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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:20:11 UTC

Update Date

2021-09-26 23:07:57 UTC

HMDB ID

HMDB0254150

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Lofepramine

Description

Lofepramine 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. Lofepramine is a very strong basic compound (based on its pKa). In humans, lofepramine is involved in imipramine metabolism pathway. This compound has been identified in human blood as reported by (PMID: 31557052 ). Lofepramine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Lofepramine 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


  Mrv1652306031607142D          

 30 33  0  0  0  0            999 V2000
    5.3385    4.0824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0876    1.6704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7676    5.6887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2992    1.4272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1628    5.1276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7674    3.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2712    2.4747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5559    5.4456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6945    1.9884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3464    4.3233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9678    3.8038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5553    4.5183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4806    3.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1951    2.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7662    2.8449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4806    1.6074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0530    2.8449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4819    2.8449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6240    2.8449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6664    3.0358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7395    4.6412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1951    2.8449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7662    2.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8780    2.7927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1347    4.0801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9096    3.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0517    1.6074    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.3385    3.2574    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1964    3.2574    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9096    4.0824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  2  0  0  0  0
  5  3  2  0  0  0  0
  7  2  1  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
 12 11  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  2  0  0  0  0
 17  6  1  0  0  0  0
 18  6  1  0  0  0  0
 20  7  2  0  0  0  0
 20 11  1  0  0  0  0
 21  8  2  0  0  0  0
 21 12  1  0  0  0  0
 22 13  2  0  0  0  0
 22 14  1  0  0  0  0
 23 15  2  0  0  0  0
 23 16  1  0  0  0  0
 24  9  2  0  0  0  0
 24 20  1  0  0  0  0
 25 10  2  0  0  0  0
 25 21  1  0  0  0  0
 26 19  1  0  0  0  0
 26 22  1  0  0  0  0
 27 23  1  0  0  0  0
 28  1  1  0  0  0  0
 28 17  1  0  0  0  0
 28 19  1  0  0  0  0
 29 18  1  0  0  0  0
 29 24  1  0  0  0  0
 29 25  1  0  0  0  0
 30 26  2  0  0  0  0
M  END

HMDB0254150
     RDKit          3D
Lofepramine
 57 60  0  0  0  0  0  0  0  0999 V2000
    2.2100   -2.3073   -0.6851 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4969   -1.0387    0.0095 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3562   -0.6746    0.7991 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1280   -0.3984   -0.1073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0615   -0.1635    0.7106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3516   -0.0063    0.1891 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1348   -1.2054    0.1185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4074   -2.3564    0.1151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0264   -3.6161    0.0451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3901   -3.7391   -0.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1463   -2.5829   -0.0192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5282   -1.3578    0.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5118   -0.2287    0.0538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2495    0.6351   -1.1359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1258    1.5525   -0.8413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4134    2.8486   -1.2162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4867    3.8330   -1.0368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2420    3.5267   -0.4709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9509    2.2382   -0.0959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8799    1.2423   -0.2735 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0399   -0.1304   -0.8999 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7097    0.9992   -0.2317 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0633    1.9334    0.2429 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1730    0.9837   -0.1483 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9055   -0.1084   -0.5738 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2999   -0.1347   -0.5389 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9946    0.9457   -0.0707 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7477    0.9277   -0.0221 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.2905    2.0379    0.3571 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8941    2.0565    0.3192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1452   -2.8870   -0.7674 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4853   -2.9033   -0.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8951   -2.0580   -1.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6054    0.2299    1.3749 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0528   -1.5383    1.4119 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3976    0.5071   -0.7614 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2120   -1.2137   -0.8162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0211   -0.9963    1.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9097    0.6443    1.5051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3463   -2.2849    0.1783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3751   -4.4794    0.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8824   -4.7201   -0.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2026   -2.6490   -0.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5318   -0.6386   -0.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4372    0.3421    1.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1340    1.2420   -1.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9619   -0.0042   -2.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4002    3.0114   -1.6475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7575    4.8309   -1.3458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5734    4.3491   -0.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0318    2.0044    0.3151 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1970    0.3001   -1.5524 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7020   -0.5960   -1.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4015   -0.9979   -0.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8281   -1.0262   -0.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8660    2.8784    0.7216 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3740    2.9412    0.6630 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  2 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  2  0
 20  6  1  0
 30 24  1  0
 12  7  1  0
 20 15  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  8 40  1  0
  9 41  1  0
 10 42  1  0
 11 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 16 48  1  0
 17 49  1  0
 18 50  1  0
 19 51  1  0
 21 52  1  0
 21 53  1  0
 25 54  1  0
 26 55  1  0
 29 56  1  0
 30 57  1  0
M  END


  Mrv1652306031607142D          

 30 33  0  0  0  0            999 V2000
    5.3385    4.0824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0876    1.6704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7676    5.6887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2992    1.4272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1628    5.1276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7674    3.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2712    2.4747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5559    5.4456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6945    1.9884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3464    4.3233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9678    3.8038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5553    4.5183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4806    3.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1951    2.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7662    2.8449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4806    1.6074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0530    2.8449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4819    2.8449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6240    2.8449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6664    3.0358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7395    4.6412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1951    2.8449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7662    2.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8780    2.7927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1347    4.0801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9096    3.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0517    1.6074    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.3385    3.2574    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1964    3.2574    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9096    4.0824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  2  0  0  0  0
  5  3  2  0  0  0  0
  7  2  1  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
 12 11  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  2  0  0  0  0
 17  6  1  0  0  0  0
 18  6  1  0  0  0  0
 20  7  2  0  0  0  0
 20 11  1  0  0  0  0
 21  8  2  0  0  0  0
 21 12  1  0  0  0  0
 22 13  2  0  0  0  0
 22 14  1  0  0  0  0
 23 15  2  0  0  0  0
 23 16  1  0  0  0  0
 24  9  2  0  0  0  0
 24 20  1  0  0  0  0
 25 10  2  0  0  0  0
 25 21  1  0  0  0  0
 26 19  1  0  0  0  0
 26 22  1  0  0  0  0
 27 23  1  0  0  0  0
 28  1  1  0  0  0  0
 28 17  1  0  0  0  0
 28 19  1  0  0  0  0
 29 18  1  0  0  0  0
 29 24  1  0  0  0  0
 29 25  1  0  0  0  0
 30 26  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254150

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(CCCN1C2=CC=CC=C2CCC2=CC=CC=C12)CC(=O)C1=CC=C(Cl)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H27ClN2O/c1-28(19-26(30)22-13-15-23(27)16-14-22)17-6-18-29-24-9-4-2-7-20(24)11-12-21-8-3-5-10-25(21)29/h2-5,7-10,13-16H,6,11-12,17-19H2,1H3

> <INCHI_KEY>
SAPNXPWPAUFAJU-UHFFFAOYSA-N

> <FORMULA>
C26H27ClN2O

> <MOLECULAR_WEIGHT>
418.97

> <EXACT_MASS>
418.1811912

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
46.65971197786423

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(3-{2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-2-yl}propyl)(methyl)amino]-1-(4-chlorophenyl)ethan-1-one

> <ALOGPS_LOGP>
5.79

> <JCHEM_LOGP>
6.114835828

> <ALOGPS_LOGS>
-5.70

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.02323073746386

> <JCHEM_PKA_STRONGEST_BASIC>
6.53055477092998

> <JCHEM_POLAR_SURFACE_AREA>
23.55

> <JCHEM_REFRACTIVITY>
125.31209999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.38e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(3-{2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-2-yl}propyl)(methyl)amino]-1-(4-chlorophenyl)ethanone

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0254150
     RDKit          3D
Lofepramine
 57 60  0  0  0  0  0  0  0  0999 V2000
    2.2100   -2.3073   -0.6851 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4969   -1.0387    0.0095 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3562   -0.6746    0.7991 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1280   -0.3984   -0.1073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0615   -0.1635    0.7106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3516   -0.0063    0.1891 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1348   -1.2054    0.1185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4074   -2.3564    0.1151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0264   -3.6161    0.0451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3901   -3.7391   -0.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1463   -2.5829   -0.0192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5282   -1.3578    0.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5118   -0.2287    0.0538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2495    0.6351   -1.1359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1258    1.5525   -0.8413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4134    2.8486   -1.2162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4867    3.8330   -1.0368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2420    3.5267   -0.4709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9509    2.2382   -0.0959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8799    1.2423   -0.2735 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0399   -0.1304   -0.8999 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7097    0.9992   -0.2317 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0633    1.9334    0.2429 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1730    0.9837   -0.1483 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9055   -0.1084   -0.5738 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2999   -0.1347   -0.5389 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9946    0.9457   -0.0707 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7477    0.9277   -0.0221 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.2905    2.0379    0.3571 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8941    2.0565    0.3192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1452   -2.8870   -0.7674 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4853   -2.9033   -0.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8951   -2.0580   -1.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6054    0.2299    1.3749 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0528   -1.5383    1.4119 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3976    0.5071   -0.7614 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2120   -1.2137   -0.8162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0211   -0.9963    1.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9097    0.6443    1.5051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3463   -2.2849    0.1783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3751   -4.4794    0.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8824   -4.7201   -0.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2026   -2.6490   -0.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5318   -0.6386   -0.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4372    0.3421    1.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1340    1.2420   -1.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9619   -0.0042   -2.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4002    3.0114   -1.6475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7575    4.8309   -1.3458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5734    4.3491   -0.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0318    2.0044    0.3151 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1970    0.3001   -1.5524 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7020   -0.5960   -1.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4015   -0.9979   -0.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8281   -1.0262   -0.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8660    2.8784    0.7216 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3740    2.9412    0.6630 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  2 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  2  0
 20  6  1  0
 30 24  1  0
 12  7  1  0
 20 15  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  8 40  1  0
  9 41  1  0
 10 42  1  0
 11 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 16 48  1  0
 17 49  1  0
 18 50  1  0
 19 51  1  0
 21 52  1  0
 21 53  1  0
 25 54  1  0
 26 55  1  0
 29 56  1  0
 30 57  1  0
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       9.965   7.621   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.830   3.118   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.499  10.619   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      17.359   2.664   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.371   9.572   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.633   6.081   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      19.173   4.619   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.971  10.165   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.230   3.712   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.713   8.070   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.607   7.100   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.837   8.434   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.630   6.081   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.964   3.771   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.297   5.311   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.630   3.001   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.299   5.311   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.966   5.311   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.632   5.311   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      18.044   5.667   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.314   8.664   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.964   5.311   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.297   3.771   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.572   5.213   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.185   7.616   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.298   6.081   0.000  0.00  0.00           C+0
HETATM   27 Cl   UNK     0       1.963   3.001   0.000  0.00  0.00          Cl+0
HETATM   28  N   UNK     0       9.965   6.081   0.000  0.00  0.00           N+0
HETATM   29  N   UNK     0      15.300   6.081   0.000  0.00  0.00           N+0
HETATM   30  O   UNK     0       7.298   7.621   0.000  0.00  0.00           O+0
CONECT    1   28                                                            
CONECT    2    4    7                                                       
CONECT    3    5    8                                                       
CONECT    4    2    9                                                       
CONECT    5    3   10                                                       
CONECT    6   17   18                                                       
CONECT    7    2   20                                                       
CONECT    8    3   21                                                       
CONECT    9    4   24                                                       
CONECT   10    5   25                                                       
CONECT   11   12   20                                                       
CONECT   12   11   21                                                       
CONECT   13   15   22                                                       
CONECT   14   16   22                                                       
CONECT   15   13   23                                                       
CONECT   16   14   23                                                       
CONECT   17    6   28                                                       
CONECT   18    6   29                                                       
CONECT   19   26   28                                                       
CONECT   20    7   11   24                                                  
CONECT   21    8   12   25                                                  
CONECT   22   13   14   26                                                  
CONECT   23   15   16   27                                                  
CONECT   24    9   20   29                                                  
CONECT   25   10   21   29                                                  
CONECT   26   19   22   30                                                  
CONECT   27   23                                                            
CONECT   28    1   17   19                                                  
CONECT   29   18   24   25                                                  
CONECT   30   26                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

COMPND    HMDB0254150
HETATM    1  C1  UNL     1       2.210  -2.307  -0.685  1.00  0.00           C  
HETATM    2  N1  UNL     1       2.497  -1.039   0.010  1.00  0.00           N  
HETATM    3  C2  UNL     1       1.356  -0.675   0.799  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.128  -0.398  -0.107  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.061  -0.163   0.711  1.00  0.00           C  
HETATM    6  N2  UNL     1      -2.352  -0.006   0.189  1.00  0.00           N  
HETATM    7  C5  UNL     1      -3.135  -1.205   0.119  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.407  -2.356   0.115  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.026  -3.616   0.045  1.00  0.00           C  
HETATM   10  C8  UNL     1      -4.390  -3.739  -0.022  1.00  0.00           C  
HETATM   11  C9  UNL     1      -5.146  -2.583  -0.019  1.00  0.00           C  
HETATM   12  C10 UNL     1      -4.528  -1.358   0.050  1.00  0.00           C  
HETATM   13  C11 UNL     1      -5.512  -0.229   0.054  1.00  0.00           C  
HETATM   14  C12 UNL     1      -5.249   0.635  -1.136  1.00  0.00           C  
HETATM   15  C13 UNL     1      -4.126   1.552  -0.841  1.00  0.00           C  
HETATM   16  C14 UNL     1      -4.413   2.849  -1.216  1.00  0.00           C  
HETATM   17  C15 UNL     1      -3.487   3.833  -1.037  1.00  0.00           C  
HETATM   18  C16 UNL     1      -2.242   3.527  -0.471  1.00  0.00           C  
HETATM   19  C17 UNL     1      -1.951   2.238  -0.096  1.00  0.00           C  
HETATM   20  C18 UNL     1      -2.880   1.242  -0.274  1.00  0.00           C  
HETATM   21  C19 UNL     1       3.040  -0.130  -0.900  1.00  0.00           C  
HETATM   22  C20 UNL     1       3.710   0.999  -0.232  1.00  0.00           C  
HETATM   23  O1  UNL     1       3.063   1.933   0.243  1.00  0.00           O  
HETATM   24  C21 UNL     1       5.173   0.984  -0.148  1.00  0.00           C  
HETATM   25  C22 UNL     1       5.905  -0.108  -0.574  1.00  0.00           C  
HETATM   26  C23 UNL     1       7.300  -0.135  -0.539  1.00  0.00           C  
HETATM   27  C24 UNL     1       7.995   0.946  -0.071  1.00  0.00           C  
HETATM   28 CL1  UNL     1       9.748   0.928  -0.022  1.00  0.00          CL  
HETATM   29  C25 UNL     1       7.291   2.038   0.357  1.00  0.00           C  
HETATM   30  C26 UNL     1       5.894   2.057   0.319  1.00  0.00           C  
HETATM   31  H1  UNL     1       3.145  -2.887  -0.767  1.00  0.00           H  
HETATM   32  H2  UNL     1       1.485  -2.903  -0.124  1.00  0.00           H  
HETATM   33  H3  UNL     1       1.895  -2.058  -1.724  1.00  0.00           H  
HETATM   34  H4  UNL     1       1.605   0.230   1.375  1.00  0.00           H  
HETATM   35  H5  UNL     1       1.053  -1.538   1.412  1.00  0.00           H  
HETATM   36  H6  UNL     1       0.398   0.507  -0.761  1.00  0.00           H  
HETATM   37  H7  UNL     1       0.212  -1.214  -0.816  1.00  0.00           H  
HETATM   38  H8  UNL     1      -1.021  -0.996   1.522  1.00  0.00           H  
HETATM   39  H9  UNL     1      -0.910   0.644   1.505  1.00  0.00           H  
HETATM   40  H10 UNL     1      -1.346  -2.285   0.178  1.00  0.00           H  
HETATM   41  H11 UNL     1      -2.375  -4.479   0.047  1.00  0.00           H  
HETATM   42  H12 UNL     1      -4.882  -4.720  -0.079  1.00  0.00           H  
HETATM   43  H13 UNL     1      -6.203  -2.649  -0.071  1.00  0.00           H  
HETATM   44  H14 UNL     1      -6.532  -0.639  -0.025  1.00  0.00           H  
HETATM   45  H15 UNL     1      -5.437   0.342   1.005  1.00  0.00           H  
HETATM   46  H16 UNL     1      -6.134   1.242  -1.431  1.00  0.00           H  
HETATM   47  H17 UNL     1      -4.962  -0.004  -2.021  1.00  0.00           H  
HETATM   48  H18 UNL     1      -5.400   3.011  -1.648  1.00  0.00           H  
HETATM   49  H19 UNL     1      -3.758   4.831  -1.346  1.00  0.00           H  
HETATM   50  H20 UNL     1      -1.573   4.349  -0.363  1.00  0.00           H  
HETATM   51  H21 UNL     1      -1.032   2.004   0.315  1.00  0.00           H  
HETATM   52  H22 UNL     1       2.197   0.300  -1.552  1.00  0.00           H  
HETATM   53  H23 UNL     1       3.702  -0.596  -1.680  1.00  0.00           H  
HETATM   54  H24 UNL     1       5.402  -0.998  -0.945  1.00  0.00           H  
HETATM   55  H25 UNL     1       7.828  -1.026  -0.889  1.00  0.00           H  
HETATM   56  H26 UNL     1       7.866   2.878   0.722  1.00  0.00           H  
HETATM   57  H27 UNL     1       5.374   2.941   0.663  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3   21
CONECT    3    4   34   35
CONECT    4    5   36   37
CONECT    5    6   38   39
CONECT    6    7   20
CONECT    7    8    8   12
CONECT    8    9   40
CONECT    9   10   10   41
CONECT   10   11   42
CONECT   11   12   12   43
CONECT   12   13
CONECT   13   14   44   45
CONECT   14   15   46   47
CONECT   15   16   16   20
CONECT   16   17   48
CONECT   17   18   18   49
CONECT   18   19   50
CONECT   19   20   20   51
CONECT   21   22   52   53
CONECT   22   23   23   24
CONECT   24   25   25   30
CONECT   25   26   54
CONECT   26   27   27   55
CONECT   27   28   29
CONECT   29   30   30   56
CONECT   30   57
END

HMDB0254150
     RDKit          3D
Lofepramine
 57 60  0  0  0  0  0  0  0  0999 V2000
    2.2100   -2.3073   -0.6851 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4969   -1.0387    0.0095 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3562   -0.6746    0.7991 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1280   -0.3984   -0.1073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0615   -0.1635    0.7106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3516   -0.0063    0.1891 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1348   -1.2054    0.1185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4074   -2.3564    0.1151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0264   -3.6161    0.0451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3901   -3.7391   -0.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1463   -2.5829   -0.0192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5282   -1.3578    0.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5118   -0.2287    0.0538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2495    0.6351   -1.1359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1258    1.5525   -0.8413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4134    2.8486   -1.2162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4867    3.8330   -1.0368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2420    3.5267   -0.4709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9509    2.2382   -0.0959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8799    1.2423   -0.2735 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0399   -0.1304   -0.8999 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7097    0.9992   -0.2317 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0633    1.9334    0.2429 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1730    0.9837   -0.1483 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9055   -0.1084   -0.5738 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2999   -0.1347   -0.5389 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9946    0.9457   -0.0707 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7477    0.9277   -0.0221 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.2905    2.0379    0.3571 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8941    2.0565    0.3192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1452   -2.8870   -0.7674 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4853   -2.9033   -0.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8951   -2.0580   -1.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6054    0.2299    1.3749 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0528   -1.5383    1.4119 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3976    0.5071   -0.7614 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2120   -1.2137   -0.8162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0211   -0.9963    1.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9097    0.6443    1.5051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3463   -2.2849    0.1783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3751   -4.4794    0.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8824   -4.7201   -0.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2026   -2.6490   -0.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5318   -0.6386   -0.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4372    0.3421    1.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1340    1.2420   -1.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9619   -0.0042   -2.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4002    3.0114   -1.6475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7575    4.8309   -1.3458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5734    4.3491   -0.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0318    2.0044    0.3151 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1970    0.3001   -1.5524 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7020   -0.5960   -1.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4015   -0.9979   -0.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8281   -1.0262   -0.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8660    2.8784    0.7216 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3740    2.9412    0.6630 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  2 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  2  0
 20  6  1  0
 30 24  1  0
 12  7  1  0
 20 15  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  8 40  1  0
  9 41  1  0
 10 42  1  0
 11 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 16 48  1  0
 17 49  1  0
 18 50  1  0
 19 51  1  0
 21 52  1  0
 21 53  1  0
 25 54  1  0
 26 55  1  0
 29 56  1  0
 30 57  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(4-Chlorophenyl)-2-{[3-(10,11-dihydro-5H-dibenzo[b,F]azepin-5-yl)propyl]methylamino}ethanone	ChEBI
4'-Chlor-2-((3-(10,11-dihydro-5H-dibenz(b,F)azepin-5-yl)propyl)methylamino)acetophenon	ChEBI
4'-Chloro-2-((3-(10,11-dihydro-5H-dibenz(b,F)azepin5-yl)propyl)methylamino)acetophenone	ChEBI
Lopramine	ChEBI
Feprapax	MeSH
Ashbourne brand OF lofepramine hydrochloride	MeSH
leo 640	MeSH
Lomont	MeSH
Gamanil	MeSH
Hydrochloride, lofepramine	MeSH
Merck brand OF lofepramine hydrochloride	MeSH
Rosemont brand OF lofepramine hydrochloride	MeSH
Deftan	MeSH
Lofepramine hydrochloride	MeSH
Gamonil	MeSH

Chemical Formula

C₂₆H₂₇ClN₂O

Average Molecular Weight

418.97

Monoisotopic Molecular Weight

418.1811912

IUPAC Name

2-[(3-{2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-2-yl}propyl)(methyl)amino]-1-(4-chlorophenyl)ethan-1-one

Traditional Name

2-[(3-{2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-2-yl}propyl)(methyl)amino]-1-(4-chlorophenyl)ethanone

CAS Registry Number

Not Available

SMILES

CN(CCCN1C2=CC=CC=C2CCC2=CC=CC=C12)CC(=O)C1=CC=C(Cl)C=C1

InChI Identifier

InChI=1S/C26H27ClN2O/c1-28(19-26(30)22-13-15-23(27)16-14-22)17-6-18-29-24-9-4-2-7-20(24)11-12-21-8-3-5-10-25(21)29/h2-5,7-10,13-16H,6,11-12,17-19H2,1H3

InChI Key

SAPNXPWPAUFAJU-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
Alkyl-phenylketone
Alkyldiarylamine
Phenylketone
Benzoyl
Tertiary aliphatic/aromatic amine
Aryl ketone
Aryl alkyl ketone
Azepine
Chlorobenzene
Halobenzene
Aryl halide
Aryl chloride
Benzenoid
Monocyclic benzene moiety
Alpha-aminoketone
Tertiary aliphatic amine
Tertiary amine
Ketone
Azacycle
Hydrocarbon derivative
Organooxygen compound
Organic nitrogen compound
Amine
Organopnictogen compound
Organic oxide
Organic oxygen compound
Organohalogen compound
Organochloride
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary amino compound (CHEBI:47782 )
monochlorobenzenes (CHEBI:47782 )
aromatic ketone (CHEBI:47782 )
dibenzoazepine (CHEBI:47782 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0254150)

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	5.79	ALOGPS
logP	6.11	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	17.02	ChemAxon
pKa (Strongest Basic)	6.53	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	23.55 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	125.31 m³·mol⁻¹	ChemAxon
Polarizability	46.66 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	225.569	30932474
DeepCCS	[M+Na]+	200.798	30932474
AllCCS	[M+H]+	204.0	32859911
AllCCS	[M+H-H2O]+	201.4	32859911
AllCCS	[M+NH4]+	206.3	32859911
AllCCS	[M+Na]+	207.0	32859911
AllCCS	[M-H]-	200.1	32859911
AllCCS	[M+Na-2H]-	199.9	32859911
AllCCS	[M+HCOO]-	199.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	15.1109 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.95 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2253.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	303.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	222.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	191.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	160.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	582.2 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	525.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	158.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1521.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	610.0 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	1565.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	411.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	422.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	229.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	123.9 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	8.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lofepramine	CN(CCCN1C2=CC=CC=C2CCC2=CC=CC=C12)CC(=O)C1=CC=C(Cl)C=C1	4969.1	Standard polar	33892256
Lofepramine	CN(CCCN1C2=CC=CC=C2CCC2=CC=CC=C12)CC(=O)C1=CC=C(Cl)C=C1	3506.2	Standard non polar	33892256
Lofepramine	CN(CCCN1C2=CC=CC=C2CCC2=CC=CC=C12)CC(=O)C1=CC=C(Cl)C=C1	3530.3	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 - Lofepramine GC-MS (Non-derivatized) - 70eV, Positive	splash10-052r-3930000000-7f3233101e9bc3c16ac2	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lofepramine 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lofepramine 35V, Positive-QTOF	splash10-00di-0190000000-939eaff7e4c449d10e95	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lofepramine 10V, Positive-QTOF	splash10-014i-0030900000-f2c1472e308c1b5aef4b	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lofepramine 20V, Positive-QTOF	splash10-00tr-1390200000-e0f7a25f6e2c3cf8cf45	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lofepramine 40V, Positive-QTOF	splash10-0017-7950000000-f7cfdbd1d08c3c9e7b07	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lofepramine 10V, Negative-QTOF	splash10-014i-0100900000-0c66d04816128a1bd142	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lofepramine 20V, Negative-QTOF	splash10-015c-0911400000-f3a351150cd2f078f73a	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lofepramine 40V, Negative-QTOF	splash10-00kf-1900000000-239b62d416a315bf9bef	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lofepramine 10V, Positive-QTOF	splash10-014i-0010900000-417d70665e251f5a9161	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lofepramine 20V, Positive-QTOF	splash10-00yr-3790300000-35b025799d6e47a8cf30	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lofepramine 40V, Positive-QTOF	splash10-000i-2950000000-3b5dd2fb9a45903de9ec	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lofepramine 10V, Negative-QTOF	splash10-014i-0000900000-b75a2d50ee5a83773f68	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lofepramine 20V, Negative-QTOF	splash10-00l6-1970700000-92d67c757a3b7ac10b0e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lofepramine 40V, Negative-QTOF	splash10-001i-9310100000-31a976888a2df4b86577	2021-10-12	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

DB13411

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

Lofepramine

METLIN ID

Not Available

PubChem Compound

3947

PDB ID

Not Available

ChEBI ID

47782

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 Lofepramine (HMDB0254150)

MOL for HMDB0254150 (Lofepramine)

3D MOL for HMDB0254150 (Lofepramine)

3D SDF for HMDB0254150 (Lofepramine)

3D-SDF for HMDB0254150 (Lofepramine)

PDB for HMDB0254150 (Lofepramine)

3D PDB for HMDB0254150 (Lofepramine)

SMILES for HMDB0254150 (Lofepramine)

INCHI for HMDB0254150 (Lofepramine)

Structure for HMDB0254150 (Lofepramine)

3D Structure for HMDB0254150 (Lofepramine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra