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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 03:59:03 UTC

Update Date

2021-09-26 23:00:23 UTC

HMDB ID

HMDB0249471

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Butriptyline

Description

Butriptyline, also known as evadyne, 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. Butriptyline is a very strong basic compound (based on its pKa). It is the isobutyl side chain homologue of amitriptyline. Butriptyline is a tricyclic antidepressant which has been used in Europe since 1974. Gastrointestinal disturbances (including nausea and vomiting), drowsiness, tremor, low blood pressure when standing, dizziness, sweating, weakness and fatigue, incoordination, epilepsy-like seizures, and speech difficulties may occur. Side effects of tricyclic antidepressants include dry mouth, sour or metallic taste, constipation, retention of urine, blurred vision and changes in focusing, palpitations, and fast heart beat. This compound has been identified in human blood as reported by (PMID: 31557052 ). Butriptyline is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Butriptyline 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

HMDB0249471
     RDKit          3D
Butriptyline
 49 51  0  0  0  0  0  0  0  0999 V2000
    1.8084   -0.5649    1.6210 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7918   -0.2577    0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5819   -0.9655   -0.4700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6443   -0.4812    0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9103   -1.1986   -0.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6189   -2.2163   -1.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6745   -2.9952   -1.6555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9714   -2.7529   -1.2987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2491   -1.7285   -0.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2057   -0.9299    0.0778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8317    0.0659    0.9531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8188    0.8460    1.7478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9582    1.5425    0.7688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2718    2.8609    0.6433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5878    3.6443   -0.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6202    3.0678   -1.0488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3232    1.7210   -0.8977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9743    0.9590   -0.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0832   -0.8109   -0.4355 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1653   -0.1099    0.2715 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4587   -0.5851   -0.1756 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0383    1.3247    0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0831    0.1081    2.0798 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8213   -0.2868    1.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5812   -1.6442    1.7754 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7847    0.8315    0.0744 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6159   -0.9953   -1.5808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7271   -2.0379   -0.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5916   -0.6957    1.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6473   -2.5106   -1.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4849   -3.8071   -2.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8096   -3.3425   -1.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2820   -1.5224   -0.1425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5897   -0.4130    1.6205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4244    0.7909    0.3086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1737    0.1168    2.3099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3129    1.5437    2.4477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0376    3.3449    1.2364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8116    4.6895   -0.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0787    3.6765   -1.7822 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4112    1.3029   -1.5422 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1993   -0.6890   -1.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1793   -1.8761   -0.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0033   -1.1185    0.6576 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2837   -1.2777   -1.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0577    0.2801   -0.5205 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4716    1.6204   -0.7527 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6645    1.7677    1.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0928    1.7083    0.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  2 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 18  4  1  0
 10  5  1  0
 18 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 14 38  1  0
 15 39  1  0
 16 40  1  0
 17 41  1  0
 19 42  1  0
 19 43  1  0
 21 44  1  0
 21 45  1  0
 21 46  1  0
 22 47  1  0
 22 48  1  0
 22 49  1  0
M  END


  Mrv0541 06231411412D          

 22 24  0  0  0  0            999 V2000
    1.6622    1.7437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8057    2.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0912    1.7437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2678    4.6505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3721    4.6505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0842    3.8462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1885    3.8462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6630    5.2117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7673    5.2117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2958    3.6030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4002    3.6030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3603    5.6135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5353    5.6135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9478    2.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3767    2.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6622    2.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8747    4.9685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0209    4.9685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6911    4.1642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2045    4.1642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9478    3.8062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0912    2.5687    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  2  0  0  0  0
  7  5  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 13 12  1  0  0  0  0
 16  1  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17  8  2  0  0  0  0
 17 12  1  0  0  0  0
 18  9  2  0  0  0  0
 18 13  1  0  0  0  0
 19 10  2  0  0  0  0
 19 17  1  0  0  0  0
 20 11  2  0  0  0  0
 20 18  1  0  0  0  0
 21 14  1  0  0  0  0
 21 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22  2  1  0  0  0  0
 22  3  1  0  0  0  0
 22 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249471

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(CC1C2=CC=CC=C2CCC2=CC=CC=C12)CN(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C21H27N/c1-16(15-22(2)3)14-21-19-10-6-4-8-17(19)12-13-18-9-5-7-11-20(18)21/h4-11,16,21H,12-15H2,1-3H3

> <INCHI_KEY>
ALELTFCQZDXAMQ-UHFFFAOYSA-N

> <FORMULA>
C21H27N

> <MOLECULAR_WEIGHT>
293.4458

> <EXACT_MASS>
293.214349869

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
35.53031790642079

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
dimethyl(2-methyl-3-{tricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-2-yl}propyl)amine

> <JCHEM_LOGP>
5.4413538893333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.005979381820191

> <JCHEM_POLAR_SURFACE_AREA>
3.24

> <JCHEM_REFRACTIVITY>
95.95309999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
butriptyline

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0249471
     RDKit          3D
Butriptyline
 49 51  0  0  0  0  0  0  0  0999 V2000
    1.8084   -0.5649    1.6210 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7918   -0.2577    0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5819   -0.9655   -0.4700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6443   -0.4812    0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9103   -1.1986   -0.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6189   -2.2163   -1.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6745   -2.9952   -1.6555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9714   -2.7529   -1.2987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2491   -1.7285   -0.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2057   -0.9299    0.0778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8317    0.0659    0.9531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8188    0.8460    1.7478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9582    1.5425    0.7688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2718    2.8609    0.6433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5878    3.6443   -0.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6202    3.0678   -1.0488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3232    1.7210   -0.8977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9743    0.9590   -0.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0832   -0.8109   -0.4355 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1653   -0.1099    0.2715 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4587   -0.5851   -0.1756 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0383    1.3247    0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0831    0.1081    2.0798 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8213   -0.2868    1.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5812   -1.6442    1.7754 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7847    0.8315    0.0744 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6159   -0.9953   -1.5808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7271   -2.0379   -0.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5916   -0.6957    1.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6473   -2.5106   -1.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4849   -3.8071   -2.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8096   -3.3425   -1.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2820   -1.5224   -0.1425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5897   -0.4130    1.6205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4244    0.7909    0.3086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1737    0.1168    2.3099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3129    1.5437    2.4477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0376    3.3449    1.2364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8116    4.6895   -0.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0787    3.6765   -1.7822 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4112    1.3029   -1.5422 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1993   -0.6890   -1.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1793   -1.8761   -0.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0033   -1.1185    0.6576 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2837   -1.2777   -1.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0577    0.2801   -0.5205 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4716    1.6204   -0.7527 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6645    1.7677    1.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0928    1.7083    0.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  2 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 18  4  1  0
 10  5  1  0
 18 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 14 38  1  0
 15 39  1  0
 16 40  1  0
 17 41  1  0
 19 42  1  0
 19 43  1  0
 21 44  1  0
 21 45  1  0
 21 46  1  0
 22 47  1  0
 22 48  1  0
 22 49  1  0
M  END

HEADER    PROTEIN                                 23-JUN-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-JUN-14         0                                  
HETATM    1  C   UNK     0       3.103   3.255   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.104   5.565   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.770   3.255   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.100   8.681   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.561   8.681   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.757   7.180   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.219   7.180   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.971   9.729   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.432   9.729   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.285   6.726   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.747   6.726   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.539  10.479   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.999  10.479   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.769   5.565   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.437   5.565   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.103   4.795   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.499   9.275   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.039   9.275   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.157   7.773   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.382   7.773   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.769   7.105   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       5.770   4.795   0.000  0.00  0.00           N+0
CONECT    1   16                                                            
CONECT    2   22                                                            
CONECT    3   22                                                            
CONECT    4    6    8                                                       
CONECT    5    7    9                                                       
CONECT    6    4   10                                                       
CONECT    7    5   11                                                       
CONECT    8    4   17                                                       
CONECT    9    5   18                                                       
CONECT   10    6   19                                                       
CONECT   11    7   20                                                       
CONECT   12   13   17                                                       
CONECT   13   12   18                                                       
CONECT   14   16   21                                                       
CONECT   15   16   22                                                       
CONECT   16    1   14   15                                                  
CONECT   17    8   12   19                                                  
CONECT   18    9   13   20                                                  
CONECT   19   10   17   21                                                  
CONECT   20   11   18   21                                                  
CONECT   21   14   19   20                                                  
CONECT   22    2    3   15                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0249471
HETATM    1  C1  UNL     1       1.808  -0.565   1.621  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.792  -0.258   0.101  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.582  -0.965  -0.470  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.644  -0.481   0.132  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.910  -1.199  -0.300  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.619  -2.216  -1.158  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.675  -2.995  -1.655  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.971  -2.753  -1.299  1.00  0.00           C  
HETATM    9  C9  UNL     1      -4.249  -1.729  -0.437  1.00  0.00           C  
HETATM   10  C10 UNL     1      -3.206  -0.930   0.078  1.00  0.00           C  
HETATM   11  C11 UNL     1      -3.832   0.066   0.953  1.00  0.00           C  
HETATM   12  C12 UNL     1      -2.819   0.846   1.748  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.958   1.543   0.769  1.00  0.00           C  
HETATM   14  C14 UNL     1      -2.272   2.861   0.643  1.00  0.00           C  
HETATM   15  C15 UNL     1      -1.588   3.644  -0.286  1.00  0.00           C  
HETATM   16  C16 UNL     1      -0.620   3.068  -1.049  1.00  0.00           C  
HETATM   17  C17 UNL     1      -0.323   1.721  -0.898  1.00  0.00           C  
HETATM   18  C18 UNL     1      -0.974   0.959  -0.003  1.00  0.00           C  
HETATM   19  C19 UNL     1       3.083  -0.811  -0.436  1.00  0.00           C  
HETATM   20  N1  UNL     1       4.165  -0.110   0.271  1.00  0.00           N  
HETATM   21  C20 UNL     1       5.459  -0.585  -0.176  1.00  0.00           C  
HETATM   22  C21 UNL     1       4.038   1.325   0.135  1.00  0.00           C  
HETATM   23  H1  UNL     1       1.083   0.108   2.080  1.00  0.00           H  
HETATM   24  H2  UNL     1       2.821  -0.287   1.960  1.00  0.00           H  
HETATM   25  H3  UNL     1       1.581  -1.644   1.775  1.00  0.00           H  
HETATM   26  H4  UNL     1       1.785   0.832   0.074  1.00  0.00           H  
HETATM   27  H5  UNL     1       0.616  -0.995  -1.581  1.00  0.00           H  
HETATM   28  H6  UNL     1       0.727  -2.038  -0.159  1.00  0.00           H  
HETATM   29  H7  UNL     1      -0.592  -0.696   1.240  1.00  0.00           H  
HETATM   30  H8  UNL     1      -0.647  -2.511  -1.515  1.00  0.00           H  
HETATM   31  H9  UNL     1      -2.485  -3.807  -2.334  1.00  0.00           H  
HETATM   32  H10 UNL     1      -4.810  -3.343  -1.670  1.00  0.00           H  
HETATM   33  H11 UNL     1      -5.282  -1.522  -0.142  1.00  0.00           H  
HETATM   34  H12 UNL     1      -4.590  -0.413   1.621  1.00  0.00           H  
HETATM   35  H13 UNL     1      -4.424   0.791   0.309  1.00  0.00           H  
HETATM   36  H14 UNL     1      -2.174   0.117   2.310  1.00  0.00           H  
HETATM   37  H15 UNL     1      -3.313   1.544   2.448  1.00  0.00           H  
HETATM   38  H16 UNL     1      -3.038   3.345   1.236  1.00  0.00           H  
HETATM   39  H17 UNL     1      -1.812   4.690  -0.409  1.00  0.00           H  
HETATM   40  H18 UNL     1      -0.079   3.676  -1.782  1.00  0.00           H  
HETATM   41  H19 UNL     1       0.411   1.303  -1.542  1.00  0.00           H  
HETATM   42  H20 UNL     1       3.199  -0.689  -1.517  1.00  0.00           H  
HETATM   43  H21 UNL     1       3.179  -1.876  -0.121  1.00  0.00           H  
HETATM   44  H22 UNL     1       6.003  -1.119   0.658  1.00  0.00           H  
HETATM   45  H23 UNL     1       5.284  -1.278  -1.023  1.00  0.00           H  
HETATM   46  H24 UNL     1       6.058   0.280  -0.521  1.00  0.00           H  
HETATM   47  H25 UNL     1       3.472   1.620  -0.753  1.00  0.00           H  
HETATM   48  H26 UNL     1       3.664   1.768   1.059  1.00  0.00           H  
HETATM   49  H27 UNL     1       5.093   1.708   0.015  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   19   26
CONECT    3    4   27   28
CONECT    4    5   18   29
CONECT    5    6    6   10
CONECT    6    7   30
CONECT    7    8    8   31
CONECT    8    9   32
CONECT    9   10   10   33
CONECT   10   11
CONECT   11   12   34   35
CONECT   12   13   36   37
CONECT   13   14   14   18
CONECT   14   15   38
CONECT   15   16   16   39
CONECT   16   17   40
CONECT   17   18   18   41
CONECT   19   20   42   43
CONECT   20   21   22
CONECT   21   44   45   46
CONECT   22   47   48   49
END

HMDB0249471
     RDKit          3D
Butriptyline
 49 51  0  0  0  0  0  0  0  0999 V2000
    1.8084   -0.5649    1.6210 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7918   -0.2577    0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5819   -0.9655   -0.4700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6443   -0.4812    0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9103   -1.1986   -0.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6189   -2.2163   -1.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6745   -2.9952   -1.6555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9714   -2.7529   -1.2987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2491   -1.7285   -0.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2057   -0.9299    0.0778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8317    0.0659    0.9531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8188    0.8460    1.7478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9582    1.5425    0.7688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2718    2.8609    0.6433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5878    3.6443   -0.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6202    3.0678   -1.0488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3232    1.7210   -0.8977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9743    0.9590   -0.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0832   -0.8109   -0.4355 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1653   -0.1099    0.2715 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4587   -0.5851   -0.1756 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0383    1.3247    0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0831    0.1081    2.0798 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8213   -0.2868    1.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5812   -1.6442    1.7754 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7847    0.8315    0.0744 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6159   -0.9953   -1.5808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7271   -2.0379   -0.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5916   -0.6957    1.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6473   -2.5106   -1.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4849   -3.8071   -2.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8096   -3.3425   -1.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2820   -1.5224   -0.1425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5897   -0.4130    1.6205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4244    0.7909    0.3086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1737    0.1168    2.3099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3129    1.5437    2.4477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0376    3.3449    1.2364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8116    4.6895   -0.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0787    3.6765   -1.7822 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4112    1.3029   -1.5422 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1993   -0.6890   -1.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1793   -1.8761   -0.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0033   -1.1185    0.6576 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2837   -1.2777   -1.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0577    0.2801   -0.5205 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4716    1.6204   -0.7527 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6645    1.7677    1.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0928    1.7083    0.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  2 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 18  4  1  0
 10  5  1  0
 18 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 14 38  1  0
 15 39  1  0
 16 40  1  0
 17 41  1  0
 19 42  1  0
 19 43  1  0
 21 44  1  0
 21 45  1  0
 21 46  1  0
 22 47  1  0
 22 48  1  0
 22 49  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Evadyne	Kegg
Butriptyline hydrochloride, (+-)-isomer	MeSH
10,11-Dihydro-N,N,beta-trimethyl-5H-dibenzo(a,D) cycloheptane-5-propylamine	MeSH
Butriptyline, (+-)-isomer	MeSH
Butriptyline hydrochloride	MeSH
Butriptylene	MeSH

Chemical Formula

C₂₁H₂₇N

Average Molecular Weight

293.4458

Monoisotopic Molecular Weight

293.214349869

IUPAC Name

dimethyl(2-methyl-3-{tricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-2-yl}propyl)amine

Traditional Name

butriptyline

CAS Registry Number

Not Available

SMILES

CC(CC1C2=CC=CC=C2CCC2=CC=CC=C12)CN(C)C

InChI Identifier

InChI=1S/C21H27N/c1-16(15-22(2)3)14-21-19-10-6-4-8-17(19)12-13-18-9-5-7-11-20(18)21/h4-11,16,21H,12-15H2,1-3H3

InChI Key

ALELTFCQZDXAMQ-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
Aralkylamine
Tertiary aliphatic amine
Tertiary amine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

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	5.44	ChemAxon
pKa (Strongest Basic)	10.01	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	3.24 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	95.95 m³·mol⁻¹	ChemAxon
Polarizability	35.53 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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]-	197.275	30932474
DeepCCS	[M+Na]+	172.61	30932474
AllCCS	[M+H]+	172.7	32859911
AllCCS	[M+H-H2O]+	169.4	32859911
AllCCS	[M+NH4]+	175.8	32859911
AllCCS	[M+Na]+	176.7	32859911
AllCCS	[M-H]-	182.0	32859911
AllCCS	[M+Na-2H]-	181.8	32859911
AllCCS	[M+HCOO]-	181.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Butriptyline	CC(CC1C2=CC=CC=C2CCC2=CC=CC=C12)CN(C)C	2869.9	Standard polar	33892256
Butriptyline	CC(CC1C2=CC=CC=C2CCC2=CC=CC=C12)CN(C)C	2205.6	Standard non polar	33892256
Butriptyline	CC(CC1C2=CC=CC=C2CCC2=CC=CC=C12)CN(C)C	2171.5	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 - Butriptyline GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9340000000-599e7b771be6e4c672d4	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Butriptyline 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 - Butriptyline 10V, Positive-QTOF	splash10-0006-0090000000-fcdc735cf1f6f87d021f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butriptyline 20V, Positive-QTOF	splash10-0005-1390000000-7e2f47992612fac4fda6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butriptyline 40V, Positive-QTOF	splash10-0006-7960000000-581cf9f5866770d25326	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butriptyline 10V, Negative-QTOF	splash10-0006-0090000000-493334f63085dc31849f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butriptyline 20V, Negative-QTOF	splash10-0006-0090000000-75fc4df499d36855eb2c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butriptyline 40V, Negative-QTOF	splash10-0006-9560000000-d618a0d44ddb3dfbc253	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butriptyline 10V, Positive-QTOF	splash10-0006-0190000000-d68da30bb5c28850f9ca	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butriptyline 20V, Positive-QTOF	splash10-0a4l-3390000000-3f62baa1e777aadc8233	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butriptyline 40V, Positive-QTOF	splash10-0a4i-7890000000-e90be0872eba21ea457f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butriptyline 10V, Negative-QTOF	splash10-0006-0090000000-25264659bc9fd0f2879e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butriptyline 20V, Negative-QTOF	splash10-0006-0190000000-f902aa459e092b518048	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butriptyline 40V, Negative-QTOF	splash10-0690-2290000000-06974eaa1a0edad3039d	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

DB09016

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Butriptyline

METLIN ID

Not Available

PubChem Compound

21772

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 Butriptyline (HMDB0249471)

MOL for HMDB0249471 (Butriptyline)

3D MOL for HMDB0249471 (Butriptyline)

3D SDF for HMDB0249471 (Butriptyline)

3D-SDF for HMDB0249471 (Butriptyline)

PDB for HMDB0249471 (Butriptyline)

3D PDB for HMDB0249471 (Butriptyline)

SMILES for HMDB0249471 (Butriptyline)

INCHI for HMDB0249471 (Butriptyline)

Structure for HMDB0249471 (Butriptyline)

3D Structure for HMDB0249471 (Butriptyline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra