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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:01:37 UTC

Update Date

2021-09-14 14:58:38 UTC

HMDB ID

HMDB0014257

Secondary Accession Numbers

HMDB14257

Metabolite Identification

Common Name

E-10-Hydroxydesmethylnortriptyline

Description

E-10-Hydroxydesmethylnortriptyline is only found in individuals that have used or taken Amitriptyline. E-10-Hydroxydesmethylnortriptyline is a metabolite of Amitriptyline. E-10-hydroxydesmethylnortriptyline belongs to the family of Dibenzocycloheptenes. These are compounds containing a dibenzocycloheptene moiety, which consists of two benzene connected by a cycloheptene ring.

Structure

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

HMDB0014257
     RDKit          3D
E-10-Hydroxydesmethylnortriptyline
 39 41  0  0  0  0  0  0  0  0999 V2000
    3.4090    1.5190    2.0362 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0860    0.1067    1.8960 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5997   -0.0412    0.3833 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4255    0.8386    0.3023 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3006    0.4036   -0.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2898   -1.0079   -0.6247 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4275   -1.2161   -1.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5812   -2.5061   -1.8312 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6189   -3.4922   -1.5679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5139   -3.1841   -0.8164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7127   -1.9141   -0.3168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9500   -1.6815    0.4400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7766   -0.5069    0.1035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5880   -0.7949   -1.0240 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1763    0.8148    0.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1563    1.7957    0.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8009    3.1479   -0.0433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4763    3.5565   -0.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4888    2.5900   -0.2307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8916    1.2957   -0.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4350    1.9985    1.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4083    1.6066    2.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2414   -0.1093    2.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9787   -0.4904    2.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5425    0.2734   -0.0228 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3907   -1.1076    0.5607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4851    1.8389    0.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1127   -0.4569   -1.6129 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4347   -2.7922   -2.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7837   -4.4844   -1.9620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2743   -3.9491   -0.6057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7843   -1.7677    1.5447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6031   -2.5793    0.2149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5413   -0.4321    0.9393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2680   -0.2630   -1.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2100    1.5743    0.1569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5613    3.9127   -0.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3042    4.6168   -0.2470 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5270    2.8874   -0.3561 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20  5  1  0
 11  6  1  0
 20 15  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
M  END

  Mrv0541 06191311032D          

 20 22  0  0  0  0            999 V2000
    7.2878   -6.3338    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1284   -2.0531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3038   -2.0531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6426   -2.6981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7895   -2.6981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7162   -3.8598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4591   -3.5019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9729   -3.5019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7162   -4.6844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4593   -2.4322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9727   -2.4322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0798   -4.0957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3526   -4.0957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0018   -5.0968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0936   -3.0114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3387   -3.0113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0017   -5.9214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9025   -3.8491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5296   -3.8491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4863   -1.3101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 17  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 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014257

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H19NO/c19-11-5-10-15-14-7-2-1-6-13(14)12-18(20)17-9-4-3-8-16(15)17/h1-4,6-10,18,20H,5,11-12,19H2/b15-10+

> <INCHI_KEY>
PIEVJGJKDMQGSG-XNTDXEJSSA-N

> <FORMULA>
C18H19NO

> <MOLECULAR_WEIGHT>
265.3496

> <EXACT_MASS>
265.146664235

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
30.36509190201028

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.88

> <JCHEM_LOGP>
2.7630955169999996

> <ALOGPS_LOGS>
-4.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.257310281564678

> <JCHEM_PKA_STRONGEST_BASIC>
10.172583284335342

> <JCHEM_POLAR_SURFACE_AREA>
46.25

> <JCHEM_REFRACTIVITY>
92.95340000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.61e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014257
     RDKit          3D
E-10-Hydroxydesmethylnortriptyline
 39 41  0  0  0  0  0  0  0  0999 V2000
    3.4090    1.5190    2.0362 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0860    0.1067    1.8960 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5997   -0.0412    0.3833 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4255    0.8386    0.3023 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3006    0.4036   -0.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2898   -1.0079   -0.6247 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4275   -1.2161   -1.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5812   -2.5061   -1.8312 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6189   -3.4922   -1.5679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5139   -3.1841   -0.8164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7127   -1.9141   -0.3168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9500   -1.6815    0.4400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7766   -0.5069    0.1035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5880   -0.7949   -1.0240 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1763    0.8148    0.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1563    1.7957    0.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8009    3.1479   -0.0433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4763    3.5565   -0.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4888    2.5900   -0.2307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8916    1.2957   -0.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4350    1.9985    1.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4083    1.6066    2.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2414   -0.1093    2.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9787   -0.4904    2.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5425    0.2734   -0.0228 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3907   -1.1076    0.5607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4851    1.8389    0.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1127   -0.4569   -1.6129 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4347   -2.7922   -2.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7837   -4.4844   -1.9620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2743   -3.9491   -0.6057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7843   -1.7677    1.5447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6031   -2.5793    0.2149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5413   -0.4321    0.9393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2680   -0.2630   -1.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2100    1.5743    0.1569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5613    3.9127   -0.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3042    4.6168   -0.2470 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5270    2.8874   -0.3561 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20  5  1  0
 11  6  1  0
 20 15  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  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      13.604 -11.823   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      17.040  -3.832   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.500  -3.832   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.000  -5.036   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.540  -5.036   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.270  -7.205   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.657  -6.537   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.883  -6.537   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.270  -8.744   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      19.524  -4.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.016  -4.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      18.816  -7.645   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.725  -7.645   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.937  -9.514   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.708  -5.621   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.832  -5.621   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.937 -11.053   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      20.351  -7.185   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.189  -7.185   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      17.708  -2.445   0.000  0.00  0.00           O+0
CONECT    1   17                                                            
CONECT    2    3    4   20                                                  
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    2                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0014257
HETATM    1  N1  UNL     1       3.409   1.519   2.036  1.00  0.00           N  
HETATM    2  C1  UNL     1       3.086   0.107   1.896  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.600  -0.041   0.383  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.426   0.839   0.302  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.301   0.404  -0.169  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.290  -1.008  -0.625  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.427  -1.216  -1.354  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.581  -2.506  -1.831  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.619  -3.492  -1.568  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.514  -3.184  -0.816  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.713  -1.914  -0.317  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.950  -1.682   0.440  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.777  -0.507   0.104  1.00  0.00           C  
HETATM   14  O1  UNL     1      -3.588  -0.795  -1.024  1.00  0.00           O  
HETATM   15  C13 UNL     1      -2.176   0.815   0.005  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.156   1.796   0.050  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.801   3.148  -0.043  1.00  0.00           C  
HETATM   18  C16 UNL     1      -1.476   3.557  -0.184  1.00  0.00           C  
HETATM   19  C17 UNL     1      -0.489   2.590  -0.231  1.00  0.00           C  
HETATM   20  C18 UNL     1      -0.892   1.296  -0.134  1.00  0.00           C  
HETATM   21  H1  UNL     1       3.435   1.998   1.091  1.00  0.00           H  
HETATM   22  H2  UNL     1       4.408   1.607   2.366  1.00  0.00           H  
HETATM   23  H3  UNL     1       2.241  -0.109   2.551  1.00  0.00           H  
HETATM   24  H4  UNL     1       3.979  -0.490   2.045  1.00  0.00           H  
HETATM   25  H5  UNL     1       3.543   0.273  -0.023  1.00  0.00           H  
HETATM   26  H6  UNL     1       2.391  -1.108   0.561  1.00  0.00           H  
HETATM   27  H7  UNL     1       1.485   1.839   0.653  1.00  0.00           H  
HETATM   28  H8  UNL     1       2.113  -0.457  -1.613  1.00  0.00           H  
HETATM   29  H9  UNL     1       2.435  -2.792  -2.414  1.00  0.00           H  
HETATM   30  H10 UNL     1       0.784  -4.484  -1.962  1.00  0.00           H  
HETATM   31  H11 UNL     1      -1.274  -3.949  -0.606  1.00  0.00           H  
HETATM   32  H12 UNL     1      -1.784  -1.768   1.545  1.00  0.00           H  
HETATM   33  H13 UNL     1      -2.603  -2.579   0.215  1.00  0.00           H  
HETATM   34  H14 UNL     1      -3.541  -0.432   0.939  1.00  0.00           H  
HETATM   35  H15 UNL     1      -3.268  -0.263  -1.814  1.00  0.00           H  
HETATM   36  H16 UNL     1      -4.210   1.574   0.157  1.00  0.00           H  
HETATM   37  H17 UNL     1      -3.561   3.913  -0.008  1.00  0.00           H  
HETATM   38  H18 UNL     1      -1.304   4.617  -0.247  1.00  0.00           H  
HETATM   39  H19 UNL     1       0.527   2.887  -0.356  1.00  0.00           H  
CONECT    1    2   21   22
CONECT    2    3   23   24
CONECT    3    4   25   26
CONECT    4    5    5   27
CONECT    5    6   20
CONECT    6    7    7   11
CONECT    7    8   28
CONECT    8    9    9   29
CONECT    9   10   30
CONECT   10   11   11   31
CONECT   11   12
CONECT   12   13   32   33
CONECT   13   14   15   34
CONECT   14   35
CONECT   15   16   16   20
CONECT   16   17   36
CONECT   17   18   18   37
CONECT   18   19   38
CONECT   19   20   20   39
END

HMDB0014257
     RDKit          3D
E-10-Hydroxydesmethylnortriptyline
 39 41  0  0  0  0  0  0  0  0999 V2000
    3.4090    1.5190    2.0362 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0860    0.1067    1.8960 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5997   -0.0412    0.3833 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4255    0.8386    0.3023 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3006    0.4036   -0.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2898   -1.0079   -0.6247 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4275   -1.2161   -1.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5812   -2.5061   -1.8312 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6189   -3.4922   -1.5679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5139   -3.1841   -0.8164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7127   -1.9141   -0.3168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9500   -1.6815    0.4400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7766   -0.5069    0.1035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5880   -0.7949   -1.0240 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1763    0.8148    0.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1563    1.7957    0.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8009    3.1479   -0.0433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4763    3.5565   -0.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4888    2.5900   -0.2307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8916    1.2957   -0.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4350    1.9985    1.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4083    1.6066    2.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2414   -0.1093    2.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9787   -0.4904    2.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5425    0.2734   -0.0228 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3907   -1.1076    0.5607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4851    1.8389    0.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1127   -0.4569   -1.6129 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4347   -2.7922   -2.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7837   -4.4844   -1.9620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2743   -3.9491   -0.6057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7843   -1.7677    1.5447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6031   -2.5793    0.2149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5413   -0.4321    0.9393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2680   -0.2630   -1.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2100    1.5743    0.1569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5613    3.9127   -0.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3042    4.6168   -0.2470 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5270    2.8874   -0.3561 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20  5  1  0
 11  6  1  0
 20 15  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₈H₁₉NO

Average Molecular Weight

265.3496

Monoisotopic Molecular Weight

265.146664235

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C18H19NO/c19-11-5-10-15-14-7-2-1-6-13(14)12-18(20)17-9-4-3-8-16(15)17/h1-4,6-10,18,20H,5,11-12,19H2/b15-10+

InChI Key

PIEVJGJKDMQGSG-XNTDXEJSSA-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
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Amine
Alcohol
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: 21059682)

Organ

Liver (HMDB: HMDB0014257)
Kidney (HMDB: HMDB0014257)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0014257)

Source

Endogenous

Endogenous (HMDB: HMDB0014257)

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	0.016 g/L	ALOGPS
logP	2.88	ALOGPS
logP	2.76	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	14.26	ChemAxon
pKa (Strongest Basic)	10.17	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	46.25 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	92.95 m³·mol⁻¹	ChemAxon
Polarizability	30.37 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	164.198	31661259
DarkChem	[M-H]-	162.907	31661259
DeepCCS	[M-2H]-	195.832	30932474
DeepCCS	[M+Na]+	171.398	30932474
AllCCS	[M+H]+	164.2	32859911
AllCCS	[M+H-H2O]+	160.6	32859911
AllCCS	[M+NH4]+	167.5	32859911
AllCCS	[M+Na]+	168.5	32859911
AllCCS	[M-H]-	168.4	32859911
AllCCS	[M+Na-2H]-	168.1	32859911
AllCCS	[M+HCOO]-	167.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
E-10-Hydroxydesmethylnortriptyline	NCC\C=C1/C2=CC=CC=C2CC(O)C2=CC=CC=C12	3461.5	Standard polar	33892256
E-10-Hydroxydesmethylnortriptyline	NCC\C=C1/C2=CC=CC=C2CC(O)C2=CC=CC=C12	2499.6	Standard non polar	33892256
E-10-Hydroxydesmethylnortriptyline	NCC\C=C1/C2=CC=CC=C2CC(O)C2=CC=CC=C12	2421.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
E-10-Hydroxydesmethylnortriptyline,1TMS,isomer #1	C[Si](C)(C)OC1CC2=CC=CC=C2/C(=C\CCN)C2=CC=CC=C21	2475.4	Semi standard non polar	33892256
E-10-Hydroxydesmethylnortriptyline,1TMS,isomer #2	C[Si](C)(C)NCC/C=C1\C2=CC=CC=C2CC(O)C2=CC=CC=C12	2650.7	Semi standard non polar	33892256
E-10-Hydroxydesmethylnortriptyline,2TMS,isomer #1	C[Si](C)(C)NCC/C=C1\C2=CC=CC=C2CC(O[Si](C)(C)C)C2=CC=CC=C12	2594.4	Semi standard non polar	33892256
E-10-Hydroxydesmethylnortriptyline,2TMS,isomer #1	C[Si](C)(C)NCC/C=C1\C2=CC=CC=C2CC(O[Si](C)(C)C)C2=CC=CC=C12	2572.1	Standard non polar	33892256
E-10-Hydroxydesmethylnortriptyline,2TMS,isomer #1	C[Si](C)(C)NCC/C=C1\C2=CC=CC=C2CC(O[Si](C)(C)C)C2=CC=CC=C12	3088.2	Standard polar	33892256
E-10-Hydroxydesmethylnortriptyline,2TMS,isomer #2	C[Si](C)(C)N(CC/C=C1\C2=CC=CC=C2CC(O)C2=CC=CC=C12)[Si](C)(C)C	2837.2	Semi standard non polar	33892256
E-10-Hydroxydesmethylnortriptyline,2TMS,isomer #2	C[Si](C)(C)N(CC/C=C1\C2=CC=CC=C2CC(O)C2=CC=CC=C12)[Si](C)(C)C	2840.9	Standard non polar	33892256
E-10-Hydroxydesmethylnortriptyline,2TMS,isomer #2	C[Si](C)(C)N(CC/C=C1\C2=CC=CC=C2CC(O)C2=CC=CC=C12)[Si](C)(C)C	3234.3	Standard polar	33892256
E-10-Hydroxydesmethylnortriptyline,3TMS,isomer #1	C[Si](C)(C)OC1CC2=CC=CC=C2/C(=C\CCN([Si](C)(C)C)[Si](C)(C)C)C2=CC=CC=C21	2756.6	Semi standard non polar	33892256
E-10-Hydroxydesmethylnortriptyline,3TMS,isomer #1	C[Si](C)(C)OC1CC2=CC=CC=C2/C(=C\CCN([Si](C)(C)C)[Si](C)(C)C)C2=CC=CC=C21	2800.3	Standard non polar	33892256
E-10-Hydroxydesmethylnortriptyline,3TMS,isomer #1	C[Si](C)(C)OC1CC2=CC=CC=C2/C(=C\CCN([Si](C)(C)C)[Si](C)(C)C)C2=CC=CC=C21	2984.4	Standard polar	33892256
E-10-Hydroxydesmethylnortriptyline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CC2=CC=CC=C2/C(=C\CCN)C2=CC=CC=C21	2732.9	Semi standard non polar	33892256
E-10-Hydroxydesmethylnortriptyline,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCC/C=C1\C2=CC=CC=C2CC(O)C2=CC=CC=C12	2906.8	Semi standard non polar	33892256
E-10-Hydroxydesmethylnortriptyline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC/C=C1\C2=CC=CC=C2CC(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C12	3018.2	Semi standard non polar	33892256
E-10-Hydroxydesmethylnortriptyline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC/C=C1\C2=CC=CC=C2CC(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C12	3059.4	Standard non polar	33892256
E-10-Hydroxydesmethylnortriptyline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC/C=C1\C2=CC=CC=C2CC(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C12	3239.6	Standard polar	33892256
E-10-Hydroxydesmethylnortriptyline,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CC/C=C1\C2=CC=CC=C2CC(O)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	3276.9	Semi standard non polar	33892256
E-10-Hydroxydesmethylnortriptyline,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CC/C=C1\C2=CC=CC=C2CC(O)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	3268.3	Standard non polar	33892256
E-10-Hydroxydesmethylnortriptyline,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CC/C=C1\C2=CC=CC=C2CC(O)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	3316.0	Standard polar	33892256
E-10-Hydroxydesmethylnortriptyline,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CC2=CC=CC=C2/C(=C\CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=CC=CC=C21	3432.0	Semi standard non polar	33892256
E-10-Hydroxydesmethylnortriptyline,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CC2=CC=CC=C2/C(=C\CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=CC=CC=C21	3464.1	Standard non polar	33892256
E-10-Hydroxydesmethylnortriptyline,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CC2=CC=CC=C2/C(=C\CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=CC=CC=C21	3156.7	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-Hydroxydesmethylnortriptyline GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9380000000-7f30b4b3e8709cb182ac	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - E-10-Hydroxydesmethylnortriptyline GC-MS (1 TMS) - 70eV, Positive	splash10-0089-9043000000-bafab0c3999454f81cca	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - E-10-Hydroxydesmethylnortriptyline 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-Hydroxydesmethylnortriptyline 10V, Positive-QTOF	splash10-00kb-0090000000-0e6ec8b5602840a75321	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - E-10-Hydroxydesmethylnortriptyline 20V, Positive-QTOF	splash10-000t-1090000000-cd2d0e452aa79e6f3b40	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - E-10-Hydroxydesmethylnortriptyline 40V, Positive-QTOF	splash10-0a5c-5390000000-506657e81c957c8770db	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - E-10-Hydroxydesmethylnortriptyline 10V, Negative-QTOF	splash10-03di-0090000000-726dea79d4f611bf635c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - E-10-Hydroxydesmethylnortriptyline 20V, Negative-QTOF	splash10-03di-0090000000-8b7a42c41e2e29c52b9c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - E-10-Hydroxydesmethylnortriptyline 40V, Negative-QTOF	splash10-00kp-4090000000-f5ce19cf845fa393bbf3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - E-10-Hydroxydesmethylnortriptyline 10V, Positive-QTOF	splash10-014i-0090000000-d7e2674b434ca547f3f9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - E-10-Hydroxydesmethylnortriptyline 20V, Positive-QTOF	splash10-00lr-0090000000-9fd9be8a426b1ce80dc4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - E-10-Hydroxydesmethylnortriptyline 40V, Positive-QTOF	splash10-0a4i-1490000000-4b9a8cf7590226dbc569	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - E-10-Hydroxydesmethylnortriptyline 10V, Negative-QTOF	splash10-03di-0090000000-f88a9abb5979da4e772d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - E-10-Hydroxydesmethylnortriptyline 20V, Negative-QTOF	splash10-08fr-0190000000-df21930d302d46ec80ba	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - E-10-Hydroxydesmethylnortriptyline 40V, Negative-QTOF	splash10-014i-1290000000-9f66f0bc1f7554e477e3	2021-09-22	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

5005861

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6506716

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-Hydroxydesmethylnortriptyline (HMDB0014257)

MOL for HMDB0014257 (E-10-Hydroxydesmethylnortriptyline)

3D MOL for HMDB0014257 (E-10-Hydroxydesmethylnortriptyline)

3D SDF for HMDB0014257 (E-10-Hydroxydesmethylnortriptyline)

3D-SDF for HMDB0014257 (E-10-Hydroxydesmethylnortriptyline)

PDB for HMDB0014257 (E-10-Hydroxydesmethylnortriptyline)

3D PDB for HMDB0014257 (E-10-Hydroxydesmethylnortriptyline)

SMILES for HMDB0014257 (E-10-Hydroxydesmethylnortriptyline)

INCHI for HMDB0014257 (E-10-Hydroxydesmethylnortriptyline)

Structure for HMDB0014257 (E-10-Hydroxydesmethylnortriptyline)

3D Structure for HMDB0014257 (E-10-Hydroxydesmethylnortriptyline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra