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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:35:52 UTC

Update Date

2021-09-26 22:52:11 UTC

HMDB ID

HMDB0244439

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N,N-Dimethyl-3-(naphthalen-1-yloxy)-1-phenylpropan-1-amine

Description

N,N-Dimethyl-3-(naphthalen-1-yloxy)-1-phenylpropan-1-amine, also known as dapoxetine or N,N-dimethyl-alpha-(2-(1-naphthalenyloxy)ethyl)benzenemethanamine, belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings. Based on a literature review very few articles have been published on N,N-Dimethyl-3-(naphthalen-1-yloxy)-1-phenylpropan-1-amine. This compound has been identified in human blood as reported by (PMID: 31557052 ). N,n-dimethyl-3-(naphthalen-1-yloxy)-1-phenylpropan-1-amine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically N,N-Dimethyl-3-(naphthalen-1-yloxy)-1-phenylpropan-1-amine 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

HMDB0250862
     RDKit          3D
Dapoxetine
 46 48  0  0  0  0  0  0  0  0999 V2000
    3.2958   -2.3017   -1.0625 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9188   -2.8311   -0.9331 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0315   -4.0580   -0.2285 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0583   -1.8298   -0.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4372   -1.4010    1.0144 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4869   -0.3353    1.5044 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5267    0.8154    0.6515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2802    1.9199    0.9333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1246    1.9592    2.0110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9028    3.0866    2.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8353    4.1679    1.3930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9808    4.1345    0.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9462    5.2457   -0.5264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0879    5.1802   -1.6039 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6898    4.0511   -1.8302 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6341    2.9693   -0.9989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2193    3.0134    0.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3760   -2.1461   -0.4305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2807   -1.2624   -1.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6291   -1.4793   -1.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1840   -2.5974   -0.5194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3312   -3.4881    0.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9488   -3.2583    0.1307 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3107   -1.2172   -0.8699 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5792   -2.4525   -2.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9955   -2.8906   -0.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0754   -4.4795   -0.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3774   -4.8356   -0.6849 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9954   -3.9889    0.8576 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2268   -0.9139   -1.0819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4760   -1.0278    1.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3772   -2.2557    1.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5526   -0.6974    1.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7339   -0.0056    2.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1722    1.0999    2.6777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5720    3.1336    3.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4284    5.0502    1.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5360    6.1260   -0.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0159    6.0083   -2.3215 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3643    4.0029   -2.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2323    2.0822   -1.1605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8346   -0.3688   -1.4933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2704   -0.7694   -1.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2664   -2.7826   -0.5470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7429   -4.3912    0.5533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3364   -3.9809    0.6299 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
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 13 14  1  0
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 17  8  1  0
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  5 32  1  0
  6 33  1  0
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  9 35  1  0
 10 36  1  0
 11 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
 22 45  1  0
 23 46  1  0
M  END


  Mrv1652309102123362D          

 23 25  0  0  0  0            999 V2000
    3.2704    1.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454    1.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    1.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9829    1.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    0.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454    0.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329   -0.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -0.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    0.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    1.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329    3.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204    4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329    5.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704    4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
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 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
  8 17  1  0  0  0  0
  4 18  1  0  0  0  0
 18 19  2  0  0  0  0
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 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0244439

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)C(CCOC1=CC=CC2=CC=CC=C12)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H23NO/c1-22(2)20(18-10-4-3-5-11-18)15-16-23-21-14-8-12-17-9-6-7-13-19(17)21/h3-14,20H,15-16H2,1-2H3

> <INCHI_KEY>
USRHYDPUVLEVMC-UHFFFAOYSA-N

> <FORMULA>
C21H23NO

> <MOLECULAR_WEIGHT>
305.421

> <EXACT_MASS>
305.177964365

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
35.66141112388072

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
dimethyl[3-(naphthalen-1-yloxy)-1-phenylpropyl]amine

> <ALOGPS_LOGP>
4.75

> <JCHEM_LOGP>
4.667895755666667

> <ALOGPS_LOGS>
-5.56

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.958904109021285

> <JCHEM_POLAR_SURFACE_AREA>
12.47

> <JCHEM_REFRACTIVITY>
96.13870000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.37e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dimethyl[3-(naphthalen-1-yloxy)-1-phenylpropyl]amine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0250862
     RDKit          3D
Dapoxetine
 46 48  0  0  0  0  0  0  0  0999 V2000
    3.2958   -2.3017   -1.0625 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9188   -2.8311   -0.9331 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0315   -4.0580   -0.2285 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0583   -1.8298   -0.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4372   -1.4010    1.0144 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4869   -0.3353    1.5044 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5267    0.8154    0.6515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2802    1.9199    0.9333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1246    1.9592    2.0110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9028    3.0866    2.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8353    4.1679    1.3930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9808    4.1345    0.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9462    5.2457   -0.5264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0879    5.1802   -1.6039 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6898    4.0511   -1.8302 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6341    2.9693   -0.9989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2193    3.0134    0.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3760   -2.1461   -0.4305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2807   -1.2624   -1.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6291   -1.4793   -1.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1840   -2.5974   -0.5194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3312   -3.4881    0.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9488   -3.2583    0.1307 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3107   -1.2172   -0.8699 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5792   -2.4525   -2.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9955   -2.8906   -0.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0754   -4.4795   -0.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3774   -4.8356   -0.6849 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9954   -3.9889    0.8576 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2268   -0.9139   -1.0819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4760   -1.0278    1.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3772   -2.2557    1.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5526   -0.6974    1.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7339   -0.0056    2.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1722    1.0999    2.6777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5720    3.1336    3.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4284    5.0502    1.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5360    6.1260   -0.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0159    6.0083   -2.3215 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3643    4.0029   -2.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2323    2.0822   -1.1605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8346   -0.3688   -1.4933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2704   -0.7694   -1.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2664   -2.7826   -0.5470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7429   -4.3912    0.5533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3364   -3.9809    0.6299 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  2  0
 15 16  1  0
 16 17  2  0
  4 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 17  8  1  0
 23 18  1  0
 17 12  1  0
  1 24  1  0
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  3 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
 22 45  1  0
 23 46  1  0
M  END

HEADER    PROTEIN                                 10-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-21         0                                  
HETATM    1  C   UNK     0       6.105   3.286   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       5.335   4.620   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       3.795   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.105   5.954   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.645   5.954   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.415   4.620   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.955   4.620   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      10.725   3.286   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.265   3.286   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.035   1.953   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.265   0.619   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.725   0.619   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.955  -0.715   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.415  -0.715   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.645   0.619   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.415   1.953   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.955   1.953   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   7.287   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.795   7.287   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.025   8.621   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.795   9.955   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335   9.955   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.105   8.621   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   18                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   17                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12    8                                                  
CONECT   18    4   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0244439
HETATM    1  C1  UNL     1      -2.644   2.768  -1.710  1.00  0.00           C  
HETATM    2  N1  UNL     1      -3.047   1.785  -0.776  1.00  0.00           N  
HETATM    3  C2  UNL     1      -4.439   1.627  -0.568  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.286   0.562  -0.816  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.861   0.926  -0.458  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.076  -0.259  -0.461  1.00  0.00           C  
HETATM    7  O1  UNL     1       1.345   0.217  -0.114  1.00  0.00           O  
HETATM    8  C6  UNL     1       2.486  -0.542  -0.006  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.458  -1.895  -0.246  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.626  -2.663  -0.135  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.810  -2.062   0.217  1.00  0.00           C  
HETATM   12  C10 UNL     1       4.854  -0.716   0.460  1.00  0.00           C  
HETATM   13  C11 UNL     1       6.064  -0.138   0.813  1.00  0.00           C  
HETATM   14  C12 UNL     1       6.130   1.214   1.061  1.00  0.00           C  
HETATM   15  C13 UNL     1       4.976   1.955   0.948  1.00  0.00           C  
HETATM   16  C14 UNL     1       3.781   1.379   0.599  1.00  0.00           C  
HETATM   17  C15 UNL     1       3.689   0.018   0.344  1.00  0.00           C  
HETATM   18  C16 UNL     1      -2.832  -0.459   0.115  1.00  0.00           C  
HETATM   19  C17 UNL     1      -3.197  -0.099   1.394  1.00  0.00           C  
HETATM   20  C18 UNL     1      -3.710  -1.013   2.300  1.00  0.00           C  
HETATM   21  C19 UNL     1      -3.864  -2.319   1.923  1.00  0.00           C  
HETATM   22  C20 UNL     1      -3.512  -2.713   0.659  1.00  0.00           C  
HETATM   23  C21 UNL     1      -2.994  -1.780  -0.247  1.00  0.00           C  
HETATM   24  H1  UNL     1      -2.396   2.391  -2.717  1.00  0.00           H  
HETATM   25  H2  UNL     1      -3.441   3.560  -1.737  1.00  0.00           H  
HETATM   26  H3  UNL     1      -1.740   3.290  -1.311  1.00  0.00           H  
HETATM   27  H4  UNL     1      -4.779   0.584  -0.443  1.00  0.00           H  
HETATM   28  H5  UNL     1      -5.078   2.136  -1.335  1.00  0.00           H  
HETATM   29  H6  UNL     1      -4.702   2.146   0.400  1.00  0.00           H  
HETATM   30  H7  UNL     1      -2.296   0.194  -1.861  1.00  0.00           H  
HETATM   31  H8  UNL     1      -0.794   1.445   0.511  1.00  0.00           H  
HETATM   32  H9  UNL     1      -0.517   1.655  -1.243  1.00  0.00           H  
HETATM   33  H10 UNL     1      -0.324  -0.966   0.322  1.00  0.00           H  
HETATM   34  H11 UNL     1       0.061  -0.789  -1.425  1.00  0.00           H  
HETATM   35  H12 UNL     1       1.552  -2.417  -0.526  1.00  0.00           H  
HETATM   36  H13 UNL     1       3.613  -3.730  -0.323  1.00  0.00           H  
HETATM   37  H14 UNL     1       5.715  -2.641   0.305  1.00  0.00           H  
HETATM   38  H15 UNL     1       6.971  -0.713   0.904  1.00  0.00           H  
HETATM   39  H16 UNL     1       7.075   1.704   1.344  1.00  0.00           H  
HETATM   40  H17 UNL     1       5.006   3.014   1.139  1.00  0.00           H  
HETATM   41  H18 UNL     1       2.849   1.947   0.501  1.00  0.00           H  
HETATM   42  H19 UNL     1      -3.081   0.941   1.711  1.00  0.00           H  
HETATM   43  H20 UNL     1      -3.989  -0.705   3.295  1.00  0.00           H  
HETATM   44  H21 UNL     1      -4.266  -3.002   2.653  1.00  0.00           H  
HETATM   45  H22 UNL     1      -3.633  -3.745   0.360  1.00  0.00           H  
HETATM   46  H23 UNL     1      -2.714  -2.090  -1.245  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    4
CONECT    3   27   28   29
CONECT    4    5   18   30
CONECT    5    6   31   32
CONECT    6    7   33   34
CONECT    7    8
CONECT    8    9    9   17
CONECT    9   10   35
CONECT   10   11   11   36
CONECT   11   12   37
CONECT   12   13   13   17
CONECT   13   14   38
CONECT   14   15   15   39
CONECT   15   16   40
CONECT   16   17   17   41
CONECT   18   19   19   23
CONECT   19   20   42
CONECT   20   21   21   43
CONECT   21   22   44
CONECT   22   23   23   45
CONECT   23   46
END

HMDB0250862
     RDKit          3D
Dapoxetine
 46 48  0  0  0  0  0  0  0  0999 V2000
    3.2958   -2.3017   -1.0625 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9188   -2.8311   -0.9331 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0315   -4.0580   -0.2285 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0583   -1.8298   -0.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4372   -1.4010    1.0144 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4869   -0.3353    1.5044 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5267    0.8154    0.6515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2802    1.9199    0.9333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1246    1.9592    2.0110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9028    3.0866    2.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8353    4.1679    1.3930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9808    4.1345    0.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9462    5.2457   -0.5264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0879    5.1802   -1.6039 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6898    4.0511   -1.8302 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6341    2.9693   -0.9989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2193    3.0134    0.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3760   -2.1461   -0.4305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2807   -1.2624   -1.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6291   -1.4793   -1.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1840   -2.5974   -0.5194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3312   -3.4881    0.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9488   -3.2583    0.1307 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3107   -1.2172   -0.8699 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5792   -2.4525   -2.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9955   -2.8906   -0.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0754   -4.4795   -0.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3774   -4.8356   -0.6849 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9954   -3.9889    0.8576 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2268   -0.9139   -1.0819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4760   -1.0278    1.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3772   -2.2557    1.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5526   -0.6974    1.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7339   -0.0056    2.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1722    1.0999    2.6777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5720    3.1336    3.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4284    5.0502    1.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5360    6.1260   -0.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0159    6.0083   -2.3215 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3643    4.0029   -2.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2323    2.0822   -1.1605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8346   -0.3688   -1.4933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2704   -0.7694   -1.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2664   -2.7826   -0.5470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7429   -4.3912    0.5533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3364   -3.9809    0.6299 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  2  0
 15 16  1  0
 16 17  2  0
  4 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 17  8  1  0
 23 18  1  0
 17 12  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
 22 45  1  0
 23 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N,N-Dimethyl-alpha-(2-(1-naphthalenyloxy)ethyl)benzenemethanamine	HMDB
Dapoxetine	HMDB
Priligy	HMDB
Dapoxetine hydrochloride	HMDB

Chemical Formula

C₂₁H₂₃NO

Average Molecular Weight

305.421

Monoisotopic Molecular Weight

305.177964365

IUPAC Name

dimethyl[3-(naphthalen-1-yloxy)-1-phenylpropyl]amine

Traditional Name

dimethyl[3-(naphthalen-1-yloxy)-1-phenylpropyl]amine

CAS Registry Number

Not Available

SMILES

CN(C)C(CCOC1=CC=CC2=CC=CC=C12)C1=CC=CC=C1

InChI Identifier

InChI=1S/C21H23NO/c1-22(2)20(18-10-4-3-5-11-18)15-16-23-21-14-8-12-17-9-6-7-13-19(17)21/h3-14,20H,15-16H2,1-2H3

InChI Key

USRHYDPUVLEVMC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Not Available

Direct Parent

Naphthalenes

Alternative Parents

Substituents

Naphthalene
Aralkylamine
Alkyl aryl ether
Monocyclic benzene moiety
Tertiary aliphatic amine
Tertiary amine
Ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	4.75	ALOGPS
logP	4.67	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Basic)	8.96	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.47 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	96.14 m³·mol⁻¹	ChemAxon
Polarizability	35.66 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	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	198.464	30932474
DeepCCS	[M+Na]+	174.03	30932474
AllCCS	[M+H]+	176.4	32859911
AllCCS	[M+H-H2O]+	173.0	32859911
AllCCS	[M+NH4]+	179.6	32859911
AllCCS	[M+Na]+	180.5	32859911
AllCCS	[M-H]-	181.8	32859911
AllCCS	[M+Na-2H]-	181.3	32859911
AllCCS	[M+HCOO]-	180.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	12.5842 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.23 minutes	32390414

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N,N-Dimethyl-3-(naphthalen-1-yloxy)-1-phenylpropan-1-amine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001l-4910000000-15ee6cee8abdd4edf381	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N,N-Dimethyl-3-(naphthalen-1-yloxy)-1-phenylpropan-1-amine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N,N-Dimethyl-3-(naphthalen-1-yloxy)-1-phenylpropan-1-amine 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 - N,N-Dimethyl-3-(naphthalen-1-yloxy)-1-phenylpropan-1-amine 10V, Positive-QTOF	splash10-0a4i-0719000000-67ad71bf704f1cae35a3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N-Dimethyl-3-(naphthalen-1-yloxy)-1-phenylpropan-1-amine 20V, Positive-QTOF	splash10-0bu1-2911000000-e8a73a6895b1773ccf64	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N-Dimethyl-3-(naphthalen-1-yloxy)-1-phenylpropan-1-amine 40V, Positive-QTOF	splash10-00lu-4900000000-56c07dfa9c1a5075c842	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N-Dimethyl-3-(naphthalen-1-yloxy)-1-phenylpropan-1-amine 10V, Negative-QTOF	splash10-0udi-0509000000-f0f54b4d84a5f26c236b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N-Dimethyl-3-(naphthalen-1-yloxy)-1-phenylpropan-1-amine 20V, Negative-QTOF	splash10-0f6x-1902000000-2be529ea231fd596d4e3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N-Dimethyl-3-(naphthalen-1-yloxy)-1-phenylpropan-1-amine 40V, Negative-QTOF	splash10-0006-0900000000-a34c510a29231c342a65	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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4805170

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6093437

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 N,N-Dimethyl-3-(naphthalen-1-yloxy)-1-phenylpropan-1-amine (HMDB0244439)

MOL for HMDB0244439 (N,N-Dimethyl-3-(naphthalen-1-yloxy)-1-phenylpropan-1-amine)

3D MOL for HMDB0244439 (N,N-Dimethyl-3-(naphthalen-1-yloxy)-1-phenylpropan-1-amine)

3D SDF for HMDB0244439 (N,N-Dimethyl-3-(naphthalen-1-yloxy)-1-phenylpropan-1-amine)

3D-SDF for HMDB0244439 (N,N-Dimethyl-3-(naphthalen-1-yloxy)-1-phenylpropan-1-amine)

PDB for HMDB0244439 (N,N-Dimethyl-3-(naphthalen-1-yloxy)-1-phenylpropan-1-amine)

3D PDB for HMDB0244439 (N,N-Dimethyl-3-(naphthalen-1-yloxy)-1-phenylpropan-1-amine)

SMILES for HMDB0244439 (N,N-Dimethyl-3-(naphthalen-1-yloxy)-1-phenylpropan-1-amine)

INCHI for HMDB0244439 (N,N-Dimethyl-3-(naphthalen-1-yloxy)-1-phenylpropan-1-amine)

Structure for HMDB0244439 (N,N-Dimethyl-3-(naphthalen-1-yloxy)-1-phenylpropan-1-amine)

3D Structure for HMDB0244439 (N,N-Dimethyl-3-(naphthalen-1-yloxy)-1-phenylpropan-1-amine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra