Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:32:22 UTC

Update Date

2022-03-07 02:52:16 UTC

HMDB ID

HMDB0029746

Secondary Accession Numbers

HMDB29746

Metabolite Identification

Common Name

3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole

Description

3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole, also known as 3-amino-1,4-dimethyl-g-carboline or TRP-1, belongs to the class of organic compounds known as gamma carbolines. These are polycyclic aromatic compounds containing a gamma-carbazole(5H-pyrido[4,3-b]indole) moiety, with a structure characterized by the presence of pyridine fused to the pyrrole ring of an indole. Based on a literature review a significant number of articles have been published on 3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole.

Structure

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

HMDB0029746
     RDKit          3D
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole
 29 31  0  0  0  0  0  0  0  0999 V2000
    2.7175    2.0714   -0.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9622    0.7837   -0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6317   -0.4254   -0.0233 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0494   -0.3720   -0.0299 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9484   -1.5817   -0.0306 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5999   -1.6629   -0.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0444   -3.0086   -0.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1000   -0.4907   -0.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5849    0.7280   -0.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3292    1.7044    0.0112 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5596    1.1626    0.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8124    1.7299    0.0238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9407    0.9368    0.0220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8178   -0.4509    0.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5694   -1.0367   -0.0031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4532   -0.2315   -0.0011 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9643    2.8922   -0.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4486    2.1136   -0.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2524    2.2196    0.9672 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5875    0.4169   -0.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5719   -1.1604    0.3932 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7515   -3.7884   -0.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5925   -3.1345    0.9239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6262   -3.2060   -0.9377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0871    2.7344    0.0195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9559    2.7978    0.0343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9113    1.4030    0.0311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7418   -1.0320    0.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5286   -2.1126   -0.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  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
  9  2  1  0
 16 11  1  0
 16  8  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  4 21  1  0
  7 22  1  0
  7 23  1  0
  7 24  1  0
 10 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
M  END


  Mrv0541 02241220152D          

 16 18  0  0  0  0            999 V2000
   -0.3296   -1.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9896   -1.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7321   -1.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7321   -0.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9896   -0.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3296   -0.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3296   -0.1642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0004    0.5767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8246    0.4942    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6496    0.4117    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1546   -0.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4846   -0.9892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7321    1.8142    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3196    1.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4121    1.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0821    1.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 11  2  0  0  0  0
  8  9  1  0  0  0  0
  8 15  2  0  0  0  0
 10 11  1  0  0  0  0
 10 14  2  0  0  0  0
 11 12  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
M  END
> <DATABASE_ID>
HMDB0029746

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C2C(NC3=CC=CC=C23)=C(C)C(N)=N1

> <INCHI_IDENTIFIER>
InChI=1S/C13H13N3/c1-7-12-11(8(2)15-13(7)14)9-5-3-4-6-10(9)16-12/h3-6,16H,1-2H3,(H2,14,15)

> <INCHI_KEY>
LVTKHGUGBGNBPL-UHFFFAOYSA-N

> <FORMULA>
C13H13N3

> <MOLECULAR_WEIGHT>
211.2624

> <EXACT_MASS>
211.110947431

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
23.86439641042199

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,4-dimethyl-5H-pyrido[4,3-b]indol-3-amine

> <ALOGPS_LOGP>
2.73

> <JCHEM_LOGP>
2.2835363966666664

> <ALOGPS_LOGS>
-3.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.453126249924537

> <JCHEM_PKA_STRONGEST_BASIC>
9.967370898006674

> <JCHEM_POLAR_SURFACE_AREA>
54.7

> <JCHEM_REFRACTIVITY>
65.9619

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.50e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,4-dimethyl-5H-pyrido[4,3-b]indol-3-amine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029746
     RDKit          3D
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole
 29 31  0  0  0  0  0  0  0  0999 V2000
    2.7175    2.0714   -0.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9622    0.7837   -0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6317   -0.4254   -0.0233 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0494   -0.3720   -0.0299 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9484   -1.5817   -0.0306 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5999   -1.6629   -0.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0444   -3.0086   -0.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1000   -0.4907   -0.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5849    0.7280   -0.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3292    1.7044    0.0112 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5596    1.1626    0.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8124    1.7299    0.0238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9407    0.9368    0.0220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8178   -0.4509    0.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5694   -1.0367   -0.0031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4532   -0.2315   -0.0011 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9643    2.8922   -0.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4486    2.1136   -0.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2524    2.2196    0.9672 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5875    0.4169   -0.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5719   -1.1604    0.3932 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7515   -3.7884   -0.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5925   -3.1345    0.9239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6262   -3.2060   -0.9377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0871    2.7344    0.0195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9559    2.7978    0.0343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9113    1.4030    0.0311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7418   -1.0320    0.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5286   -2.1126   -0.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  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
  9  2  1  0
 16 11  1  0
 16  8  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  4 21  1  0
  7 22  1  0
  7 23  1  0
  7 24  1  0
 10 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.615  -2.925   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.847  -3.695   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.233  -2.925   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.233  -1.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.847  -0.615   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.615  -1.385   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.615  -0.307   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.001   1.077   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -1.539   0.923   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       3.079   0.769   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       2.155  -0.461   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.771  -1.847   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       3.233   3.387   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       2.463   2.155   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.769   2.309   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.153   3.695   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    1    5    7                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7    9   15                                                  
CONECT    9    5    8                                                       
CONECT   10   11   14                                                       
CONECT   11    7   10   12                                                  
CONECT   12   11                                                            
CONECT   13   14                                                            
CONECT   14   10   13   15                                                  
CONECT   15    8   14   16                                                  
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

COMPND    HMDB0029746
HETATM    1  C1  UNL     1       2.717   2.071  -0.001  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.962   0.784  -0.009  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.632  -0.425  -0.023  1.00  0.00           C  
HETATM    4  N1  UNL     1       4.049  -0.372  -0.030  1.00  0.00           N  
HETATM    5  N2  UNL     1       1.948  -1.582  -0.031  1.00  0.00           N  
HETATM    6  C4  UNL     1       0.600  -1.663  -0.025  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.044  -3.009  -0.034  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.100  -0.491  -0.010  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.585   0.728  -0.002  1.00  0.00           C  
HETATM   10  N3  UNL     1      -0.329   1.704   0.011  1.00  0.00           N  
HETATM   11  C8  UNL     1      -1.560   1.163   0.012  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.812   1.730   0.024  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.941   0.937   0.022  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.818  -0.451   0.009  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.569  -1.037  -0.003  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.453  -0.231  -0.001  1.00  0.00           C  
HETATM   17  H1  UNL     1       1.964   2.892  -0.052  1.00  0.00           H  
HETATM   18  H2  UNL     1       3.449   2.114  -0.828  1.00  0.00           H  
HETATM   19  H3  UNL     1       3.252   2.220   0.967  1.00  0.00           H  
HETATM   20  H4  UNL     1       4.587   0.417  -0.437  1.00  0.00           H  
HETATM   21  H5  UNL     1       4.572  -1.160   0.393  1.00  0.00           H  
HETATM   22  H6  UNL     1       0.752  -3.788  -0.019  1.00  0.00           H  
HETATM   23  H7  UNL     1      -0.592  -3.135   0.924  1.00  0.00           H  
HETATM   24  H8  UNL     1      -0.626  -3.206  -0.938  1.00  0.00           H  
HETATM   25  H9  UNL     1      -0.087   2.734   0.020  1.00  0.00           H  
HETATM   26  H10 UNL     1      -2.956   2.798   0.034  1.00  0.00           H  
HETATM   27  H11 UNL     1      -4.911   1.403   0.031  1.00  0.00           H  
HETATM   28  H12 UNL     1      -4.742  -1.032   0.008  1.00  0.00           H  
HETATM   29  H13 UNL     1      -2.529  -2.113  -0.013  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    3    9
CONECT    3    4    5
CONECT    4   20   21
CONECT    5    6    6
CONECT    6    7    8
CONECT    7   22   23   24
CONECT    8    9    9   16
CONECT    9   10
CONECT   10   11   25
CONECT   11   12   12   16
CONECT   12   13   26
CONECT   13   14   14   27
CONECT   14   15   28
CONECT   15   16   16   29
END

HMDB0029746
     RDKit          3D
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole
 29 31  0  0  0  0  0  0  0  0999 V2000
    2.7175    2.0714   -0.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9622    0.7837   -0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6317   -0.4254   -0.0233 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0494   -0.3720   -0.0299 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9484   -1.5817   -0.0306 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5999   -1.6629   -0.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0444   -3.0086   -0.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1000   -0.4907   -0.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5849    0.7280   -0.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3292    1.7044    0.0112 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5596    1.1626    0.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8124    1.7299    0.0238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9407    0.9368    0.0220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8178   -0.4509    0.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5694   -1.0367   -0.0031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4532   -0.2315   -0.0011 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9643    2.8922   -0.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4486    2.1136   -0.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2524    2.2196    0.9672 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5875    0.4169   -0.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5719   -1.1604    0.3932 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7515   -3.7884   -0.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5925   -3.1345    0.9239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6262   -3.2060   -0.9377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0871    2.7344    0.0195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9559    2.7978    0.0343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9113    1.4030    0.0311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7418   -1.0320    0.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5286   -2.1126   -0.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  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
  9  2  1  0
 16 11  1  0
 16  8  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  4 21  1  0
  7 22  1  0
  7 23  1  0
  7 24  1  0
 10 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,4-Dimethyl-5H-pyrido(4,3-b)indol-3-amine	HMDB
1,4-Dimethyl-5H-pyrido[4,3-b]indol-3-amine, 9ci	HMDB
1,4-Dimethyl-9H-pyrido(4,3-b)indol-3-amine	HMDB
3-Amino-1,4-dimethyl-5H-pyrido(4,3-b)indole	HMDB
3-Amino-1,4-dimethyl-g-carboline	HMDB
3-Amino-1,4-dimethyl-gamma-carboline	HMDB
TRP-1	HMDB
TRP-p-1	HMDB
TRP-P1	HMDB
Tryptophan P1	HMDB
Tryptophan-p-1	HMDB
Trytophan pyrolysate 1	HMDB
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole	KEGG

Chemical Formula

C₁₃H₁₃N₃

Average Molecular Weight

211.2624

Monoisotopic Molecular Weight

211.110947431

IUPAC Name

1,4-dimethyl-5H-pyrido[4,3-b]indol-3-amine

Traditional Name

1,4-dimethyl-5H-pyrido[4,3-b]indol-3-amine

CAS Registry Number

62450-06-0

SMILES

CC1=C2C(NC3=CC=CC=C23)=C(C)C(N)=N1

InChI Identifier

InChI=1S/C13H13N3/c1-7-12-11(8(2)15-13(7)14)9-5-3-4-6-10(9)16-12/h3-6,16H,1-2H3,(H2,14,15)

InChI Key

LVTKHGUGBGNBPL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma carbolines. These are polycyclic aromatic compounds containing a gamma-carbazole(5H-pyrido[4,3-b]indole) moiety, with a structure characterized by the presence of pyridine fused to the pyrrole ring of an indole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyridoindoles

Direct Parent

Gamma carbolines

Alternative Parents

Substituents

Gamma-carboline
Indole
Pyrrolopyridine
Aminopyridine
Methylpyridine
Imidolactam
Benzenoid
Pyridine
Heteroaromatic compound
Pyrrole
Azacycle
Hydrocarbon derivative
Primary amine
Organonitrogen compound
Amine
Organic nitrogen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

pyridoindole (CHEBI:82376 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0029746)

Cellular substructure

Source

Endogenous

Endogenous (HMDB: HMDB0029746)

Exogenous

Food

Food (HMDB: HMDB0029746)

Environmental

Tobacco smoke (HMDB: HMDB0029746)

Process

Naturally occurring process

Biological process

Biochemical pathway

Signaling pathway

Apoptosis (HMDB: HMDB0029746)

Cellular process

Apoptosis (HMDB: HMDB0029746)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	252 - 262 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	61.72 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.055 g/L	ALOGPS
logP	2.73	ALOGPS
logP	2.28	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	13.45	ChemAxon
pKa (Strongest Basic)	9.97	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	54.7 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	65.96 m³·mol⁻¹	ChemAxon
Polarizability	23.86 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	186.647	30932474
DeepCCS	[M+Na]+	161.997	30932474
AllCCS	[M+H]+	146.4	32859911
AllCCS	[M+H-H2O]+	142.1	32859911
AllCCS	[M+NH4]+	150.3	32859911
AllCCS	[M+Na]+	151.5	32859911
AllCCS	[M-H]-	152.0	32859911
AllCCS	[M+Na-2H]-	151.6	32859911
AllCCS	[M+HCOO]-	151.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole	CC1=C2C(NC3=CC=CC=C23)=C(C)C(N)=N1	3436.1	Standard polar	33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole	CC1=C2C(NC3=CC=CC=C23)=C(C)C(N)=N1	2255.5	Standard non polar	33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole	CC1=C2C(NC3=CC=CC=C23)=C(C)C(N)=N1	2537.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole,1TMS,isomer #1	CC1=C(N[Si](C)(C)C)N=C(C)C2=C1[NH]C1=CC=CC=C12	2537.5	Semi standard non polar	33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole,1TMS,isomer #1	CC1=C(N[Si](C)(C)C)N=C(C)C2=C1[NH]C1=CC=CC=C12	2129.8	Standard non polar	33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole,1TMS,isomer #2	CC1=NC(N)=C(C)C2=C1C1=CC=CC=C1N2[Si](C)(C)C	2507.9	Semi standard non polar	33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole,1TMS,isomer #2	CC1=NC(N)=C(C)C2=C1C1=CC=CC=C1N2[Si](C)(C)C	2162.3	Standard non polar	33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole,2TMS,isomer #1	CC1=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(C)C2=C1[NH]C1=CC=CC=C12	2540.7	Semi standard non polar	33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole,2TMS,isomer #1	CC1=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(C)C2=C1[NH]C1=CC=CC=C12	2275.4	Standard non polar	33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole,2TMS,isomer #2	CC1=NC(N[Si](C)(C)C)=C(C)C2=C1C1=CC=CC=C1N2[Si](C)(C)C	2484.7	Semi standard non polar	33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole,2TMS,isomer #2	CC1=NC(N[Si](C)(C)C)=C(C)C2=C1C1=CC=CC=C1N2[Si](C)(C)C	2190.5	Standard non polar	33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole,3TMS,isomer #1	CC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=C(C)C2=C1C1=CC=CC=C1N2[Si](C)(C)C	2503.4	Semi standard non polar	33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole,3TMS,isomer #1	CC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=C(C)C2=C1C1=CC=CC=C1N2[Si](C)(C)C	2324.9	Standard non polar	33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole,1TBDMS,isomer #1	CC1=C(N[Si](C)(C)C(C)(C)C)N=C(C)C2=C1[NH]C1=CC=CC=C12	2761.9	Semi standard non polar	33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole,1TBDMS,isomer #1	CC1=C(N[Si](C)(C)C(C)(C)C)N=C(C)C2=C1[NH]C1=CC=CC=C12	2330.7	Standard non polar	33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole,1TBDMS,isomer #2	CC1=NC(N)=C(C)C2=C1C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C	2734.3	Semi standard non polar	33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole,1TBDMS,isomer #2	CC1=NC(N)=C(C)C2=C1C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C	2349.9	Standard non polar	33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole,2TBDMS,isomer #1	CC1=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(C)C2=C1[NH]C1=CC=CC=C12	2898.5	Semi standard non polar	33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole,2TBDMS,isomer #1	CC1=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(C)C2=C1[NH]C1=CC=CC=C12	2672.7	Standard non polar	33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole,2TBDMS,isomer #2	CC1=NC(N[Si](C)(C)C(C)(C)C)=C(C)C2=C1C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C	2837.3	Semi standard non polar	33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole,2TBDMS,isomer #2	CC1=NC(N[Si](C)(C)C(C)(C)C)=C(C)C2=C1C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C	2614.6	Standard non polar	33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole,3TBDMS,isomer #1	CC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(C)C2=C1C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C	2974.8	Semi standard non polar	33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole,3TBDMS,isomer #1	CC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(C)C2=C1C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C	2903.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole EI-B (Non-derivatized)	splash10-01ox-6920000000-bc93105c1d081ec984b7	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole EI-B (Non-derivatized)	splash10-01ox-6920000000-bc93105c1d081ec984b7	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole GC-MS (Non-derivatized) - 70eV, Positive	splash10-03dj-0930000000-36b5d2d7bf0b59d1b39b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole 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 - 3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole 10V, Positive-QTOF	splash10-03di-0090000000-99d523d2d9b243b038af	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole 20V, Positive-QTOF	splash10-03di-0690000000-2b58ed661612ed6a86a7	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole 40V, Positive-QTOF	splash10-00kb-0900000000-47965f0b341d97a19de6	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole 10V, Negative-QTOF	splash10-03di-1090000000-f592d074259bb2ab388f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole 20V, Negative-QTOF	splash10-03di-1190000000-dd2a6c3bfecff2ce6023	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole 40V, Negative-QTOF	splash10-0006-9600000000-81184911da8b853890ff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole 10V, Negative-QTOF	splash10-03di-0090000000-4dafdcd63f1115768fe9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole 20V, Negative-QTOF	splash10-03di-0090000000-bda0e0b196243b2f2b49	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole 40V, Negative-QTOF	splash10-0296-0910000000-9ff4ea4f5ec8709952f7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole 10V, Positive-QTOF	splash10-03di-0090000000-151eb25ddf9df2d6bfbe	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole 20V, Positive-QTOF	splash10-03di-0090000000-151eb25ddf9df2d6bfbe	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole 40V, Positive-QTOF	splash10-0007-0910000000-59be513918c2decfcf14	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB000947

KNApSAcK ID

Not Available

Chemspider ID

4447538

KEGG Compound ID

C19306

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5284474

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1379871

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Bae YK, Qin H, Knobel KM, Hu J, Rosenbaum JL, Barr MM: General and cell-type specific mechanisms target TRPP2/PKD-2 to cilia. Development. 2006 Oct;133(19):3859-70. Epub 2006 Aug 30. [PubMed:16943275 ]
Awney HA, Sindi H: The effect of rosemary on the mutagenic activity of heterocyclic amines extracted from common food consumed in Saudi Arabia. Int J Food Sci Nutr. 2010 Mar;61(2):192-203. doi: 10.3109/09637480903294953. [PubMed:19939197 ]
Woudenberg-Vrenken TE, Bindels RJ, Hoenderop JG: The role of transient receptor potential channels in kidney disease. Nat Rev Nephrol. 2009 Aug;5(8):441-9. doi: 10.1038/nrneph.2009.100. Epub 2009 Jun 23. [PubMed:19546862 ]
Mene P: Transient receptor potential channels in the kidney: calcium signaling, transport and beyond. J Nephrol. 2006 Jan-Feb;19(1):21-9. [PubMed:16523421 ]
Yin J, Kuebler WM: Mechanotransduction by TRP channels: general concepts and specific role in the vasculature. Cell Biochem Biophys. 2010;56(1):1-18. doi: 10.1007/s12013-009-9067-2. [PubMed:19842065 ]
Sharif-Naeini R, Folgering JH, Bichet D, Duprat F, Lauritzen I, Arhatte M, Jodar M, Dedman A, Chatelain FC, Schulte U, Retailleau K, Loufrani L, Patel A, Sachs F, Delmas P, Peters DJ, Honore E: Polycystin-1 and -2 dosage regulates pressure sensing. Cell. 2009 Oct 30;139(3):587-96. doi: 10.1016/j.cell.2009.08.045. [PubMed:19879844 ]
Kwan HY, Huang Y, Yao X: TRP channels in endothelial function and dysfunction. Biochim Biophys Acta. 2007 Aug;1772(8):907-14. Epub 2007 Mar 12. [PubMed:17434294 ]
Laycock S, Taylor HC, Haigh C, Lee AT, Cooper GJ, Ong AC, Robson L: A novel dephosphorylation-activated conductance in a mouse renal collecting duct cell line. Exp Physiol. 2009 Aug;94(8):914-27. doi: 10.1113/expphysiol.2009.047753. Epub 2009 May 8. [PubMed:19429644 ]
Beech DJ, Muraki K, Flemming R: Non-selective cationic channels of smooth muscle and the mammalian homologues of Drosophila TRP. J Physiol. 2004 Sep 15;559(Pt 3):685-706. Epub 2004 Jul 22. [PubMed:15272031 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole (HMDB0029746)

MOL for HMDB0029746 (3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole)

3D MOL for HMDB0029746 (3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole)

3D SDF for HMDB0029746 (3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole)

3D-SDF for HMDB0029746 (3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole)

PDB for HMDB0029746 (3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole)

3D PDB for HMDB0029746 (3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole)

SMILES for HMDB0029746 (3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole)

INCHI for HMDB0029746 (3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole)

Structure for HMDB0029746 (3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole)

3D Structure for HMDB0029746 (3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra