2.0734    1.2969 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2529    1.1950    0.4559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1287   -2.0498   -0.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2574   -1.2621    1.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6715   -1.6035    0.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8986   -0.4741   -2.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6870    0.0468   -0.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9109    1.2854   -1.8016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2941    2.0026   -0.9348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2906    1.4441    0.8017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9911    2.0670   -0.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3518    0.8391   -1.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2044   -0.8917   -0.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3018   -0.0988    1.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6270   -2.0133    1.2630 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1129   -4.3574    1.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3270   -4.9577    0.4388 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8303   -3.1791   -0.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4279   -0.7273   -0.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8965   -1.3186   -1.6020 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1440    1.1294   -1.3718 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6882    0.5428   -2.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8757    3.0070   -0.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7958    4.6453    0.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2759    1.7144    1.7831 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  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
 22  7  1  0
 13  8  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 17 43  1  0
 18 44  1  0
 21 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-(3-Chloro-10,11-dihydro-5H-dibenzo[b,F]azepin-5-yl)-N,N-dimethyl-1-propanamine	ChEBI
3-(3-CHLORO-5H-dibenzo[b,F]azepin-5-yl)-N,N-dimethylpropan-1-amine	ChEBI
3-Chloroimipramine	ChEBI
Chlorimipramine	ChEBI
g 34586	ChEBI
Monochlorimipramine	ChEBI
Anafranil	Kegg
Monohydrochloride, clomipramine	HMDB
Clomipramine maleate (1:1)	HMDB
Clomipramine monohydrochloride	HMDB
Hydiphen	HMDB
Hydrochloride, clomipramine	HMDB
Chlomipramine	HMDB
Clomipramine hydrochloride	HMDB

Chemical Formula

C₁₉H₂₃ClN₂

Average Molecular Weight

314.852

Monoisotopic Molecular Weight

314.154976453

IUPAC Name

(3-{14-chloro-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaen-2-yl}propyl)dimethylamine

Traditional Name

clomipramine

CAS Registry Number

303-49-1

SMILES

CN(C)CCCN1C2=CC=CC=C2CCC2=C1C=C(Cl)C=C2

InChI Identifier

InChI=1S/C19H23ClN2/c1-21(2)12-5-13-22-18-7-4-3-6-15(18)8-9-16-10-11-17(20)14-19(16)22/h3-4,6-7,10-11,14H,5,8-9,12-13H2,1-2H3

InChI Key

GDLIGKIOYRNHDA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzazepines. Dibenzazepines are compounds with two benzene rings connected by an azepine ring. Azepine is an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzazepines

Sub Class

Dibenzazepines

Direct Parent

Dibenzazepines

Alternative Parents

Substituents

Dibenzazepine
Alkyldiarylamine
Tertiary aliphatic/aromatic amine
Azepine
Benzenoid
Aryl halide
Aryl chloride
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organopnictogen compound
Amine
Organonitrogen compound
Organochloride
Organohalogen compound
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dibenzoazepine (CHEBI:47780 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015372)

Source

Exogenous

Exogenous (HMDB: HMDB0015372)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Clomipramine Metabolism Pathway (PathBank: SMP0000639)

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Antidepressant (HMDB: HMDB0015372)

Serotonergic antagonist (HMDB: HMDB0015372)

Pharmaceutical industry

Serotonergic drug (HMDB: HMDB0015372)

Biological role

Modulator

Inhibitor

EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor (HMDB: HMDB0015372)

Serotonin uptake inhibitor (HMDB: HMDB0015372)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	189.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.014 g/L	Not Available
LogP	4.5	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	174.3	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.014 g/L	ALOGPS
logP	5.04	ALOGPS
logP	4.88	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Basic)	9.2	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	6.48 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	95.41 m³·mol⁻¹	ChemAxon
Polarizability	35.73 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	170.32	30932474
DeepCCS	[M-H]-	167.962	30932474
DeepCCS	[M-2H]-	200.848	30932474
DeepCCS	[M+Na]+	176.414	30932474
AllCCS	[M+H]+	173.6	32859911
AllCCS	[M+H-H2O]+	170.3	32859911
AllCCS	[M+NH4]+	176.7	32859911
AllCCS	[M+Na]+	177.6	32859911
AllCCS	[M-H]-	181.0	32859911
AllCCS	[M+Na-2H]-	180.7	32859911
AllCCS	[M+HCOO]-	180.6	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.	7.31 minutes	32390414
Predicted by Siyang on May 30, 2022	12.2555 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.29 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	37.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1350.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	268.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	176.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	184.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	122.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	419.1 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	427.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	498.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1194.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	429.3 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	1336.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	283.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	362.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	316.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	217.1 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	8.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Clomipramine	CN(C)CCCN1C2=CC=CC=C2CCC2=C1C=C(Cl)C=C2	3590.2	Standard polar	33892256
Clomipramine	CN(C)CCCN1C2=CC=CC=C2CCC2=C1C=C(Cl)C=C2	2413.6	Standard non polar	33892256
Clomipramine	CN(C)CCCN1C2=CC=CC=C2CCC2=C1C=C(Cl)C=C2	2397.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Clomipramine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9060000000-34352b7b1b6a78a55cd8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Clomipramine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-066r-6391000000-e57dc447a97807ce527a	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clomipramine LC-ESI-QTOF , positive-QTOF	splash10-052r-9010000000-77a0afe2d49df71431d8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clomipramine LC-ESI-QFT , positive-QTOF	splash10-014i-2009000000-a1cc70dad4bb4c19ab7b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clomipramine LC-ESI-QFT , positive-QTOF	splash10-000i-9000000000-a9af3369f8d6da434fd0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clomipramine LC-ESI-QFT , positive-QTOF	splash10-052r-9000000000-3f1941447bc096ea9d73	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clomipramine LC-ESI-QFT , positive-QTOF	splash10-0a4r-9010000000-c6b5c5a56ac456cd8845	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clomipramine LC-ESI-QFT , positive-QTOF	splash10-0a4i-9010000000-8b5307526ea875a06881	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clomipramine LC-ESI-QFT , positive-QTOF	splash10-0a4i-9010000000-98746d4db184914ce871	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clomipramine LC-ESI-QFT , positive-QTOF	splash10-0a4i-9310000000-194486cca11709cd1b80	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clomipramine LC-ESI-QFT , positive-QTOF	splash10-0a4i-9600000000-da861dd5252aaff30e89	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clomipramine LC-ESI-QFT , positive-QTOF	splash10-0a4i-6900000000-efdead8e50e8b700d4bd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clomipramine Linear Ion Trap , positive-QTOF	splash10-00di-0090000000-558a68c9d4919e7945a2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clomipramine Linear Ion Trap , positive-QTOF	splash10-00di-0090000000-489c71d87d96f5bafd40	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clomipramine Linear Ion Trap , positive-QTOF	splash10-014i-0009002000-3318f523b446a8d9d68e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clomipramine Linear Ion Trap , positive-QTOF	splash10-014i-0009000000-8b8a1763c5358415b2b0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clomipramine 60V, Positive-QTOF	splash10-0a4r-9000000000-5c2c7aa10719beb2c160	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clomipramine 45V, Positive-QTOF	splash10-052r-9000000000-252b037815db33ff1554	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clomipramine 15V, Positive-QTOF	splash10-014i-4009000000-f6fbb8f3c1432560c648	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clomipramine 30V, Positive-QTOF	splash10-000i-9000000000-96e4294b38c6773a9dff	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clomipramine 10V, Positive-QTOF	splash10-014r-8009000000-47296607dea9797c1439	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clomipramine 10V, Positive-QTOF	splash10-014i-1029000000-68c9c186daeb14b564b2	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clomipramine 20V, Positive-QTOF	splash10-01bl-7095000000-7aeedc02e87a2acd87ab	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clomipramine 40V, Positive-QTOF	splash10-0076-9140000000-201084960b40747f3339	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clomipramine 10V, Negative-QTOF	splash10-03di-0009000000-0d5e3470f9eae466d2e1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clomipramine 20V, Negative-QTOF	splash10-03fr-1089000000-bda0b94a0a3d33589f39	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clomipramine 40V, Negative-QTOF	splash10-0fbc-2390000000-f1f3b5dec72ac0b8b633	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Clomipramine Metabolism Pathway		Not Available

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 DB01242	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01242	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

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

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01242

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2699

KEGG Compound ID

C06918

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Clomipramine

METLIN ID

Not Available

PubChem Compound

2801

PDB ID

CXX

ChEBI ID

47780

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

(). FDA label . .

Only showing the first 10 proteins. There are 11 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Glutathione S-transferase P

General function:: Involved in glutathione transferase activity
Specific function:: Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Regulates negatively CDK5 activity via p25/p35 translocation to prevent neurodegeneration.
Gene Name:: GSTP1
Uniprot ID:: P09211
Molecular weight:: 23355.625

References

Baranczyk-Kuzma A, Sawicki J, Kuzma M, Jagiello J: [Tricyclic antidepressants as inhibitors of brain glutathione-S-transferase]. Pol Merkur Lekarski. 2001 Dec;11(66):472-5. [PubMed:11899840 ]
Baranczyk-Kuzma A, Kuzma M, Gutowicz M, Kazmierczak B, Sawicki J: Glutathione S-transferase pi as a target for tricyclic antidepressants in human brain. Acta Biochim Pol. 2004;51(1):207-12. [PubMed:15094841 ]
Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Enzyme Details

2. 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

3. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

References

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

Enzyme Details

4. Cytochrome P450 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

5. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

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

6. 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

References

Sargent PA, Quested DJ, Cowen PJ: Clomipramine enhances the cortisol response to 5-HTP: implications for the therapeutic role of 5-HT2 receptors. Psychopharmacology (Berl). 1998 Nov;140(1):120-2. [PubMed:9862411 ]
Sugimoto Y, Inoue K, Yamada J: The tricyclic antidepressant clomipramine increases plasma glucose levels of mice. J Pharmacol Sci. 2003 Sep;93(1):74-9. [PubMed:14501155 ]
Contreras CM, Marvan ML, Munoz-Mendez A, Ramirez-Morales A: Cortical and septal responses to dorsal raphe nucleus stimulation in the rat: long-term clomipramine actions. Bol Estud Med Biol. 1992 Jan-Dec;40(1-4):3-7. [PubMed:1296670 ]

Enzyme Details

7. 5-hydroxytryptamine receptor 2A

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

References

Hentall ID, Kurle PJ, White TR: Correlations between serotonin level and single-cell firing in the rat's nucleus raphe magnus. Neuroscience. 2000;95(4):1081-8. [PubMed:10682715 ]
Contreras CM, Marvan ML, Munoz-Mendez A, Ramirez-Morales A: Cortical and septal responses to dorsal raphe nucleus stimulation in the rat: long-term clomipramine actions. Bol Estud Med Biol. 1992 Jan-Dec;40(1-4):3-7. [PubMed:1296670 ]
Sugimoto Y, Inoue K, Yamada J: The tricyclic antidepressant clomipramine increases plasma glucose levels of mice. J Pharmacol Sci. 2003 Sep;93(1):74-9. [PubMed:14501155 ]
Trifunovic RD, Brodie MS: The effects of clomipramine on the excitatory action of ethanol on dopaminergic neurons of the ventral tegmental area in vitro. J Pharmacol Exp Ther. 1996 Jan;276(1):34-40. [PubMed:8558452 ]
Sargent PA, Quested DJ, Cowen PJ: Clomipramine enhances the cortisol response to 5-HTP: implications for the therapeutic role of 5-HT2 receptors. Psychopharmacology (Berl). 1998 Nov;140(1):120-2. [PubMed:9862411 ]

Enzyme Details

8. 5-hydroxytryptamine receptor 2C

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

References

Sargent PA, Quested DJ, Cowen PJ: Clomipramine enhances the cortisol response to 5-HTP: implications for the therapeutic role of 5-HT2 receptors. Psychopharmacology (Berl). 1998 Nov;140(1):120-2. [PubMed:9862411 ]
Sugimoto Y, Inoue K, Yamada J: The tricyclic antidepressant clomipramine increases plasma glucose levels of mice. J Pharmacol Sci. 2003 Sep;93(1):74-9. [PubMed:14501155 ]
Contreras CM, Marvan ML, Munoz-Mendez A, Ramirez-Morales A: Cortical and septal responses to dorsal raphe nucleus stimulation in the rat: long-term clomipramine actions. Bol Estud Med Biol. 1992 Jan-Dec;40(1-4):3-7. [PubMed:1296670 ]

Transporters

Enzyme Details

1. Multidrug resistance protein 1

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

References

Mahar Doan KM, Humphreys JE, Webster LO, Wring SA, Shampine LJ, Serabjit-Singh CJ, Adkison KK, Polli JW: Passive permeability and P-glycoprotein-mediated efflux differentiate central nervous system (CNS) and non-CNS marketed drugs. J Pharmacol Exp Ther. 2002 Dec;303(3):1029-37. [PubMed:12438524 ]

Enzyme Details

2. Sodium-dependent noradrenaline transporter

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

References

Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [PubMed:9537821 ]
Jungkun G, Kuss HJ, Gsell W: Long-term effects of tricyclic antidepressants on norepinephrine kinetics in humans. J Neural Transm (Vienna). 2001;108(3):349-62. [PubMed:11341486 ]

Enzyme Details

3. Sodium-dependent serotonin transporter

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

References

Alvarez JC, Gluck N, Arnulf I, Quintin P, Leboyer M, Pecquery R, Launay JM, Perez-Diaz F, Spreux-Varoquaux O: Decreased platelet serotonin transporter sites and increased platelet inositol triphosphate levels in patients with unipolar depression: effects of clomipramine and fluoxetine. Clin Pharmacol Ther. 1999 Dec;66(6):617-24. [PubMed:10613618 ]
Borkowska A, Pilaczynska E, Araszkiewicz A, Rybakowski J: [The effect of sertraline on cognitive functions in patients with obsessive-compulsive disorder]. Psychiatr Pol. 2002 Nov-Dec;36(6 Suppl):289-95. [PubMed:12647451 ]
Suhara T, Takano A, Sudo Y, Ichimiya T, Inoue M, Yasuno F, Ikoma Y, Okubo Y: High levels of serotonin transporter occupancy with low-dose clomipramine in comparative occupancy study with fluvoxamine using positron emission tomography. Arch Gen Psychiatry. 2003 Apr;60(4):386-91. [PubMed:12695316 ]
Larsen AK, Brennum LT, Egebjerg J, Sanchez C, Halldin C, Andersen PH: Selectivity of (3)H-MADAM binding to 5-hydroxytryptamine transporters in vitro and in vivo in mice; correlation with behavioural effects. Br J Pharmacol. 2004 Mar;141(6):1015-23. Epub 2004 Mar 1. [PubMed:14993096 ]
Malizia AL, Melichar JM, Brown DJ, Gunn RN, Reynolds A, Jones T, Nutt DJ: Demonstration of clomipramine and venlafaxine occupation at serotonin reuptake sites in man in vivo. J Psychopharmacol. 1997;11(3):279-81. [PubMed:9305421 ]
Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [PubMed:9537821 ]
Gillman PK: Tricyclic antidepressant pharmacology and therapeutic drug interactions updated. Br J Pharmacol. 2007 Jul;151(6):737-48. Epub 2007 Apr 30. [PubMed:17471183 ]

Only showing the first 10 proteins. There are 11 proteins in total.

Show all enzymes and transporters

Showing metabocard for Clomipramine (HMDB0015372)

MOL for HMDB0015372 (Clomipramine)

3D MOL for HMDB0015372 (Clomipramine)

3D SDF for HMDB0015372 (Clomipramine)

3D-SDF for HMDB0015372 (Clomipramine)

PDB for HMDB0015372 (Clomipramine)

3D PDB for HMDB0015372 (Clomipramine)

SMILES for HMDB0015372 (Clomipramine)

INCHI for HMDB0015372 (Clomipramine)

Structure for HMDB0015372 (Clomipramine)

3D Structure for HMDB0015372 (Clomipramine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References

References

References

Transporters

References

References

References