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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:11:34 UTC

Update Date

2022-03-07 02:53:43 UTC

HMDB ID

HMDB0033459

Secondary Accession Numbers

HMDB33459

Metabolite Identification

Common Name

Flazine

Description

Flazine 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. Flazine has been detected, but not quantified in, a few different foods, such as beverages, herbs and spices, and soy beans (Glycine max). This could make flazine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Flazine.

Structure

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

HMDB0033459
     RDKit          3D
Flazine
 35 38  0  0  0  0  0  0  0  0999 V2000
   -2.9541    4.3242    0.3008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7390    4.0533    0.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8122    5.0723    0.3141 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3014    2.6728    0.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2530    1.6758    0.1576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8513    0.3711    0.0864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5097    0.0781    0.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4172   -1.2663   -0.0137 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6421   -1.8154   -0.0275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1297   -3.1242   -0.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4725   -3.3669   -0.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4058   -2.3598   -0.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9473   -1.0607    0.0378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5875   -0.8203    0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4331    1.0819    0.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8588    0.7401    0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9052    1.6388    0.0959 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0804    0.9234    0.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6884   -0.4060   -0.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6230   -1.5525   -0.0867 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8891   -1.8295   -1.4384 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3796   -0.4385   -0.0039 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0285    2.3576    0.1659 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1212    4.9316    0.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3154    1.9097    0.1819 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4809   -1.8015   -0.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4092   -3.9242   -0.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7950   -4.4144   -0.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4651   -2.6149   -0.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6463   -0.2361    0.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8444    2.7301    0.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1022    1.3033    0.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5738   -1.2608    0.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1692   -2.4588    0.3856 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4761   -1.1133   -1.7978 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
 20 21  1  0
 19 22  1  0
 15 23  2  0
 23  4  1  0
 14  6  1  0
 22 16  1  0
 14  9  1  0
  3 24  1  0
  5 25  1  0
  8 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 17 31  1  0
 18 32  1  0
 20 33  1  0
 20 34  1  0
 21 35  1  0
M  END


  Mrv0541 05061307082D          

 23 26  0  0  0  0            999 V2000
    3.7054   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5800    3.0617    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
    0.9694   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595    4.1012    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
    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
   -0.0925    4.7143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1966   -0.6422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -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
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  1  0  0  0  0
  9  5  2  0  0  0  0
  9  8  1  0  0  0  0
 10  3  2  0  0  0  0
 11  7  2  0  0  0  0
 11 10  1  0  0  0  0
 12  4  2  0  0  0  0
 12 10  1  0  0  0  0
 13  7  1  0  0  0  0
 14  6  2  0  0  0  0
 15 11  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  2  0  0  0  0
 17 13  1  0  0  0  0
 18 12  1  0  0  0  0
 18 15  1  0  0  0  0
 19 13  2  0  0  0  0
 19 16  1  0  0  0  0
 20  8  1  0  0  0  0
 21 17  1  0  0  0  0
 22 17  2  0  0  0  0
 23  9  1  0  0  0  0
 23 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033459

> <DATABASE_NAME>
hmdb

> <SMILES>
OCC1=CC=C(O1)C1=C2NC3=CC=CC=C3C2=CC(=N1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H12N2O4/c20-8-9-5-6-14(23-9)16-15-11(7-13(19-16)17(21)22)10-3-1-2-4-12(10)18-15/h1-7,18,20H,8H2,(H,21,22)

> <INCHI_KEY>
USBWYUYKHHILLZ-UHFFFAOYSA-N

> <FORMULA>
C17H12N2O4

> <MOLECULAR_WEIGHT>
308.2882

> <EXACT_MASS>
308.079706882

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
32.08935918608638

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[5-(hydroxymethyl)furan-2-yl]-9H-pyrido[3,4-b]indole-3-carboxylic acid

> <ALOGPS_LOGP>
2.64

> <JCHEM_LOGP>
2.1626201839999997

> <ALOGPS_LOGS>
-3.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.810302584183646

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.895044051693421

> <JCHEM_PKA_STRONGEST_BASIC>
0.27944288769682946

> <JCHEM_POLAR_SURFACE_AREA>
99.35000000000001

> <JCHEM_REFRACTIVITY>
82.04799999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.25e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[5-(hydroxymethyl)furan-2-yl]-9H-pyrido[3,4-b]indole-3-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033459
     RDKit          3D
Flazine
 35 38  0  0  0  0  0  0  0  0999 V2000
   -2.9541    4.3242    0.3008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7390    4.0533    0.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8122    5.0723    0.3141 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3014    2.6728    0.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2530    1.6758    0.1576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8513    0.3711    0.0864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5097    0.0781    0.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4172   -1.2663   -0.0137 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6421   -1.8154   -0.0275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1297   -3.1242   -0.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4725   -3.3669   -0.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4058   -2.3598   -0.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9473   -1.0607    0.0378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5875   -0.8203    0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4331    1.0819    0.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8588    0.7401    0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9052    1.6388    0.0959 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0804    0.9234    0.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6884   -0.4060   -0.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6230   -1.5525   -0.0867 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8891   -1.8295   -1.4384 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3796   -0.4385   -0.0039 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0285    2.3576    0.1659 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1212    4.9316    0.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3154    1.9097    0.1819 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4809   -1.8015   -0.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4092   -3.9242   -0.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7950   -4.4144   -0.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4651   -2.6149   -0.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6463   -0.2361    0.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8444    2.7301    0.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1022    1.3033    0.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5738   -1.2608    0.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1692   -2.4588    0.3856 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4761   -1.1133   -1.7978 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
 20 21  1  0
 19 22  1  0
 15 23  2  0
 23  4  1  0
 14  6  1  0
 22 16  1  0
 14  9  1  0
  3 24  1  0
  5 25  1  0
  8 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 17 31  1  0
 18 32  1  0
 20 33  1  0
 20 34  1  0
 21 35  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       6.917  -0.374   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.393   1.090   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.411  -0.695   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.362   2.235   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.083   5.715   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       1.810  -0.695   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.858   7.656   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.382   6.191   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.380   0.450   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.840   0.450   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.856   1.914   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.303  -0.374   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.382   3.699   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.364   1.914   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.858   2.235   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.727  -1.519   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       3.610   2.820   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0      -0.173   1.090   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0      -0.173   8.800   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.234  -1.199   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -0.251  -2.983   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.287   4.945   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1   10                                                       
CONECT    4    2   12                                                       
CONECT    5    6    9                                                       
CONECT    6    5   14                                                       
CONECT    7   11   13                                                       
CONECT    8    9   20                                                       
CONECT    9    5    8   23                                                  
CONECT   10    3   11   12                                                  
CONECT   11    7   10   15                                                  
CONECT   12    4   10   18                                                  
CONECT   13    7   17   19                                                  
CONECT   14    6   16   23                                                  
CONECT   15   11   16   18                                                  
CONECT   16   14   15   19                                                  
CONECT   17   13   21   22                                                  
CONECT   18   12   15                                                       
CONECT   19   13   16                                                       
CONECT   20    8                                                            
CONECT   21   17                                                            
CONECT   22   17                                                            
CONECT   23    9   14                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0033459
HETATM    1  O1  UNL     1      -2.954   4.324   0.301  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.739   4.053   0.273  1.00  0.00           C  
HETATM    3  O2  UNL     1      -0.812   5.072   0.314  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.301   2.673   0.197  1.00  0.00           C  
HETATM    5  C3  UNL     1      -2.253   1.676   0.158  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.851   0.371   0.086  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.510   0.078   0.056  1.00  0.00           C  
HETATM    8  N1  UNL     1      -0.417  -1.266  -0.014  1.00  0.00           N  
HETATM    9  C6  UNL     1      -1.642  -1.815  -0.027  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.130  -3.124  -0.089  1.00  0.00           C  
HETATM   11  C8  UNL     1      -3.472  -3.367  -0.085  1.00  0.00           C  
HETATM   12  C9  UNL     1      -4.406  -2.360  -0.023  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.947  -1.061   0.038  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.587  -0.820   0.034  1.00  0.00           C  
HETATM   15  C12 UNL     1       0.433   1.082   0.096  1.00  0.00           C  
HETATM   16  C13 UNL     1       1.859   0.740   0.062  1.00  0.00           C  
HETATM   17  C14 UNL     1       2.905   1.639   0.096  1.00  0.00           C  
HETATM   18  C15 UNL     1       4.080   0.923   0.046  1.00  0.00           C  
HETATM   19  C16 UNL     1       3.688  -0.406  -0.017  1.00  0.00           C  
HETATM   20  C17 UNL     1       4.623  -1.553  -0.087  1.00  0.00           C  
HETATM   21  O3  UNL     1       4.889  -1.829  -1.438  1.00  0.00           O  
HETATM   22  O4  UNL     1       2.380  -0.439  -0.004  1.00  0.00           O  
HETATM   23  N2  UNL     1       0.028   2.358   0.166  1.00  0.00           N  
HETATM   24  H1  UNL     1       0.121   4.932   0.712  1.00  0.00           H  
HETATM   25  H2  UNL     1      -3.315   1.910   0.182  1.00  0.00           H  
HETATM   26  H3  UNL     1       0.481  -1.802  -0.051  1.00  0.00           H  
HETATM   27  H4  UNL     1      -1.409  -3.924  -0.138  1.00  0.00           H  
HETATM   28  H5  UNL     1      -3.795  -4.414  -0.135  1.00  0.00           H  
HETATM   29  H6  UNL     1      -5.465  -2.615  -0.024  1.00  0.00           H  
HETATM   30  H7  UNL     1      -4.646  -0.236   0.088  1.00  0.00           H  
HETATM   31  H8  UNL     1       2.844   2.730   0.152  1.00  0.00           H  
HETATM   32  H9  UNL     1       5.102   1.303   0.053  1.00  0.00           H  
HETATM   33  H10 UNL     1       5.574  -1.261   0.434  1.00  0.00           H  
HETATM   34  H11 UNL     1       4.169  -2.459   0.386  1.00  0.00           H  
HETATM   35  H12 UNL     1       5.476  -1.113  -1.798  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   24
CONECT    4    5    5   23
CONECT    5    6   25
CONECT    6    7    7   14
CONECT    7    8   15
CONECT    8    9   26
CONECT    9   10   10   14
CONECT   10   11   27
CONECT   11   12   12   28
CONECT   12   13   29
CONECT   13   14   14   30
CONECT   15   16   23   23
CONECT   16   17   17   22
CONECT   17   18   31
CONECT   18   19   19   32
CONECT   19   20   22
CONECT   20   21   33   34
CONECT   21   35
END

HMDB0033459
     RDKit          3D
Flazine
 35 38  0  0  0  0  0  0  0  0999 V2000
   -2.9541    4.3242    0.3008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7390    4.0533    0.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8122    5.0723    0.3141 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3014    2.6728    0.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2530    1.6758    0.1576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8513    0.3711    0.0864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5097    0.0781    0.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4172   -1.2663   -0.0137 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6421   -1.8154   -0.0275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1297   -3.1242   -0.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4725   -3.3669   -0.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4058   -2.3598   -0.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9473   -1.0607    0.0378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5875   -0.8203    0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4331    1.0819    0.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8588    0.7401    0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9052    1.6388    0.0959 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0804    0.9234    0.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6884   -0.4060   -0.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6230   -1.5525   -0.0867 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8891   -1.8295   -1.4384 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3796   -0.4385   -0.0039 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0285    2.3576    0.1659 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1212    4.9316    0.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3154    1.9097    0.1819 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4809   -1.8015   -0.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4092   -3.9242   -0.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7950   -4.4144   -0.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4651   -2.6149   -0.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6463   -0.2361    0.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8444    2.7301    0.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1022    1.3033    0.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5738   -1.2608    0.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1692   -2.4588    0.3856 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4761   -1.1133   -1.7978 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
 20 21  1  0
 19 22  1  0
 15 23  2  0
 23  4  1  0
 14  6  1  0
 22 16  1  0
 14  9  1  0
  3 24  1  0
  5 25  1  0
  8 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 17 31  1  0
 18 32  1  0
 20 33  1  0
 20 34  1  0
 21 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-[5-(Hydroxymethyl)-2-furanyl]-9H-pyrido[3,4-b]indole-3-carboxylic acid, 9ci	HMDB
Flazin	HMDB
1-[5-(Hydroxymethyl)furan-2-yl]-9H-pyrido[3,4-b]indole-3-carboxylate	Generator
Flazine	MeSH

Chemical Formula

C₁₇H₁₂N₂O₄

Average Molecular Weight

308.2882

Monoisotopic Molecular Weight

308.079706882

IUPAC Name

1-[5-(hydroxymethyl)furan-2-yl]-9H-pyrido[3,4-b]indole-3-carboxylic acid

Traditional Name

1-[5-(hydroxymethyl)furan-2-yl]-9H-pyrido[3,4-b]indole-3-carboxylic acid

CAS Registry Number

100041-05-2

SMILES

OCC1=CC=C(O1)C1=C2NC3=CC=CC=C3C2=CC(=N1)C(O)=O

InChI Identifier

InChI=1S/C17H12N2O4/c20-8-9-5-6-14(23-9)16-15-11(7-13(19-16)17(21)22)10-3-1-2-4-12(10)18-15/h1-7,18,20H,8H2,(H,21,22)

InChI Key

USBWYUYKHHILLZ-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
Benzenoid
Pyridine
Heteroaromatic compound
Pyrrole
Furan
Azacycle
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organonitrogen compound
Organooxygen compound
Alcohol
Organic oxygen compound
Primary alcohol
Organic nitrogen compound
Organopnictogen compound
Aromatic alcohol
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

harmala alkaloid (CHEBI:69443 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0033459)
Cell membrane (HMDB: HMDB0033459)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033459)

Source

Exogenous

Exogenous (HMDB: HMDB0033459)

Food

Food (HMDB: HMDB0033459)

Soy

Soy bean (FooDB: FOOD00085)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Beverage

Beverages (FooDB: FOOD00870)

Endogenous

Plant

Plant (HMDB: HMDB0033459)
Glycine Max (HMDB: HMDB0033459)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033459)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	231 - 233 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	11.26 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	0.12 g/L	ALOGPS
logP	2.64	ALOGPS
logP	2.16	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	3.9	ChemAxon
pKa (Strongest Basic)	0.28	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	99.35 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	82.05 m³·mol⁻¹	ChemAxon
Polarizability	32.09 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]+	172.982	31661259
DarkChem	[M-H]-	172.464	31661259
DeepCCS	[M+H]+	170.009	30932474
DeepCCS	[M-H]-	167.651	30932474
DeepCCS	[M-2H]-	200.913	30932474
DeepCCS	[M+Na]+	176.14	30932474
AllCCS	[M+H]+	172.1	32859911
AllCCS	[M+H-H2O]+	168.5	32859911
AllCCS	[M+NH4]+	175.5	32859911
AllCCS	[M+Na]+	176.4	32859911
AllCCS	[M-H]-	173.3	32859911
AllCCS	[M+Na-2H]-	172.4	32859911
AllCCS	[M+HCOO]-	171.6	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.	5.74 minutes	32390414
Predicted by Siyang on May 30, 2022	11.7368 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.92 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	60.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1604.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	291.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	115.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	188.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	198.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	414.4 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	396.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	71.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	714.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	426.9 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	1391.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	307.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	246.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	453.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	185.3 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	124.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Flazine	OCC1=CC=C(O1)C1=C2NC3=CC=CC=C3C2=CC(=N1)C(O)=O	4039.2	Standard polar	33892256
Flazine	OCC1=CC=C(O1)C1=C2NC3=CC=CC=C3C2=CC(=N1)C(O)=O	3005.9	Standard non polar	33892256
Flazine	OCC1=CC=C(O1)C1=C2NC3=CC=CC=C3C2=CC(=N1)C(O)=O	3348.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Flazine,1TMS,isomer #1	C[Si](C)(C)OCC1=CC=C(C2=NC(C(=O)O)=CC3=C2[NH]C2=CC=CC=C23)O1	3292.6	Semi standard non polar	33892256
Flazine,1TMS,isomer #2	C[Si](C)(C)OC(=O)C1=CC2=C([NH]C3=CC=CC=C32)C(C2=CC=C(CO)O2)=N1	3282.6	Semi standard non polar	33892256
Flazine,1TMS,isomer #3	C[Si](C)(C)N1C2=CC=CC=C2C2=CC(C(=O)O)=NC(C3=CC=C(CO)O3)=C21	3267.1	Semi standard non polar	33892256
Flazine,2TMS,isomer #1	C[Si](C)(C)OCC1=CC=C(C2=NC(C(=O)O[Si](C)(C)C)=CC3=C2[NH]C2=CC=CC=C23)O1	3304.3	Semi standard non polar	33892256
Flazine,2TMS,isomer #2	C[Si](C)(C)OCC1=CC=C(C2=NC(C(=O)O)=CC3=C2N([Si](C)(C)C)C2=CC=CC=C32)O1	3239.6	Semi standard non polar	33892256
Flazine,2TMS,isomer #3	C[Si](C)(C)OC(=O)C1=CC2=C(C(C3=CC=C(CO)O3)=N1)N([Si](C)(C)C)C1=CC=CC=C21	3250.7	Semi standard non polar	33892256
Flazine,3TMS,isomer #1	C[Si](C)(C)OCC1=CC=C(C2=NC(C(=O)O[Si](C)(C)C)=CC3=C2N([Si](C)(C)C)C2=CC=CC=C32)O1	3248.8	Semi standard non polar	33892256
Flazine,3TMS,isomer #1	C[Si](C)(C)OCC1=CC=C(C2=NC(C(=O)O[Si](C)(C)C)=CC3=C2N([Si](C)(C)C)C2=CC=CC=C32)O1	3160.3	Standard non polar	33892256
Flazine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=CC=C(C2=NC(C(=O)O)=CC3=C2[NH]C2=CC=CC=C23)O1	3516.5	Semi standard non polar	33892256
Flazine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=C([NH]C3=CC=CC=C32)C(C2=CC=C(CO)O2)=N1	3503.4	Semi standard non polar	33892256
Flazine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C2=CC=CC=C2C2=CC(C(=O)O)=NC(C3=CC=C(CO)O3)=C21	3514.2	Semi standard non polar	33892256
Flazine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=CC=C(C2=NC(C(=O)O[Si](C)(C)C(C)(C)C)=CC3=C2[NH]C2=CC=CC=C23)O1	3709.2	Semi standard non polar	33892256
Flazine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC1=CC=C(C2=NC(C(=O)O)=CC3=C2N([Si](C)(C)C(C)(C)C)C2=CC=CC=C32)O1	3680.6	Semi standard non polar	33892256
Flazine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=C(C(C3=CC=C(CO)O3)=N1)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C21	3655.6	Semi standard non polar	33892256
Flazine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=CC=C(C2=NC(C(=O)O[Si](C)(C)C(C)(C)C)=CC3=C2N([Si](C)(C)C(C)(C)C)C2=CC=CC=C32)O1	3790.3	Semi standard non polar	33892256
Flazine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=CC=C(C2=NC(C(=O)O[Si](C)(C)C(C)(C)C)=CC3=C2N([Si](C)(C)C(C)(C)C)C2=CC=CC=C32)O1	3656.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Flazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-01p6-0090000000-0deb89f70a9d79179146	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Flazine GC-MS (2 TMS) - 70eV, Positive	splash10-01w0-7009300000-ecca7acccf29e0231cd1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Flazine 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 - Flazine 10V, Positive-QTOF	splash10-0a4l-0095000000-1263d337948d7d371f36	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flazine 20V, Positive-QTOF	splash10-03dl-0191000000-598b7ee60742ff605b5e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flazine 40V, Positive-QTOF	splash10-014i-1190000000-cff9b067455a02de6a04	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flazine 10V, Negative-QTOF	splash10-0a4i-0079000000-5e0da435e9075614bcf4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flazine 20V, Negative-QTOF	splash10-0bwi-0091000000-f18ea79c8ce1382efea8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flazine 40V, Negative-QTOF	splash10-0lec-2190000000-5e89b4135dd0b11d55dc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flazine 10V, Positive-QTOF	splash10-0a4i-0019000000-fa17a10e8a34d55baebc	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flazine 20V, Positive-QTOF	splash10-0a4l-0198000000-3c7bc5bdeed93fc7e77b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flazine 40V, Positive-QTOF	splash10-01p9-0190000000-54a40d43b14592b5553b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flazine 10V, Negative-QTOF	splash10-0a59-0098000000-d4f29a6ad1adfa42a238	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flazine 20V, Negative-QTOF	splash10-0bu0-0094000000-8fe6fad8f6880ecc505d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flazine 40V, Negative-QTOF	splash10-00lu-1790000000-7e9c1f226e8cbbbb8f65	2021-09-24	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

FDB011500

KNApSAcK ID

C00050461

Chemspider ID

4526683

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5377686

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1835811

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 Flazine (HMDB0033459)

MOL for HMDB0033459 (Flazine)

3D MOL for HMDB0033459 (Flazine)

3D SDF for HMDB0033459 (Flazine)

3D-SDF for HMDB0033459 (Flazine)

PDB for HMDB0033459 (Flazine)

3D PDB for HMDB0033459 (Flazine)

SMILES for HMDB0033459 (Flazine)

INCHI for HMDB0033459 (Flazine)

Structure for HMDB0033459 (Flazine)

3D Structure for HMDB0033459 (Flazine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra