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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:11:28 UTC

Update Date

2022-03-07 02:53:43 UTC

HMDB ID

HMDB0033457

Secondary Accession Numbers

HMDB33457

Metabolite Identification

Common Name

Flazine methyl ether

Description

Flazine methyl ether, also known as proadifen or SK and F 525 a, 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 methyl ether is found, on average, in the highest concentration within blackcurrants (Ribes nigrum). Flazine methyl ether has also been detected, but not quantified in, fruits. This could make flazine methyl ether a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Flazine methyl ether.

Structure

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

HMDB0033457
     RDKit          3D
Flazine methyl ether
 38 41  0  0  0  0  0  0  0  0999 V2000
    5.7077   -0.7499   -0.6425 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6050    0.3569    0.1955 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8874    1.3758   -0.3904 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914    0.9281   -0.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0618    0.3978   -1.8880 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6918    0.1402   -1.7206 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3607    0.5229   -0.4697 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1290    0.5272    0.3111 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0644    1.2539    1.4633 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0119    1.3823    2.2263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0406    2.1726    3.4526 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0284    2.7535    3.7817 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1514    2.3057    4.2393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1609    0.7314    1.8297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1966   -0.0344    0.6729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0171   -0.1154   -0.0714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3314   -0.9181   -1.1009 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6236   -1.3233   -1.0263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4205   -2.1289   -1.8094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7539   -2.3745   -1.4751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3041   -1.8133   -0.3487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5153   -1.0049    0.4429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1993   -0.7765    0.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4993    0.9914    0.0790 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6974   -1.1388   -0.8835 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2269   -0.4080   -1.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3153   -1.5441   -0.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3743    1.7525   -1.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8159    2.1996    0.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5834    0.1822   -2.8024 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0360   -0.2619   -2.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3081    3.2110    4.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0944    0.7842    2.4002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7108   -1.2321   -1.8675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0249   -2.5778   -2.6871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3860   -2.9984   -2.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3531   -1.9931   -0.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9724   -0.5761    1.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
  7 24  1  0
 24  4  1  0
 16  8  1  0
 23 18  1  0
 23 15  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  5 30  1  0
  6 31  1  0
 13 32  1  0
 14 33  1  0
 17 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
 22 38  1  0
M  END


  Mrv0541 05061307082D          

 24 27  0  0  0  0            999 V2000
    0.1624    5.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
   -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
   -0.0925    4.7143    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
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  7  6  1  0  0  0  0
 10  6  2  0  0  0  0
 10  9  1  0  0  0  0
 11  4  2  0  0  0  0
 12  8  2  0  0  0  0
 12 11  1  0  0  0  0
 13  5  2  0  0  0  0
 13 11  1  0  0  0  0
 14  8  1  0  0  0  0
 15  7  2  0  0  0  0
 16 12  1  0  0  0  0
 17 15  1  0  0  0  0
 17 16  2  0  0  0  0
 18 14  1  0  0  0  0
 19 13  1  0  0  0  0
 19 16  1  0  0  0  0
 20 14  2  0  0  0  0
 20 17  1  0  0  0  0
 21 18  1  0  0  0  0
 22 18  2  0  0  0  0
 23  1  1  0  0  0  0
 23  9  1  0  0  0  0
 24 10  1  0  0  0  0
 24 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033457

> <DATABASE_NAME>
hmdb

> <SMILES>
COCC1=CC=C(O1)C1=C2NC3=CC=CC=C3C2=CC(=N1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H14N2O4/c1-23-9-10-6-7-15(24-10)17-16-12(8-14(20-17)18(21)22)11-4-2-3-5-13(11)19-16/h2-8,19H,9H2,1H3,(H,21,22)

> <INCHI_KEY>
DTVVELLZKPXBHH-UHFFFAOYSA-N

> <FORMULA>
C18H14N2O4

> <MOLECULAR_WEIGHT>
322.3148

> <EXACT_MASS>
322.095356946

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
34.325414803713684

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.23

> <JCHEM_LOGP>
2.8057466876666664

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.868772367209985

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.895036074921488

> <JCHEM_PKA_STRONGEST_BASIC>
0.2793821659274064

> <JCHEM_POLAR_SURFACE_AREA>
88.35

> <JCHEM_REFRACTIVITY>
86.7992

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.10e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033457
     RDKit          3D
Flazine methyl ether
 38 41  0  0  0  0  0  0  0  0999 V2000
    5.7077   -0.7499   -0.6425 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6050    0.3569    0.1955 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8874    1.3758   -0.3904 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914    0.9281   -0.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0618    0.3978   -1.8880 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6918    0.1402   -1.7206 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3607    0.5229   -0.4697 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1290    0.5272    0.3111 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0644    1.2539    1.4633 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0119    1.3823    2.2263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0406    2.1726    3.4526 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0284    2.7535    3.7817 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1514    2.3057    4.2393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1609    0.7314    1.8297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1966   -0.0344    0.6729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0171   -0.1154   -0.0714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3314   -0.9181   -1.1009 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6236   -1.3233   -1.0263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4205   -2.1289   -1.8094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7539   -2.3745   -1.4751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3041   -1.8133   -0.3487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5153   -1.0049    0.4429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1993   -0.7765    0.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4993    0.9914    0.0790 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6974   -1.1388   -0.8835 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2269   -0.4080   -1.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3153   -1.5441   -0.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3743    1.7525   -1.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8159    2.1996    0.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5834    0.1822   -2.8024 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0360   -0.2619   -2.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3081    3.2110    4.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0944    0.7842    2.4002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7108   -1.2321   -1.8675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0249   -2.5778   -2.6871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3860   -2.9984   -2.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3531   -1.9931   -0.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9724   -0.5761    1.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
  7 24  1  0
 24  4  1  0
 16  8  1  0
 23 18  1  0
 23 15  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  5 30  1  0
  6 31  1  0
 13 32  1  0
 14 33  1  0
 17 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
 22 38  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       0.303  10.265   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.917  -0.374   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.393   1.090   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   5.715   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.083   4.175   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       0.858   7.656   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.382   6.191   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.380   0.450   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.840   0.450   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.856   1.914   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.303  -0.374   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.382   3.699   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.364   1.914   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.858   2.235   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.727  -1.519   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       3.610   2.820   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0      -0.173   1.090   0.000  0.00  0.00           N+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      -0.173   8.800   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       1.287   4.945   0.000  0.00  0.00           O+0
CONECT    1   23                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2   11                                                       
CONECT    5    3   13                                                       
CONECT    6    7   10                                                       
CONECT    7    6   15                                                       
CONECT    8   12   14                                                       
CONECT    9   10   23                                                       
CONECT   10    6    9   24                                                  
CONECT   11    4   12   13                                                  
CONECT   12    8   11   16                                                  
CONECT   13    5   11   19                                                  
CONECT   14    8   18   20                                                  
CONECT   15    7   17   24                                                  
CONECT   16   12   17   19                                                  
CONECT   17   15   16   20                                                  
CONECT   18   14   21   22                                                  
CONECT   19   13   16                                                       
CONECT   20   14   17                                                       
CONECT   21   18                                                            
CONECT   22   18                                                            
CONECT   23    1    9                                                       
CONECT   24   10   15                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0033457
HETATM    1  C1  UNL     1       5.708  -0.750  -0.642  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.605   0.357   0.195  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.887   1.376  -0.390  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.491   0.928  -0.721  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.062   0.398  -1.888  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.692   0.140  -1.721  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.361   0.523  -0.470  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.129   0.527   0.311  1.00  0.00           C  
HETATM    9  N1  UNL     1       0.064   1.254   1.463  1.00  0.00           N  
HETATM   10  C8  UNL     1      -1.012   1.382   2.226  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.041   2.173   3.453  1.00  0.00           C  
HETATM   12  O2  UNL     1       0.028   2.753   3.782  1.00  0.00           O  
HETATM   13  O3  UNL     1      -2.151   2.306   4.239  1.00  0.00           O  
HETATM   14  C10 UNL     1      -2.161   0.731   1.830  1.00  0.00           C  
HETATM   15  C11 UNL     1      -2.197  -0.034   0.673  1.00  0.00           C  
HETATM   16  C12 UNL     1      -1.017  -0.115  -0.071  1.00  0.00           C  
HETATM   17  N2  UNL     1      -1.331  -0.918  -1.101  1.00  0.00           N  
HETATM   18  C13 UNL     1      -2.624  -1.323  -1.026  1.00  0.00           C  
HETATM   19  C14 UNL     1      -3.421  -2.129  -1.809  1.00  0.00           C  
HETATM   20  C15 UNL     1      -4.754  -2.374  -1.475  1.00  0.00           C  
HETATM   21  C16 UNL     1      -5.304  -1.813  -0.349  1.00  0.00           C  
HETATM   22  C17 UNL     1      -4.515  -1.005   0.443  1.00  0.00           C  
HETATM   23  C18 UNL     1      -3.199  -0.777   0.092  1.00  0.00           C  
HETATM   24  O4  UNL     1       2.499   0.991   0.079  1.00  0.00           O  
HETATM   25  H1  UNL     1       4.697  -1.139  -0.884  1.00  0.00           H  
HETATM   26  H2  UNL     1       6.227  -0.408  -1.586  1.00  0.00           H  
HETATM   27  H3  UNL     1       6.315  -1.544  -0.173  1.00  0.00           H  
HETATM   28  H4  UNL     1       5.374   1.753  -1.303  1.00  0.00           H  
HETATM   29  H5  UNL     1       4.816   2.200   0.358  1.00  0.00           H  
HETATM   30  H6  UNL     1       3.583   0.182  -2.802  1.00  0.00           H  
HETATM   31  H7  UNL     1       1.036  -0.262  -2.453  1.00  0.00           H  
HETATM   32  H8  UNL     1      -2.308   3.211   4.691  1.00  0.00           H  
HETATM   33  H9  UNL     1      -3.094   0.784   2.400  1.00  0.00           H  
HETATM   34  H10 UNL     1      -0.711  -1.232  -1.867  1.00  0.00           H  
HETATM   35  H11 UNL     1      -3.025  -2.578  -2.687  1.00  0.00           H  
HETATM   36  H12 UNL     1      -5.386  -2.998  -2.074  1.00  0.00           H  
HETATM   37  H13 UNL     1      -6.353  -1.993  -0.066  1.00  0.00           H  
HETATM   38  H14 UNL     1      -4.972  -0.576   1.323  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4   28   29
CONECT    4    5    5   24
CONECT    5    6   30
CONECT    6    7    7   31
CONECT    7    8   24
CONECT    8    9    9   16
CONECT    9   10
CONECT   10   11   14   14
CONECT   11   12   12   13
CONECT   13   32
CONECT   14   15   33
CONECT   15   16   16   23
CONECT   16   17
CONECT   17   18   34
CONECT   18   19   19   23
CONECT   19   20   35
CONECT   20   21   21   36
CONECT   21   22   37
CONECT   22   23   23   38
END

HMDB0033457
     RDKit          3D
Flazine methyl ether
 38 41  0  0  0  0  0  0  0  0999 V2000
    5.7077   -0.7499   -0.6425 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6050    0.3569    0.1955 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8874    1.3758   -0.3904 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914    0.9281   -0.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0618    0.3978   -1.8880 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6918    0.1402   -1.7206 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3607    0.5229   -0.4697 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1290    0.5272    0.3111 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0644    1.2539    1.4633 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0119    1.3823    2.2263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0406    2.1726    3.4526 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0284    2.7535    3.7817 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1514    2.3057    4.2393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1609    0.7314    1.8297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1966   -0.0344    0.6729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0171   -0.1154   -0.0714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3314   -0.9181   -1.1009 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6236   -1.3233   -1.0263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4205   -2.1289   -1.8094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7539   -2.3745   -1.4751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3041   -1.8133   -0.3487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5153   -1.0049    0.4429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1993   -0.7765    0.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4993    0.9914    0.0790 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6974   -1.1388   -0.8835 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2269   -0.4080   -1.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3153   -1.5441   -0.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3743    1.7525   -1.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8159    2.1996    0.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5834    0.1822   -2.8024 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0360   -0.2619   -2.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3081    3.2110    4.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0944    0.7842    2.4002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7108   -1.2321   -1.8675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0249   -2.5778   -2.6871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3860   -2.9984   -2.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3531   -1.9931   -0.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9724   -0.5761    1.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
  7 24  1  0
 24  4  1  0
 16  8  1  0
 23 18  1  0
 23 15  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  5 30  1  0
  6 31  1  0
 13 32  1  0
 14 33  1  0
 17 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
 22 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
SK And F 525 a	MeSH
SK And F-525-a	MeSH
Proadifen	MeSH
Propyladiphenin	MeSH
SK And F525a	MeSH
SKF-525a	MeSH
Acetate, diethylaminoethyldiphenylpropyl	MeSH
Diethylaminoethyldiphenylpropyl acetate	MeSH
Hydrochloride, proadifen	MeSH
SK 525a	MeSH
SKF-525-a	MeSH
Proadifen hydrochloride	MeSH
SK-525a	MeSH
SKF 525 a	MeSH
SKF525a	MeSH
2-(diethylamino)Ethyl 2,2-diphenylpentanoate	HMDB
2-(diethylamino)Ethyl 2,2-diphenylvalerate hydrochloride	HMDB
2-Diethylaminoethyl propyldiphenylacetate	HMDB
2-Diethylaminoethyl-2,2-diphenylvalerate	HMDB
Acetic acid, propyldiphenyl-, 2-(diethylamino)ethyl ester	HMDB
BCTB	HMDB
Ethyl aprofen	HMDB
O-Methylflazine	HMDB
Proadifene	HMDB
Proadifeno	HMDB
Proadifenum	HMDB
SKF-525a Hydrochloride	HMDB
Valeric acid, 2,2-diphenyl-, 2-(diethylamino)ethyl ester	HMDB
1-[5-(Methoxymethyl)furan-2-yl]-9H-pyrido[3,4-b]indole-3-carboxylate	Generator

Chemical Formula

C₁₈H₁₄N₂O₄

Average Molecular Weight

322.3148

Monoisotopic Molecular Weight

322.095356946

IUPAC Name

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

Traditional Name

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

CAS Registry Number

159898-11-0

SMILES

COCC1=CC=C(O1)C1=C2NC3=CC=CC=C3C2=CC(=N1)C(O)=O

InChI Identifier

InChI=1S/C18H14N2O4/c1-23-9-10-6-7-15(24-10)17-16-12(8-14(20-17)18(21)22)11-4-2-3-5-13(11)19-16/h2-8,19H,9H2,1H3,(H,21,22)

InChI Key

DTVVELLZKPXBHH-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
Furan
Pyrrole
Azacycle
Oxacycle
Dialkyl ether
Ether
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Organic nitrogen compound
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organic oxide
Organic oxygen compound
Organopnictogen 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: HMDB0033457)
Cell membrane (HMDB: HMDB0033457)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033457)

Source

Exogenous

Exogenous (HMDB: HMDB0033457)

Food

Food (HMDB: HMDB0033457)

Fruit

Berry

Blackcurrant (FooDB: FOOD00155)

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0033457)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033457)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	199 - 200 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	2.35 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	0.061 g/L	ALOGPS
logP	3.23	ALOGPS
logP	2.81	ChemAxon
logS	-3.7	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	2	ChemAxon
Polar Surface Area	88.35 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	86.8 m³·mol⁻¹	ChemAxon
Polarizability	34.33 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]+	175.036	31661259
DarkChem	[M-H]-	177.117	31661259
DeepCCS	[M+H]+	176.029	30932474
DeepCCS	[M-H]-	173.671	30932474
DeepCCS	[M-2H]-	207.224	30932474
DeepCCS	[M+Na]+	182.451	30932474
AllCCS	[M+H]+	176.1	32859911
AllCCS	[M+H-H2O]+	172.6	32859911
AllCCS	[M+NH4]+	179.3	32859911
AllCCS	[M+Na]+	180.3	32859911
AllCCS	[M-H]-	178.1	32859911
AllCCS	[M+Na-2H]-	177.4	32859911
AllCCS	[M+HCOO]-	176.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Flazine methyl ether	COCC1=CC=C(O1)C1=C2NC3=CC=CC=C3C2=CC(=N1)C(O)=O	3952.9	Standard polar	33892256
Flazine methyl ether	COCC1=CC=C(O1)C1=C2NC3=CC=CC=C3C2=CC(=N1)C(O)=O	3048.5	Standard non polar	33892256
Flazine methyl ether	COCC1=CC=C(O1)C1=C2NC3=CC=CC=C3C2=CC(=N1)C(O)=O	3238.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Flazine methyl ether,1TMS,isomer #1	COCC1=CC=C(C2=NC(C(=O)O[Si](C)(C)C)=CC3=C2[NH]C2=CC=CC=C23)O1	3203.8	Semi standard non polar	33892256
Flazine methyl ether,1TMS,isomer #2	COCC1=CC=C(C2=NC(C(=O)O)=CC3=C2N([Si](C)(C)C)C2=CC=CC=C32)O1	3171.2	Semi standard non polar	33892256
Flazine methyl ether,2TMS,isomer #1	COCC1=CC=C(C2=NC(C(=O)O[Si](C)(C)C)=CC3=C2N([Si](C)(C)C)C2=CC=CC=C32)O1	3164.9	Semi standard non polar	33892256
Flazine methyl ether,2TMS,isomer #1	COCC1=CC=C(C2=NC(C(=O)O[Si](C)(C)C)=CC3=C2N([Si](C)(C)C)C2=CC=CC=C32)O1	3032.4	Standard non polar	33892256
Flazine methyl ether,1TBDMS,isomer #1	COCC1=CC=C(C2=NC(C(=O)O[Si](C)(C)C(C)(C)C)=CC3=C2[NH]C2=CC=CC=C23)O1	3423.3	Semi standard non polar	33892256
Flazine methyl ether,1TBDMS,isomer #2	COCC1=CC=C(C2=NC(C(=O)O)=CC3=C2N([Si](C)(C)C(C)(C)C)C2=CC=CC=C32)O1	3398.1	Semi standard non polar	33892256
Flazine methyl ether,2TBDMS,isomer #1	COCC1=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	3525.8	Semi standard non polar	33892256
Flazine methyl ether,2TBDMS,isomer #1	COCC1=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	3385.6	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Flazine methyl ether GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ffy-1191000000-6e9180f8f8ef299e14db	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Flazine methyl ether GC-MS (1 TMS) - 70eV, Positive	splash10-00b9-8039000000-0e2908375d652444c3e7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Flazine methyl ether 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 methyl ether 10V, Positive-QTOF	splash10-05fr-0049000000-a0baa21fab01a433d56f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flazine methyl ether 20V, Positive-QTOF	splash10-004i-0193000000-98926adc0579c26cccd4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flazine methyl ether 40V, Positive-QTOF	splash10-014j-2090000000-12a5b7da081d667bc5c3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flazine methyl ether 10V, Negative-QTOF	splash10-00di-0049000000-bd5865221dbb1cb0ec7d	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flazine methyl ether 20V, Negative-QTOF	splash10-00fr-1094000000-680b32a2b9650aa78868	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flazine methyl ether 40V, Negative-QTOF	splash10-0mlv-2090000000-3e18312aabfa3474be73	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flazine methyl ether 10V, Negative-QTOF	splash10-00b9-0093000000-85c8b5fcfa754a604b22	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flazine methyl ether 20V, Negative-QTOF	splash10-0032-0090000000-ca8ec19d93778becae6f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flazine methyl ether 40V, Negative-QTOF	splash10-003s-0490000000-84ddfaded7f431940ed9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flazine methyl ether 10V, Positive-QTOF	splash10-00di-0019000000-2cc40adb6ad968451ad6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flazine methyl ether 20V, Positive-QTOF	splash10-00fr-0098000000-213233d9b4fce0029415	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flazine methyl ether 40V, Positive-QTOF	splash10-01p2-0090000000-ba31bcb2be19286b1b6e	2021-09-22	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

FDB011498

KNApSAcK ID

Not Available

Chemspider ID

30777003

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751427

PDB ID

Not Available

ChEBI ID

175110

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1835791

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 methyl ether (HMDB0033457)

MOL for HMDB0033457 (Flazine methyl ether)

3D MOL for HMDB0033457 (Flazine methyl ether)

3D SDF for HMDB0033457 (Flazine methyl ether)

3D-SDF for HMDB0033457 (Flazine methyl ether)

PDB for HMDB0033457 (Flazine methyl ether)

3D PDB for HMDB0033457 (Flazine methyl ether)

SMILES for HMDB0033457 (Flazine methyl ether)

INCHI for HMDB0033457 (Flazine methyl ether)

Structure for HMDB0033457 (Flazine methyl ether)

3D Structure for HMDB0033457 (Flazine methyl ether)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra