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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:40:29 UTC

Update Date

2022-03-07 02:54:35 UTC

HMDB ID

HMDB0035665

Secondary Accession Numbers

HMDB35665

Metabolite Identification

Common Name

L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid

Description

L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid, also known as 3-carboxy-1,2,3,4-tetrahydro-2-carboline or ccris 6486, belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety. L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid has been detected, but not quantified in, garden tomato (var.). This could make L-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid a potential biomarker for the consumption of these foods. L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid.

Structure

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

HMDB0035665
     RDKit          3D
L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid
 28 30  0  0  0  0  0  0  0  0999 V2000
   -3.4023    0.0599   -1.3144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9952    0.7736   -0.3768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0927    2.1441   -0.4841 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4123    0.1869    0.8433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0378    0.8021    1.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0063    0.0036    0.3555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2229   -1.2277   -0.1951 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9351   -1.6854   -0.7454 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9066   -0.7705   -0.5589 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2418   -0.7079   -0.8988 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0292    0.3770   -0.5763 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4283    1.4091    0.1057 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1025    1.3940    0.4666 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3312    0.2904    0.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5705   -1.8497   -0.1309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3551   -1.2239    0.8598 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8686    2.5810   -0.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0909    0.4966    1.6932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8668    0.8861    2.1349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0022    1.8188    0.5971 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0564   -2.6159   -1.2434 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6903   -1.5511   -1.4441 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0878    0.3928   -0.8627 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0601    2.2623    0.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6756    2.2449    1.0099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4674   -2.9369    0.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0093   -1.8285   -1.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1569   -1.7257    1.2249 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  7 15  1  0
 15 16  1  0
 16  4  1  0
 14  6  1  0
 14  9  1  0
  3 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  8 21  1  0
 10 22  1  0
 11 23  1  0
 12 24  1  0
 13 25  1  0
 15 26  1  0
 15 27  1  0
 16 28  1  0
M  END


  Mrv0541 05061308372D          

 16 18  0  0  0  0            999 V2000
    3.7054   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3896   -0.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.5840    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339    1.5105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1347   -1.5983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1966   -0.6422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  7  3  2  0  0  0  0
  8  5  1  0  0  0  0
  8  7  1  0  0  0  0
  9  4  2  0  0  0  0
  9  7  1  0  0  0  0
 10  5  1  0  0  0  0
 11  6  1  0  0  0  0
 11  8  2  0  0  0  0
 12 10  1  0  0  0  0
 13  6  1  0  0  0  0
 13 10  1  0  0  0  0
 14  9  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  2  0  0  0  0
 16 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035665

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C1CC2=C(CN1)NC1=CC=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C12H12N2O2/c15-12(16)10-5-8-7-3-1-2-4-9(7)14-11(8)6-13-10/h1-4,10,13-14H,5-6H2,(H,15,16)

> <INCHI_KEY>
FSNCEEGOMTYXKY-UHFFFAOYSA-N

> <FORMULA>
C12H12N2O2

> <MOLECULAR_WEIGHT>
216.2359

> <EXACT_MASS>
216.089877638

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
22.851196643315806

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylic acid

> <ALOGPS_LOGP>
-0.47

> <JCHEM_LOGP>
-1.1886015525830436

> <ALOGPS_LOGS>
-2.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.386404689795448

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.9711947636796197

> <JCHEM_PKA_STRONGEST_BASIC>
8.990963781121424

> <JCHEM_POLAR_SURFACE_AREA>
65.12

> <JCHEM_REFRACTIVITY>
59.409499999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035665
     RDKit          3D
L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid
 28 30  0  0  0  0  0  0  0  0999 V2000
   -3.4023    0.0599   -1.3144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9952    0.7736   -0.3768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0927    2.1441   -0.4841 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4123    0.1869    0.8433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0378    0.8021    1.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0063    0.0036    0.3555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2229   -1.2277   -0.1951 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9351   -1.6854   -0.7454 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9066   -0.7705   -0.5589 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2418   -0.7079   -0.8988 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0292    0.3770   -0.5763 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4283    1.4091    0.1057 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1025    1.3940    0.4666 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3312    0.2904    0.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5705   -1.8497   -0.1309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3551   -1.2239    0.8598 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8686    2.5810   -0.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0909    0.4966    1.6932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8668    0.8861    2.1349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0022    1.8188    0.5971 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0564   -2.6159   -1.2434 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6903   -1.5511   -1.4441 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0878    0.3928   -0.8627 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0601    2.2623    0.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6756    2.2449    1.0099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4674   -2.9369    0.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0093   -1.8285   -1.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1569   -1.7257    1.2249 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  7 15  1  0
 15 16  1  0
 16  4  1  0
 14  6  1  0
 14  9  1  0
  3 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  8 21  1  0
 10 22  1  0
 11 23  1  0
 12 24  1  0
 13 25  1  0
 15 26  1  0
 15 27  1  0
 16 28  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       6.917  -0.374   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.393   1.090   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.411  -0.695   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.362   2.235   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.810  -0.695   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.858   2.235   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.380   0.450   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.840   0.450   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.856   1.914   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.303  -0.374   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.364   1.914   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.727  -1.519   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -0.173   1.090   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       3.610   2.820   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0      -0.251  -2.983   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -2.234  -1.199   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    7                                                       
CONECT    4    2    9                                                       
CONECT    5    8   10                                                       
CONECT    6   11   13                                                       
CONECT    7    3    8    9                                                  
CONECT    8    5    7   11                                                  
CONECT    9    4    7   14                                                  
CONECT   10    5   12   13                                                  
CONECT   11    6    8   14                                                  
CONECT   12   10   15   16                                                  
CONECT   13    6   10                                                       
CONECT   14    9   11                                                       
CONECT   15   12                                                            
CONECT   16   12                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

COMPND    HMDB0035665
HETATM    1  O1  UNL     1      -3.402   0.060  -1.314  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.995   0.774  -0.377  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.093   2.144  -0.484  1.00  0.00           O  
HETATM    4  C2  UNL     1      -2.412   0.187   0.843  1.00  0.00           C  
HETATM    5  C3  UNL     1      -1.038   0.802   1.044  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.006   0.004   0.356  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.223  -1.228  -0.195  1.00  0.00           C  
HETATM    8  N1  UNL     1       0.935  -1.685  -0.745  1.00  0.00           N  
HETATM    9  C6  UNL     1       1.907  -0.770  -0.559  1.00  0.00           C  
HETATM   10  C7  UNL     1       3.242  -0.708  -0.899  1.00  0.00           C  
HETATM   11  C8  UNL     1       4.029   0.377  -0.576  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.428   1.409   0.106  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.103   1.394   0.467  1.00  0.00           C  
HETATM   14  C11 UNL     1       1.331   0.290   0.130  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.570  -1.850  -0.131  1.00  0.00           C  
HETATM   16  N2  UNL     1      -2.355  -1.224   0.860  1.00  0.00           N  
HETATM   17  H1  UNL     1      -3.869   2.581  -0.966  1.00  0.00           H  
HETATM   18  H2  UNL     1      -3.091   0.497   1.693  1.00  0.00           H  
HETATM   19  H3  UNL     1      -0.867   0.886   2.135  1.00  0.00           H  
HETATM   20  H4  UNL     1      -1.002   1.819   0.597  1.00  0.00           H  
HETATM   21  H5  UNL     1       1.056  -2.616  -1.243  1.00  0.00           H  
HETATM   22  H6  UNL     1       3.690  -1.551  -1.444  1.00  0.00           H  
HETATM   23  H7  UNL     1       5.088   0.393  -0.863  1.00  0.00           H  
HETATM   24  H8  UNL     1       4.060   2.262   0.356  1.00  0.00           H  
HETATM   25  H9  UNL     1       1.676   2.245   1.010  1.00  0.00           H  
HETATM   26  H10 UNL     1      -1.467  -2.937   0.139  1.00  0.00           H  
HETATM   27  H11 UNL     1      -2.009  -1.828  -1.164  1.00  0.00           H  
HETATM   28  H12 UNL     1      -3.157  -1.726   1.225  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   17
CONECT    4    5   16   18
CONECT    5    6   19   20
CONECT    6    7    7   14
CONECT    7    8   15
CONECT    8    9   21
CONECT    9   10   10   14
CONECT   10   11   22
CONECT   11   12   12   23
CONECT   12   13   24
CONECT   13   14   14   25
CONECT   15   16   26   27
CONECT   16   28
END

HMDB0035665
     RDKit          3D
L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid
 28 30  0  0  0  0  0  0  0  0999 V2000
   -3.4023    0.0599   -1.3144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9952    0.7736   -0.3768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0927    2.1441   -0.4841 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4123    0.1869    0.8433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0378    0.8021    1.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0063    0.0036    0.3555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2229   -1.2277   -0.1951 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9351   -1.6854   -0.7454 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9066   -0.7705   -0.5589 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2418   -0.7079   -0.8988 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0292    0.3770   -0.5763 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4283    1.4091    0.1057 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1025    1.3940    0.4666 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3312    0.2904    0.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5705   -1.8497   -0.1309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3551   -1.2239    0.8598 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8686    2.5810   -0.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0909    0.4966    1.6932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8668    0.8861    2.1349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0022    1.8188    0.5971 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0564   -2.6159   -1.2434 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6903   -1.5511   -1.4441 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0878    0.3928   -0.8627 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0601    2.2623    0.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6756    2.2449    1.0099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4674   -2.9369    0.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0093   -1.8285   -1.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1569   -1.7257    1.2249 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  7 15  1  0
 15 16  1  0
 16  4  1  0
 14  6  1  0
 14  9  1  0
  3 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  8 21  1  0
 10 22  1  0
 11 23  1  0
 12 24  1  0
 13 25  1  0
 15 26  1  0
 15 27  1  0
 16 28  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-Carboxy-1,2,3,4-tetrahydro-2-carboline	ChEBI
CCRIS 6486	ChEBI
NSC 96912	ChEBI
L-1,2,3,4-Tetrahydro-b-carboline-3-carboxylate	Generator
L-1,2,3,4-Tetrahydro-b-carboline-3-carboxylic acid	Generator
L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylate	Generator
L-1,2,3,4-Tetrahydro-β-carboline-3-carboxylate	Generator
L-1,2,3,4-Tetrahydro-β-carboline-3-carboxylic acid	Generator
(-)-3-Carboxy-1,2,3,4-tetrahydro-beta-carboline	HMDB
3-Carboxy-1,2,3,4-tetrahydro-beta-carboline	HMDB
Cyclomethyltryptophan	HMDB
L-1,2,3,4-Tetrahydronorharman-3-carboxylic acid	HMDB
1,2,3,4-Tetrahydro-b-carboline-3-carboxylate	Generator
1,2,3,4-Tetrahydro-b-carboline-3-carboxylic acid	Generator
1,2,3,4-Tetrahydro-beta-carboline-3-carboxylate	Generator
1,2,3,4-Tetrahydro-β-carboline-3-carboxylate	Generator
1,2,3,4-Tetrahydro-β-carboline-3-carboxylic acid	Generator
3S-Tetrahydro-beta-carboline-3-carboxylic acid	MeSH
1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid, (S)-isomer	MeSH
1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid,(+-)-isomer	MeSH
THBC-CA	MeSH
1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid	MeSH

Chemical Formula

C₁₂H₁₂N₂O₂

Average Molecular Weight

216.2359

Monoisotopic Molecular Weight

216.089877638

IUPAC Name

1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylic acid

Traditional Name

1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylic acid

CAS Registry Number

42438-90-4

SMILES

OC(=O)C1CC2=C(CN1)NC1=CC=CC=C21

InChI Identifier

InChI=1S/C12H12N2O2/c15-12(16)10-5-8-7-3-1-2-4-9(7)14-11(8)6-13-10/h1-4,10,13-14H,5-6H2,(H,15,16)

InChI Key

FSNCEEGOMTYXKY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyridoindoles

Direct Parent

Beta carbolines

Alternative Parents

Substituents

Beta-carboline
Alpha-amino acid
Alpha-amino acid or derivatives
3-alkylindole
Indole
Aralkylamine
Benzenoid
Pyrrole
Heteroaromatic compound
Amino acid
Amino acid or derivatives
Carboxylic acid derivative
Secondary amine
Carboxylic acid
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Azacycle
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Amine
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0035665)
Cytoplasm (HMDB: HMDB0035665)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035665)

Source

Exogenous

Exogenous (HMDB: HMDB0035665)

Food

Food (HMDB: HMDB0035665)

Vegetable

Fruit vegetable

Garden tomato (var.) (FooDB: FOOD00173)

Endogenous

Plant

Plant (HMDB: HMDB0035665)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0035665)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	282 - 284 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.92 g/L	ALOGPS
logP	-0.47	ALOGPS
logP	-1.2	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	1.97	ChemAxon
pKa (Strongest Basic)	8.99	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	65.12 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	59.41 m³·mol⁻¹	ChemAxon
Polarizability	22.85 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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
DarkChem	[M+H]+	149.516	31661259
DarkChem	[M-H]-	145.194	31661259
DeepCCS	[M-2H]-	174.672	30932474
DeepCCS	[M+Na]+	149.272	30932474
AllCCS	[M+H]+	149.1	32859911
AllCCS	[M+H-H2O]+	145.0	32859911
AllCCS	[M+NH4]+	153.0	32859911
AllCCS	[M+Na]+	154.1	32859911
AllCCS	[M-H]-	151.6	32859911
AllCCS	[M+Na-2H]-	151.3	32859911
AllCCS	[M+HCOO]-	151.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	3.1 minutes	32390414
Predicted by Siyang on May 30, 2022	9.6888 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.4 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	710.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	269.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	79.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	171.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	111.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	284.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	271.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	801.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	612.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	276.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	753.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	180.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	202.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	544.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	441.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	238.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid	OC(=O)C1CC2=C(CN1)NC1=CC=CC=C21	3750.9	Standard polar	33892256
L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid	OC(=O)C1CC2=C(CN1)NC1=CC=CC=C21	2203.3	Standard non polar	33892256
L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid	OC(=O)C1CC2=C(CN1)NC1=CC=CC=C21	2447.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)C1CC2=C(CN1)[NH]C1=CC=CC=C21	2336.6	Semi standard non polar	33892256
L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid,1TMS,isomer #2	C[Si](C)(C)N1CC2=C(CC1C(=O)O)C1=CC=CC=C1[NH]2	2416.4	Semi standard non polar	33892256
L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid,1TMS,isomer #3	C[Si](C)(C)N1C2=C(CC(C(=O)O)NC2)C2=CC=CC=C21	2407.7	Semi standard non polar	33892256
L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1CC2=C(CN1)N([Si](C)(C)C)C1=CC=CC=C21	2331.7	Semi standard non polar	33892256
L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1CC2=C(CN1)N([Si](C)(C)C)C1=CC=CC=C21	2159.3	Standard non polar	33892256
L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)C1CC2=C(CN1[Si](C)(C)C)[NH]C1=CC=CC=C21	2399.4	Semi standard non polar	33892256
L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)C1CC2=C(CN1[Si](C)(C)C)[NH]C1=CC=CC=C21	2268.8	Standard non polar	33892256
L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid,2TMS,isomer #3	C[Si](C)(C)N1CC2=C(CC1C(=O)O)C1=CC=CC=C1N2[Si](C)(C)C	2356.1	Semi standard non polar	33892256
L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid,2TMS,isomer #3	C[Si](C)(C)N1CC2=C(CC1C(=O)O)C1=CC=CC=C1N2[Si](C)(C)C	2302.9	Standard non polar	33892256
L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1CC2=C(CN1[Si](C)(C)C)N([Si](C)(C)C)C1=CC=CC=C21	2368.8	Semi standard non polar	33892256
L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1CC2=C(CN1[Si](C)(C)C)N([Si](C)(C)C)C1=CC=CC=C21	2341.4	Standard non polar	33892256
L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1CC2=C(CN1)[NH]C1=CC=CC=C21	2597.2	Semi standard non polar	33892256
L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1CC2=C(CC1C(=O)O)C1=CC=CC=C1[NH]2	2715.4	Semi standard non polar	33892256
L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C2=C(CC(C(=O)O)NC2)C2=CC=CC=C21	2641.1	Semi standard non polar	33892256
L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1CC2=C(CN1)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C21	2786.0	Semi standard non polar	33892256
L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1CC2=C(CN1)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C21	2592.0	Standard non polar	33892256
L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1CC2=C(CN1[Si](C)(C)C(C)(C)C)[NH]C1=CC=CC=C21	2877.1	Semi standard non polar	33892256
L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1CC2=C(CN1[Si](C)(C)C(C)(C)C)[NH]C1=CC=CC=C21	2739.6	Standard non polar	33892256
L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1CC2=C(CC1C(=O)O)C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C	2847.2	Semi standard non polar	33892256
L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1CC2=C(CC1C(=O)O)C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C	2733.9	Standard non polar	33892256
L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1CC2=C(CN1[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C21	3002.0	Semi standard non polar	33892256
L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1CC2=C(CN1[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C21	2972.5	Standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB014381

KNApSAcK ID

C00026660

Chemspider ID

88749

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

98285

PDB ID

Not Available

ChEBI ID

91151

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid (HMDB0035665)

MOL for HMDB0035665 (L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid)

3D MOL for HMDB0035665 (L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid)

3D SDF for HMDB0035665 (L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid)

3D-SDF for HMDB0035665 (L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid)

PDB for HMDB0035665 (L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid)

3D PDB for HMDB0035665 (L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid)

SMILES for HMDB0035665 (L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid)

INCHI for HMDB0035665 (L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid)

Structure for HMDB0035665 (L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid)

3D Structure for HMDB0035665 (L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized