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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:26:23 UTC

Update Date

2021-09-26 22:51:54 UTC

HMDB ID

HMDB0244270

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(Z)-10-Hydroxyamitriptyline

Description

(Z)-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. Based on a literature review very few articles have been published on (Z)-10-Hydroxyamitriptyline. This compound has been identified in human blood as reported by (PMID: 31557052 ). (z)-10-hydroxyamitriptyline is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (Z)-10-Hydroxyamitriptyline is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0244270
     RDKit          3D
(Z)-10-Hydroxyamitriptyline
 45 47  0  0  0  0  0  0  0  0999 V2000
    5.3293    0.5847   -0.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2314   -0.1405    0.3799 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1433   -1.4227   -0.2617 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0372    0.6532    0.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8279   -0.0064    0.8147 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5748    0.7323    0.6754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5758    0.4181    0.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7608   -0.9016   -0.4631 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3180   -1.2220   -1.2735 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3114   -2.4202   -1.8910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7318   -3.2909   -1.7227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7977   -2.9431   -0.9091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8446   -1.7178   -0.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0304   -1.4850    0.5630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7255   -0.1979    0.4975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5563   -0.1259    1.6479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0061    1.0526    0.4373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9037    2.1222    0.5631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4628    3.4276    0.5151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1270    3.7292    0.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2116    2.7038    0.2132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6727    1.4298    0.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2657    0.1382    0.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2847    0.4303   -1.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2513    1.6532   -0.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8350   -1.3618   -1.3319 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5089   -2.1007    0.3347 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1955   -1.8303   -0.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8783    0.9463   -0.8476 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1469    1.6348    0.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7751   -1.0679    0.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0766    0.0204    1.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6480    1.7456    1.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0713   -0.4690   -1.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1593   -2.6824   -2.5292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7105   -4.2575   -2.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6374   -3.6137   -0.7591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7852   -2.2727    0.2434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8158   -1.7798    1.6319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4797   -0.1904   -0.3465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9586    0.2771    2.3523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9572    1.9385    0.7000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1896    4.2462    0.6172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7833    4.7514    0.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1456    2.8648    0.0485 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  3
  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


  Mrv1652309102123262D          

 22 24  0  0  0  0            999 V2000
    2.3747    3.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3747    2.8070    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6603    2.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0892    2.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0892    1.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8037    1.1570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8037    0.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5470   -0.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1517    0.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9401    0.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1237   -0.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5189   -1.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7305   -0.8303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2162   -1.4753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3912   -1.4753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8768   -0.8303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0884   -1.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4837   -0.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6673    0.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4556    0.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0604   -0.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0332   -2.2186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
  7 21  1  0  0  0  0
 15 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0244270

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)CCC=C1C2=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

> <INCHI_KEY>
GHWBJXOKAFHZAI-UHFFFAOYSA-N

> <FORMULA>
C20H23NO

> <MOLECULAR_WEIGHT>
293.41

> <EXACT_MASS>
293.177964365

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
34.40476746646465

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[3-(dimethylamino)propylidene]tricyclo[9.4.0.0^{3,8}]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>
103.0227

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.56e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[3-(dimethylamino)propylidene]tricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-9-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0244270
     RDKit          3D
(Z)-10-Hydroxyamitriptyline
 45 47  0  0  0  0  0  0  0  0999 V2000
    5.3293    0.5847   -0.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2314   -0.1405    0.3799 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1433   -1.4227   -0.2617 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0372    0.6532    0.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8279   -0.0064    0.8147 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5748    0.7323    0.6754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5758    0.4181    0.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7608   -0.9016   -0.4631 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3180   -1.2220   -1.2735 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3114   -2.4202   -1.8910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7318   -3.2909   -1.7227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7977   -2.9431   -0.9091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8446   -1.7178   -0.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0304   -1.4850    0.5630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7255   -0.1979    0.4975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5563   -0.1259    1.6479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0061    1.0526    0.4373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9037    2.1222    0.5631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4628    3.4276    0.5151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1270    3.7292    0.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2116    2.7038    0.2132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6727    1.4298    0.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2657    0.1382    0.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2847    0.4303   -1.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2513    1.6532   -0.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8350   -1.3618   -1.3319 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5089   -2.1007    0.3347 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1955   -1.8303   -0.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8783    0.9463   -0.8476 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1469    1.6348    0.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7751   -1.0679    0.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0766    0.0204    1.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6480    1.7456    1.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0713   -0.4690   -1.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1593   -2.6824   -2.5292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7105   -4.2575   -2.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6374   -3.6137   -0.7591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7852   -2.2727    0.2434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8158   -1.7798    1.6319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4797   -0.1904   -0.3465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9586    0.2771    2.3523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9572    1.9385    0.7000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1896    4.2462    0.6172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7833    4.7514    0.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1456    2.8648    0.0485 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  3
  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                                 10-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-21         0                                  
HETATM    1  C   UNK     0       4.433   6.780   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       4.433   5.240   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       3.099   4.470   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.766   4.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.766   2.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.100   2.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.100   0.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.488  -0.048   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.617   0.999   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.088   0.545   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.431  -0.956   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.302  -2.004   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.830  -1.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.870  -2.754   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.330  -2.754   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.370  -1.550   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.898  -2.004   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.770  -0.956   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.112   0.545   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.584   0.999   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.713  -0.048   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.662  -4.141   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   21                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16    7                                                  
CONECT   22   15                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0244270
HETATM    1  C1  UNL     1       5.329   0.585  -0.241  1.00  0.00           C  
HETATM    2  N1  UNL     1       4.231  -0.140   0.380  1.00  0.00           N  
HETATM    3  C2  UNL     1       4.143  -1.423  -0.262  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.037   0.653   0.205  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.828  -0.006   0.815  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.575   0.732   0.675  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.576   0.418   0.145  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.761  -0.902  -0.463  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.318  -1.222  -1.274  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.311  -2.420  -1.891  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.732  -3.291  -1.723  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.798  -2.943  -0.909  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.845  -1.718  -0.244  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.030  -1.485   0.563  1.00  0.00           C  
HETATM   15  C14 UNL     1      -3.726  -0.198   0.497  1.00  0.00           C  
HETATM   16  O1  UNL     1      -4.556  -0.126   1.648  1.00  0.00           O  
HETATM   17  C15 UNL     1      -3.006   1.053   0.437  1.00  0.00           C  
HETATM   18  C16 UNL     1      -3.904   2.122   0.563  1.00  0.00           C  
HETATM   19  C17 UNL     1      -3.463   3.428   0.515  1.00  0.00           C  
HETATM   20  C18 UNL     1      -2.127   3.729   0.341  1.00  0.00           C  
HETATM   21  C19 UNL     1      -1.212   2.704   0.213  1.00  0.00           C  
HETATM   22  C20 UNL     1      -1.673   1.430   0.266  1.00  0.00           C  
HETATM   23  H1  UNL     1       6.266   0.138   0.146  1.00  0.00           H  
HETATM   24  H2  UNL     1       5.285   0.430  -1.350  1.00  0.00           H  
HETATM   25  H3  UNL     1       5.251   1.653  -0.032  1.00  0.00           H  
HETATM   26  H4  UNL     1       3.835  -1.362  -1.332  1.00  0.00           H  
HETATM   27  H5  UNL     1       3.509  -2.101   0.335  1.00  0.00           H  
HETATM   28  H6  UNL     1       5.196  -1.830  -0.298  1.00  0.00           H  
HETATM   29  H7  UNL     1       2.878   0.946  -0.848  1.00  0.00           H  
HETATM   30  H8  UNL     1       3.147   1.635   0.753  1.00  0.00           H  
HETATM   31  H9  UNL     1       1.775  -1.068   0.631  1.00  0.00           H  
HETATM   32  H10 UNL     1       2.077   0.020   1.958  1.00  0.00           H  
HETATM   33  H11 UNL     1       0.648   1.746   1.132  1.00  0.00           H  
HETATM   34  H12 UNL     1       1.071  -0.469  -1.380  1.00  0.00           H  
HETATM   35  H13 UNL     1       1.159  -2.682  -2.529  1.00  0.00           H  
HETATM   36  H14 UNL     1      -0.710  -4.258  -2.236  1.00  0.00           H  
HETATM   37  H15 UNL     1      -2.637  -3.614  -0.759  1.00  0.00           H  
HETATM   38  H16 UNL     1      -3.785  -2.273   0.243  1.00  0.00           H  
HETATM   39  H17 UNL     1      -2.816  -1.780   1.632  1.00  0.00           H  
HETATM   40  H18 UNL     1      -4.480  -0.190  -0.347  1.00  0.00           H  
HETATM   41  H19 UNL     1      -3.959   0.277   2.352  1.00  0.00           H  
HETATM   42  H20 UNL     1      -4.957   1.938   0.700  1.00  0.00           H  
HETATM   43  H21 UNL     1      -4.190   4.246   0.617  1.00  0.00           H  
HETATM   44  H22 UNL     1      -1.783   4.751   0.304  1.00  0.00           H  
HETATM   45  H23 UNL     1      -0.146   2.865   0.049  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

HMDB0244270
     RDKit          3D
(Z)-10-Hydroxyamitriptyline
 45 47  0  0  0  0  0  0  0  0999 V2000
    5.3293    0.5847   -0.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2314   -0.1405    0.3799 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1433   -1.4227   -0.2617 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0372    0.6532    0.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8279   -0.0064    0.8147 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5748    0.7323    0.6754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5758    0.4181    0.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7608   -0.9016   -0.4631 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3180   -1.2220   -1.2735 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3114   -2.4202   -1.8910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7318   -3.2909   -1.7227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7977   -2.9431   -0.9091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8446   -1.7178   -0.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0304   -1.4850    0.5630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7255   -0.1979    0.4975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5563   -0.1259    1.6479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0061    1.0526    0.4373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9037    2.1222    0.5631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4628    3.4276    0.5151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1270    3.7292    0.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2116    2.7038    0.2132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6727    1.4298    0.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2657    0.1382    0.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2847    0.4303   -1.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2513    1.6532   -0.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8350   -1.3618   -1.3319 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5089   -2.1007    0.3347 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1955   -1.8303   -0.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8783    0.9463   -0.8476 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1469    1.6348    0.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7751   -1.0679    0.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0766    0.0204    1.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6480    1.7456    1.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0713   -0.4690   -1.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1593   -2.6824   -2.5292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7105   -4.2575   -2.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6374   -3.6137   -0.7591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7852   -2.2727    0.2434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8158   -1.7798    1.6319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4797   -0.1904   -0.3465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9586    0.2771    2.3523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9572    1.9385    0.7000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1896    4.2462    0.6172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7833    4.7514    0.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1456    2.8648    0.0485 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  3
  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

Value	Source
10-Hydroxyamitriptyline, (e)-isomer	HMDB
10-Hydroxyamitriptyline, (Z)-isomer	HMDB

Chemical Formula

C₂₀H₂₃NO

Average Molecular Weight

293.41

Monoisotopic Molecular Weight

293.177964365

IUPAC Name

2-[3-(dimethylamino)propylidene]tricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-9-ol

Traditional Name

2-[3-(dimethylamino)propylidene]tricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-9-ol

CAS Registry Number

Not Available

SMILES

CN(C)CCC=C1C2=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

InChI Key

GHWBJXOKAFHZAI-UHFFFAOYSA-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
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
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: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	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	34.4 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
DeepCCS	[M-2H]-	199.45	30932474
DeepCCS	[M+Na]+	175.015	30932474
AllCCS	[M+H]+	173.1	32859911
AllCCS	[M+H-H2O]+	169.9	32859911
AllCCS	[M+NH4]+	176.1	32859911
AllCCS	[M+Na]+	176.9	32859911
AllCCS	[M-H]-	175.6	32859911
AllCCS	[M+Na-2H]-	175.3	32859911
AllCCS	[M+HCOO]-	175.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.97 minutes	32390414
Predicted by Siyang on May 30, 2022	10.9014 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.48 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1255.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	229.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	162.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	185.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	104.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	356.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	441.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	707.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	906.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	290.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1143.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	228.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	332.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	357.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	432.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(Z)-10-Hydroxyamitriptyline	CN(C)CCC=C1C2=CC=CC=C2CC(O)C2=CC=CC=C12	3446.5	Standard polar	33892256
(Z)-10-Hydroxyamitriptyline	CN(C)CCC=C1C2=CC=CC=C2CC(O)C2=CC=CC=C12	2342.3	Standard non polar	33892256
(Z)-10-Hydroxyamitriptyline	CN(C)CCC=C1C2=CC=CC=C2CC(O)C2=CC=CC=C12	2390.7	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 - (Z)-10-Hydroxyamitriptyline GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6r-7090000000-07b31b93f1a8400df99f	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (Z)-10-Hydroxyamitriptyline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (Z)-10-Hydroxyamitriptyline GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (Z)-10-Hydroxyamitriptyline GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	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 - (Z)-10-Hydroxyamitriptyline 10V, Positive-QTOF	splash10-0006-0090000000-30d07353bc3aa408628f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-10-Hydroxyamitriptyline 20V, Positive-QTOF	splash10-054o-1090000000-d0ae9ffdc4dbc85f5497	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-10-Hydroxyamitriptyline 40V, Positive-QTOF	splash10-0a4i-4190000000-b6da53f18b8b57b4314b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-10-Hydroxyamitriptyline 10V, Negative-QTOF	splash10-0006-0090000000-7eeb2b0b68aedf3d9ea7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-10-Hydroxyamitriptyline 20V, Negative-QTOF	splash10-000x-0090000000-f3fcdb89eb4d28527d4b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-10-Hydroxyamitriptyline 40V, Negative-QTOF	splash10-014i-0090000000-c9759d12aa0574ca2c06	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

32675185

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

155720

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for (Z)-10-Hydroxyamitriptyline (HMDB0244270)

MOL for HMDB0244270 ((Z)-10-Hydroxyamitriptyline)

3D MOL for HMDB0244270 ((Z)-10-Hydroxyamitriptyline)

3D SDF for HMDB0244270 ((Z)-10-Hydroxyamitriptyline)

3D-SDF for HMDB0244270 ((Z)-10-Hydroxyamitriptyline)

PDB for HMDB0244270 ((Z)-10-Hydroxyamitriptyline)

3D PDB for HMDB0244270 ((Z)-10-Hydroxyamitriptyline)

SMILES for HMDB0244270 ((Z)-10-Hydroxyamitriptyline)

INCHI for HMDB0244270 ((Z)-10-Hydroxyamitriptyline)

Structure for HMDB0244270 ((Z)-10-Hydroxyamitriptyline)

3D Structure for HMDB0244270 ((Z)-10-Hydroxyamitriptyline)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra