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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:05:53 UTC

Update Date

2022-03-07 02:54:03 UTC

HMDB ID

HMDB0034292

Secondary Accession Numbers

HMDB34292

Metabolite Identification

Common Name

Nb-Methyltetrahydroharmol

Description

Nb-Methyltetrahydroharmol 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. Nb-Methyltetrahydroharmol has been detected, but not quantified in, fruits. This could make NB-methyltetrahydroharmol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Nb-Methyltetrahydroharmol.

Structure

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

HMDB0034292
     RDKit          3D
Nb-Methyltetrahydroharmol
 32 34  0  0  0  0  0  0  0  0999 V2000
   -2.3796   -0.7095    1.7900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9546    0.3095    0.7320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4833    0.4075    0.6496 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4848    1.1798    1.1721 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6902    0.7686    0.7044 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9617    1.2435    0.9512 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0374    0.6327    0.3352 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.1141    0.5846 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8739   -0.4382   -0.5191 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5949   -0.8977   -0.7526 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5086   -0.3012   -0.1470 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1481   -0.5229   -0.1777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6648   -1.5091   -0.8914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0299   -1.0498   -1.2644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5918   -0.0224   -0.4817 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1838    1.0645   -1.1872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3825   -0.1945    2.7784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6817   -1.5586    1.7444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3869   -1.1087    1.5237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3731    1.2984    1.0836 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2764    1.9606    1.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1269    2.0971    1.6283 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7097    1.8298   -0.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6959   -0.9243   -1.0056 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3900   -1.7322   -1.4097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7174   -2.4433   -0.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1281   -1.7976   -1.8190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0609   -0.7540   -2.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7092   -1.9500   -1.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9073    0.6533   -1.9207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4105    1.6870   -1.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7863    1.6673   -0.4469 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15  2  1  0
 12  3  2  0
 11  5  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  4 21  1  0
  6 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 13 26  1  0
 13 27  1  0
 14 28  1  0
 14 29  1  0
 16 30  1  0
 16 31  1  0
 16 32  1  0
M  END


  Mrv0541 05061307422D          

 16 18  0  0  0  0            999 V2000
    0.2046   -1.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8995    0.0694    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
    2.8985    1.1971    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
    0.1624    1.0256    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
    0.4595   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    0.2410    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
    1.5214    0.5840    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
    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
   -0.0925    0.2410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7674    0.0694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  6  5  1  0  0  0  0
  8  1  1  0  0  0  0
  9  3  1  0  0  0  0
  9  7  2  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
 11 10  1  0  0  0  0
 12  7  1  0  0  0  0
 12 10  2  0  0  0  0
 13  8  1  0  0  0  0
 13 11  2  0  0  0  0
 14 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15  2  1  0  0  0  0
 15  6  1  0  0  0  0
 15  8  1  0  0  0  0
 16  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034292

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1N(C)CCC2=C1NC1=C2C=CC(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H16N2O/c1-8-13-11(5-6-15(8)2)10-4-3-9(16)7-12(10)14-13/h3-4,7-8,14,16H,5-6H2,1-2H3

> <INCHI_KEY>
AGILGFCOHSGLIT-UHFFFAOYSA-N

> <FORMULA>
C13H16N2O

> <MOLECULAR_WEIGHT>
216.2789

> <EXACT_MASS>
216.126263144

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
24.583323945215184

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,2-dimethyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-7-ol

> <ALOGPS_LOGP>
2.37

> <JCHEM_LOGP>
2.0863039089999997

> <ALOGPS_LOGS>
-1.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
17.3024470862984

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.733657342372875

> <JCHEM_PKA_STRONGEST_BASIC>
9.839001943968787

> <JCHEM_POLAR_SURFACE_AREA>
39.260000000000005

> <JCHEM_REFRACTIVITY>
65.274

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.24e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,2-dimethyl-1H,3H,4H,9H-pyrido[3,4-b]indol-7-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0034292
     RDKit          3D
Nb-Methyltetrahydroharmol
 32 34  0  0  0  0  0  0  0  0999 V2000
   -2.3796   -0.7095    1.7900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9546    0.3095    0.7320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4833    0.4075    0.6496 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4848    1.1798    1.1721 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6902    0.7686    0.7044 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9617    1.2435    0.9512 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0374    0.6327    0.3352 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.1141    0.5846 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8739   -0.4382   -0.5191 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5949   -0.8977   -0.7526 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5086   -0.3012   -0.1470 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1481   -0.5229   -0.1777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6648   -1.5091   -0.8914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0299   -1.0498   -1.2644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5918   -0.0224   -0.4817 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1838    1.0645   -1.1872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3825   -0.1945    2.7784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6817   -1.5586    1.7444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3869   -1.1087    1.5237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3731    1.2984    1.0836 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2764    1.9606    1.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1269    2.0971    1.6283 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7097    1.8298   -0.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6959   -0.9243   -1.0056 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3900   -1.7322   -1.4097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7174   -2.4433   -0.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1281   -1.7976   -1.8190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0609   -0.7540   -2.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7092   -1.9500   -1.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9073    0.6533   -1.9207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4105    1.6870   -1.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7863    1.6673   -0.4469 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15  2  1  0
 12  3  2  0
 11  5  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  4 21  1  0
  6 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 13 26  1  0
 13 27  1  0
 14 28  1  0
 14 29  1  0
 16 30  1  0
 16 31  1  0
 16 32  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       0.382  -2.159   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.679   0.130   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.917   1.914   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.411   2.235   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.810   2.235   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.303   1.914   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.362  -0.695   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.858  -0.695   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.393   0.450   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.380   1.090   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.840   1.090   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.856  -0.374   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.364  -0.374   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       3.610  -1.280   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0      -0.173   0.450   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       8.899   0.130   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2   15                                                            
CONECT    3    4    9                                                       
CONECT    4    3   10                                                       
CONECT    5    6   11                                                       
CONECT    6    5   15                                                       
CONECT    7    9   12                                                       
CONECT    8    1   13   15                                                  
CONECT    9    3    7   16                                                  
CONECT   10    4   11   12                                                  
CONECT   11    5   10   13                                                  
CONECT   12    7   10   14                                                  
CONECT   13    8   11   14                                                  
CONECT   14   12   13                                                       
CONECT   15    2    6    8                                                  
CONECT   16    9                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

COMPND    HMDB0034292
HETATM    1  C1  UNL     1      -2.380  -0.709   1.790  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.955   0.309   0.732  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.483   0.407   0.650  1.00  0.00           C  
HETATM    4  N1  UNL     1       0.485   1.180   1.172  1.00  0.00           N  
HETATM    5  C4  UNL     1       1.690   0.769   0.704  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.962   1.243   0.951  1.00  0.00           C  
HETATM    7  C6  UNL     1       4.037   0.633   0.335  1.00  0.00           C  
HETATM    8  O1  UNL     1       5.333   1.114   0.585  1.00  0.00           O  
HETATM    9  C7  UNL     1       3.874  -0.438  -0.519  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.595  -0.898  -0.753  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.509  -0.301  -0.147  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.148  -0.523  -0.178  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.665  -1.509  -0.891  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.030  -1.050  -1.264  1.00  0.00           C  
HETATM   15  N2  UNL     1      -2.592  -0.022  -0.482  1.00  0.00           N  
HETATM   16  C13 UNL     1      -3.184   1.065  -1.187  1.00  0.00           C  
HETATM   17  H1  UNL     1      -2.383  -0.194   2.778  1.00  0.00           H  
HETATM   18  H2  UNL     1      -1.682  -1.559   1.744  1.00  0.00           H  
HETATM   19  H3  UNL     1      -3.387  -1.109   1.524  1.00  0.00           H  
HETATM   20  H4  UNL     1      -2.373   1.298   1.084  1.00  0.00           H  
HETATM   21  H5  UNL     1       0.276   1.961   1.831  1.00  0.00           H  
HETATM   22  H6  UNL     1       3.127   2.097   1.628  1.00  0.00           H  
HETATM   23  H7  UNL     1       5.710   1.830  -0.002  1.00  0.00           H  
HETATM   24  H8  UNL     1       4.696  -0.924  -1.006  1.00  0.00           H  
HETATM   25  H9  UNL     1       2.390  -1.732  -1.410  1.00  0.00           H  
HETATM   26  H10 UNL     1      -0.717  -2.443  -0.267  1.00  0.00           H  
HETATM   27  H11 UNL     1      -0.128  -1.798  -1.819  1.00  0.00           H  
HETATM   28  H12 UNL     1      -2.061  -0.754  -2.337  1.00  0.00           H  
HETATM   29  H13 UNL     1      -2.709  -1.950  -1.201  1.00  0.00           H  
HETATM   30  H14 UNL     1      -3.907   0.653  -1.921  1.00  0.00           H  
HETATM   31  H15 UNL     1      -2.411   1.687  -1.679  1.00  0.00           H  
HETATM   32  H16 UNL     1      -3.786   1.667  -0.447  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   15   20
CONECT    3    4   12   12
CONECT    4    5   21
CONECT    5    6    6   11
CONECT    6    7   22
CONECT    7    8    9    9
CONECT    8   23
CONECT    9   10   24
CONECT   10   11   11   25
CONECT   11   12
CONECT   12   13
CONECT   13   14   26   27
CONECT   14   15   28   29
CONECT   15   16
CONECT   16   30   31   32
END

HMDB0034292
     RDKit          3D
Nb-Methyltetrahydroharmol
 32 34  0  0  0  0  0  0  0  0999 V2000
   -2.3796   -0.7095    1.7900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9546    0.3095    0.7320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4833    0.4075    0.6496 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4848    1.1798    1.1721 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6902    0.7686    0.7044 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9617    1.2435    0.9512 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0374    0.6327    0.3352 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.1141    0.5846 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8739   -0.4382   -0.5191 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5949   -0.8977   -0.7526 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5086   -0.3012   -0.1470 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1481   -0.5229   -0.1777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6648   -1.5091   -0.8914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0299   -1.0498   -1.2644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5918   -0.0224   -0.4817 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1838    1.0645   -1.1872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3825   -0.1945    2.7784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6817   -1.5586    1.7444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3869   -1.1087    1.5237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3731    1.2984    1.0836 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2764    1.9606    1.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1269    2.0971    1.6283 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7097    1.8298   -0.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6959   -0.9243   -1.0056 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3900   -1.7322   -1.4097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7174   -2.4433   -0.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1281   -1.7976   -1.8190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0609   -0.7540   -2.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7092   -1.9500   -1.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9073    0.6533   -1.9207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4105    1.6870   -1.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7863    1.6673   -0.4469 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15  2  1  0
 12  3  2  0
 11  5  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  4 21  1  0
  6 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 13 26  1  0
 13 27  1  0
 14 28  1  0
 14 29  1  0
 16 30  1  0
 16 31  1  0
 16 32  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₃H₁₆N₂O

Average Molecular Weight

216.2789

Monoisotopic Molecular Weight

216.126263144

IUPAC Name

1,2-dimethyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-7-ol

Traditional Name

1,2-dimethyl-1H,3H,4H,9H-pyrido[3,4-b]indol-7-ol

CAS Registry Number

Not Available

SMILES

CC1N(C)CCC2=C1NC1=C2C=CC(O)=C1

InChI Identifier

InChI=1S/C13H16N2O/c1-8-13-11(5-6-15(8)2)10-4-3-9(16)7-12(10)14-13/h3-4,7-8,14,16H,5-6H2,1-2H3

InChI Key

AGILGFCOHSGLIT-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

Harmaline
Harmalol
Harman
Beta-carboline
Pyridoindole
Hydroxyindole
3-alkylindole
Indole
Indole or derivatives
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Benzenoid
Heteroaromatic compound
Pyrrole
Tertiary amine
Tertiary aliphatic amine
Organoheterocyclic compound
Azacycle
Organooxygen compound
Organonitrogen compound
Amine
Hydrocarbon derivative
Organopnictogen compound
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

Cellular substructure

Extracellular (HMDB: HMDB0034292)
Cytoplasm (HMDB: HMDB0034292)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034292)

Source

Exogenous

Food

Food (HMDB: HMDB0034292)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0034292)

Not Available

Nutrient (HMDB: HMDB0034292)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	268 - 270 °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	2.24 g/L	ALOGPS
logP	2.37	ALOGPS
logP	2.09	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	6.73	ChemAxon
pKa (Strongest Basic)	9.84	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	39.26 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	65.27 m³·mol⁻¹	ChemAxon
Polarizability	24.58 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]+	151.514	31661259
DarkChem	[M-H]-	150.854	31661259
DeepCCS	[M+H]+	148.488	30932474
DeepCCS	[M-H]-	146.093	30932474
DeepCCS	[M-2H]-	179.305	30932474
DeepCCS	[M+Na]+	154.479	30932474
AllCCS	[M+H]+	149.4	32859911
AllCCS	[M+H-H2O]+	145.3	32859911
AllCCS	[M+NH4]+	153.3	32859911
AllCCS	[M+Na]+	154.4	32859911
AllCCS	[M-H]-	155.5	32859911
AllCCS	[M+Na-2H]-	155.4	32859911
AllCCS	[M+HCOO]-	155.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nb-Methyltetrahydroharmol	CC1N(C)CCC2=C1NC1=C2C=CC(O)=C1	3278.1	Standard polar	33892256
Nb-Methyltetrahydroharmol	CC1N(C)CCC2=C1NC1=C2C=CC(O)=C1	2143.8	Standard non polar	33892256
Nb-Methyltetrahydroharmol	CC1N(C)CCC2=C1NC1=C2C=CC(O)=C1	2302.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nb-Methyltetrahydroharmol,1TMS,isomer #1	CC1C2=C(CCN1C)C1=CC=C(O[Si](C)(C)C)C=C1[NH]2	2297.4	Semi standard non polar	33892256
Nb-Methyltetrahydroharmol,1TMS,isomer #2	CC1C2=C(CCN1C)C1=CC=C(O)C=C1N2[Si](C)(C)C	2280.2	Semi standard non polar	33892256
Nb-Methyltetrahydroharmol,2TMS,isomer #1	CC1C2=C(CCN1C)C1=CC=C(O[Si](C)(C)C)C=C1N2[Si](C)(C)C	2261.3	Semi standard non polar	33892256
Nb-Methyltetrahydroharmol,2TMS,isomer #1	CC1C2=C(CCN1C)C1=CC=C(O[Si](C)(C)C)C=C1N2[Si](C)(C)C	2154.6	Standard non polar	33892256
Nb-Methyltetrahydroharmol,1TBDMS,isomer #1	CC1C2=C(CCN1C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1[NH]2	2540.2	Semi standard non polar	33892256
Nb-Methyltetrahydroharmol,1TBDMS,isomer #2	CC1C2=C(CCN1C)C1=CC=C(O)C=C1N2[Si](C)(C)C(C)(C)C	2496.3	Semi standard non polar	33892256
Nb-Methyltetrahydroharmol,2TBDMS,isomer #1	CC1C2=C(CCN1C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1N2[Si](C)(C)C(C)(C)C	2663.2	Semi standard non polar	33892256
Nb-Methyltetrahydroharmol,2TBDMS,isomer #1	CC1C2=C(CCN1C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1N2[Si](C)(C)C(C)(C)C	2639.6	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Nb-Methyltetrahydroharmol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-0950000000-0c3b46091825d032b047	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nb-Methyltetrahydroharmol GC-MS (1 TMS) - 70eV, Positive	splash10-00di-2390000000-0be10bd44b86e95f1e8e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nb-Methyltetrahydroharmol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nb-Methyltetrahydroharmol 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 - Nb-Methyltetrahydroharmol 10V, Positive-QTOF	splash10-014i-0190000000-8bce7c20dd3a07a2c2a3	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nb-Methyltetrahydroharmol 20V, Positive-QTOF	splash10-014i-2970000000-aa384d5437113ca562cd	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nb-Methyltetrahydroharmol 40V, Positive-QTOF	splash10-0r04-0900000000-ef31831b29a57352df30	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nb-Methyltetrahydroharmol 10V, Negative-QTOF	splash10-014i-0090000000-92957fb69a746837ef1b	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nb-Methyltetrahydroharmol 20V, Negative-QTOF	splash10-014i-0190000000-05dfe2ef23082a5cdb1f	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nb-Methyltetrahydroharmol 40V, Negative-QTOF	splash10-059t-1900000000-79b63723580dae7a4101	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nb-Methyltetrahydroharmol 10V, Negative-QTOF	splash10-014i-0090000000-810ec31dac75bb9d724b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nb-Methyltetrahydroharmol 20V, Negative-QTOF	splash10-014i-0090000000-9936bc70c64ddaa3b4d9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nb-Methyltetrahydroharmol 40V, Negative-QTOF	splash10-06si-0910000000-6d60af9f1356f2a61f8a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nb-Methyltetrahydroharmol 10V, Positive-QTOF	splash10-014i-0090000000-b3b3217a7e594f652193	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nb-Methyltetrahydroharmol 20V, Positive-QTOF	splash10-014i-0290000000-d844a7c1554295e39ddc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nb-Methyltetrahydroharmol 40V, Positive-QTOF	splash10-05fu-1900000000-9edefd7c517635e551b2	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

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

FDB012631

KNApSAcK ID

C00054104

Chemspider ID

26770427

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14219281

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

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

Showing metabocard for Nb-Methyltetrahydroharmol (HMDB0034292)

MOL for HMDB0034292 (Nb-Methyltetrahydroharmol)

3D MOL for HMDB0034292 (Nb-Methyltetrahydroharmol)

3D SDF for HMDB0034292 (Nb-Methyltetrahydroharmol)

3D-SDF for HMDB0034292 (Nb-Methyltetrahydroharmol)

PDB for HMDB0034292 (Nb-Methyltetrahydroharmol)

3D PDB for HMDB0034292 (Nb-Methyltetrahydroharmol)

SMILES for HMDB0034292 (Nb-Methyltetrahydroharmol)

INCHI for HMDB0034292 (Nb-Methyltetrahydroharmol)

Structure for HMDB0034292 (Nb-Methyltetrahydroharmol)

3D Structure for HMDB0034292 (Nb-Methyltetrahydroharmol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra