Hmdb loader

Showing metabocard for Harmine (HMDB0030311)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:36:03 UTC
Update Date2022-03-07 02:52:30 UTC
HMDB IDHMDB0030311
Secondary Accession Numbers
  • HMDB30311
Metabolite Identification
Common NameHarmine
DescriptionHarmine, also known as banisterine or leucoharmine, 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. Harmine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Harmine.
Structure
Data?1563861967
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0030311 (Harmine)

HRM
  Mrv0541 02241213442D          

 16 18  0  0  0  0            999 V2000
    2.0116   -1.1543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7566   -0.3697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3087    0.2434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0537    1.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2467    1.1995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6947    0.5864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9497   -0.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2822   -0.6831    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3852   -0.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1922   -0.3697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1303    0.5864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6823    1.1995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4893    1.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7442    0.2434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5512    0.0719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8061   -0.7128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  7  1  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
  6  7  2  0  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 10 14  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
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
Download

3D MOL for HMDB0030311 (Harmine)

HMDB0030311
     RDKit          3D
Harmine
 28 30  0  0  0  0  0  0  0  0999 V2000
    5.0160    0.4081   -0.4330 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8687    1.2342   -0.4579 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6170    0.6090   -0.3380 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4963   -0.7579   -0.2006 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2840   -1.4103   -0.0800 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1480   -0.6260   -0.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2289    0.7496   -0.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4602    1.3589   -0.3551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0187    1.2682   -0.2282 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9086    0.2500   -0.0877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2859    0.2699   -0.0239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9806    1.5735   -0.1164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9177   -0.8972    0.1187 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2556   -2.0792    0.2010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8791   -2.1009    0.1374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1783   -0.9238   -0.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1858   -0.0638    0.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8969   -0.3966   -1.1960 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8733    1.0559   -0.7389 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4139   -1.3684   -0.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2432   -2.4908    0.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4970    2.4437   -0.4614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2556    2.2703   -0.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0793    1.4532   -0.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6422    2.1784    0.7573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6527    2.0493   -1.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8033   -2.9945    0.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3715   -3.0628    0.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  8  3  1  0
 16 10  1  0
 16  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  5 21  1  0
  8 22  1  0
  9 23  1  0
 12 24  1  0
 12 25  1  0
 12 26  1  0
 14 27  1  0
 15 28  1  0
M  END
Download

3D SDF for HMDB0030311 (Harmine)

HRM
  Mrv0541 02241213442D          

 16 18  0  0  0  0            999 V2000
    2.0116   -1.1543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7566   -0.3697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3087    0.2434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0537    1.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2467    1.1995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6947    0.5864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9497   -0.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2822   -0.6831    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3852   -0.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1922   -0.3697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1303    0.5864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6823    1.1995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4893    1.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7442    0.2434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5512    0.0719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8061   -0.7128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  7  1  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
  6  7  2  0  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 10 14  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
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030311

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C2C(NC3=C2C=CN=C3C)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H12N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-7,15H,1-2H3

> <INCHI_KEY>
BXNJHAXVSOCGBA-UHFFFAOYSA-N

> <FORMULA>
C13H12N2O

> <MOLECULAR_WEIGHT>
212.2472

> <EXACT_MASS>
212.094963016

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
23.45017546276285

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-methoxy-1-methyl-9H-pyrido[3,4-b]indole

> <ALOGPS_LOGP>
3.05

> <JCHEM_LOGP>
1.8469121656666667

> <ALOGPS_LOGS>
-3.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.542985998251854

> <JCHEM_PKA_STRONGEST_BASIC>
6.153844207655581

> <JCHEM_POLAR_SURFACE_AREA>
37.91

> <JCHEM_REFRACTIVITY>
62.370000000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.13e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
harmine

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0030311 (Harmine)

HMDB0030311
     RDKit          3D
Harmine
 28 30  0  0  0  0  0  0  0  0999 V2000
    5.0160    0.4081   -0.4330 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8687    1.2342   -0.4579 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6170    0.6090   -0.3380 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4963   -0.7579   -0.2006 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2840   -1.4103   -0.0800 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1480   -0.6260   -0.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2289    0.7496   -0.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4602    1.3589   -0.3551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0187    1.2682   -0.2282 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9086    0.2500   -0.0877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2859    0.2699   -0.0239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9806    1.5735   -0.1164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9177   -0.8972    0.1187 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2556   -2.0792    0.2010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8791   -2.1009    0.1374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1783   -0.9238   -0.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1858   -0.0638    0.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8969   -0.3966   -1.1960 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8733    1.0559   -0.7389 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4139   -1.3684   -0.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2432   -2.4908    0.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4970    2.4437   -0.4614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2556    2.2703   -0.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0793    1.4532   -0.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6422    2.1784    0.7573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6527    2.0493   -1.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8033   -2.9945    0.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3715   -3.0628    0.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  8  3  1  0
 16 10  1  0
 16  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  5 21  1  0
  8 22  1  0
  9 23  1  0
 12 24  1  0
 12 25  1  0
 12 26  1  0
 14 27  1  0
 15 28  1  0
M  END
Download

PDB for HMDB0030311 (Harmine)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: HRM                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       3.755  -2.155   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.279  -0.690   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       4.310   0.454   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       3.834   1.919   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.327   2.239   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.297   1.095   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.773  -0.370   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       0.527  -1.275   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -0.719  -0.370   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.225  -0.690   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.243   1.095   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.274   2.239   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.780   1.919   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.256   0.454   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.762   0.134   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -5.238  -1.331   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    2    6    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9   14                                                       
CONECT   11    6    9   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   10   13   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END
Download

3D PDB for HMDB0030311 (Harmine)

COMPND    HMDB0030311
HETATM    1  C1  UNL     1       5.016   0.408  -0.433  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.869   1.234  -0.458  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.617   0.609  -0.338  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.496  -0.758  -0.201  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.284  -1.410  -0.080  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.148  -0.626  -0.101  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.229   0.750  -0.238  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.460   1.359  -0.355  1.00  0.00           C  
HETATM    9  N1  UNL     1      -1.019   1.268  -0.228  1.00  0.00           N  
HETATM   10  C8  UNL     1      -1.909   0.250  -0.088  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.286   0.270  -0.024  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.981   1.573  -0.116  1.00  0.00           C  
HETATM   13  N2  UNL     1      -3.918  -0.897   0.119  1.00  0.00           N  
HETATM   14  C11 UNL     1      -3.256  -2.079   0.201  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.879  -2.101   0.137  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.178  -0.924  -0.009  1.00  0.00           C  
HETATM   17  H1  UNL     1       5.186  -0.064   0.554  1.00  0.00           H  
HETATM   18  H2  UNL     1       4.897  -0.397  -1.196  1.00  0.00           H  
HETATM   19  H3  UNL     1       5.873   1.056  -0.739  1.00  0.00           H  
HETATM   20  H4  UNL     1       3.414  -1.368  -0.186  1.00  0.00           H  
HETATM   21  H5  UNL     1       1.243  -2.491   0.026  1.00  0.00           H  
HETATM   22  H6  UNL     1       1.497   2.444  -0.461  1.00  0.00           H  
HETATM   23  H7  UNL     1      -1.256   2.270  -0.313  1.00  0.00           H  
HETATM   24  H8  UNL     1      -5.079   1.453  -0.089  1.00  0.00           H  
HETATM   25  H9  UNL     1      -3.642   2.178   0.757  1.00  0.00           H  
HETATM   26  H10 UNL     1      -3.653   2.049  -1.058  1.00  0.00           H  
HETATM   27  H11 UNL     1      -3.803  -2.995   0.315  1.00  0.00           H  
HETATM   28  H12 UNL     1      -1.372  -3.063   0.206  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   20
CONECT    5    6    6   21
CONECT    6    7   16
CONECT    7    8    8    9
CONECT    8   22
CONECT    9   10   23
CONECT   10   11   11   16
CONECT   11   12   13
CONECT   12   24   25   26
CONECT   13   14   14
CONECT   14   15   27
CONECT   15   16   16   28
END
Download

SMILES for HMDB0030311 (Harmine)

COC1=CC=C2C(NC3=C2C=CN=C3C)=C1
Download

INCHI for HMDB0030311 (Harmine)

InChI=1S/C13H12N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-7,15H,1-2H3
Download
View in JSmolView Stereo Labels
Synonyms
ValueSource
6-MethoxyharmanChEBI
7-Methoxy-1-methyl-9H-beta-carbolineChEBI
BanisterineChEBI
LeucoharmineChEBI
TelepathineChEBI
YageineChEBI
YajeineChEBI
7-Methoxy-1-methyl-9H-b-carbolineGenerator
7-Methoxy-1-methyl-9H-β-carbolineGenerator
1-Methyl-7-methoxy-beta -carbolineHMDB
1-Methyl-7-methoxy-beta-carbolineHMDB
442-51-3 (FREE base)HMDB
7-Methoxy-1-methyl-9H-pyrido(3,4-b)indoleHMDB
7-Methoxy-1-methyl-9H-pyrido[3,4-b]indoleHMDB
7-Methoxy-1-methyl-9H-pyrido[3,4-b]indole, 9ciHMDB
BanisterinHMDB
GarminHMDB
HarminHMDB
Harmin hydrochlorideHMDB
HRMHMDB
TelepathienHMDB
TelepathinHMDB
YageinHMDB
Chemical FormulaC13H12N2O
Average Molecular Weight212.2472
Monoisotopic Molecular Weight212.094963016
IUPAC Name7-methoxy-1-methyl-9H-pyrido[3,4-b]indole
Traditional Nameharmine
CAS Registry Number442-51-3
SMILES
COC1=CC=C2C(NC3=C2C=CN=C3C)=C1
InChI Identifier
InChI=1S/C13H12N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-7,15H,1-2H3
InChI KeyBXNJHAXVSOCGBA-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.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassHarmala alkaloids
Sub ClassNot Available
Direct ParentHarmala alkaloids
Alternative Parents
Substituents
  • Harman
  • Beta-carboline
  • Pyridoindole
  • Indole
  • Indole or derivatives
  • Anisole
  • Methylpyridine
  • Alkyl aryl ether
  • Benzenoid
  • Pyridine
  • Heteroaromatic compound
  • Pyrrole
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial applicationBiological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point264 - 265 °CNot Available
Boiling Point421.40 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility2.68 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.56Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg145.27530932474
[M+H]+MetCCS_train_pos146.03330932474
[M+H]+Not Available144.507http://allccs.zhulab.cn/database/detail?ID=AllCCS00001371
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.061 g/LALOGPS
logP3.05ALOGPS
logP1.85ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)13.54ChemAxon
pKa (Strongest Basic)6.15ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.91 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity62.37 m³·mol⁻¹ChemAxon
Polarizability23.45 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+150.031661259
DarkChem[M-H]-150.59531661259
DeepCCS[M+H]+151.430932474
DeepCCS[M-H]-149.00530932474
DeepCCS[M-2H]-182.09130932474
DeepCCS[M+Na]+157.42130932474
AllCCS[M+H]+146.432859911
AllCCS[M+H-H2O]+142.132859911
AllCCS[M+NH4]+150.432859911
AllCCS[M+Na]+151.632859911
AllCCS[M-H]-151.932859911
AllCCS[M+Na-2H]-151.632859911
AllCCS[M+HCOO]-151.332859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
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. Predicted by Afia on May 17, 2022.4.57 minutes32390414
Predicted by Siyang on May 30, 20229.8317 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.2 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid56.4 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1484.9 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid305.0 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid90.6 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid177.3 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid133.4 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid342.0 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid302.4 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)57.6 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid570.0 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid192.1 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid922.6 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid220.8 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid251.0 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate670.7 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA205.6 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water111.8 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
HarmineCOC1=CC=C2C(NC3=C2C=CN=C3C)=C12697.4Standard polar33892256
HarmineCOC1=CC=C2C(NC3=C2C=CN=C3C)=C12282.3Standard non polar33892256
HarmineCOC1=CC=C2C(NC3=C2C=CN=C3C)=C12239.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Harmine,1TMS,isomer #1COC1=CC=C2C3=CC=NC(C)=C3N([Si](C)(C)C)C2=C12434.1Semi standard non polar33892256
Harmine,1TMS,isomer #1COC1=CC=C2C3=CC=NC(C)=C3N([Si](C)(C)C)C2=C12108.3Standard non polar33892256
Harmine,1TBDMS,isomer #1COC1=CC=C2C3=CC=NC(C)=C3N([Si](C)(C)C(C)(C)C)C2=C12597.1Semi standard non polar33892256
Harmine,1TBDMS,isomer #1COC1=CC=C2C3=CC=NC(C)=C3N([Si](C)(C)C(C)(C)C)C2=C12304.6Standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB07919
Phenol Explorer Compound IDNot Available
FooDB IDFDB002149
KNApSAcK IDC00001737
Chemspider ID4444445
KEGG Compound IDC06538
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHarmine
METLIN IDNot Available
PubChem Compound5280953
PDB IDHRM
ChEBI ID28121
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1249111
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Gambelunghe C, Aroni K, Rossi R, Moretti L, Bacci M: Identification of N,N-dimethyltryptamine and beta-carbolines in psychotropic ayahuasca beverage. Biomed Chromatogr. 2008 Oct;22(10):1056-9. doi: 10.1002/bmc.1023. [PubMed:18506697 ]
  2. Yonezawa T, Lee JW, Hibino A, Asai M, Hojo H, Cha BY, Teruya T, Nagai K, Chung UI, Yagasaki K, Woo JT: Harmine promotes osteoblast differentiation through bone morphogenetic protein signaling. Biochem Biophys Res Commun. 2011 Jun 3;409(2):260-5. doi: 10.1016/j.bbrc.2011.05.001. Epub 2011 May 6. [PubMed:21570953 ]
  3. Hamsa TP, Kuttan G: Harmine inhibits tumour specific neo-vessel formation by regulating VEGF, MMP, TIMP and pro-inflammatory mediators both in vivo and in vitro. Eur J Pharmacol. 2010 Dec 15;649(1-3):64-73. doi: 10.1016/j.ejphar.2010.09.010. Epub 2010 Sep 19. [PubMed:20858484 ]
  4. Reus GZ, Stringari RB, de Souza B, Petronilho F, Dal-Pizzol F, Hallak JE, Zuardi AW, Crippa JA, Quevedo J: Harmine and imipramine promote antioxidant activities in prefrontal cortex and hippocampus. Oxid Med Cell Longev. 2010 Sep-Oct;3(5):325-31. Epub 2010 Sep 1. [PubMed:21150338 ]
  5. Carpentier RG: The effect of harmine on the action potential of the guinea-pig atrial muscle depends on the external calcium concentration. Br J Pharmacol. 1981 Oct;74(2):415-8. [PubMed:7317690 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .