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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1)transporters (3) Show 4 proteins XML

enzymes (1)transporters (3) Show 4 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:38 UTC

HMDB ID

HMDB0014488

Secondary Accession Numbers

HMDB14488

Metabolite Identification

Common Name

Protriptyline

Description

Protriptyline hydrochloride is a dibenzocycloheptene-derivative tricyclic antidepressant (TCA). TCAs are structurally similar to phenothiazines. They contain a tricyclic ring system with an alkyl amine substituent on the central ring. In non-depressed individuals, protriptyline does not affect mood or arousal, but may cause sedation. In depressed individuals, protriptyline exerts a positive effect on mood. TCAs are potent inhibitors of serotonin and norepinephrine reuptake. In addition, TCAs down-regulate cerebral cortical β-adrenergic receptors and sensitize post-synaptic serotonergic receptors with chronic use. The antidepressant effects of TCAs are thought to be due to an overall increase in serotonergic neurotransmission. TCAs also block histamine H₁ receptors, α₁-adrenergic receptors and muscarinic receptors, which accounts for their sedative, hypotensive and anticholinergic effects (e.g. blurred vision, dry mouth, constipation, urinary retention), respectively. See toxicity section below for a complete listing of side effects. Protriptyline may be used for the treatment of depression.

Structure

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

HMDB0014488
     RDKit          3D
Protriptyline
 41 43  0  0  0  0  0  0  0  0999 V2000
    4.4262    0.6529    0.5733 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1348    0.5059    1.2284 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5920   -0.8049    0.9953 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2316   -0.9269   -0.4838 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2129    0.0879   -0.9294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1048    0.0368   -0.3048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9171   -1.1816   -0.4847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5420   -2.0503   -1.4769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2297   -3.2360   -1.7139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3144   -3.5358   -0.9278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7096   -2.6676    0.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0187   -1.4962    0.3009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6455   -0.6892    1.3767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6501    0.6406    1.4501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0278    1.5696    0.4684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6609    2.7723    0.3649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1928    3.7216   -0.5247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0872    3.4256   -1.2914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4132    2.1961   -1.2065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9031    1.2874   -0.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9711   -0.3219    0.5036 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2796    1.1050   -0.4314 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0075    1.3836    1.1764 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1353    0.8091    2.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6867   -1.0121    1.5762 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3377   -1.6113    1.1803 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9792   -1.9724   -0.6186 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1859   -0.6547   -1.0354 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6949    1.0725   -0.6182 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1995    0.1808   -2.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1566   -0.0189    0.8373 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2828   -1.8051   -2.1009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8673   -3.8585   -2.5094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8609   -4.4502   -1.0948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5719   -2.8734    0.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1486   -1.2330    2.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1321    1.1411    2.2563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5283    2.9242    1.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7048    4.6876   -0.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7455    4.1699   -1.9676 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4619    2.0293   -1.8520 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  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20  6  1  0
 12  7  1  0
 20 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  8 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 13 36  1  0
 14 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
M  END

344
  Mrv0541 02231214372D          

 20 22  0  0  0  0            999 V2000
    2.5989   -1.7283    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0276    0.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0276   -0.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7706    1.1040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2842    1.1040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3131   -0.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9542    1.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1007    1.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3130   -1.3158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3914    0.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6637    0.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4398    2.5530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6151    2.5530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7710    2.1739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2838    2.1739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2142    0.7568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8406    0.7568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4054    1.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6497    1.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5989   -2.5530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  1 20  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4 10  2  0  0  0  0
  5  8  1  0  0  0  0
  5 11  2  0  0  0  0
  6  9  1  0  0  0  0
  7 12  1  0  0  0  0
  7 14  2  0  0  0  0
  8 13  1  0  0  0  0
  8 15  2  0  0  0  0
 10 16  1  0  0  0  0
 11 17  1  0  0  0  0
 12 13  2  0  0  0  0
 14 18  1  0  0  0  0
 15 19  1  0  0  0  0
 16 18  2  0  0  0  0
 17 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014488

> <DATABASE_NAME>
hmdb

> <SMILES>
CNCCCC1C2=CC=CC=C2C=CC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C19H21N/c1-20-14-6-11-19-17-9-4-2-7-15(17)12-13-16-8-3-5-10-18(16)19/h2-5,7-10,12-13,19-20H,6,11,14H2,1H3

> <INCHI_KEY>
BWPIARFWQZKAIA-UHFFFAOYSA-N

> <FORMULA>
C19H21N

> <MOLECULAR_WEIGHT>
263.3767

> <EXACT_MASS>
263.167399677

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
31.60441131093086

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl(3-{tricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,9,11,13-heptaen-2-yl}propyl)amine

> <ALOGPS_LOGP>
4.65

> <JCHEM_LOGP>
4.496811469000001

> <ALOGPS_LOGS>
-6.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.54323028083324

> <JCHEM_POLAR_SURFACE_AREA>
12.03

> <JCHEM_REFRACTIVITY>
87.30340000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.31e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
protriptyline

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014488
     RDKit          3D
Protriptyline
 41 43  0  0  0  0  0  0  0  0999 V2000
    4.4262    0.6529    0.5733 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1348    0.5059    1.2284 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5920   -0.8049    0.9953 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2316   -0.9269   -0.4838 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2129    0.0879   -0.9294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1048    0.0368   -0.3048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9171   -1.1816   -0.4847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5420   -2.0503   -1.4769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2297   -3.2360   -1.7139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3144   -3.5358   -0.9278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7096   -2.6676    0.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0187   -1.4962    0.3009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6455   -0.6892    1.3767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6501    0.6406    1.4501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0278    1.5696    0.4684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6609    2.7723    0.3649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1928    3.7216   -0.5247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0872    3.4256   -1.2914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4132    2.1961   -1.2065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9031    1.2874   -0.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9711   -0.3219    0.5036 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2796    1.1050   -0.4314 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0075    1.3836    1.1764 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1353    0.8091    2.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6867   -1.0121    1.5762 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3377   -1.6113    1.1803 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9792   -1.9724   -0.6186 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1859   -0.6547   -1.0354 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6949    1.0725   -0.6182 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1995    0.1808   -2.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1566   -0.0189    0.8373 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2828   -1.8051   -2.1009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8673   -3.8585   -2.5094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8609   -4.4502   -1.0948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5719   -2.8734    0.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1486   -1.2330    2.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1321    1.1411    2.2563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5283    2.9242    1.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7048    4.6876   -0.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7455    4.1699   -1.9676 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4619    2.0293   -1.8520 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  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20  6  1  0
 12  7  1  0
 20 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  8 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 13 36  1  0
 14 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 344                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       4.851  -3.226   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       7.518   1.393   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.518  -0.147   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.905   2.061   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.131   2.061   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.185  -0.917   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.248   3.562   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.788   3.562   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.184  -2.456   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.064   0.952   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.972   0.952   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.288   4.766   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.748   4.766   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.773   4.058   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.263   4.058   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.600   1.413   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.436   1.413   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.957   2.977   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.079   2.977   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.851  -4.766   0.000  0.00  0.00           C+0
CONECT    1    9   20                                                       
CONECT    2    3    4    5                                                  
CONECT    3    2    6                                                       
CONECT    4    2    7   10                                                  
CONECT    5    2    8   11                                                  
CONECT    6    3    9                                                       
CONECT    7    4   12   14                                                  
CONECT    8    5   13   15                                                  
CONECT    9    1    6                                                       
CONECT   10    4   16                                                       
CONECT   11    5   17                                                       
CONECT   12    7   13                                                       
CONECT   13    8   12                                                       
CONECT   14    7   18                                                       
CONECT   15    8   19                                                       
CONECT   16   10   18                                                       
CONECT   17   11   19                                                       
CONECT   18   14   16                                                       
CONECT   19   15   17                                                       
CONECT   20    1                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0014488
HETATM    1  C1  UNL     1       4.426   0.653   0.573  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.135   0.506   1.228  1.00  0.00           N  
HETATM    3  C2  UNL     1       2.592  -0.805   0.995  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.232  -0.927  -0.484  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.213   0.088  -0.929  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.105   0.037  -0.305  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.917  -1.182  -0.485  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.542  -2.050  -1.477  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.230  -3.236  -1.714  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.314  -3.536  -0.928  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.710  -2.668   0.079  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.019  -1.496   0.301  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.645  -0.689   1.377  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.650   0.641   1.450  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.028   1.570   0.468  1.00  0.00           C  
HETATM   16  C15 UNL     1      -2.661   2.772   0.365  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.193   3.722  -0.525  1.00  0.00           C  
HETATM   18  C17 UNL     1      -1.087   3.426  -1.291  1.00  0.00           C  
HETATM   19  C18 UNL     1      -0.413   2.196  -1.207  1.00  0.00           C  
HETATM   20  C19 UNL     1      -0.903   1.287  -0.320  1.00  0.00           C  
HETATM   21  H1  UNL     1       4.971  -0.322   0.504  1.00  0.00           H  
HETATM   22  H2  UNL     1       4.280   1.105  -0.431  1.00  0.00           H  
HETATM   23  H3  UNL     1       5.007   1.384   1.176  1.00  0.00           H  
HETATM   24  H4  UNL     1       3.135   0.809   2.219  1.00  0.00           H  
HETATM   25  H5  UNL     1       1.687  -1.012   1.576  1.00  0.00           H  
HETATM   26  H6  UNL     1       3.338  -1.611   1.180  1.00  0.00           H  
HETATM   27  H7  UNL     1       1.979  -1.972  -0.619  1.00  0.00           H  
HETATM   28  H8  UNL     1       3.186  -0.655  -1.035  1.00  0.00           H  
HETATM   29  H9  UNL     1       1.695   1.073  -0.618  1.00  0.00           H  
HETATM   30  H10 UNL     1       1.200   0.181  -2.053  1.00  0.00           H  
HETATM   31  H11 UNL     1       0.157  -0.019   0.837  1.00  0.00           H  
HETATM   32  H12 UNL     1       0.283  -1.805  -2.101  1.00  0.00           H  
HETATM   33  H13 UNL     1      -0.867  -3.858  -2.509  1.00  0.00           H  
HETATM   34  H14 UNL     1      -2.861  -4.450  -1.095  1.00  0.00           H  
HETATM   35  H15 UNL     1      -3.572  -2.873   0.725  1.00  0.00           H  
HETATM   36  H16 UNL     1      -3.149  -1.233   2.156  1.00  0.00           H  
HETATM   37  H17 UNL     1      -3.132   1.141   2.256  1.00  0.00           H  
HETATM   38  H18 UNL     1      -3.528   2.924   1.008  1.00  0.00           H  
HETATM   39  H19 UNL     1      -2.705   4.688  -0.601  1.00  0.00           H  
HETATM   40  H20 UNL     1      -0.745   4.170  -1.968  1.00  0.00           H  
HETATM   41  H21 UNL     1       0.462   2.029  -1.852  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   24
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6   29   30
CONECT    6    7   20   31
CONECT    7    8    8   12
CONECT    8    9   32
CONECT    9   10   10   33
CONECT   10   11   34
CONECT   11   12   12   35
CONECT   12   13
CONECT   13   14   14   36
CONECT   14   15   37
CONECT   15   16   16   20
CONECT   16   17   38
CONECT   17   18   18   39
CONECT   18   19   40
CONECT   19   20   20   41
END

HMDB0014488
     RDKit          3D
Protriptyline
 41 43  0  0  0  0  0  0  0  0999 V2000
    4.4262    0.6529    0.5733 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1348    0.5059    1.2284 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5920   -0.8049    0.9953 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2316   -0.9269   -0.4838 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2129    0.0879   -0.9294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1048    0.0368   -0.3048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9171   -1.1816   -0.4847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5420   -2.0503   -1.4769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2297   -3.2360   -1.7139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3144   -3.5358   -0.9278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7096   -2.6676    0.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0187   -1.4962    0.3009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6455   -0.6892    1.3767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6501    0.6406    1.4501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0278    1.5696    0.4684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6609    2.7723    0.3649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1928    3.7216   -0.5247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0872    3.4256   -1.2914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4132    2.1961   -1.2065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9031    1.2874   -0.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9711   -0.3219    0.5036 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2796    1.1050   -0.4314 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0075    1.3836    1.1764 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1353    0.8091    2.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6867   -1.0121    1.5762 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3377   -1.6113    1.1803 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9792   -1.9724   -0.6186 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1859   -0.6547   -1.0354 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6949    1.0725   -0.6182 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1995    0.1808   -2.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1566   -0.0189    0.8373 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2828   -1.8051   -2.1009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8673   -3.8585   -2.5094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8609   -4.4502   -1.0948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5719   -2.8734    0.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1486   -1.2330    2.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1321    1.1411    2.2563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5283    2.9242    1.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7048    4.6876   -0.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7455    4.1699   -1.9676 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4619    2.0293   -1.8520 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  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20  6  1  0
 12  7  1  0
 20 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  8 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 13 36  1  0
 14 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-(5H-Dibenzo[a,D]cyclohepten-5-yl)-N-methyl-1-propanamine	ChEBI
5-(3-Methylaminopropyl)-5H-dibenzo[a,D]cycloheptene	ChEBI
7-(3-Methylaminopropyl)-1,2:5,6-dibenzocycloheptatriene	ChEBI
Amimetilina	ChEBI
N-Methyl-5H-dibenzo[a,D]cycloheptene-5-propanamine	ChEBI
N-Methyl-5H-dibenzo[a,D]cycloheptene-5-propylamine	ChEBI
Protryptyline	HMDB
Odyssey brand OF protriptyline hydrochloride	HMDB
Hydrochloride, protriptyline	HMDB
Vivactil	HMDB
Protriptyline hydrochloride	HMDB

Chemical Formula

C₁₉H₂₁N

Average Molecular Weight

263.3767

Monoisotopic Molecular Weight

263.167399677

IUPAC Name

methyl(3-{tricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,9,11,13-heptaen-2-yl}propyl)amine

Traditional Name

protriptyline

CAS Registry Number

438-60-8

SMILES

CNCCCC1C2=CC=CC=C2C=CC2=CC=CC=C12

InChI Identifier

InChI=1S/C19H21N/c1-20-14-6-11-19-17-9-4-2-7-15(17)12-13-16-8-3-5-10-18(16)19/h2-5,7-10,12-13,19-20H,6,11,14H2,1H3

InChI Key

BWPIARFWQZKAIA-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
Secondary amine
Secondary aliphatic amine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

organic tricyclic compound (CHEBI:8597 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014488)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

antidepressant (HMDB: HMDB0014488)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	169 - 171 °C (protriptyline hydrochloride)	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.00023 g/L	Not Available
LogP	4.7	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	162.8	30932474
[M+H]+	Not Available	162.762	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000876

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00023 g/L	ALOGPS
logP	4.65	ALOGPS
logP	4.5	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Basic)	10.54	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	12.03 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	87.3 m³·mol⁻¹	ChemAxon
Polarizability	31.6 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]+	161.992	31661259
DarkChem	[M-H]-	164.38	31661259
DeepCCS	[M-2H]-	193.04	30932474
DeepCCS	[M+Na]+	168.605	30932474
AllCCS	[M+H]+	164.1	32859911
AllCCS	[M+H-H2O]+	160.5	32859911
AllCCS	[M+NH4]+	167.5	32859911
AllCCS	[M+Na]+	168.5	32859911
AllCCS	[M-H]-	171.3	32859911
AllCCS	[M+Na-2H]-	171.0	32859911
AllCCS	[M+HCOO]-	170.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Protriptyline	CNCCCC1C2=CC=CC=C2C=CC2=CC=CC=C12	3108.7	Standard polar	33892256
Protriptyline	CNCCCC1C2=CC=CC=C2C=CC2=CC=CC=C12	2324.1	Standard non polar	33892256
Protriptyline	CNCCCC1C2=CC=CC=C2C=CC2=CC=CC=C12	2296.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Protriptyline,1TMS,isomer #1	CN(CCCC1C2=CC=CC=C2C=CC2=CC=CC=C21)[Si](C)(C)C	2511.8	Semi standard non polar	33892256
Protriptyline,1TMS,isomer #1	CN(CCCC1C2=CC=CC=C2C=CC2=CC=CC=C21)[Si](C)(C)C	2584.1	Standard non polar	33892256
Protriptyline,1TMS,isomer #1	CN(CCCC1C2=CC=CC=C2C=CC2=CC=CC=C21)[Si](C)(C)C	3281.9	Standard polar	33892256
Protriptyline,1TBDMS,isomer #1	CN(CCCC1C2=CC=CC=C2C=CC2=CC=CC=C21)[Si](C)(C)C(C)(C)C	2724.0	Semi standard non polar	33892256
Protriptyline,1TBDMS,isomer #1	CN(CCCC1C2=CC=CC=C2C=CC2=CC=CC=C21)[Si](C)(C)C(C)(C)C	2808.1	Standard non polar	33892256
Protriptyline,1TBDMS,isomer #1	CN(CCCC1C2=CC=CC=C2C=CC2=CC=CC=C21)[Si](C)(C)C(C)(C)C	3391.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Protriptyline GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9040000000-6498574fa1f4eead1816	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protriptyline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protriptyline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-006x-8910000000-ec599ee02d998905757e	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protriptyline 10V, Positive-QTOF	splash10-03e9-0090000000-2ab870bf797378caf1c5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protriptyline 20V, Positive-QTOF	splash10-01q9-2190000000-b7468843989ba53316aa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protriptyline 40V, Positive-QTOF	splash10-052f-8890000000-d9505145b3d35ed27be8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protriptyline 10V, Negative-QTOF	splash10-03di-0090000000-13fe8faae8c2bed47e30	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protriptyline 20V, Negative-QTOF	splash10-03di-1090000000-8781e71c0e0ae6ea19be	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protriptyline 40V, Negative-QTOF	splash10-001l-5490000000-349b95c342d47d80f512	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protriptyline 10V, Negative-QTOF	splash10-03di-0090000000-330f29be739abf456d25	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protriptyline 20V, Negative-QTOF	splash10-03di-0090000000-45344afe501cffed83b8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protriptyline 40V, Negative-QTOF	splash10-0j6u-0590000000-16a1cb7e0b6aa13171c8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protriptyline 10V, Positive-QTOF	splash10-03di-0090000000-0f92e6ab1c1e69d00ae5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protriptyline 20V, Positive-QTOF	splash10-03di-0090000000-049efc86fef6b36591c4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protriptyline 40V, Positive-QTOF	splash10-0a4l-1690000000-6edf1174a6d682928acd	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

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 DB00344	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00344	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00344

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4805

KEGG Compound ID

C07408

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Protriptyline

METLIN ID

Not Available

PubChem Compound

4976

PDB ID

Not Available

ChEBI ID

8597

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

Enzymes

Enzyme Details

1. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Enzyme Details

1. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Ibrahim S, Peggins J, Knapton A, Licht T, Aszalos A: Influence of antipsychotic, antiemetic, and Ca(2+) channel blocker drugs on the cellular accumulation of the anticancer drug daunorubicin: P-glycoprotein modulation. J Pharmacol Exp Ther. 2000 Dec;295(3):1276-83. [PubMed:11082465 ]

Enzyme Details

2. Sodium-dependent noradrenaline transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:: SLC6A2
Uniprot ID:: P23975
Molecular weight:: 69331.42

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [PubMed:9537821 ]
Cheetham SC, Viggers JA, Butler SA, Prow MR, Heal DJ: [3H]nisoxetine--a radioligand for noradrenaline reuptake sites: correlation with inhibition of [3H]noradrenaline uptake and effect of DSP-4 lesioning and antidepressant treatments. Neuropharmacology. 1996 Jan;35(1):63-70. [PubMed:8684598 ]

Enzyme Details

3. Sodium-dependent serotonin transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into the pre-synaptic terminal for re-utilization. Plays a key role in mediating regulation of the availability of serotonin to other receptors of serotonergic systems. Terminates the action of serotonin and recycles it in a sodium-dependent manner.
Gene Name:: SLC6A4
Uniprot ID:: P31645
Molecular weight:: 70324.165

References

McDougle CJ, Epperson CN, Price LH, Gelernter J: Evidence for linkage disequilibrium between serotonin transporter protein gene (SLC6A4) and obsessive compulsive disorder. Mol Psychiatry. 1998 May;3(3):270-3. [PubMed:9672904 ]
Rouillon F, Blachier C, Dreyfus JP, Bouhassira M, Allicar MP: [Pharmaco-epidemiologic study of the use of antidepressant drugs in the general population]. Encephale. 1996 May;22 Spec No 1:39-48. [PubMed:8767026 ]
Frazer A, Daws LC: Serotonin transporter function in vivo: assessment by chronoamperometry. Ann N Y Acad Sci. 1998 Dec 15;861:217-29. [PubMed:9928259 ]
Daws LC, Toney GM, Gerhardt GA, Frazer A: In vivo chronoamperometric measures of extracellular serotonin clearance in rat dorsal hippocampus: contribution of serotonin and norepinephrine transporters. J Pharmacol Exp Ther. 1998 Aug;286(2):967-76. [PubMed:9694957 ]
Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [PubMed:9537821 ]
Kovachich GB, Aronson CE, Brunswick DJ: Effect of repeated administration of antidepressants on serotonin uptake sites in limbic and neocortical structures of rat brain determined by quantitative autoradiography. Neuropsychopharmacology. 1992 Dec;7(4):317-24. [PubMed:1476595 ]

Showing metabocard for Protriptyline (HMDB0014488)

MOL for HMDB0014488 (Protriptyline)

3D MOL for HMDB0014488 (Protriptyline)

3D SDF for HMDB0014488 (Protriptyline)

3D-SDF for HMDB0014488 (Protriptyline)

PDB for HMDB0014488 (Protriptyline)

3D PDB for HMDB0014488 (Protriptyline)

SMILES for HMDB0014488 (Protriptyline)

INCHI for HMDB0014488 (Protriptyline)

Structure for HMDB0014488 (Protriptyline)

3D Structure for HMDB0014488 (Protriptyline)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

Transporters

References

References

References