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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 14:59:05 UTC

HMDB ID

HMDB0013888

Secondary Accession Numbers

HMDB13888

Metabolite Identification

Common Name

E-10-Hydroxyamitriptyline

Description

E-10-Hydroxyamitriptyline 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-Hydroxyamitriptyline is a very strong basic compound (based on its pKa). These are compounds containing a dibenzocycloheptene moiety, which consists of two benzene connected by a cycloheptene ring. E-10-Hydroxyamitriptyline is only found in individuals that have used or taken Amitriptyline. E-10-Hydroxyamitriptyline is a metabolite of Amitriptyline.

Structure

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

HMDB0013888
     RDKit          3D
E-10-Hydroxyamitriptyline
 45 47  0  0  0  0  0  0  0  0999 V2000
    4.7568    1.1529    0.1319 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4481    0.4340    0.2675 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8578   -0.6857    1.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0728   -0.0867   -1.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6642   -0.5147   -1.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6396    0.5179   -0.9102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4757    0.3017   -0.3147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7225   -1.0672    0.1961 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4165   -1.4857    0.8224 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3818   -2.7730    1.3185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7739   -3.5608    1.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8941   -3.0518    0.5186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8996   -1.7739    0.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1365   -1.3144   -0.6458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6854   -0.0001   -0.2556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3942   -0.1534    0.9536 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8391    1.1801   -0.2594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6061    2.3413   -0.2389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0124    3.6065   -0.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6214    3.7491   -0.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8282    2.6035   -0.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4784    1.4114   -0.2590 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9649    1.6037    1.1181 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4769    0.3531   -0.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6610    1.8621   -0.6954 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9359   -0.6835    1.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6063   -1.6253    0.6499 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2955   -0.6020    2.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3117    0.7636   -1.7452 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8256   -0.8287   -1.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6227   -0.5325   -2.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3909   -1.5670   -1.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8320    1.5058   -1.3138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2225   -0.8441    0.9819 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2410   -3.1957    1.8281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8091   -4.5732    1.5546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8001   -3.6459    0.3927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0511   -1.4222   -1.7576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9264   -2.0684   -0.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5125    0.2084   -1.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8982    0.2148    1.7155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6890    2.3348   -0.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6210    4.4946   -0.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1855    4.7219   -0.2042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2360    2.6945   -0.2169 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  2  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  1  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22  7  1  0
 13  8  1  0
 22 17  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  0
 21 45  1  0
M  END


  Mrv0541 06191310272D          

 22 24  0  0  0  0            999 V2000
    7.6503   -6.0812    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6667   -1.7993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4916   -1.7993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0792   -3.6063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1523   -2.4442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0060   -2.4442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3359   -3.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8225   -3.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0792   -4.4313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3647   -4.8438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3352   -2.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8231   -2.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7150   -3.8426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4432   -3.8426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3646   -5.6687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7008   -2.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4575   -2.7579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8920   -3.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2662   -3.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6503   -6.9062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9358   -5.6687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8496   -1.0560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 15  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  2  3  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  2  0  0  0  0
  5  7  1  0  0  0  0
  5 11  2  0  0  0  0
  6  8  1  0  0  0  0
  6 12  2  0  0  0  0
  7 13  2  0  0  0  0
  8 14  2  0  0  0  0
  9 10  1  0  0  0  0
 10 15  1  0  0  0  0
 11 16  1  0  0  0  0
 12 17  1  0  0  0  0
 13 18  1  0  0  0  0
 14 19  1  0  0  0  0
 16 18  2  0  0  0  0
 17 19  2  0  0  0  0
  3 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013888

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H23NO/c1-21(2)13-7-12-17-16-9-4-3-8-15(16)14-20(22)19-11-6-5-10-18(17)19/h3-6,8-12,20,22H,7,13-14H2,1-2H3/b17-12+

> <INCHI_KEY>
GHWBJXOKAFHZAI-SFQUDFHCSA-N

> <FORMULA>
C20H23NO

> <MOLECULAR_WEIGHT>
293.4027

> <EXACT_MASS>
293.177964363

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
34.42331733475349

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.84

> <JCHEM_LOGP>
3.5787238479999997

> <ALOGPS_LOGS>
-3.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.257286784588839

> <JCHEM_PKA_STRONGEST_BASIC>
9.760724866463432

> <JCHEM_POLAR_SURFACE_AREA>
23.47

> <JCHEM_REFRACTIVITY>
103.02270000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.56e-02 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0013888
     RDKit          3D
E-10-Hydroxyamitriptyline
 45 47  0  0  0  0  0  0  0  0999 V2000
    4.7568    1.1529    0.1319 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4481    0.4340    0.2675 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8578   -0.6857    1.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0728   -0.0867   -1.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6642   -0.5147   -1.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6396    0.5179   -0.9102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4757    0.3017   -0.3147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7225   -1.0672    0.1961 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4165   -1.4857    0.8224 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3818   -2.7730    1.3185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7739   -3.5608    1.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8941   -3.0518    0.5186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8996   -1.7739    0.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1365   -1.3144   -0.6458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6854   -0.0001   -0.2556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3942   -0.1534    0.9536 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8391    1.1801   -0.2594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6061    2.3413   -0.2389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0124    3.6065   -0.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6214    3.7491   -0.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8282    2.6035   -0.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4784    1.4114   -0.2590 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9649    1.6037    1.1181 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4769    0.3531   -0.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6610    1.8621   -0.6954 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9359   -0.6835    1.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6063   -1.6253    0.6499 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2955   -0.6020    2.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3117    0.7636   -1.7452 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8256   -0.8287   -1.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6227   -0.5325   -2.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3909   -1.5670   -1.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8320    1.5058   -1.3138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2225   -0.8441    0.9819 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2410   -3.1957    1.8281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8091   -4.5732    1.5546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8001   -3.6459    0.3927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0511   -1.4222   -1.7576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9264   -2.0684   -0.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5125    0.2084   -1.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8982    0.2148    1.7155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6890    2.3348   -0.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6210    4.4946   -0.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1855    4.7219   -0.2042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2360    2.6945   -0.2169 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  2  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  1  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22  7  1  0
 13  8  1  0
 22 17  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  0
 21 45  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      14.280 -11.352   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      16.178  -3.359   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.718  -3.359   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.948  -6.732   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.218  -4.563   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.678  -4.563   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.560  -6.064   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.335  -6.064   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.948  -8.272   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.614  -9.042   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.692  -4.066   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      20.203  -4.066   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.401  -7.173   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      19.494  -7.173   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.614 -10.582   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.508  -5.148   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      21.387  -5.148   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.865  -6.712   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      21.030  -6.712   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.280 -12.892   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.947 -10.582   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      18.386  -1.971   0.000  0.00  0.00           O+0
CONECT    1   15   20   21                                                  
CONECT    2    3    5                                                       
CONECT    3    2    6   22                                                  
CONECT    4    7    8    9                                                  
CONECT    5    2    7   11                                                  
CONECT    6    3    8   12                                                  
CONECT    7    4    5   13                                                  
CONECT    8    4    6   14                                                  
CONECT    9    4   10                                                       
CONECT   10    9   15                                                       
CONECT   11    5   16                                                       
CONECT   12    6   17                                                       
CONECT   13    7   18                                                       
CONECT   14    8   19                                                       
CONECT   15    1   10                                                       
CONECT   16   11   18                                                       
CONECT   17   12   19                                                       
CONECT   18   13   16                                                       
CONECT   19   14   17                                                       
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    3                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0013888
HETATM    1  C1  UNL     1       4.757   1.153   0.132  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.448   0.434   0.268  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.858  -0.686   1.168  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.073  -0.087  -1.016  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.664  -0.515  -1.107  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.640   0.518  -0.910  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.476   0.302  -0.315  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.723  -1.067   0.196  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.417  -1.486   0.822  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.382  -2.773   1.319  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.774  -3.561   1.168  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.894  -3.052   0.519  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.900  -1.774   0.008  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.136  -1.314  -0.646  1.00  0.00           C  
HETATM   15  C14 UNL     1      -3.685  -0.000  -0.256  1.00  0.00           C  
HETATM   16  O1  UNL     1      -4.394  -0.153   0.954  1.00  0.00           O  
HETATM   17  C15 UNL     1      -2.839   1.180  -0.259  1.00  0.00           C  
HETATM   18  C16 UNL     1      -3.606   2.341  -0.239  1.00  0.00           C  
HETATM   19  C17 UNL     1      -3.012   3.607  -0.219  1.00  0.00           C  
HETATM   20  C18 UNL     1      -1.621   3.749  -0.219  1.00  0.00           C  
HETATM   21  C19 UNL     1      -0.828   2.603  -0.240  1.00  0.00           C  
HETATM   22  C20 UNL     1      -1.478   1.411  -0.259  1.00  0.00           C  
HETATM   23  H1  UNL     1       4.965   1.604   1.118  1.00  0.00           H  
HETATM   24  H2  UNL     1       5.477   0.353  -0.130  1.00  0.00           H  
HETATM   25  H3  UNL     1       4.661   1.862  -0.695  1.00  0.00           H  
HETATM   26  H4  UNL     1       4.936  -0.684   1.347  1.00  0.00           H  
HETATM   27  H5  UNL     1       3.606  -1.625   0.650  1.00  0.00           H  
HETATM   28  H6  UNL     1       3.295  -0.602   2.140  1.00  0.00           H  
HETATM   29  H7  UNL     1       3.312   0.764  -1.745  1.00  0.00           H  
HETATM   30  H8  UNL     1       3.826  -0.829  -1.296  1.00  0.00           H  
HETATM   31  H9  UNL     1       1.623  -0.532  -2.297  1.00  0.00           H  
HETATM   32  H10 UNL     1       1.391  -1.567  -1.151  1.00  0.00           H  
HETATM   33  H11 UNL     1       0.832   1.506  -1.314  1.00  0.00           H  
HETATM   34  H12 UNL     1       1.222  -0.844   0.982  1.00  0.00           H  
HETATM   35  H13 UNL     1       1.241  -3.196   1.828  1.00  0.00           H  
HETATM   36  H14 UNL     1      -0.809  -4.573   1.555  1.00  0.00           H  
HETATM   37  H15 UNL     1      -2.800  -3.646   0.393  1.00  0.00           H  
HETATM   38  H16 UNL     1      -3.051  -1.422  -1.758  1.00  0.00           H  
HETATM   39  H17 UNL     1      -3.926  -2.068  -0.344  1.00  0.00           H  
HETATM   40  H18 UNL     1      -4.513   0.208  -1.004  1.00  0.00           H  
HETATM   41  H19 UNL     1      -3.898   0.215   1.716  1.00  0.00           H  
HETATM   42  H20 UNL     1      -4.689   2.335  -0.237  1.00  0.00           H  
HETATM   43  H21 UNL     1      -3.621   4.495  -0.204  1.00  0.00           H  
HETATM   44  H22 UNL     1      -1.186   4.722  -0.204  1.00  0.00           H  
HETATM   45  H23 UNL     1       0.236   2.695  -0.217  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    4
CONECT    3   26   27   28
CONECT    4    5   29   30
CONECT    5    6   31   32
CONECT    6    7    7   33
CONECT    7    8   22
CONECT    8    9    9   13
CONECT    9   10   34
CONECT   10   11   11   35
CONECT   11   12   36
CONECT   12   13   13   37
CONECT   13   14
CONECT   14   15   38   39
CONECT   15   16   17   40
CONECT   16   41
CONECT   17   18   18   22
CONECT   18   19   42
CONECT   19   20   20   43
CONECT   20   21   44
CONECT   21   22   22   45
END

HMDB0013888
     RDKit          3D
E-10-Hydroxyamitriptyline
 45 47  0  0  0  0  0  0  0  0999 V2000
    4.7568    1.1529    0.1319 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4481    0.4340    0.2675 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8578   -0.6857    1.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0728   -0.0867   -1.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6642   -0.5147   -1.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6396    0.5179   -0.9102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4757    0.3017   -0.3147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7225   -1.0672    0.1961 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4165   -1.4857    0.8224 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3818   -2.7730    1.3185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7739   -3.5608    1.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8941   -3.0518    0.5186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8996   -1.7739    0.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1365   -1.3144   -0.6458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6854   -0.0001   -0.2556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3942   -0.1534    0.9536 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8391    1.1801   -0.2594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6061    2.3413   -0.2389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0124    3.6065   -0.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6214    3.7491   -0.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8282    2.6035   -0.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4784    1.4114   -0.2590 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9649    1.6037    1.1181 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4769    0.3531   -0.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6610    1.8621   -0.6954 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9359   -0.6835    1.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6063   -1.6253    0.6499 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2955   -0.6020    2.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3117    0.7636   -1.7452 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8256   -0.8287   -1.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6227   -0.5325   -2.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3909   -1.5670   -1.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8320    1.5058   -1.3138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2225   -0.8441    0.9819 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2410   -3.1957    1.8281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8091   -4.5732    1.5546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8001   -3.6459    0.3927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0511   -1.4222   -1.7576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9264   -2.0684   -0.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5125    0.2084   -1.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8982    0.2148    1.7155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6890    2.3348   -0.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6210    4.4946   -0.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1855    4.7219   -0.2042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2360    2.6945   -0.2169 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  2  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  1  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22  7  1  0
 13  8  1  0
 22 17  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  0
 21 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₀H₂₃NO

Average Molecular Weight

293.4027

Monoisotopic Molecular Weight

293.177964363

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H23NO/c1-21(2)13-7-12-17-16-9-4-3-8-15(16)14-20(22)19-11-6-5-10-18(17)19/h3-6,8-12,20,22H,7,13-14H2,1-2H3/b17-12+

InChI Key

GHWBJXOKAFHZAI-SFQUDFHCSA-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
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
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: HMDB0013888)
Kidney (HMDB: HMDB0013888)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0013888)

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	0.066 g/L	ALOGPS
logP	3.84	ALOGPS
logP	3.58	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	14.26	ChemAxon
pKa (Strongest Basic)	9.76	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	23.47 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	103.02 m³·mol⁻¹	ChemAxon
Polarizability	34.42 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]+	170.71	31661259
DarkChem	[M-H]-	168.935	31661259
DeepCCS	[M-2H]-	202.912	30932474
DeepCCS	[M+Na]+	178.477	30932474
AllCCS	[M+H]+	172.1	32859911
AllCCS	[M+H-H2O]+	168.7	32859911
AllCCS	[M+NH4]+	175.2	32859911
AllCCS	[M+Na]+	176.1	32859911
AllCCS	[M-H]-	178.4	32859911
AllCCS	[M+Na-2H]-	178.2	32859911
AllCCS	[M+HCOO]-	178.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
E-10-Hydroxyamitriptyline	CN(C)CC\C=C1/C2=CC=CC=C2CC(O)C2=CC=CC=C12	3446.4	Standard polar	33892256
E-10-Hydroxyamitriptyline	CN(C)CC\C=C1/C2=CC=CC=C2CC(O)C2=CC=CC=C12	2342.4	Standard non polar	33892256
E-10-Hydroxyamitriptyline	CN(C)CC\C=C1/C2=CC=CC=C2CC(O)C2=CC=CC=C12	2390.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
E-10-Hydroxyamitriptyline,1TMS,isomer #1	CN(C)CC/C=C1\C2=CC=CC=C2CC(O[Si](C)(C)C)C2=CC=CC=C12	2496.7	Semi standard non polar	33892256
E-10-Hydroxyamitriptyline,1TBDMS,isomer #1	CN(C)CC/C=C1\C2=CC=CC=C2CC(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2741.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - E-10-Hydroxyamitriptyline GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6r-7090000000-07b31b93f1a8400df99f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - E-10-Hydroxyamitriptyline GC-MS (1 TMS) - 70eV, Positive	splash10-0a4i-9024000000-b354676abc0f3d58b38b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - E-10-Hydroxyamitriptyline 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-Hydroxyamitriptyline 10V, Positive-QTOF	splash10-004l-0090000000-f56812898df243a35394	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - E-10-Hydroxyamitriptyline 20V, Positive-QTOF	splash10-005d-1090000000-1189e985404461b4865d	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - E-10-Hydroxyamitriptyline 40V, Positive-QTOF	splash10-0abc-4390000000-b6c4477918c155b76301	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - E-10-Hydroxyamitriptyline 10V, Negative-QTOF	splash10-0006-0090000000-a0a8455f1734afe4e7b1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - E-10-Hydroxyamitriptyline 20V, Negative-QTOF	splash10-0006-1090000000-4c8601908fafdad5e0e8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - E-10-Hydroxyamitriptyline 40V, Negative-QTOF	splash10-0006-7090000000-305f0a55abc7763582ba	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - E-10-Hydroxyamitriptyline 10V, Positive-QTOF	splash10-0006-0090000000-30d07353bc3aa408628f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - E-10-Hydroxyamitriptyline 20V, Positive-QTOF	splash10-054o-1090000000-d0ae9ffdc4dbc85f5497	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - E-10-Hydroxyamitriptyline 40V, Positive-QTOF	splash10-0a4i-4190000000-b6da53f18b8b57b4314b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - E-10-Hydroxyamitriptyline 10V, Negative-QTOF	splash10-0006-0090000000-7eeb2b0b68aedf3d9ea7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - E-10-Hydroxyamitriptyline 20V, Negative-QTOF	splash10-000x-0090000000-f3fcdb89eb4d28527d4b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - E-10-Hydroxyamitriptyline 40V, Negative-QTOF	splash10-014i-0090000000-c9759d12aa0574ca2c06	2021-09-24	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

4957199

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6454906

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-Hydroxyamitriptyline (HMDB0013888)

MOL for HMDB0013888 (E-10-Hydroxyamitriptyline)

3D MOL for HMDB0013888 (E-10-Hydroxyamitriptyline)

3D SDF for HMDB0013888 (E-10-Hydroxyamitriptyline)

3D-SDF for HMDB0013888 (E-10-Hydroxyamitriptyline)

PDB for HMDB0013888 (E-10-Hydroxyamitriptyline)

3D PDB for HMDB0013888 (E-10-Hydroxyamitriptyline)

SMILES for HMDB0013888 (E-10-Hydroxyamitriptyline)

INCHI for HMDB0013888 (E-10-Hydroxyamitriptyline)

Structure for HMDB0013888 (E-10-Hydroxyamitriptyline)

3D Structure for HMDB0013888 (E-10-Hydroxyamitriptyline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra