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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 20:50:23 UTC

Update Date

2022-11-23 21:39:02 UTC

HMDB ID

HMDB0258959

Secondary Accession Numbers

None

Metabolite Identification

Common Name

1-Methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-5-ol

Description

1-Methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-5-ol, also known as tryptoline or 1,2,3,4-tetrahydro-beta-carboline, belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole. Based on a literature review very few articles have been published on 1-Methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-5-ol. This compound has been identified in human blood as reported by (PMID: 31557052 ). 1-methyl-2,3,4,9-tetrahydro-1h-pyrido[3,4-b]indol-5-ol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 1-Methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-5-ol is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0258959
     RDKit          3D
THbetaC
 29 31  0  0  0  0  0  0  0  0999 V2000
   -3.0936    1.5818   -0.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3073    0.4202    0.2268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6467   -0.8058   -0.4521 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0139   -1.9498    0.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7166   -1.6974    0.7888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0473   -0.4633    0.3322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8425    0.6256    0.0414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0426    1.6054   -0.3429 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2374    1.1966   -0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4477    1.8138   -0.6121 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6633    1.1735   -0.5016 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6776   -0.1382   -0.0749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4695   -0.7767    0.2310 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4354   -2.0876    0.6613 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2653   -0.1145    0.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1472    1.4782    0.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9549    1.6951   -1.3379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7130    2.4969    0.2666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4606    0.2346    1.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3042   -0.7017   -1.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8200   -2.7003   -0.7110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7015   -2.4440    0.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9146   -1.5610    1.8862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0379   -2.5673    0.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3745    2.5530   -0.6251 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4568    2.8390   -0.9472 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6137    1.6356   -0.7291 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6189   -0.6784    0.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2532   -2.6634    0.7830 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  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  1  0
 13 15  2  0
  7  2  1  0
 15  9  1  0
 15  6  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  8 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 14 29  1  0
M  END

  Mrv1652309112122502D          

 15 17  0  0  0  0            999 V2000
    3.6633   -1.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    0.2410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339   -0.6855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2243    1.9817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  3 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0258959

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1NCCC2=C1NC1=C2C(O)=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H14N2O/c1-7-12-8(5-6-13-7)11-9(14-12)3-2-4-10(11)15/h2-4,7,13-15H,5-6H2,1H3

> <INCHI_KEY>
CKAPKIRGAPRHBU-UHFFFAOYSA-N

> <FORMULA>
C12H14N2O

> <MOLECULAR_WEIGHT>
202.257

> <EXACT_MASS>
202.110613079

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
22.57868174709654

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-5-ol

> <ALOGPS_LOGP>
1.51

> <JCHEM_LOGP>
1.1040217241154509

> <ALOGPS_LOGS>
-2.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
18.11521443021026

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.830508721878042

> <JCHEM_PKA_STRONGEST_BASIC>
9.518147725574298

> <JCHEM_POLAR_SURFACE_AREA>
48.05

> <JCHEM_REFRACTIVITY>
59.9793

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.72e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-5-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0258959
     RDKit          3D
THbetaC
 29 31  0  0  0  0  0  0  0  0999 V2000
   -3.0936    1.5818   -0.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3073    0.4202    0.2268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6467   -0.8058   -0.4521 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0139   -1.9498    0.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7166   -1.6974    0.7888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0473   -0.4633    0.3322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8425    0.6256    0.0414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0426    1.6054   -0.3429 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2374    1.1966   -0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4477    1.8138   -0.6121 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6633    1.1735   -0.5016 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6776   -0.1382   -0.0749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4695   -0.7767    0.2310 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4354   -2.0876    0.6613 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2653   -0.1145    0.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1472    1.4782    0.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9549    1.6951   -1.3379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7130    2.4969    0.2666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4606    0.2346    1.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3042   -0.7017   -1.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8200   -2.7003   -0.7110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7015   -2.4440    0.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9146   -1.5610    1.8862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0379   -2.5673    0.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3745    2.5530   -0.6251 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4568    2.8390   -0.9472 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6137    1.6356   -0.7291 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6189   -0.6784    0.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2532   -2.6634    0.7830 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  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  1  0
 13 15  2  0
  7  2  1  0
 15  9  1  0
 15  6  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  8 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 14 29  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       6.838  -2.159   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.362  -0.695   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.856  -0.374   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.380   1.090   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.410   2.235   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.917   1.914   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       7.393   0.450   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       2.840   1.090   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.364  -0.374   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       3.610  -1.280   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       0.858  -0.695   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.173   0.450   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.303   1.914   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.810   2.235   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.285   3.699   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8    4    9   14                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    3                                                       
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    8   15                                                  
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   34    0
END

COMPND    HMDB0258959
HETATM    1  C1  UNL     1      -3.094   1.582  -0.259  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.307   0.420   0.227  1.00  0.00           C  
HETATM    3  N1  UNL     1      -2.647  -0.806  -0.452  1.00  0.00           N  
HETATM    4  C3  UNL     1      -2.014  -1.950   0.105  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.717  -1.697   0.789  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.047  -0.463   0.332  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.843   0.626   0.041  1.00  0.00           C  
HETATM    8  N2  UNL     1      -0.043   1.605  -0.343  1.00  0.00           N  
HETATM    9  C7  UNL     1       1.237   1.197  -0.313  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.448   1.814  -0.612  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.663   1.173  -0.502  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.678  -0.138  -0.075  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.469  -0.777   0.231  1.00  0.00           C  
HETATM   14  O1  UNL     1       2.435  -2.088   0.661  1.00  0.00           O  
HETATM   15  C12 UNL     1       1.265  -0.115   0.112  1.00  0.00           C  
HETATM   16  H1  UNL     1      -4.147   1.478   0.047  1.00  0.00           H  
HETATM   17  H2  UNL     1      -2.955   1.695  -1.338  1.00  0.00           H  
HETATM   18  H3  UNL     1      -2.713   2.497   0.267  1.00  0.00           H  
HETATM   19  H4  UNL     1      -2.461   0.235   1.323  1.00  0.00           H  
HETATM   20  H5  UNL     1      -2.304  -0.702  -1.449  1.00  0.00           H  
HETATM   21  H6  UNL     1      -1.820  -2.700  -0.711  1.00  0.00           H  
HETATM   22  H7  UNL     1      -2.701  -2.444   0.832  1.00  0.00           H  
HETATM   23  H8  UNL     1      -0.915  -1.561   1.886  1.00  0.00           H  
HETATM   24  H9  UNL     1      -0.038  -2.567   0.692  1.00  0.00           H  
HETATM   25  H10 UNL     1      -0.374   2.553  -0.625  1.00  0.00           H  
HETATM   26  H11 UNL     1       2.457   2.839  -0.947  1.00  0.00           H  
HETATM   27  H12 UNL     1       4.614   1.636  -0.729  1.00  0.00           H  
HETATM   28  H13 UNL     1       4.619  -0.678   0.025  1.00  0.00           H  
HETATM   29  H14 UNL     1       3.253  -2.663   0.783  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    7   19
CONECT    3    4   20
CONECT    4    5   21   22
CONECT    5    6   23   24
CONECT    6    7    7   15
CONECT    7    8
CONECT    8    9   25
CONECT    9   10   10   15
CONECT   10   11   26
CONECT   11   12   12   27
CONECT   12   13   28
CONECT   13   14   15   15
CONECT   14   29
END

HMDB0258959
     RDKit          3D
THbetaC
 29 31  0  0  0  0  0  0  0  0999 V2000
   -3.0936    1.5818   -0.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3073    0.4202    0.2268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6467   -0.8058   -0.4521 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0139   -1.9498    0.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7166   -1.6974    0.7888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0473   -0.4633    0.3322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8425    0.6256    0.0414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0426    1.6054   -0.3429 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2374    1.1966   -0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4477    1.8138   -0.6121 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6633    1.1735   -0.5016 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6776   -0.1382   -0.0749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4695   -0.7767    0.2310 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4354   -2.0876    0.6613 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2653   -0.1145    0.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1472    1.4782    0.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9549    1.6951   -1.3379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7130    2.4969    0.2666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4606    0.2346    1.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3042   -0.7017   -1.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8200   -2.7003   -0.7110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7015   -2.4440    0.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9146   -1.5610    1.8862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0379   -2.5673    0.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3745    2.5530   -0.6251 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4568    2.8390   -0.9472 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6137    1.6356   -0.7291 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6189   -0.6784    0.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2532   -2.6634    0.7830 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  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  1  0
 13 15  2  0
  7  2  1  0
 15  9  1  0
 15  6  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  8 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 14 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,2,3,4-Tetrahydro-beta-carboline	HMDB
Tryptoline	HMDB
Tryptoline monohydrochloride	HMDB
Tetrahydronorharmane	HMDB
Triptoline	HMDB
Tryptoline hydrochloride	HMDB
9H-1,2,3,4-Tetrahydropyrido(3,4-b)indole	HMDB
Noreleagnine	HMDB
Tetrahydro-beta-carboline	HMDB

Chemical Formula

C₁₂H₁₄N₂O

Average Molecular Weight

202.257

Monoisotopic Molecular Weight

202.110613079

IUPAC Name

1-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-5-ol

Traditional Name

1-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-5-ol

CAS Registry Number

Not Available

SMILES

CC1NCCC2=C1NC1=C2C(O)=CC=C1

InChI Identifier

InChI=1S/C12H14N2O/c1-7-12-8(5-6-13-7)11-9(14-12)3-2-4-10(11)15/h2-4,7,13-15H,5-6H2,1H3

InChI Key

CKAPKIRGAPRHBU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Harmala alkaloids

Sub Class

Not Available

Direct Parent

Harmala alkaloids

Alternative Parents

Substituents

Harman
Beta-carboline
Pyridoindole
Hydroxyindole
3-alkylindole
Indole
Indole or derivatives
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Benzenoid
Heteroaromatic compound
Pyrrole
Organoheterocyclic compound
Azacycle
Secondary aliphatic amine
Secondary amine
Organooxygen compound
Organonitrogen compound
Amine
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.51	ALOGPS
logP	1.1	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	8.83	ChemAxon
pKa (Strongest Basic)	9.52	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	48.05 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	59.98 m³·mol⁻¹	ChemAxon
Polarizability	22.58 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+H]+	142.405	30932474
DeepCCS	[M-H]-	140.047	30932474
DeepCCS	[M-2H]-	174.695	30932474
DeepCCS	[M+Na]+	150.143	30932474
AllCCS	[M+H]+	147.5	32859911
AllCCS	[M+H-H2O]+	143.5	32859911
AllCCS	[M+NH4]+	151.3	32859911
AllCCS	[M+Na]+	152.3	32859911
AllCCS	[M-H]-	146.6	32859911
AllCCS	[M+Na-2H]-	146.5	32859911
AllCCS	[M+HCOO]-	146.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
THbetaC	CC1NCCC2=C1NC1=C2C(O)=CC=C1	3199.1	Standard polar	33892256
THbetaC	CC1NCCC2=C1NC1=C2C(O)=CC=C1	2103.2	Standard non polar	33892256
THbetaC	CC1NCCC2=C1NC1=C2C(O)=CC=C1	2272.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
THbetaC,2TMS,isomer #1	CC1C2=C(CCN1[Si](C)(C)C)C1=C(O[Si](C)(C)C)C=CC=C1[NH]2	2326.4	Semi standard non polar	33892256
THbetaC,2TMS,isomer #1	CC1C2=C(CCN1[Si](C)(C)C)C1=C(O[Si](C)(C)C)C=CC=C1[NH]2	2194.0	Standard non polar	33892256
THbetaC,2TMS,isomer #1	CC1C2=C(CCN1[Si](C)(C)C)C1=C(O[Si](C)(C)C)C=CC=C1[NH]2	2523.5	Standard polar	33892256
THbetaC,2TMS,isomer #2	CC1NCCC2=C1N([Si](C)(C)C)C1=CC=CC(O[Si](C)(C)C)=C21	2282.3	Semi standard non polar	33892256
THbetaC,2TMS,isomer #2	CC1NCCC2=C1N([Si](C)(C)C)C1=CC=CC(O[Si](C)(C)C)=C21	2001.6	Standard non polar	33892256
THbetaC,2TMS,isomer #2	CC1NCCC2=C1N([Si](C)(C)C)C1=CC=CC(O[Si](C)(C)C)=C21	2380.7	Standard polar	33892256
THbetaC,2TMS,isomer #3	CC1C2=C(CCN1[Si](C)(C)C)C1=C(O)C=CC=C1N2[Si](C)(C)C	2292.7	Semi standard non polar	33892256
THbetaC,2TMS,isomer #3	CC1C2=C(CCN1[Si](C)(C)C)C1=C(O)C=CC=C1N2[Si](C)(C)C	2284.4	Standard non polar	33892256
THbetaC,2TMS,isomer #3	CC1C2=C(CCN1[Si](C)(C)C)C1=C(O)C=CC=C1N2[Si](C)(C)C	2436.1	Standard polar	33892256
THbetaC,3TMS,isomer #1	CC1C2=C(CCN1[Si](C)(C)C)C1=C(O[Si](C)(C)C)C=CC=C1N2[Si](C)(C)C	2304.7	Semi standard non polar	33892256
THbetaC,3TMS,isomer #1	CC1C2=C(CCN1[Si](C)(C)C)C1=C(O[Si](C)(C)C)C=CC=C1N2[Si](C)(C)C	2236.8	Standard non polar	33892256
THbetaC,3TMS,isomer #1	CC1C2=C(CCN1[Si](C)(C)C)C1=C(O[Si](C)(C)C)C=CC=C1N2[Si](C)(C)C	2331.9	Standard polar	33892256
THbetaC,2TBDMS,isomer #1	CC1C2=C(CCN1[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C=CC=C1[NH]2	2774.7	Semi standard non polar	33892256
THbetaC,2TBDMS,isomer #1	CC1C2=C(CCN1[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C=CC=C1[NH]2	2660.4	Standard non polar	33892256
THbetaC,2TBDMS,isomer #1	CC1C2=C(CCN1[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C=CC=C1[NH]2	2786.3	Standard polar	33892256
THbetaC,2TBDMS,isomer #2	CC1NCCC2=C1N([Si](C)(C)C(C)(C)C)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C21	2662.0	Semi standard non polar	33892256
THbetaC,2TBDMS,isomer #2	CC1NCCC2=C1N([Si](C)(C)C(C)(C)C)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C21	2449.1	Standard non polar	33892256
THbetaC,2TBDMS,isomer #2	CC1NCCC2=C1N([Si](C)(C)C(C)(C)C)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C21	2611.6	Standard polar	33892256
THbetaC,2TBDMS,isomer #3	CC1C2=C(CCN1[Si](C)(C)C(C)(C)C)C1=C(O)C=CC=C1N2[Si](C)(C)C(C)(C)C	2679.6	Semi standard non polar	33892256
THbetaC,2TBDMS,isomer #3	CC1C2=C(CCN1[Si](C)(C)C(C)(C)C)C1=C(O)C=CC=C1N2[Si](C)(C)C(C)(C)C	2742.3	Standard non polar	33892256
THbetaC,2TBDMS,isomer #3	CC1C2=C(CCN1[Si](C)(C)C(C)(C)C)C1=C(O)C=CC=C1N2[Si](C)(C)C(C)(C)C	2673.4	Standard polar	33892256
THbetaC,3TBDMS,isomer #1	CC1C2=C(CCN1[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C=CC=C1N2[Si](C)(C)C(C)(C)C	2877.1	Semi standard non polar	33892256
THbetaC,3TBDMS,isomer #1	CC1C2=C(CCN1[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C=CC=C1N2[Si](C)(C)C(C)(C)C	2877.7	Standard non polar	33892256
THbetaC,3TBDMS,isomer #1	CC1C2=C(CCN1[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C=CC=C1N2[Si](C)(C)C(C)(C)C	2691.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-5-ol GC-MS (Non-derivatized) - 70eV, Positive	splash10-059i-0910000000-a95b2a0165114d5c587b	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-5-ol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-5-ol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-5-ol GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-5-ol GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-5-ol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-5-ol GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-5-ol GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

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

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10519387

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21788252

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for 1-Methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-5-ol (HMDB0258959)

MOL for HMDB0258959 (1-Methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-5-ol)

3D MOL for HMDB0258959 (1-Methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-5-ol)

3D SDF for HMDB0258959 (1-Methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-5-ol)

3D-SDF for HMDB0258959 (1-Methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-5-ol)

PDB for HMDB0258959 (1-Methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-5-ol)

3D PDB for HMDB0258959 (1-Methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-5-ol)

SMILES for HMDB0258959 (1-Methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-5-ol)

INCHI for HMDB0258959 (1-Methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-5-ol)

Structure for HMDB0258959 (1-Methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-5-ol)

3D Structure for HMDB0258959 (1-Methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-5-ol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra