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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 11:52:21 UTC

Update Date

2021-09-26 23:06:39 UTC

HMDB ID

HMDB0253434

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Imipraminoxide

Description

Imipramine oxide 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. Imipraminoxide is both an analogue and a metabolite of imipramine, and has similar effects. Imipramine oxide is a strong basic compound (based on its pKa). Imipraminoxide's pharmacology has not been well elucidated, but based on its very close relationship with imipramine, it likely acts as a serotonin and norepinephrine reuptake inhibitor and serotonin, adrenenaline, histamine, and muscarinic acetylcholine receptor antagonist, though with weaker antiadrenergic and anticholinergic actions. Imipraminoxide has been said to be a prodrug of imipramine. However, in clinical trials, imipraminoxide was found to have a faster onset of action, slightly higher efficacy, and fewer and less marked side effects, including diminished orthostatic hypotension and anticholinergic effects like dry mouth, sweating, dizziness, and fatigue. Imipraminoxide (brand names Imiprex, Elepsin), or imipramine N-oxide, is a tricyclic antidepressant (TCA) that was introduced in Europe in the 1960s for the treatment of depression. This compound has been identified in human blood as reported by (PMID: 31557052 ). Imipraminoxide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Imipraminoxide is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0253434
     RDKit          3D
Imipraminoxide
 46 48  0  0  0  0  0  0  0  0999 V2000
    4.3000   -1.8684    0.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7467   -0.5918    0.7989 N   0  0  0  0  0  4  0  0  0  0  0  0
    4.8389    0.3408    1.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9698   -0.6684    1.9143 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.9289   -0.0786   -0.2706 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4587   -0.1710    0.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5991    0.3878   -1.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7862    0.3122   -0.7679 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4760    1.5589   -0.4694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9937    2.5627   -1.2879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5312    3.8073   -1.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5178    4.0315   -0.1998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9833    3.0043    0.6075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4612    1.7367    0.4816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0281    0.7110    1.3869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6275   -0.3873    0.5794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6544   -1.2583   -0.1234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1120   -2.5664   -0.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3285   -3.5232   -0.8086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1237   -3.2163   -1.3926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6472   -1.9082   -1.3569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4294   -0.9845   -0.7251 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6415   -2.7262    0.7861 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2514   -2.0040    1.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4482   -1.8891   -0.6421 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5560    1.1480    1.7240 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0711    0.8242    0.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7396   -0.1911    1.4117 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2203    0.9462   -0.5720 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0755   -0.7382   -1.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695   -1.2146    0.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2900    0.4841    0.9625 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9631    0.1534   -2.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9102    1.4733   -0.9278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2332    2.2915   -2.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1549    4.5947   -1.7770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9408    5.0013   -0.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7482    3.1539    1.3422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1501    0.2616    1.9407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7560    1.1250    2.0976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3267   -1.0301    1.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2561    0.0923   -0.2281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0533   -2.8542    0.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7286   -4.5309   -0.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5227   -3.9672   -1.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2923   -1.6348   -1.8114 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
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22  8  1  0
 14  9  1  0
 22 17  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
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
M  CHG  2   2   1   4  -1
M  END

  Mrv1652306031609512D          

 22 24  0  0  0  0            999 V2000
    1.6603   -3.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7872   -4.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1237   -0.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4837   -0.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9401   -0.8303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6673   -0.8303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0892   -2.1078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5189    0.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0884    0.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1517   -1.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4556   -1.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2162    0.9370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3912    0.9370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8037   -1.6953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0892   -2.9328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7305    0.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8768    0.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5470   -0.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0604   -0.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8037   -0.8703    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3747   -3.3453    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9622   -2.6308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
  8  3  1  0  0  0  0
  9  4  1  0  0  0  0
 10  5  1  0  0  0  0
 11  6  1  0  0  0  0
 13 12  1  0  0  0  0
 14  7  1  0  0  0  0
 15  7  1  0  0  0  0
 16  8  2  0  0  0  0
 16 12  1  0  0  0  0
 17  9  2  0  0  0  0
 17 13  1  0  0  0  0
 18 10  2  0  0  0  0
 18 16  1  0  0  0  0
 19 11  2  0  0  0  0
 19 17  1  0  0  0  0
 20 14  1  0  0  0  0
 20 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21  1  1  0  0  0  0
 21  2  1  0  0  0  0
 21 15  1  0  0  0  0
 22 21  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253434

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C19H24N2O/c1-21(2,22)15-7-14-20-18-10-5-3-8-16(18)12-13-17-9-4-6-11-19(17)20/h3-6,8-11H,7,12-15H2,1-2H3

> <INCHI_KEY>
QZIQORUGXBPDSU-UHFFFAOYSA-N

> <FORMULA>
C19H24N2O

> <MOLECULAR_WEIGHT>
296.414

> <EXACT_MASS>
296.188863401

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
34.58557437622472

> <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}-N,N-dimethylpropanamine oxide

> <ALOGPS_LOGP>
1.10

> <JCHEM_LOGP>
3.154193611

> <ALOGPS_LOGS>
-4.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
4.124860970033837

> <JCHEM_POLAR_SURFACE_AREA>
30.12

> <JCHEM_REFRACTIVITY>
92.65049999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.28e-03 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}-N,N-dimethylpropanamine oxide

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0253434
     RDKit          3D
Imipraminoxide
 46 48  0  0  0  0  0  0  0  0999 V2000
    4.3000   -1.8684    0.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7467   -0.5918    0.7989 N   0  0  0  0  0  4  0  0  0  0  0  0
    4.8389    0.3408    1.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9698   -0.6684    1.9143 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.9289   -0.0786   -0.2706 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4587   -0.1710    0.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5991    0.3878   -1.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7862    0.3122   -0.7679 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4760    1.5589   -0.4694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9937    2.5627   -1.2879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5312    3.8073   -1.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5178    4.0315   -0.1998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9833    3.0043    0.6075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4612    1.7367    0.4816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0281    0.7110    1.3869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6275   -0.3873    0.5794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6544   -1.2583   -0.1234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1120   -2.5664   -0.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3285   -3.5232   -0.8086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1237   -3.2163   -1.3926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6472   -1.9082   -1.3569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4294   -0.9845   -0.7251 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6415   -2.7262    0.7861 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2514   -2.0040    1.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4482   -1.8891   -0.6421 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5560    1.1480    1.7240 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0711    0.8242    0.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7396   -0.1911    1.4117 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2203    0.9462   -0.5720 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0755   -0.7382   -1.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695   -1.2146    0.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2900    0.4841    0.9625 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9631    0.1534   -2.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9102    1.4733   -0.9278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2332    2.2915   -2.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1549    4.5947   -1.7770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9408    5.0013   -0.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7482    3.1539    1.3422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1501    0.2616    1.9407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7560    1.1250    2.0976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3267   -1.0301    1.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2561    0.0923   -0.2281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0533   -2.8542    0.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7286   -4.5309   -0.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5227   -3.9672   -1.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2923   -1.6348   -1.8114 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
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22  8  1  0
 14  9  1  0
 22 17  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
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
M  CHG  2   2   1   4  -1
M  END

HEADER    PROTEIN                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0       3.099  -7.015   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.203  -7.578   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.431  -0.048   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.770  -0.048   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.088  -1.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.112  -1.550   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.766  -3.935   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.302   0.999   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.898   0.999   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.617  -2.004   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.584  -2.004   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.870   1.749   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.330   1.749   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.100  -3.165   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.766  -5.475   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.830   0.545   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.370   0.545   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.488  -0.956   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.713  -0.956   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       7.100  -1.625   0.000  0.00  0.00           N+0
HETATM   21  N   UNK     0       4.433  -6.245   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0       3.663  -4.911   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2   21                                                            
CONECT    3    5    8                                                       
CONECT    4    6    9                                                       
CONECT    5    3   10                                                       
CONECT    6    4   11                                                       
CONECT    7   14   15                                                       
CONECT    8    3   16                                                       
CONECT    9    4   17                                                       
CONECT   10    5   18                                                       
CONECT   11    6   19                                                       
CONECT   12   13   16                                                       
CONECT   13   12   17                                                       
CONECT   14    7   20                                                       
CONECT   15    7   21                                                       
CONECT   16    8   12   18                                                  
CONECT   17    9   13   19                                                  
CONECT   18   10   16   20                                                  
CONECT   19   11   17   20                                                  
CONECT   20   14   18   19                                                  
CONECT   21    1    2   15   22                                             
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0253434
HETATM    1  C1  UNL     1       4.300  -1.868   0.464  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.747  -0.592   0.799  1.00  0.00           N1+
HETATM    3  C2  UNL     1       4.839   0.341   1.014  1.00  0.00           C  
HETATM    4  O1  UNL     1       2.970  -0.668   1.914  1.00  0.00           O1-
HETATM    5  C3  UNL     1       2.929  -0.079  -0.271  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.459  -0.171   0.086  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.599   0.388  -1.082  1.00  0.00           C  
HETATM    8  N2  UNL     1      -0.786   0.312  -0.768  1.00  0.00           N  
HETATM    9  C6  UNL     1      -1.476   1.559  -0.469  1.00  0.00           C  
HETATM   10  C7  UNL     1      -0.994   2.563  -1.288  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.531   3.807  -1.138  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.518   4.031  -0.200  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.983   3.004   0.608  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.461   1.737   0.482  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.028   0.711   1.387  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.627  -0.387   0.579  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.654  -1.258  -0.123  1.00  0.00           C  
HETATM   18  C15 UNL     1      -3.112  -2.566  -0.169  1.00  0.00           C  
HETATM   19  C16 UNL     1      -2.328  -3.523  -0.809  1.00  0.00           C  
HETATM   20  C17 UNL     1      -1.124  -3.216  -1.393  1.00  0.00           C  
HETATM   21  C18 UNL     1      -0.647  -1.908  -1.357  1.00  0.00           C  
HETATM   22  C19 UNL     1      -1.429  -0.984  -0.725  1.00  0.00           C  
HETATM   23  H1  UNL     1       3.642  -2.726   0.786  1.00  0.00           H  
HETATM   24  H2  UNL     1       5.251  -2.004   1.022  1.00  0.00           H  
HETATM   25  H3  UNL     1       4.448  -1.889  -0.642  1.00  0.00           H  
HETATM   26  H4  UNL     1       4.556   1.148   1.724  1.00  0.00           H  
HETATM   27  H5  UNL     1       5.071   0.824   0.059  1.00  0.00           H  
HETATM   28  H6  UNL     1       5.740  -0.191   1.412  1.00  0.00           H  
HETATM   29  H7  UNL     1       3.220   0.946  -0.572  1.00  0.00           H  
HETATM   30  H8  UNL     1       3.075  -0.738  -1.156  1.00  0.00           H  
HETATM   31  H9  UNL     1       1.270  -1.215   0.272  1.00  0.00           H  
HETATM   32  H10 UNL     1       1.290   0.484   0.962  1.00  0.00           H  
HETATM   33  H11 UNL     1       0.963   0.153  -2.055  1.00  0.00           H  
HETATM   34  H12 UNL     1       0.910   1.473  -0.928  1.00  0.00           H  
HETATM   35  H13 UNL     1      -0.233   2.292  -2.005  1.00  0.00           H  
HETATM   36  H14 UNL     1      -1.155   4.595  -1.777  1.00  0.00           H  
HETATM   37  H15 UNL     1      -2.941   5.001  -0.079  1.00  0.00           H  
HETATM   38  H16 UNL     1      -3.748   3.154   1.342  1.00  0.00           H  
HETATM   39  H17 UNL     1      -2.150   0.262   1.941  1.00  0.00           H  
HETATM   40  H18 UNL     1      -3.756   1.125   2.098  1.00  0.00           H  
HETATM   41  H19 UNL     1      -4.327  -1.030   1.154  1.00  0.00           H  
HETATM   42  H20 UNL     1      -4.256   0.092  -0.228  1.00  0.00           H  
HETATM   43  H21 UNL     1      -4.053  -2.854   0.276  1.00  0.00           H  
HETATM   44  H22 UNL     1      -2.729  -4.531  -0.818  1.00  0.00           H  
HETATM   45  H23 UNL     1      -0.523  -3.967  -1.887  1.00  0.00           H  
HETATM   46  H24 UNL     1       0.292  -1.635  -1.811  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    4    5
CONECT    3   26   27   28
CONECT    5    6   29   30
CONECT    6    7   31   32
CONECT    7    8   33   34
CONECT    8    9   22
CONECT    9   10   10   14
CONECT   10   11   35
CONECT   11   12   12   36
CONECT   12   13   37
CONECT   13   14   14   38
CONECT   14   15
CONECT   15   16   39   40
CONECT   16   17   41   42
CONECT   17   18   18   22
CONECT   18   19   43
CONECT   19   20   20   44
CONECT   20   21   45
CONECT   21   22   22   46
END

HMDB0253434
     RDKit          3D
Imipraminoxide
 46 48  0  0  0  0  0  0  0  0999 V2000
    4.3000   -1.8684    0.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7467   -0.5918    0.7989 N   0  0  0  0  0  4  0  0  0  0  0  0
    4.8389    0.3408    1.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9698   -0.6684    1.9143 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.9289   -0.0786   -0.2706 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4587   -0.1710    0.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5991    0.3878   -1.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7862    0.3122   -0.7679 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4760    1.5589   -0.4694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9937    2.5627   -1.2879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5312    3.8073   -1.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5178    4.0315   -0.1998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9833    3.0043    0.6075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4612    1.7367    0.4816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0281    0.7110    1.3869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6275   -0.3873    0.5794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6544   -1.2583   -0.1234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1120   -2.5664   -0.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3285   -3.5232   -0.8086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1237   -3.2163   -1.3926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6472   -1.9082   -1.3569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4294   -0.9845   -0.7251 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6415   -2.7262    0.7861 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2514   -2.0040    1.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4482   -1.8891   -0.6421 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5560    1.1480    1.7240 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0711    0.8242    0.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7396   -0.1911    1.4117 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2203    0.9462   -0.5720 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0755   -0.7382   -1.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695   -1.2146    0.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2900    0.4841    0.9625 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9631    0.1534   -2.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9102    1.4733   -0.9278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2332    2.2915   -2.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1549    4.5947   -1.7770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9408    5.0013   -0.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7482    3.1539    1.3422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1501    0.2616    1.9407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7560    1.1250    2.0976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3267   -1.0301    1.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2561    0.0923   -0.2281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0533   -2.8542    0.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7286   -4.5309   -0.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5227   -3.9672   -1.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2923   -1.6348   -1.8114 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
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22  8  1  0
 14  9  1  0
 22 17  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
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
M  CHG  2   2   1   4  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Imipramine N-oxide hydrochloride	MeSH
5-(3-(Dimethylamino)propyl)-10,11-dihydro-5H- dibenz(b,F)azepine 5-(3-N-oxide)	MeSH
Imipramine-N-oxide	MeSH
Imipramine N-oxide	MeSH

Chemical Formula

C₁₉H₂₄N₂O

Average Molecular Weight

296.414

Monoisotopic Molecular Weight

296.188863401

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C19H24N2O/c1-21(2,22)15-7-14-20-18-10-5-3-8-16(18)12-13-17-9-4-6-11-19(17)20/h3-6,8-11H,7,12-15H2,1-2H3

InChI Key

QZIQORUGXBPDSU-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
Trialkyl amine oxide
Tertiary amine
Azacycle
N-oxide
Trisubstituted n-oxide
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.1	ALOGPS
logP	3.15	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	4.12	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	30.12 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	92.65 m³·mol⁻¹	ChemAxon
Polarizability	34.59 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-2H]-	192.572	30932474
DeepCCS	[M+Na]+	168.137	30932474
AllCCS	[M+H]+	171.7	32859911
AllCCS	[M+H-H2O]+	168.3	32859911
AllCCS	[M+NH4]+	174.8	32859911
AllCCS	[M+Na]+	175.7	32859911
AllCCS	[M-H]-	182.0	32859911
AllCCS	[M+Na-2H]-	182.3	32859911
AllCCS	[M+HCOO]-	182.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Imipraminoxide	CN(C)(=O)CCCN1C2=CC=CC=C2CCC2=CC=CC=C12	3681.9	Standard polar	33892256
Imipraminoxide	CN(C)(=O)CCCN1C2=CC=CC=C2CCC2=CC=CC=C12	2060.5	Standard non polar	33892256
Imipraminoxide	CN(C)(=O)CCCN1C2=CC=CC=C2CCC2=CC=CC=C12	2341.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Imipraminoxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a5i-1390000000-5afdfd31ebc015d57de8	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Imipraminoxide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imipraminoxide 10V, Positive-QTOF	splash10-0002-0090000000-8b1d8694a0b277893cf1	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imipraminoxide 20V, Positive-QTOF	splash10-0f72-1490000000-627961206bbaba03fed0	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imipraminoxide 40V, Positive-QTOF	splash10-0006-9820000000-498a1a429385f0ad9f15	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imipraminoxide 10V, Negative-QTOF	splash10-0002-0090000000-4d827b5259e10aa2edb9	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imipraminoxide 20V, Negative-QTOF	splash10-0005-1590000000-5f67a40fb89ec9b37a4b	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imipraminoxide 40V, Negative-QTOF	splash10-0006-0900000000-946fb0db05f67672a64d	2019-02-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB13782

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Imipraminoxide

METLIN ID

Not Available

PubChem Compound

65589

PDB ID

Not Available

ChEBI ID

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Imipraminoxide (HMDB0253434)

MOL for HMDB0253434 (Imipraminoxide)

3D MOL for HMDB0253434 (Imipraminoxide)

3D SDF for HMDB0253434 (Imipraminoxide)

3D-SDF for HMDB0253434 (Imipraminoxide)

PDB for HMDB0253434 (Imipraminoxide)

3D PDB for HMDB0253434 (Imipraminoxide)

SMILES for HMDB0253434 (Imipraminoxide)

INCHI for HMDB0253434 (Imipraminoxide)

Structure for HMDB0253434 (Imipraminoxide)

3D Structure for HMDB0253434 (Imipraminoxide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra