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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (9)transporters (2) Show 11 proteins XML

enzymes (9)transporters (2) Show 11 proteins

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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-02-16 08:59:19 UTC

Update Date

2022-03-07 02:49:10 UTC

HMDB ID

HMDB0001848

Secondary Accession Numbers

HMDB01848

Metabolite Identification

Common Name

Imipramine

Description

Imipramine, also known as tofranil or imizine, 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. A dibenzoazepine that is 5H-dibenzoazepine substituted by a 3-(dimethylamino)propyl group at the nitrogen atom. Imipramine is a drug which is used for the relief of symptoms of depression and as temporary adjunctive therapy in reducing enuresis in children aged 6 years and older [fda label]. may also be used off-label to manage panic disorders with or without agoraphobia, as a second line agent for adhd in children and adolescents, to manage bulimia nervosa, for short-term management of acute depressive episodes in bipolar disorder and schizophrenia, for the treatment of acute stress disorder and posttraumatic stress disorder, and for symptomatic treatment of postherpetic neuralgia and painful diabetic neuropathy [l1349,l1348,a31900,l1351,l1352,l1353,a31904]. . Imipramine is a very strong basic compound (based on its pKa). Within humans, imipramine participates in a number of enzymatic reactions. In particular, imipramine can be converted into 2-hydroxyimipramine; which is mediated by the enzyme cytochrome P450 2D6. In addition, imipramine can be converted into desipramine and formaldehyde; which is mediated by the enzymes cytochrome P450 2C19, cytochrome P450 1A2, and cytochrome P450 3A4. In humans, imipramine is involved in imipramine action pathway. Imipramine is a potentially toxic compound.

Structure

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

HMDB0001848
     RDKit          3D
Imipramine
 45 47  0  0  0  0  0  0  0  0999 V2000
    4.6573   -1.0244   -0.5623 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2189    0.2657   -0.2134 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1356    1.3316   -0.2667 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0412    0.4239    0.5281 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7756    0.0282   -0.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6392    0.2449    0.5870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7074    0.0189    0.2801 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2688   -1.2895    0.1460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3395   -2.2577    0.3892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6770   -3.5850    0.3184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9674   -3.9861   -0.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9113   -3.0168   -0.2466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5739   -1.6842   -0.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7293   -0.8082   -0.4566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8653    0.2821    0.6060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8971    1.3433    0.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5443    2.5332    0.0444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7856    3.6205   -0.3188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4251    3.5268   -0.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7975    2.2875   -0.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5228    1.1823    0.1000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9717   -1.1549   -1.6135 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9099   -1.7753   -0.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5795   -1.2496    0.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2620    1.7562    0.7640 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1303    0.9395   -0.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8962    2.1367   -0.9839 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9044    1.4845    0.7904 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0943   -0.1537    1.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9335   -0.9065   -0.8123 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9291    0.7887   -1.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8150    1.2449    1.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8232   -0.3435    1.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6262   -1.9727    0.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0727   -4.3709    0.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2083   -5.0505   -0.0505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9394   -3.2770   -0.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7068   -0.3197   -1.4343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6792   -1.4126   -0.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5476   -0.1856    1.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9013    0.6577    0.6696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6275    2.6196    0.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2474    4.5839   -0.4876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7887    4.3550   -0.7649 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2429    2.1691   -0.3909 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
 20 21  2  0
 21  7  1  0
 13  8  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 15 41  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
M  END

458
  Mrv1652305271900162D          

 21 23  0  0  0  0            999 V2000
    3.8680    0.7167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4959   -1.6597    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8680   -0.0755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5817    1.0603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1542    1.0603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2641    2.4519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4719    2.4519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7580    1.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9780    1.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1820   -0.4715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1819   -1.2637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1777    0.4899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5581    0.4899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5425    2.0879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1934    2.0879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9680    0.7269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7678    0.7269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1516    1.5314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5843    1.5315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4959   -2.4519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8099   -1.2637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  1  5  1  0  0  0  0
  2 11  1  0  0  0  0
  2 20  1  0  0  0  0
  2 21  1  0  0  0  0
  3 10  1  0  0  0  0
  4  8  1  0  0  0  0
  4 12  2  0  0  0  0
  5  9  1  0  0  0  0
  5 13  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 14  2  0  0  0  0
  9 15  2  0  0  0  0
 10 11  1  0  0  0  0
 12 16  1  0  0  0  0
 13 17  1  0  0  0  0
 14 18  1  0  0  0  0
 15 19  1  0  0  0  0
 16 18  2  0  0  0  0
 17 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001848

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)CCCN1C2=CC=CC=C2CCC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C19H24N2/c1-20(2)14-7-15-21-18-10-5-3-8-16(18)12-13-17-9-4-6-11-19(17)21/h3-6,8-11H,7,12-15H2,1-2H3

> <INCHI_KEY>
BCGWQEUPMDMJNV-UHFFFAOYSA-N

> <FORMULA>
C19H24N2

> <MOLECULAR_WEIGHT>
280.4073

> <EXACT_MASS>
280.193948778

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
33.391729961948194

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3-{2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-2-yl}propyl)dimethylamine

> <ALOGPS_LOGP>
4.53

> <JCHEM_LOGP>
4.278568794333333

> <ALOGPS_LOGS>
-3.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.196977071904843

> <JCHEM_POLAR_SURFACE_AREA>
6.48

> <JCHEM_REFRACTIVITY>
90.60560000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.64e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3-{2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-2-yl}propyl)dimethylamine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0001848
     RDKit          3D
Imipramine
 45 47  0  0  0  0  0  0  0  0999 V2000
    4.6573   -1.0244   -0.5623 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2189    0.2657   -0.2134 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1356    1.3316   -0.2667 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0412    0.4239    0.5281 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7756    0.0282   -0.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6392    0.2449    0.5870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7074    0.0189    0.2801 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2688   -1.2895    0.1460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3395   -2.2577    0.3892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6770   -3.5850    0.3184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9674   -3.9861   -0.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9113   -3.0168   -0.2466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5739   -1.6842   -0.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7293   -0.8082   -0.4566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8653    0.2821    0.6060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8971    1.3433    0.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5443    2.5332    0.0444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7856    3.6205   -0.3188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4251    3.5268   -0.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7975    2.2875   -0.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5228    1.1823    0.1000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9717   -1.1549   -1.6135 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9099   -1.7753   -0.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5795   -1.2496    0.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2620    1.7562    0.7640 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1303    0.9395   -0.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8962    2.1367   -0.9839 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9044    1.4845    0.7904 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0943   -0.1537    1.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9335   -0.9065   -0.8123 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9291    0.7887   -1.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8150    1.2449    1.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8232   -0.3435    1.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6262   -1.9727    0.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0727   -4.3709    0.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2083   -5.0505   -0.0505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9394   -3.2770   -0.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7068   -0.3197   -1.4343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6792   -1.4126   -0.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5476   -0.1856    1.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9013    0.6577    0.6696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6275    2.6196    0.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2474    4.5839   -0.4876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7887    4.3550   -0.7649 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2429    2.1691   -0.3909 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
 20 21  2  0
 21  7  1  0
 13  8  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 15 41  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 458                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  N   UNK     0       7.220   1.338   0.000  0.00  0.00           N+0
HETATM    2  N   UNK     0       4.659  -3.098   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       7.220  -0.141   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.553   1.979   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.888   1.979   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.960   4.577   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.481   4.577   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.882   3.421   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.559   3.421   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.940  -0.880   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.940  -2.359   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.665   0.914   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.775   0.914   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.346   3.897   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.094   3.897   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.140   1.357   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.300   1.357   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.483   2.859   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.957   2.859   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.659  -4.577   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.378  -2.359   0.000  0.00  0.00           C+0
CONECT    1    3    4    5                                                  
CONECT    2   11   20   21                                                  
CONECT    3    1   10                                                       
CONECT    4    1    8   12                                                  
CONECT    5    1    9   13                                                  
CONECT    6    7    8                                                       
CONECT    7    6    9                                                       
CONECT    8    4    6   14                                                  
CONECT    9    5    7   15                                                  
CONECT   10    3   11                                                       
CONECT   11    2   10                                                       
CONECT   12    4   16                                                       
CONECT   13    5   17                                                       
CONECT   14    8   18                                                       
CONECT   15    9   19                                                       
CONECT   16   12   18                                                       
CONECT   17   13   19                                                       
CONECT   18   14   16                                                       
CONECT   19   15   17                                                       
CONECT   20    2                                                            
CONECT   21    2                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0001848
HETATM    1  C1  UNL     1       4.657  -1.024  -0.562  1.00  0.00           C  
HETATM    2  N1  UNL     1       4.219   0.266  -0.213  1.00  0.00           N  
HETATM    3  C2  UNL     1       5.136   1.332  -0.267  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.041   0.424   0.528  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.776   0.028  -0.285  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.639   0.245   0.587  1.00  0.00           C  
HETATM    7  N2  UNL     1      -0.707   0.019   0.280  1.00  0.00           N  
HETATM    8  C6  UNL     1      -1.269  -1.289   0.146  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.339  -2.258   0.389  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.677  -3.585   0.318  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.967  -3.986  -0.001  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.911  -3.017  -0.247  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.574  -1.684  -0.176  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.729  -0.808  -0.457  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.865   0.282   0.606  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.897   1.343   0.244  1.00  0.00           C  
HETATM   17  C15 UNL     1      -3.544   2.533   0.044  1.00  0.00           C  
HETATM   18  C16 UNL     1      -2.786   3.620  -0.319  1.00  0.00           C  
HETATM   19  C17 UNL     1      -1.425   3.527  -0.479  1.00  0.00           C  
HETATM   20  C18 UNL     1      -0.798   2.288  -0.265  1.00  0.00           C  
HETATM   21  C19 UNL     1      -1.523   1.182   0.100  1.00  0.00           C  
HETATM   22  H1  UNL     1       4.972  -1.155  -1.613  1.00  0.00           H  
HETATM   23  H2  UNL     1       3.910  -1.775  -0.229  1.00  0.00           H  
HETATM   24  H3  UNL     1       5.579  -1.250   0.051  1.00  0.00           H  
HETATM   25  H4  UNL     1       5.262   1.756   0.764  1.00  0.00           H  
HETATM   26  H5  UNL     1       6.130   0.940  -0.561  1.00  0.00           H  
HETATM   27  H6  UNL     1       4.896   2.137  -0.984  1.00  0.00           H  
HETATM   28  H7  UNL     1       2.904   1.484   0.790  1.00  0.00           H  
HETATM   29  H8  UNL     1       3.094  -0.154   1.459  1.00  0.00           H  
HETATM   30  H9  UNL     1       1.933  -0.907  -0.812  1.00  0.00           H  
HETATM   31  H10 UNL     1       1.929   0.789  -1.122  1.00  0.00           H  
HETATM   32  H11 UNL     1       0.815   1.245   1.124  1.00  0.00           H  
HETATM   33  H12 UNL     1       0.823  -0.344   1.577  1.00  0.00           H  
HETATM   34  H13 UNL     1       0.626  -1.973   0.640  1.00  0.00           H  
HETATM   35  H14 UNL     1       0.073  -4.371   0.514  1.00  0.00           H  
HETATM   36  H15 UNL     1      -2.208  -5.051  -0.050  1.00  0.00           H  
HETATM   37  H16 UNL     1      -3.939  -3.277  -0.501  1.00  0.00           H  
HETATM   38  H17 UNL     1      -3.707  -0.320  -1.434  1.00  0.00           H  
HETATM   39  H18 UNL     1      -4.679  -1.413  -0.356  1.00  0.00           H  
HETATM   40  H19 UNL     1      -3.548  -0.186   1.575  1.00  0.00           H  
HETATM   41  H20 UNL     1      -4.901   0.658   0.670  1.00  0.00           H  
HETATM   42  H21 UNL     1      -4.627   2.620   0.170  1.00  0.00           H  
HETATM   43  H22 UNL     1      -3.247   4.584  -0.488  1.00  0.00           H  
HETATM   44  H23 UNL     1      -0.789   4.355  -0.765  1.00  0.00           H  
HETATM   45  H24 UNL     1       0.243   2.169  -0.391  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    4
CONECT    3   25   26   27
CONECT    4    5   28   29
CONECT    5    6   30   31
CONECT    6    7   32   33
CONECT    7    8   21
CONECT    8    9    9   13
CONECT    9   10   34
CONECT   10   11   11   35
CONECT   11   12   36
CONECT   12   13   13   37
CONECT   13   14
CONECT   14   15   38   39
CONECT   15   16   40   41
CONECT   16   17   17   21
CONECT   17   18   42
CONECT   18   19   19   43
CONECT   19   20   44
CONECT   20   21   21   45
END

HMDB0001848
     RDKit          3D
Imipramine
 45 47  0  0  0  0  0  0  0  0999 V2000
    4.6573   -1.0244   -0.5623 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2189    0.2657   -0.2134 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1356    1.3316   -0.2667 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0412    0.4239    0.5281 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7756    0.0282   -0.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6392    0.2449    0.5870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7074    0.0189    0.2801 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2688   -1.2895    0.1460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3395   -2.2577    0.3892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6770   -3.5850    0.3184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9674   -3.9861   -0.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9113   -3.0168   -0.2466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5739   -1.6842   -0.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7293   -0.8082   -0.4566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8653    0.2821    0.6060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8971    1.3433    0.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5443    2.5332    0.0444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7856    3.6205   -0.3188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4251    3.5268   -0.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7975    2.2875   -0.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5228    1.1823    0.1000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9717   -1.1549   -1.6135 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9099   -1.7753   -0.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5795   -1.2496    0.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2620    1.7562    0.7640 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1303    0.9395   -0.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8962    2.1367   -0.9839 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9044    1.4845    0.7904 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0943   -0.1537    1.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9335   -0.9065   -0.8123 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9291    0.7887   -1.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8150    1.2449    1.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8232   -0.3435    1.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6262   -1.9727    0.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0727   -4.3709    0.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2083   -5.0505   -0.0505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9394   -3.2770   -0.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7068   -0.3197   -1.4343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6792   -1.4126   -0.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5476   -0.1856    1.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9013    0.6577    0.6696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6275    2.6196    0.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2474    4.5839   -0.4876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7887    4.3550   -0.7649 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2429    2.1691   -0.3909 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
 20 21  2  0
 21  7  1  0
 13  8  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 15 41  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
10,11-Dihydro-N,N-dimethyl-5H-dibenz[b,F]azepine-5-propanamine	ChEBI
3-(5H-DIBENZO[b,F]azepin-5-yl)-N,N-dimethylpropan-1-amine	ChEBI
5-[3-(Dimethylamino)propyl]-10,11-dihydro-5H-dibenz[b,F]azepine	ChEBI
Antideprin	ChEBI
Imipramin	ChEBI
Imipraminum	ChEBI
Imizine	ChEBI
Irmin	ChEBI
Melipramine	ChEBI
N-(gamma-Dimethylaminopropyl)iminodibenzyl	ChEBI
Tofranil	Kegg
N-(g-Dimethylaminopropyl)iminodibenzyl	Generator
N-(Γ-dimethylaminopropyl)iminodibenzyl	Generator
Berkomine	HMDB
Chimoreptin	HMDB
Declomipramine	HMDB
Dimipressin	HMDB
DPID	HMDB
Dyna-zina	HMDB
Dynaprin	HMDB
Eupramin	HMDB
Feinalmin	HMDB
Imavate	HMDB
Imidobenzyle	HMDB
Imilanyle	HMDB
Janimine	HMDB
Lofepramine	HMDB
Melipramin	HMDB
Psychoforin	HMDB
Surmontil	HMDB
Surplix	HMDB
Teperine	HMDB
Timolet	HMDB
Tofranil base	HMDB
Tofranil-PM	HMDB
Trimipramine maleate	HMDB
Imipramine hydrochloride	HMDB
Norchlorimipramine	HMDB
Imipramine monohydrochloride	HMDB
Imizin	HMDB
Pryleugan	HMDB
4,4'-Methylenebis(3-hydroxy-2-naphthoic acid)-3-(10,11-dihydro-5H-dibenzo(b,F)azepin-5-yl)-N,N-dimethyl-1-propanamine (1:2)	HMDB
Imipramine pamoate	HMDB

Chemical Formula

C₁₉H₂₄N₂

Average Molecular Weight

280.4073

Monoisotopic Molecular Weight

280.193948778

IUPAC Name

(3-{2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-2-yl}propyl)dimethylamine

Traditional Name

(3-{2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-2-yl}propyl)dimethylamine

CAS Registry Number

50-49-7

SMILES

CN(C)CCCN1C2=CC=CC=C2CCC2=CC=CC=C12

InChI Identifier

InChI=1S/C19H24N2/c1-20(2)14-7-15-21-18-10-5-3-8-16(18)12-13-17-9-4-6-11-19(17)21/h3-6,8-11H,7,12-15H2,1-2H3

InChI Key

BCGWQEUPMDMJNV-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
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dibenzoazepine (CHEBI:47499 )
a small molecule (CPD-11438 )

Ontology

Physiological effect

Health effect

Circulatory system disorder

Vascular disorder

Hypertension (HMDB: HMDB0001848)
Hypotension (HMDB: HMDB0001848)

Cardiac disorder

Heart failure (HMDB: HMDB0001848)
Congestive heart failure (HMDB: HMDB0001848)

Observation

Nervous system disorder

Central nervous system disorder

Psychiatric disorder

Neurotic, stress-related, or somatoform disorder

Anxiety (HMDB: HMDB0001848)

Mood disorder

Bipolar disorder (HMDB: HMDB0001848)

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0001848)
Cell membrane (HMDB: HMDB0001848)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0001848)

Source

Exogenous

Exogenous (HMDB: HMDB0001848)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Imipramine Metabolism Pathway (HMDB: HMDB0001848)
Imipramine Metabolism Pathway (PathBank: SMP0000625)

Drug action pathway

Imipramine Action Pathway (HMDB: HMDB0001848)
Imipramine Action Pathway (PathBank: SMP0000422)

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0001848)

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Antidepressant (HMDB: HMDB0001848)
Antidepressant (HMDB: HMDB0001848)

Biological role

Modulator

Adrenergic uptake inhibitor (HMDB: HMDB0001848)

Inhibitor

EC 3.4.21.26 (prolyl oligopeptidase) inhibitor (HMDB: HMDB0001848)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	174.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	18.2 mg/L at 24 °C	Not Available
LogP	4.80	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	166.5	30932474
[M+H]+	Not Available	165.149	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000993

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.066 g/L	ALOGPS
logP	4.53	ALOGPS
logP	4.28	ChemAxon
logS	-3.6	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	90.61 m³·mol⁻¹	ChemAxon
Polarizability	33.39 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
DarkChem	[M+H]+	167.21	31661259
DarkChem	[M-H]-	165.828	31661259
AllCCS	[M+H]+	167.78	32859911
AllCCS	[M-H]-	177.655	32859911
DeepCCS	[M-2H]-	192.667	30932474
DeepCCS	[M+Na]+	168.233	30932474
AllCCS	[M+H]+	167.8	32859911
AllCCS	[M+H-H2O]+	164.2	32859911
AllCCS	[M+NH4]+	171.1	32859911
AllCCS	[M+Na]+	172.1	32859911
AllCCS	[M-H]-	177.7	32859911
AllCCS	[M+Na-2H]-	177.4	32859911
AllCCS	[M+HCOO]-	177.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Imipramine	CN(C)CCCN1C2=CC=CC=C2CCC2=CC=CC=C12	3380.2	Standard polar	33892256
Imipramine	CN(C)CCCN1C2=CC=CC=C2CCC2=CC=CC=C12	2246.0	Standard non polar	33892256
Imipramine	CN(C)CCCN1C2=CC=CC=C2CCC2=CC=CC=C12	2207.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Imipramine EI-B (Non-derivatized)	splash10-0019-7490000000-3fb4d40b6a219f088ec8	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Imipramine EI-B (Non-derivatized)	splash10-0019-7490000000-3fb4d40b6a219f088ec8	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Imipramine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-7490000000-746fcd08b0a7d6e7bc83	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Imipramine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Imipramine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0543-8890000000-6cf8e84f007ce7c750f2	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 - Imipramine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-000i-9000000000-55d924fd00e5b357ce9e	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Imipramine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-000i-9000000000-eb3c0ecdffc5d9d95e33	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Imipramine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0ab9-9432000000-033c51459b692622ee7d	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Imipramine EI-B (Unknown) , Positive-QTOF	splash10-0019-7490000000-bb99ef31a755d9f6ba14	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Imipramine LC-ESI-QTOF , positive-QTOF	splash10-052r-9010000000-961429188e57c1480db8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Imipramine 40V, Positive-QTOF	splash10-0a4i-9000000000-6272981565b197d622f1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Imipramine -1V, Positive-QTOF	splash10-052r-9010000000-be8c371ae701a7225d13	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Imipramine 40V, Positive-QTOF	splash10-0a4i-9000000000-6c56d64b8822a435898c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Imipramine 75V, Positive-QTOF	splash10-0a4i-9000000000-2671c52504aa0680b918	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Imipramine 90V, Positive-QTOF	splash10-0a4i-9100000000-a756ccfcc744eec6e5ab	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Imipramine 10V, Positive-QTOF	splash10-0019-9050000000-ad820fcbaa90ad01f5ed	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Imipramine 20V, Positive-QTOF	splash10-000i-9010000000-7b329c019f10b027904f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Imipramine 45V, Positive-QTOF	splash10-000i-9000000000-18201fd6a82e596bb8bd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Imipramine 10V, Positive-QTOF	splash10-0019-9050000000-eafe5899fec7b49f5f30	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Imipramine 20V, Positive-QTOF	splash10-000i-9000000000-9adbfb340afaa417fda3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Imipramine 60V, Positive-QTOF	splash10-0a4r-9000000000-9bb5a8512a91de12e786	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Imipramine 30V, Positive-QTOF	splash10-000i-9000000000-48bfa7137f4eaa6b17e6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Imipramine 15V, Positive-QTOF	splash10-0019-9080000000-680701a3db1bd34f0e6f	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imipramine 10V, Positive-QTOF	splash10-001i-1090000000-d8b2753be1e55651ebe7	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imipramine 20V, Positive-QTOF	splash10-0019-5190000000-884d5f80618ae379a408	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imipramine 40V, Positive-QTOF	splash10-000f-9420000000-655018838b0eb1b10c77	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imipramine 10V, Negative-QTOF	splash10-004i-0090000000-115aa4768e53e232aa16	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imipramine 20V, Negative-QTOF	splash10-004l-1590000000-bf5870eaefcecc8340c7	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imipramine 40V, Negative-QTOF	splash10-00kf-2910000000-568ea79e9375b6365408	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imipramine 10V, Negative-QTOF	splash10-004i-0090000000-fa0545de4a4dc60fd062	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	2012-12-04	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Imipramine Action Pathway		Not Available
Imipramine Metabolism Pathway		Not Available

Normal Concentrations

Not Available

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

DB00458

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022706

KNApSAcK ID

Not Available

Chemspider ID

3568

KEGG Compound ID

C07049

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Imipramine

METLIN ID

500

PubChem Compound

3696

PDB ID

Not Available

ChEBI ID

47499

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

Not Available

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

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Dimethylaniline monooxygenase [N-oxide-forming] 2

General function:: Involved in flavin-containing monooxygenase activity
Specific function:: Catalyzes the N-oxidation of certain primary alkylamines to their oximes via an N-hydroxylamine intermediate. Inactive toward certain tertiary amines, such as imipramine or chloropromazine. Can catalyze the S-oxidation of methimazole. The truncated form is catalytically inactive.
Gene Name:: FMO2
Uniprot ID:: Q99518
Molecular weight:: 53643.29

Enzyme Details

2. Amine oxidase [flavin-containing] B

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:: MAOB
Uniprot ID:: P27338
Molecular weight:: 58762.475

Enzyme Details

3. Amine oxidase [flavin-containing] A

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:: MAOA
Uniprot ID:: P21397
Molecular weight:: 59681.27

Enzyme Details

4. UDP-glucuronosyltransferase 1-4

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
Gene Name:: UGT1A4
Uniprot ID:: P22310
Molecular weight:: 60024.535

Enzyme Details

5. Cytochrome P450 2C9

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. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

Enzyme Details

6. 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

Enzyme Details

7. 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

8. 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

Enzyme Details

9. Adenosine receptor A1

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Receptor for adenosine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:: ADORA1
Uniprot ID:: P30542
Molecular weight:: 36511.3

Transporters

Enzyme Details

1. 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

Enzyme Details

2. Sodium-dependent serotonin transporter

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

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

Show all enzymes and transporters

Showing metabocard for Imipramine (HMDB0001848)

MOL for HMDB0001848 (Imipramine)

3D MOL for HMDB0001848 (Imipramine)

3D SDF for HMDB0001848 (Imipramine)

3D-SDF for HMDB0001848 (Imipramine)

PDB for HMDB0001848 (Imipramine)

3D PDB for HMDB0001848 (Imipramine)

SMILES for HMDB0001848 (Imipramine)

INCHI for HMDB0001848 (Imipramine)

Structure for HMDB0001848 (Imipramine)

3D Structure for HMDB0001848 (Imipramine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Transporters