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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:00:21 UTC

Update Date

2021-09-14 14:58:52 UTC

HMDB ID

HMDB0013889

Secondary Accession Numbers

HMDB13889

Metabolite Identification

Common Name

E-10-Hydroxynortriptyline

Description

E-10-Hydroxynortriptyline belongs to the class of organic compounds known as dibenzocycloheptenes. Dibenzocycloheptenes are compounds containing a dibenzocycloheptene moiety, which consists of two benzene rings connected by a cycloheptene ring. E-10-Hydroxynortriptyline is a very strong basic compound (based on its pKa). E-10-Hydroxynortriptyline is only found in individuals that have used or taken Amitriptyline. These are compounds containing a dibenzocycloheptene moiety, which consists of two benzene connected by a cycloheptene ring. E-10-Hydroxynortriptyline is a metabolite of Amitriptyline.

Structure

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

HMDB0013889
     RDKit          3D
E-10-Hydroxynortriptyline
 42 44  0  0  0  0  0  0  0  0999 V2000
    4.9994    0.4159   -0.8747 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8590    1.0289   -1.5341 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7306    0.1678   -1.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2332    0.0740    0.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1212   -0.8679   -0.1973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0921   -0.6004    0.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2346    0.6698    0.9333 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7630    0.7755    1.8429 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7629    1.9390    2.5879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2251    2.9182    2.3845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2185    2.7243    1.4260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2525    1.5841    0.6660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3597    1.4479   -0.3160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1676    0.2044   -0.1324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3905    0.2604   -0.7948 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5130   -1.0978   -0.3403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4043   -2.0907   -0.7374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9672   -3.3778   -0.9310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6202   -3.7218   -0.7339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7226   -2.7528   -0.3412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2192   -1.5054   -0.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0225    0.7454    0.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8623   -0.6887   -0.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9436    0.6005   -1.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6781    1.9965   -1.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0261   -0.8585   -1.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8747    0.4482   -2.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1498   -0.2813    0.4859 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9774    1.1433    0.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2877   -1.7963   -0.7619 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4495    0.0023    2.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5186    2.1310    3.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2287    3.8329    2.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9821    3.4681    1.2608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9610    1.5316   -1.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0352    2.3067   -0.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4455    0.2016    0.9736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0356    0.7282   -0.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4377   -1.7936   -0.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6673   -4.1582   -1.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3726   -4.7557   -0.9099 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2932   -2.9997   -0.1601 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  2  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
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21  6  1  0
 12  7  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
M  END


  Mrv0541 06191310272D          

 21 23  0  0  0  0            999 V2000
    7.6453   -6.0784    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4860   -1.7976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6614   -1.7976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0004   -2.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1471   -2.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0739   -3.6043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8168   -3.2464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3306   -3.2464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0739   -4.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8171   -2.1766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3303   -2.1766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4376   -3.8401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7101   -3.8401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3595   -4.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4515   -2.7559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6962   -2.7558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3593   -5.6660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2603   -3.5936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8871   -3.5936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6453   -6.9030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8440   -1.0545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 17  1  0  0  0  0
  1 20  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  7  1  0  0  0  0
  4 10  2  0  0  0  0
  5  8  1  0  0  0  0
  5 11  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  2  0  0  0  0
  7 12  2  0  0  0  0
  8 13  2  0  0  0  0
  9 14  1  0  0  0  0
 10 15  1  0  0  0  0
 11 16  1  0  0  0  0
 12 18  1  0  0  0  0
 13 19  1  0  0  0  0
 14 17  1  0  0  0  0
 15 18  2  0  0  0  0
 16 19  2  0  0  0  0
  2 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013889

> <DATABASE_NAME>
hmdb

> <SMILES>
CNCC\C=C1/C2=CC=CC=C2CC(O)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C19H21NO/c1-20-12-6-11-16-15-8-3-2-7-14(15)13-19(21)18-10-5-4-9-17(16)18/h2-5,7-11,19-21H,6,12-13H2,1H3/b16-11+

> <INCHI_KEY>
VAGXZGJKNUNLHK-LFIBNONCSA-N

> <FORMULA>
C19H21NO

> <MOLECULAR_WEIGHT>
279.3761

> <EXACT_MASS>
279.162314299

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
32.56484837351674

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-2-[3-(methylamino)propylidene]tricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-9-ol

> <ALOGPS_LOGP>
3.25

> <JCHEM_LOGP>
3.195675910666667

> <ALOGPS_LOGS>
-4.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.25734500320744

> <JCHEM_PKA_STRONGEST_BASIC>
10.471537711756177

> <JCHEM_POLAR_SURFACE_AREA>
32.26

> <JCHEM_REFRACTIVITY>
97.72800000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.38e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-2-[3-(methylamino)propylidene]tricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-9-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0013889
     RDKit          3D
E-10-Hydroxynortriptyline
 42 44  0  0  0  0  0  0  0  0999 V2000
    4.9994    0.4159   -0.8747 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8590    1.0289   -1.5341 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7306    0.1678   -1.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2332    0.0740    0.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1212   -0.8679   -0.1973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0921   -0.6004    0.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2346    0.6698    0.9333 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7630    0.7755    1.8429 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7629    1.9390    2.5879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2251    2.9182    2.3845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2185    2.7243    1.4260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2525    1.5841    0.6660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3597    1.4479   -0.3160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1676    0.2044   -0.1324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3905    0.2604   -0.7948 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5130   -1.0978   -0.3403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4043   -2.0907   -0.7374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9672   -3.3778   -0.9310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6202   -3.7218   -0.7339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7226   -2.7528   -0.3412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2192   -1.5054   -0.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0225    0.7454    0.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8623   -0.6887   -0.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9436    0.6005   -1.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6781    1.9965   -1.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0261   -0.8585   -1.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8747    0.4482   -2.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1498   -0.2813    0.4859 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9774    1.1433    0.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2877   -1.7963   -0.7619 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4495    0.0023    2.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5186    2.1310    3.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2287    3.8329    2.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9821    3.4681    1.2608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9610    1.5316   -1.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0352    2.3067   -0.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4455    0.2016    0.9736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0356    0.7282   -0.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4377   -1.7936   -0.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6673   -4.1582   -1.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3726   -4.7557   -0.9099 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2932   -2.9997   -0.1601 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  2  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
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21  6  1  0
 12  7  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
M  END

HEADER    PROTEIN                                 19-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-13         0                                  
HETATM    1  N   UNK     0      14.271 -11.346   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      17.707  -3.356   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.168  -3.356   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.667  -4.559   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.208  -4.559   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.938  -6.728   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.325  -6.060   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.550  -6.060   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.938  -8.267   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.192  -4.063   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.683  -4.063   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      19.483  -7.168   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.392  -7.168   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.604  -9.037   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.376  -5.144   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.500  -5.144   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.604 -10.576   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      21.019  -6.708   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.856  -6.708   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.271 -12.886   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      18.375  -1.968   0.000  0.00  0.00           O+0
CONECT    1   17   20                                                       
CONECT    2    3    4   21                                                  
CONECT    3    2    5                                                       
CONECT    4    2    7   10                                                  
CONECT    5    3    8   11                                                  
CONECT    6    7    8    9                                                  
CONECT    7    4    6   12                                                  
CONECT    8    5    6   13                                                  
CONECT    9    6   14                                                       
CONECT   10    4   15                                                       
CONECT   11    5   16                                                       
CONECT   12    7   18                                                       
CONECT   13    8   19                                                       
CONECT   14    9   17                                                       
CONECT   15   10   18                                                       
CONECT   16   11   19                                                       
CONECT   17    1   14                                                       
CONECT   18   12   15                                                       
CONECT   19   13   16                                                       
CONECT   20    1                                                            
CONECT   21    2                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0013889
HETATM    1  C1  UNL     1       4.999   0.416  -0.875  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.859   1.029  -1.534  1.00  0.00           N  
HETATM    3  C2  UNL     1       2.731   0.168  -1.433  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.233   0.074   0.076  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.121  -0.868  -0.197  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.092  -0.600   0.202  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.235   0.670   0.933  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.763   0.776   1.843  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.763   1.939   2.588  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.225   2.918   2.385  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.218   2.724   1.426  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.253   1.584   0.666  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.360   1.448  -0.316  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.168   0.204  -0.132  1.00  0.00           C  
HETATM   15  O1  UNL     1      -4.390   0.260  -0.795  1.00  0.00           O  
HETATM   16  C14 UNL     1      -2.513  -1.098  -0.340  1.00  0.00           C  
HETATM   17  C15 UNL     1      -3.404  -2.091  -0.737  1.00  0.00           C  
HETATM   18  C16 UNL     1      -2.967  -3.378  -0.931  1.00  0.00           C  
HETATM   19  C17 UNL     1      -1.620  -3.722  -0.734  1.00  0.00           C  
HETATM   20  C18 UNL     1      -0.723  -2.753  -0.341  1.00  0.00           C  
HETATM   21  C19 UNL     1      -1.219  -1.505  -0.171  1.00  0.00           C  
HETATM   22  H1  UNL     1       5.023   0.745   0.190  1.00  0.00           H  
HETATM   23  H2  UNL     1       4.862  -0.689  -0.842  1.00  0.00           H  
HETATM   24  H3  UNL     1       5.944   0.600  -1.412  1.00  0.00           H  
HETATM   25  H4  UNL     1       3.678   1.997  -1.202  1.00  0.00           H  
HETATM   26  H5  UNL     1       3.026  -0.858  -1.717  1.00  0.00           H  
HETATM   27  H6  UNL     1       1.875   0.448  -2.062  1.00  0.00           H  
HETATM   28  H7  UNL     1       3.150  -0.281   0.486  1.00  0.00           H  
HETATM   29  H8  UNL     1       1.977   1.143   0.094  1.00  0.00           H  
HETATM   30  H9  UNL     1       1.288  -1.796  -0.762  1.00  0.00           H  
HETATM   31  H10 UNL     1       1.449   0.002   2.018  1.00  0.00           H  
HETATM   32  H11 UNL     1       1.519   2.131   3.347  1.00  0.00           H  
HETATM   33  H12 UNL     1      -0.229   3.833   2.967  1.00  0.00           H  
HETATM   34  H13 UNL     1      -1.982   3.468   1.261  1.00  0.00           H  
HETATM   35  H14 UNL     1      -1.961   1.532  -1.373  1.00  0.00           H  
HETATM   36  H15 UNL     1      -3.035   2.307  -0.143  1.00  0.00           H  
HETATM   37  H16 UNL     1      -3.446   0.202   0.974  1.00  0.00           H  
HETATM   38  H17 UNL     1      -5.036   0.728  -0.213  1.00  0.00           H  
HETATM   39  H18 UNL     1      -4.438  -1.794  -0.879  1.00  0.00           H  
HETATM   40  H19 UNL     1      -3.667  -4.158  -1.244  1.00  0.00           H  
HETATM   41  H20 UNL     1      -1.373  -4.756  -0.910  1.00  0.00           H  
HETATM   42  H21 UNL     1       0.293  -3.000  -0.160  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   25
CONECT    3    4   26   27
CONECT    4    5   28   29
CONECT    5    6    6   30
CONECT    6    7   21
CONECT    7    8    8   12
CONECT    8    9   31
CONECT    9   10   10   32
CONECT   10   11   33
CONECT   11   12   12   34
CONECT   12   13
CONECT   13   14   35   36
CONECT   14   15   16   37
CONECT   15   38
CONECT   16   17   17   21
CONECT   17   18   39
CONECT   18   19   19   40
CONECT   19   20   41
CONECT   20   21   21   42
END

HMDB0013889
     RDKit          3D
E-10-Hydroxynortriptyline
 42 44  0  0  0  0  0  0  0  0999 V2000
    4.9994    0.4159   -0.8747 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8590    1.0289   -1.5341 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7306    0.1678   -1.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2332    0.0740    0.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1212   -0.8679   -0.1973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0921   -0.6004    0.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2346    0.6698    0.9333 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7630    0.7755    1.8429 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7629    1.9390    2.5879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2251    2.9182    2.3845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2185    2.7243    1.4260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2525    1.5841    0.6660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3597    1.4479   -0.3160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1676    0.2044   -0.1324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3905    0.2604   -0.7948 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5130   -1.0978   -0.3403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4043   -2.0907   -0.7374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9672   -3.3778   -0.9310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6202   -3.7218   -0.7339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7226   -2.7528   -0.3412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2192   -1.5054   -0.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0225    0.7454    0.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8623   -0.6887   -0.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9436    0.6005   -1.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6781    1.9965   -1.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0261   -0.8585   -1.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8747    0.4482   -2.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1498   -0.2813    0.4859 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9774    1.1433    0.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2877   -1.7963   -0.7619 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4495    0.0023    2.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5186    2.1310    3.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2287    3.8329    2.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9821    3.4681    1.2608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9610    1.5316   -1.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0352    2.3067   -0.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4455    0.2016    0.9736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0356    0.7282   -0.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4377   -1.7936   -0.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6673   -4.1582   -1.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3726   -4.7557   -0.9099 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2932   -2.9997   -0.1601 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  2  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
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21  6  1  0
 12  7  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
10-Hydroxynortriptyline	HMDB
10-Hydroxynortriptyline maleate (1:1)	HMDB
10-Hydroxynortriptyline hydrochloride	HMDB
10-Hydroxynortriptyline, (+-)-isomer	HMDB
10-Hydroxynortriptyline, (e)-isomer	HMDB
10-Hydroxynortriptyline, (Z)-isomer	HMDB

Chemical Formula

C₁₉H₂₁NO

Average Molecular Weight

279.3761

Monoisotopic Molecular Weight

279.162314299

IUPAC Name

(2E)-2-[3-(methylamino)propylidene]tricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-9-ol

Traditional Name

(2E)-2-[3-(methylamino)propylidene]tricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-9-ol

CAS Registry Number

Not Available

SMILES

CNCC\C=C1/C2=CC=CC=C2CC(O)C2=CC=CC=C12

InChI Identifier

InChI=1S/C19H21NO/c1-20-12-6-11-16-15-8-3-2-7-14(15)13-19(21)18-10-5-4-9-17(16)18/h2-5,7-11,19-21H,6,12-13H2,1H3/b16-11+

InChI Key

VAGXZGJKNUNLHK-LFIBNONCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzocycloheptenes. Dibenzocycloheptenes are compounds containing a dibenzocycloheptene moiety, which consists of two benzene rings connected by a cycloheptene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Dibenzocycloheptenes

Sub Class

Not Available

Direct Parent

Dibenzocycloheptenes

Alternative Parents

Substituents

Dibenzocycloheptene
Secondary alcohol
Secondary amine
Secondary aliphatic amine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Liver (HMDB: HMDB0013889)
Kidney (HMDB: HMDB0013889)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0013889)

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
Water Solubility	0.0074 g/L	ALOGPS
logP	3.25	ALOGPS
logP	3.2	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	14.26	ChemAxon
pKa (Strongest Basic)	10.47	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	32.26 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	97.73 m³·mol⁻¹	ChemAxon
Polarizability	32.56 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	170.221	31661259
DarkChem	[M-H]-	166.924	31661259
DeepCCS	[M-2H]-	200.576	30932474
DeepCCS	[M+Na]+	176.141	30932474
AllCCS	[M+H]+	168.5	32859911
AllCCS	[M+H-H2O]+	165.0	32859911
AllCCS	[M+NH4]+	171.7	32859911
AllCCS	[M+Na]+	172.7	32859911
AllCCS	[M-H]-	173.5	32859911
AllCCS	[M+Na-2H]-	173.2	32859911
AllCCS	[M+HCOO]-	173.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
E-10-Hydroxynortriptyline	CNCC\C=C1/C2=CC=CC=C2CC(O)C2=CC=CC=C12	3553.0	Standard polar	33892256
E-10-Hydroxynortriptyline	CNCC\C=C1/C2=CC=CC=C2CC(O)C2=CC=CC=C12	2347.4	Standard non polar	33892256
E-10-Hydroxynortriptyline	CNCC\C=C1/C2=CC=CC=C2CC(O)C2=CC=CC=C12	2418.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
E-10-Hydroxynortriptyline,1TMS,isomer #1	CNCC/C=C1\C2=CC=CC=C2CC(O[Si](C)(C)C)C2=CC=CC=C12	2491.9	Semi standard non polar	33892256
E-10-Hydroxynortriptyline,1TMS,isomer #2	CN(CC/C=C1\C2=CC=CC=C2CC(O)C2=CC=CC=C12)[Si](C)(C)C	2768.6	Semi standard non polar	33892256
E-10-Hydroxynortriptyline,2TMS,isomer #1	CN(CC/C=C1\C2=CC=CC=C2CC(O[Si](C)(C)C)C2=CC=CC=C12)[Si](C)(C)C	2667.2	Semi standard non polar	33892256
E-10-Hydroxynortriptyline,2TMS,isomer #1	CN(CC/C=C1\C2=CC=CC=C2CC(O[Si](C)(C)C)C2=CC=CC=C12)[Si](C)(C)C	2644.5	Standard non polar	33892256
E-10-Hydroxynortriptyline,2TMS,isomer #1	CN(CC/C=C1\C2=CC=CC=C2CC(O[Si](C)(C)C)C2=CC=CC=C12)[Si](C)(C)C	3021.5	Standard polar	33892256
E-10-Hydroxynortriptyline,1TBDMS,isomer #1	CNCC/C=C1\C2=CC=CC=C2CC(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2717.3	Semi standard non polar	33892256
E-10-Hydroxynortriptyline,1TBDMS,isomer #2	CN(CC/C=C1\C2=CC=CC=C2CC(O)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2961.8	Semi standard non polar	33892256
E-10-Hydroxynortriptyline,2TBDMS,isomer #1	CN(CC/C=C1\C2=CC=CC=C2CC(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	3114.0	Semi standard non polar	33892256
E-10-Hydroxynortriptyline,2TBDMS,isomer #1	CN(CC/C=C1\C2=CC=CC=C2CC(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	3141.2	Standard non polar	33892256
E-10-Hydroxynortriptyline,2TBDMS,isomer #1	CN(CC/C=C1\C2=CC=CC=C2CC(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	3183.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - E-10-Hydroxynortriptyline GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ox-6190000000-6bdfc002b8164f38a92c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - E-10-Hydroxynortriptyline GC-MS (1 TMS) - 70eV, Positive	splash10-0006-9033000000-6a9e01111b58310ed9e0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - E-10-Hydroxynortriptyline 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 - E-10-Hydroxynortriptyline 10V, Positive-QTOF	splash10-01q9-0090000000-1ca30bf7f4a64fbff1af	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - E-10-Hydroxynortriptyline 20V, Positive-QTOF	splash10-01q9-2090000000-bd2d6746902ad67f5563	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - E-10-Hydroxynortriptyline 40V, Positive-QTOF	splash10-052f-4290000000-b4df1745e201740cfb55	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - E-10-Hydroxynortriptyline 10V, Negative-QTOF	splash10-004i-0090000000-a23f7b604598473d807d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - E-10-Hydroxynortriptyline 20V, Negative-QTOF	splash10-004i-0090000000-0e2b231634f3bedce478	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - E-10-Hydroxynortriptyline 40V, Negative-QTOF	splash10-000y-5090000000-17ebb38f8c1ca1a708ee	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - E-10-Hydroxynortriptyline 10V, Positive-QTOF	splash10-001i-0090000000-72bd97d6e51f59b35b9e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - E-10-Hydroxynortriptyline 20V, Positive-QTOF	splash10-001i-0090000000-f5bea9330037bfa19f74	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - E-10-Hydroxynortriptyline 40V, Positive-QTOF	splash10-0a4i-1290000000-0c74e557da6ec34f303a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - E-10-Hydroxynortriptyline 10V, Negative-QTOF	splash10-004i-0090000000-345ef089afddc416f7fc	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - E-10-Hydroxynortriptyline 20V, Negative-QTOF	splash10-06w9-0090000000-34b91c92d338a43242c4	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - E-10-Hydroxynortriptyline 40V, Negative-QTOF	splash10-014i-1190000000-5103dd9b9878439ab144	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry	21059682	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

4944825

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6440567

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

Not Available

Showing metabocard for E-10-Hydroxynortriptyline (HMDB0013889)

MOL for HMDB0013889 (E-10-Hydroxynortriptyline)

3D MOL for HMDB0013889 (E-10-Hydroxynortriptyline)

3D SDF for HMDB0013889 (E-10-Hydroxynortriptyline)

3D-SDF for HMDB0013889 (E-10-Hydroxynortriptyline)

PDB for HMDB0013889 (E-10-Hydroxynortriptyline)

3D PDB for HMDB0013889 (E-10-Hydroxynortriptyline)

SMILES for HMDB0013889 (E-10-Hydroxynortriptyline)

INCHI for HMDB0013889 (E-10-Hydroxynortriptyline)

Structure for HMDB0013889 (E-10-Hydroxynortriptyline)

3D Structure for HMDB0013889 (E-10-Hydroxynortriptyline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra