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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:51:56 UTC

Update Date

2022-03-07 02:56:55 UTC

HMDB ID

HMDB0041200

Secondary Accession Numbers

HMDB41200

Metabolite Identification

Common Name

Dehydroxymethylflazine

Description

Dehydroxymethylflazine 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. Dehydroxymethylflazine is found, on average, in the highest concentration within blackcurrants (Ribes nigrum). Dehydroxymethylflazine has also been detected, but not quantified in, fruits. This could make dehydroxymethylflazine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Dehydroxymethylflazine.

Structure

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

HMDB0041200
     RDKit          3D
Dehydroxymethylflazine
 31 34  0  0  0  0  0  0  0  0999 V2000
    0.1169    4.4528   -1.5580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8282    3.6308   -1.5052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0980    3.9228   -1.9229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5592    2.2814   -0.9660 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6948    1.9092   -0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9852    0.6640   -0.0160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0677   -0.2496    0.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4482   -1.3728    0.5635 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7728   -1.1995    0.8320 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7610   -2.0047    1.3594 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0634   -1.5764    1.5332 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4195   -0.2916    1.1719 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4333    0.5195    0.6430 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1353    0.0798    0.4743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3229    0.1184   -0.3987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4246   -0.8454   -0.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7268   -0.6568   -0.7247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3862   -1.8441   -0.4730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4728   -2.7001    0.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3444   -2.0756    0.1154 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5288    1.3561   -0.8831 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6511    4.6002   -1.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5029    2.6189   -0.5717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0572   -2.2654    0.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4816   -3.0251    1.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8149   -2.2349    1.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4221    0.0967    1.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6784    1.5333    0.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1044    0.2663   -1.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4506   -1.9837   -0.6887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7074   -3.7247    0.3539 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  2  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 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 15 21  2  0
 21  4  1  0
 14  6  1  0
 20 16  1  0
 14  9  1  0
  3 22  1  0
  5 23  1  0
  8 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  0
M  END


  Mrv0541 05061312282D          

 21 24  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
   -0.5800    3.0617    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
   -0.5800    2.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2046    3.3166    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
    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
    0.2046    1.9817    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
    0.4595    1.1971    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
    1.9339    1.5105    0.0000 N   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
   -1.1966   -0.6422    0.0000 O   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
    0.6895    2.6492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  3  1  0  0  0  0
  7  3  2  0  0  0  0
  9  4  2  0  0  0  0
 10  8  2  0  0  0  0
 10  9  1  0  0  0  0
 11  5  2  0  0  0  0
 11  9  1  0  0  0  0
 12  8  1  0  0  0  0
 13  6  2  0  0  0  0
 14 10  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  2  0  0  0  0
 16 12  1  0  0  0  0
 17 11  1  0  0  0  0
 17 14  1  0  0  0  0
 18 12  2  0  0  0  0
 18 15  1  0  0  0  0
 19 16  1  0  0  0  0
 20 16  2  0  0  0  0
 21  7  1  0  0  0  0
 21 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041200

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C1=NC(C2=CC=CO2)=C2NC3=CC=CC=C3C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H10N2O3/c19-16(20)12-8-10-9-4-1-2-5-11(9)17-14(10)15(18-12)13-6-3-7-21-13/h1-8,17H,(H,19,20)

> <INCHI_KEY>
LTTIWDNLMMLJOI-UHFFFAOYSA-N

> <FORMULA>
C16H10N2O3

> <MOLECULAR_WEIGHT>
278.2622

> <EXACT_MASS>
278.069142196

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.7853631298846

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.36

> <JCHEM_LOGP>
3.0099688276666665

> <ALOGPS_LOGS>
-3.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.878333501357158

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8978486234482936

> <JCHEM_PKA_STRONGEST_BASIC>
0.30514386047715525

> <JCHEM_POLAR_SURFACE_AREA>
79.11999999999999

> <JCHEM_REFRACTIVITY>
75.35459999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.42e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041200
     RDKit          3D
Dehydroxymethylflazine
 31 34  0  0  0  0  0  0  0  0999 V2000
    0.1169    4.4528   -1.5580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8282    3.6308   -1.5052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0980    3.9228   -1.9229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5592    2.2814   -0.9660 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6948    1.9092   -0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9852    0.6640   -0.0160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0677   -0.2496    0.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4482   -1.3728    0.5635 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7728   -1.1995    0.8320 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7610   -2.0047    1.3594 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0634   -1.5764    1.5332 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4195   -0.2916    1.1719 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4333    0.5195    0.6430 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1353    0.0798    0.4743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3229    0.1184   -0.3987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4246   -0.8454   -0.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7268   -0.6568   -0.7247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3862   -1.8441   -0.4730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4728   -2.7001    0.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3444   -2.0756    0.1154 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5288    1.3561   -0.8831 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6511    4.6002   -1.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5029    2.6189   -0.5717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0572   -2.2654    0.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4816   -3.0251    1.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8149   -2.2349    1.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4221    0.0967    1.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6784    1.5333    0.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1044    0.2663   -1.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4506   -1.9837   -0.6887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7074   -3.7247    0.3539 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  2  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 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 15 21  2  0
 21  4  1  0
 14  6  1  0
 20 16  1  0
 14  9  1  0
  3 22  1  0
  5 23  1  0
  8 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  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      -1.083   5.715   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.411  -0.695   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.362   2.235   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.083   4.175   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.382   6.191   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.810  -0.695   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.380   0.450   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.840   0.450   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.856   1.914   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.303  -0.374   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.382   3.699   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.364   1.914   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.858   2.235   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.727  -1.519   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       3.610   2.820   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0      -0.173   1.090   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0      -2.234  -1.199   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -0.251  -2.983   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.287   4.945   0.000  0.00  0.00           O+0
CONECT    1    2    4                                                       
CONECT    2    1    5                                                       
CONECT    3    6    7                                                       
CONECT    4    1    9                                                       
CONECT    5    2   11                                                       
CONECT    6    3   13                                                       
CONECT    7    3   21                                                       
CONECT    8   10   12                                                       
CONECT    9    4   10   11                                                  
CONECT   10    8    9   14                                                  
CONECT   11    5    9   17                                                  
CONECT   12    8   16   18                                                  
CONECT   13    6   15   21                                                  
CONECT   14   10   15   17                                                  
CONECT   15   13   14   18                                                  
CONECT   16   12   19   20                                                  
CONECT   17   11   14                                                       
CONECT   18   12   15                                                       
CONECT   19   16                                                            
CONECT   20   16                                                            
CONECT   21    7   13                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0041200
HETATM    1  O1  UNL     1       0.117   4.453  -1.558  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.828   3.631  -1.505  1.00  0.00           C  
HETATM    3  O2  UNL     1      -2.098   3.923  -1.923  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.559   2.281  -0.966  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.695   1.909  -0.524  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.985   0.664  -0.016  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.068  -0.250   0.042  1.00  0.00           C  
HETATM    8  N1  UNL     1       0.448  -1.373   0.563  1.00  0.00           N  
HETATM    9  C6  UNL     1       1.773  -1.199   0.832  1.00  0.00           C  
HETATM   10  C7  UNL     1       2.761  -2.005   1.359  1.00  0.00           C  
HETATM   11  C8  UNL     1       4.063  -1.576   1.533  1.00  0.00           C  
HETATM   12  C9  UNL     1       4.419  -0.292   1.172  1.00  0.00           C  
HETATM   13  C10 UNL     1       3.433   0.519   0.643  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.135   0.080   0.474  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.323   0.118  -0.399  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.425  -0.845  -0.335  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.727  -0.657  -0.725  1.00  0.00           C  
HETATM   18  C15 UNL     1      -4.386  -1.844  -0.473  1.00  0.00           C  
HETATM   19  C16 UNL     1      -3.473  -2.700   0.054  1.00  0.00           C  
HETATM   20  O3  UNL     1      -2.344  -2.076   0.115  1.00  0.00           O  
HETATM   21  N2  UNL     1      -1.529   1.356  -0.883  1.00  0.00           N  
HETATM   22  H1  UNL     1      -2.651   4.600  -1.416  1.00  0.00           H  
HETATM   23  H2  UNL     1       1.503   2.619  -0.572  1.00  0.00           H  
HETATM   24  H3  UNL     1      -0.057  -2.265   0.750  1.00  0.00           H  
HETATM   25  H4  UNL     1       2.482  -3.025   1.647  1.00  0.00           H  
HETATM   26  H5  UNL     1       4.815  -2.235   1.950  1.00  0.00           H  
HETATM   27  H6  UNL     1       5.422   0.097   1.285  1.00  0.00           H  
HETATM   28  H7  UNL     1       3.678   1.533   0.349  1.00  0.00           H  
HETATM   29  H8  UNL     1      -4.104   0.266  -1.142  1.00  0.00           H  
HETATM   30  H9  UNL     1      -5.451  -1.984  -0.689  1.00  0.00           H  
HETATM   31  H10 UNL     1      -3.707  -3.725   0.354  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   22
CONECT    4    5    5   21
CONECT    5    6   23
CONECT    6    7    7   14
CONECT    7    8   15
CONECT    8    9   24
CONECT    9   10   10   14
CONECT   10   11   25
CONECT   11   12   12   26
CONECT   12   13   27
CONECT   13   14   14   28
CONECT   15   16   21   21
CONECT   16   17   17   20
CONECT   17   18   29
CONECT   18   19   19   30
CONECT   19   20   31
END

HMDB0041200
     RDKit          3D
Dehydroxymethylflazine
 31 34  0  0  0  0  0  0  0  0999 V2000
    0.1169    4.4528   -1.5580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8282    3.6308   -1.5052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0980    3.9228   -1.9229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5592    2.2814   -0.9660 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6948    1.9092   -0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9852    0.6640   -0.0160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0677   -0.2496    0.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4482   -1.3728    0.5635 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7728   -1.1995    0.8320 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7610   -2.0047    1.3594 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0634   -1.5764    1.5332 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4195   -0.2916    1.1719 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4333    0.5195    0.6430 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1353    0.0798    0.4743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3229    0.1184   -0.3987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4246   -0.8454   -0.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7268   -0.6568   -0.7247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3862   -1.8441   -0.4730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4728   -2.7001    0.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3444   -2.0756    0.1154 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5288    1.3561   -0.8831 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6511    4.6002   -1.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5029    2.6189   -0.5717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0572   -2.2654    0.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4816   -3.0251    1.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8149   -2.2349    1.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4221    0.0967    1.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6784    1.5333    0.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1044    0.2663   -1.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4506   -1.9837   -0.6887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7074   -3.7247    0.3539 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  2  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 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 15 21  2  0
 21  4  1  0
 14  6  1  0
 20 16  1  0
 14  9  1  0
  3 22  1  0
  5 23  1  0
  8 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(2-Furanyl)-9H-pyrido[3,4-b]indole-3-carboxylic acid	HMDB
1-(2-Furyl)-9H-pyrido(3,4-b)indole-3-carboxylic acid	HMDB
1-(2-Furyl)pyrido(3,4-b)indole-3-carboxylic acid	HMDB
1-(Furan-2-yl)-9H-pyrido[3,4-b]indole-3-carboxylate	Generator

Chemical Formula

C₁₆H₁₀N₂O₃

Average Molecular Weight

278.2622

Monoisotopic Molecular Weight

278.069142196

IUPAC Name

1-(furan-2-yl)-9H-pyrido[3,4-b]indole-3-carboxylic acid

Traditional Name

1-(furan-2-yl)-9H-pyrido[3,4-b]indole-3-carboxylic acid

CAS Registry Number

76135-36-9

SMILES

OC(=O)C1=NC(C2=CC=CO2)=C2NC3=CC=CC=C3C2=C1

InChI Identifier

InChI=1S/C16H10N2O3/c19-16(20)12-8-10-9-4-1-2-5-11(9)17-14(10)15(18-12)13-6-3-7-21-13/h1-8,17H,(H,19,20)

InChI Key

LTTIWDNLMMLJOI-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
Indole
Indole or derivatives
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Pyridine
Benzenoid
Furan
Heteroaromatic compound
Pyrrole
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Azacycle
Carboxylic acid
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
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

Membrane (HMDB: HMDB0041200)
Cell membrane (HMDB: HMDB0041200)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041200)

Source

Exogenous

Exogenous (HMDB: HMDB0041200)

Food

Food (HMDB: HMDB0041200)

Fruit

Berry

Blackcurrant (FooDB: FOOD00155)

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0041200)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0041200)

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	2.77 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.074 g/L	ALOGPS
logP	3.36	ALOGPS
logP	3.01	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	3.9	ChemAxon
pKa (Strongest Basic)	0.31	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	79.12 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	75.35 m³·mol⁻¹	ChemAxon
Polarizability	28.79 Å³	ChemAxon
Number of Rings	4	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
DarkChem	[M+H]+	163.852	31661259
DarkChem	[M-H]-	163.456	31661259
DeepCCS	[M+H]+	165.447	30932474
DeepCCS	[M-H]-	163.089	30932474
DeepCCS	[M-2H]-	196.375	30932474
DeepCCS	[M+Na]+	171.602	30932474
AllCCS	[M+H]+	163.1	32859911
AllCCS	[M+H-H2O]+	159.2	32859911
AllCCS	[M+NH4]+	166.8	32859911
AllCCS	[M+Na]+	167.8	32859911
AllCCS	[M-H]-	164.5	32859911
AllCCS	[M+Na-2H]-	163.4	32859911
AllCCS	[M+HCOO]-	162.3	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. Predicted by Afia on May 17, 2022.	5.48 minutes	32390414
Predicted by Siyang on May 30, 2022	12.1416 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.49 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	51.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2219.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	355.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	129.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	212.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	289.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	499.0 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	493.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	73.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	769.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	445.5 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	1370.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	340.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	310.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	455.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	229.7 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	96.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dehydroxymethylflazine	OC(=O)C1=NC(C2=CC=CO2)=C2NC3=CC=CC=C3C2=C1	3780.4	Standard polar	33892256
Dehydroxymethylflazine	OC(=O)C1=NC(C2=CC=CO2)=C2NC3=CC=CC=C3C2=C1	2777.9	Standard non polar	33892256
Dehydroxymethylflazine	OC(=O)C1=NC(C2=CC=CO2)=C2NC3=CC=CC=C3C2=C1	2907.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dehydroxymethylflazine,1TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC2=C([NH]C3=CC=CC=C32)C(C2=CC=CO2)=N1	2959.1	Semi standard non polar	33892256
Dehydroxymethylflazine,1TMS,isomer #2	C[Si](C)(C)N1C2=CC=CC=C2C2=CC(C(=O)O)=NC(C3=CC=CO3)=C21	2881.4	Semi standard non polar	33892256
Dehydroxymethylflazine,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC2=C(C(C3=CC=CO3)=N1)N([Si](C)(C)C)C1=CC=CC=C21	2931.5	Semi standard non polar	33892256
Dehydroxymethylflazine,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC2=C(C(C3=CC=CO3)=N1)N([Si](C)(C)C)C1=CC=CC=C21	2781.7	Standard non polar	33892256
Dehydroxymethylflazine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=C([NH]C3=CC=CC=C32)C(C2=CC=CO2)=N1	3179.7	Semi standard non polar	33892256
Dehydroxymethylflazine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C2=CC=CC=C2C2=CC(C(=O)O)=NC(C3=CC=CO3)=C21	3115.7	Semi standard non polar	33892256
Dehydroxymethylflazine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=C(C(C3=CC=CO3)=N1)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C21	3294.2	Semi standard non polar	33892256
Dehydroxymethylflazine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=C(C(C3=CC=CO3)=N1)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C21	3109.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydroxymethylflazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0in9-1090000000-b8ac0b7cb73278776082	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydroxymethylflazine GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9074000000-1d23a98378bf7f3d140c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydroxymethylflazine 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 - Dehydroxymethylflazine 10V, Positive-QTOF	splash10-01t9-0090000000-7b485c676f0743e63e50	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroxymethylflazine 20V, Positive-QTOF	splash10-03fr-0090000000-f66fa3c938036add9497	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroxymethylflazine 40V, Positive-QTOF	splash10-0uyr-1190000000-ce52efd1d739765e5d50	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroxymethylflazine 10V, Negative-QTOF	splash10-004i-0090000000-a175ebd335accba2b0a6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroxymethylflazine 20V, Negative-QTOF	splash10-0560-0090000000-1e69fe205a1f4ffb906a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroxymethylflazine 40V, Negative-QTOF	splash10-0zgj-0090000000-19fdf8160961162351aa	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroxymethylflazine 10V, Negative-QTOF	splash10-001i-0090000000-5d8c1b0e4e119c794cb8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroxymethylflazine 20V, Negative-QTOF	splash10-001i-0090000000-5d8c1b0e4e119c794cb8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroxymethylflazine 40V, Negative-QTOF	splash10-000x-6970000000-2ca9cf1f74528a218f4c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroxymethylflazine 10V, Positive-QTOF	splash10-004i-0090000000-878b730bb42bf868e998	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroxymethylflazine 20V, Positive-QTOF	splash10-01t9-0090000000-cba2dc304071d202ee53	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroxymethylflazine 40V, Positive-QTOF	splash10-01s9-0290000000-3b2cf0f1615ae313628c	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021099

KNApSAcK ID

C00055012

Chemspider ID

4589673

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5488120

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1890421

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 Dehydroxymethylflazine (HMDB0041200)

MOL for HMDB0041200 (Dehydroxymethylflazine)

3D MOL for HMDB0041200 (Dehydroxymethylflazine)

3D SDF for HMDB0041200 (Dehydroxymethylflazine)

3D-SDF for HMDB0041200 (Dehydroxymethylflazine)

PDB for HMDB0041200 (Dehydroxymethylflazine)

3D PDB for HMDB0041200 (Dehydroxymethylflazine)

SMILES for HMDB0041200 (Dehydroxymethylflazine)

INCHI for HMDB0041200 (Dehydroxymethylflazine)

Structure for HMDB0041200 (Dehydroxymethylflazine)

3D Structure for HMDB0041200 (Dehydroxymethylflazine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra