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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:23:35 UTC

Update Date

2021-09-26 23:08:01 UTC

HMDB ID

HMDB0254201

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Lumiflavin

Description

Lumiflavin, also known as lumilactoflavin, belongs to the class of organic compounds known as flavins. Flavins are compounds containing a flavin (7,8-dimethyl-benzo[g]pteridine-2,4-dione) moiety, with a structure characterized by an isoalloaxzine tricyclic ring. Lumiflavin is an extremely weak basic (essentially neutral) compound (based on its pKa). A compound showing yellow-green fluorescence, formed by a photolysis of riboflavin in alkaline solution. This compound has been identified in human blood as reported by (PMID: 31557052 ). Lumiflavin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Lumiflavin is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0254201
     RDKit          3D
Lumiflavin
 31 33  0  0  0  0  0  0  0  0999 V2000
   -3.8981    1.4202   -0.2311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5630    0.7963   -0.1334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4259    1.5779   -0.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1707    1.0099    0.0218 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9272    1.7782    0.0829 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1659    1.2367    0.1730 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2958    2.0138    0.2361 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1900    3.2667    0.2104 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5011    1.4260    0.3246 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5981    0.0841    0.3511 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7611   -0.4042    0.4354 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5185   -0.7285    0.2919 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2949   -0.2066    0.2031 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1696   -0.9632    0.1400 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2784   -2.4109    0.1689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0329   -0.3722    0.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1730   -1.1472   -0.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4361   -0.5756   -0.1044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6068   -1.4891   -0.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5879    0.9407    0.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8053    2.4993    0.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2527    1.3433   -1.2800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4689    2.6633   -0.0889 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3872    2.0162    0.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0174   -2.8058   -0.8263 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6438   -2.8559    0.9841 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3270   -2.6892    0.4564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0357   -2.2253    0.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5421   -0.9430   -0.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6571   -2.0993    0.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4198   -2.1564   -1.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18  2  1  0
 16  4  2  0
 13  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  9 24  1  0
 15 25  1  0
 15 26  1  0
 15 27  1  0
 17 28  1  0
 19 29  1  0
 19 30  1  0
 19 31  1  0
M  END


  Mrv0541 02231217522D          

 19 21  0  0  0  0            999 V2000
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 12 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254201

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C2=C(C=C(C)C(C)=C2)N=C2C(=O)NC(=O)N=C12

> <INCHI_IDENTIFIER>
InChI=1S/C13H12N4O2/c1-6-4-8-9(5-7(6)2)17(3)11-10(14-8)12(18)16-13(19)15-11/h4-5H,1-3H3,(H,16,18,19)

> <INCHI_KEY>
KPDQZGKJTJRBGU-UHFFFAOYSA-N

> <FORMULA>
C13H12N4O2

> <MOLECULAR_WEIGHT>
256.26

> <EXACT_MASS>
256.096025648

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
26.327097475426683

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7,8,10-trimethyl-2H,3H,4H,10H-benzo[g]pteridine-2,4-dione

> <ALOGPS_LOGP>
0.52

> <JCHEM_LOGP>
1.664566578

> <ALOGPS_LOGS>
-3.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.970145933434437

> <JCHEM_PKA_STRONGEST_BASIC>
0.77388198485297

> <JCHEM_POLAR_SURFACE_AREA>
74.13

> <JCHEM_REFRACTIVITY>
72.08860000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.18e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lumiflavin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0254201
     RDKit          3D
Lumiflavin
 31 33  0  0  0  0  0  0  0  0999 V2000
   -3.8981    1.4202   -0.2311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5630    0.7963   -0.1334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4259    1.5779   -0.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1707    1.0099    0.0218 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9272    1.7782    0.0829 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1659    1.2367    0.1730 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2958    2.0138    0.2361 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1900    3.2667    0.2104 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5011    1.4260    0.3246 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5981    0.0841    0.3511 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7611   -0.4042    0.4354 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5185   -0.7285    0.2919 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2949   -0.2066    0.2031 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1696   -0.9632    0.1400 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2784   -2.4109    0.1689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0329   -0.3722    0.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1730   -1.1472   -0.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4361   -0.5756   -0.1044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6068   -1.4891   -0.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5879    0.9407    0.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8053    2.4993    0.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2527    1.3433   -1.2800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4689    2.6633   -0.0889 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3872    2.0162    0.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0174   -2.8058   -0.8263 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6438   -2.8559    0.9841 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3270   -2.6892    0.4564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0357   -2.2253    0.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5421   -0.9430   -0.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6571   -2.0993    0.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4198   -2.1564   -1.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18  2  1  0
 16  4  2  0
 13  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  9 24  1  0
 15 25  1  0
 15 26  1  0
 15 27  1  0
 17 28  1  0
 19 29  1  0
 19 30  1  0
 19 31  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       6.668  -0.770   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0       8.002   1.540   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       4.001   2.310   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    3   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12    2   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   12                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0254201
HETATM    1  C1  UNL     1      -3.898   1.420  -0.231  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.563   0.796  -0.133  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.426   1.578  -0.070  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.171   1.010   0.022  1.00  0.00           C  
HETATM    5  N1  UNL     1       0.927   1.778   0.083  1.00  0.00           N  
HETATM    6  C5  UNL     1       2.166   1.237   0.173  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.296   2.014   0.236  1.00  0.00           C  
HETATM    8  O1  UNL     1       3.190   3.267   0.210  1.00  0.00           O  
HETATM    9  N2  UNL     1       4.501   1.426   0.325  1.00  0.00           N  
HETATM   10  C7  UNL     1       4.598   0.084   0.351  1.00  0.00           C  
HETATM   11  O2  UNL     1       5.761  -0.404   0.435  1.00  0.00           O  
HETATM   12  N3  UNL     1       3.518  -0.729   0.292  1.00  0.00           N  
HETATM   13  C8  UNL     1       2.295  -0.207   0.203  1.00  0.00           C  
HETATM   14  N4  UNL     1       1.170  -0.963   0.140  1.00  0.00           N  
HETATM   15  C9  UNL     1       1.278  -2.411   0.169  1.00  0.00           C  
HETATM   16  C10 UNL     1      -0.033  -0.372   0.052  1.00  0.00           C  
HETATM   17  C11 UNL     1      -1.173  -1.147  -0.012  1.00  0.00           C  
HETATM   18  C12 UNL     1      -2.436  -0.576  -0.104  1.00  0.00           C  
HETATM   19  C13 UNL     1      -3.607  -1.489  -0.168  1.00  0.00           C  
HETATM   20  H1  UNL     1      -4.588   0.941   0.491  1.00  0.00           H  
HETATM   21  H2  UNL     1      -3.805   2.499   0.012  1.00  0.00           H  
HETATM   22  H3  UNL     1      -4.253   1.343  -1.280  1.00  0.00           H  
HETATM   23  H4  UNL     1      -1.469   2.663  -0.089  1.00  0.00           H  
HETATM   24  H5  UNL     1       5.387   2.016   0.374  1.00  0.00           H  
HETATM   25  H6  UNL     1       1.017  -2.806  -0.826  1.00  0.00           H  
HETATM   26  H7  UNL     1       0.644  -2.856   0.984  1.00  0.00           H  
HETATM   27  H8  UNL     1       2.327  -2.689   0.456  1.00  0.00           H  
HETATM   28  H9  UNL     1      -1.036  -2.225   0.013  1.00  0.00           H  
HETATM   29  H10 UNL     1      -4.542  -0.943  -0.292  1.00  0.00           H  
HETATM   30  H11 UNL     1      -3.657  -2.099   0.755  1.00  0.00           H  
HETATM   31  H12 UNL     1      -3.420  -2.156  -1.055  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    3   18
CONECT    3    4   23
CONECT    4    5   16   16
CONECT    5    6    6
CONECT    6    7   13
CONECT    7    8    8    9
CONECT    9   10   24
CONECT   10   11   11   12
CONECT   12   13   13
CONECT   13   14
CONECT   14   15   16
CONECT   15   25   26   27
CONECT   16   17
CONECT   17   18   18   28
CONECT   18   19
CONECT   19   29   30   31
END

HMDB0254201
     RDKit          3D
Lumiflavin
 31 33  0  0  0  0  0  0  0  0999 V2000
   -3.8981    1.4202   -0.2311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5630    0.7963   -0.1334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4259    1.5779   -0.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1707    1.0099    0.0218 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9272    1.7782    0.0829 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1659    1.2367    0.1730 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2958    2.0138    0.2361 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1900    3.2667    0.2104 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5011    1.4260    0.3246 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5981    0.0841    0.3511 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7611   -0.4042    0.4354 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5185   -0.7285    0.2919 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2949   -0.2066    0.2031 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1696   -0.9632    0.1400 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2784   -2.4109    0.1689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0329   -0.3722    0.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1730   -1.1472   -0.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4361   -0.5756   -0.1044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6068   -1.4891   -0.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5879    0.9407    0.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8053    2.4993    0.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2527    1.3433   -1.2800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4689    2.6633   -0.0889 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3872    2.0162    0.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0174   -2.8058   -0.8263 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6438   -2.8559    0.9841 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3270   -2.6892    0.4564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0357   -2.2253    0.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5421   -0.9430   -0.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6571   -2.0993    0.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4198   -2.1564   -1.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18  2  1  0
 16  4  2  0
 13  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  9 24  1  0
 15 25  1  0
 15 26  1  0
 15 27  1  0
 17 28  1  0
 19 29  1  0
 19 30  1  0
 19 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
7,8,10-Trimethylisoalloxazine	ChEBI
Lumiflavine	ChEBI
Lumilactoflavin	ChEBI
Lumiflavin	MeSH

Chemical Formula

C₁₃H₁₂N₄O₂

Average Molecular Weight

256.26

Monoisotopic Molecular Weight

256.096025648

IUPAC Name

7,8,10-trimethyl-2H,3H,4H,10H-benzo[g]pteridine-2,4-dione

Traditional Name

lumiflavin

CAS Registry Number

Not Available

SMILES

CN1C2=C(C=C(C)C(C)=C2)N=C2C(=O)NC(=O)N=C12

InChI Identifier

InChI=1S/C13H12N4O2/c1-6-4-8-9(5-7(6)2)17(3)11-10(14-8)12(18)16-13(19)15-11/h4-5H,1-3H3,(H,16,18,19)

InChI Key

KPDQZGKJTJRBGU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavins. Flavins are compounds containing a flavin (7,8-dimethyl-benzo[g]pteridine-2,4-dione) moiety, with a structure characterized by an isoalloaxzine tricyclic ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pteridines and derivatives

Sub Class

Alloxazines and isoalloxazines

Direct Parent

Flavins

Alternative Parents

Substituents

Flavin
Diazanaphthalene
Quinoxaline
Pyrimidone
Pyrazine
Pyrimidine
Benzenoid
Heteroaromatic compound
Vinylogous amide
Lactam
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

flavin (CHEBI:43661 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.52	ALOGPS
logP	1.66	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	6.97	ChemAxon
pKa (Strongest Basic)	0.77	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.13 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	72.09 m³·mol⁻¹	ChemAxon
Polarizability	26.33 Å³	ChemAxon
Number of Rings	3	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
DeepCCS	[M-2H]-	189.698	30932474
DeepCCS	[M+Na]+	165.264	30932474
AllCCS	[M+H]+	156.0	32859911
AllCCS	[M+H-H2O]+	152.2	32859911
AllCCS	[M+NH4]+	159.5	32859911
AllCCS	[M+Na]+	160.5	32859911
AllCCS	[M-H]-	162.0	32859911
AllCCS	[M+Na-2H]-	161.4	32859911
AllCCS	[M+HCOO]-	160.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lumiflavin	CN1C2=C(C=C(C)C(C)=C2)N=C2C(=O)NC(=O)N=C12	3017.1	Standard polar	33892256
Lumiflavin	CN1C2=C(C=C(C)C(C)=C2)N=C2C(=O)NC(=O)N=C12	2332.4	Standard non polar	33892256
Lumiflavin	CN1C2=C(C=C(C)C(C)=C2)N=C2C(=O)NC(=O)N=C12	2994.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lumiflavin,1TMS,isomer #1	CC1=CC2=C(C=C1C)N(C)C1=NC(=O)N([Si](C)(C)C)C(=O)C1=N2	2717.9	Semi standard non polar	33892256
Lumiflavin,1TMS,isomer #1	CC1=CC2=C(C=C1C)N(C)C1=NC(=O)N([Si](C)(C)C)C(=O)C1=N2	2720.2	Standard non polar	33892256
Lumiflavin,1TMS,isomer #1	CC1=CC2=C(C=C1C)N(C)C1=NC(=O)N([Si](C)(C)C)C(=O)C1=N2	3350.2	Standard polar	33892256
Lumiflavin,1TBDMS,isomer #1	CC1=CC2=C(C=C1C)N(C)C1=NC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1=N2	2886.2	Semi standard non polar	33892256
Lumiflavin,1TBDMS,isomer #1	CC1=CC2=C(C=C1C)N(C)C1=NC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1=N2	2863.8	Standard non polar	33892256
Lumiflavin,1TBDMS,isomer #1	CC1=CC2=C(C=C1C)N(C)C1=NC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1=N2	3364.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Lumiflavin GC-MS (Non-derivatized) - 70eV, Positive	splash10-03yi-0890000000-dbe02eaee912fa1a8953	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lumiflavin 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 - Lumiflavin 10V, Positive-QTOF	splash10-0a4i-0090000000-d0844d3a5415c21e87a6	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumiflavin 20V, Positive-QTOF	splash10-0a4i-0090000000-43818d25b122cb562c0f	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumiflavin 40V, Positive-QTOF	splash10-06ri-0960000000-d8a5e6f0d4fbd21a4f37	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumiflavin 10V, Negative-QTOF	splash10-0006-9050000000-82384b993e08d43cb060	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumiflavin 20V, Negative-QTOF	splash10-0006-9040000000-0f64682ef3537d60d328	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumiflavin 40V, Negative-QTOF	splash10-0006-9220000000-64cf26577bf34143befb	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumiflavin 10V, Positive-QTOF	splash10-0a4i-0090000000-fc9b52eb1ec38416d276	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumiflavin 20V, Positive-QTOF	splash10-0a4i-0090000000-a7a0981ed4637f044112	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumiflavin 40V, Positive-QTOF	splash10-053i-0920000000-70fc1497c971a9355477	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumiflavin 10V, Negative-QTOF	splash10-0a4i-0090000000-99576519415bbb115d55	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumiflavin 20V, Negative-QTOF	splash10-0a4i-0190000000-c998705b3850de3cbcb2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumiflavin 40V, Negative-QTOF	splash10-000x-8960000000-c6e1bd0b53ea1e7b0026	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB04726

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lumiflavin

METLIN ID

Not Available

PubChem Compound

66184

PDB ID

Not Available

ChEBI ID

43661

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Lumiflavin (HMDB0254201)

MOL for HMDB0254201 (Lumiflavin)

3D MOL for HMDB0254201 (Lumiflavin)

3D SDF for HMDB0254201 (Lumiflavin)

3D-SDF for HMDB0254201 (Lumiflavin)

PDB for HMDB0254201 (Lumiflavin)

3D PDB for HMDB0254201 (Lumiflavin)

SMILES for HMDB0254201 (Lumiflavin)

INCHI for HMDB0254201 (Lumiflavin)

Structure for HMDB0254201 (Lumiflavin)

3D Structure for HMDB0254201 (Lumiflavin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra