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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 03:40:55 UTC

Update Date

2022-03-07 02:57:11 UTC

HMDB ID

HMDB0041758

Secondary Accession Numbers

HMDB41758

Metabolite Identification

Common Name

Melanettin

Description

Melanettin belongs to the class of organic compounds known as neoflavones. These are neoflavonoids with a structure based on the 4-phenylcoumarin skeleton. Thus, melanettin is considered to be a flavonoid. Based on a literature review very few articles have been published on Melanettin.

Structure

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

HMDB0041758
     RDKit          3D
Melanettin
 33 35  0  0  0  0  0  0  0  0999 V2000
   -5.4205   -0.6132    0.8755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1718   -0.5642    1.4911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9850   -0.3741    0.8147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9327   -0.2139   -0.5483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7260   -0.0245   -1.1992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7212    0.1239   -2.5198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5925    0.3022   -3.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5438    0.4475   -4.4189 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6036    0.3394   -2.4747 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6349    0.1876   -1.0865 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9326    0.2718   -0.3971 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9389   -0.5803   -0.8022 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1866   -0.5698   -0.2464 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4214    0.3488    0.7671 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6904    0.3891    1.3621 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4295    1.1985    1.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1885    1.1713    0.6060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5631    0.0008   -0.4404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5805   -0.1574    0.9263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7977   -0.3441    1.5450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8481   -0.5046    2.9101 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4090   -1.0685   -0.1315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8439    0.4313    0.8436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1627   -1.2175    1.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8513   -0.2333   -1.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5631    0.4856   -2.9709 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7536   -1.3083   -1.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9942   -1.2245   -0.5426 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4067   -0.2398    1.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6528    1.8978    1.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4077    1.8685    0.9403 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3552   -0.1462    1.5027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0099   -0.4859    3.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 10 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20  3  1  0
 18  5  2  0
 17 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  9 26  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 19 32  1  0
 21 33  1  0
M  END


  Mrv0541 02271201322D          

 21 23  0  0  0  0            999 V2000
   -3.2705    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9850    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9850    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2705   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5561    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5561    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8416    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8416   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1271    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1271    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8416   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5561   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5561   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8416   -2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1271   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1271   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6995    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4139    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6995   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4127    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8416   -3.7126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  7  6  1  0  0  0  0
  6  5  1  0  0  0  0
  5  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 16  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
  2 17  1  0  0  0  0
 17 18  1  0  0  0  0
  3 19  1  0  0  0  0
 10 20  2  0  0  0  0
 14 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041758

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=C2C(OC(=O)C=C2C2=CC=C(O)C=C2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O5/c1-20-15-8-14-12(6-13(15)18)11(7-16(19)21-14)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3

> <INCHI_KEY>
HUGUGFBIYQBLCS-UHFFFAOYSA-N

> <FORMULA>
C16H12O5

> <MOLECULAR_WEIGHT>
284.2635

> <EXACT_MASS>
284.068473494

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
28.493678933281462

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-hydroxy-4-(4-hydroxyphenyl)-7-methoxy-2H-chromen-2-one

> <ALOGPS_LOGP>
2.70

> <JCHEM_LOGP>
2.451756284

> <ALOGPS_LOGS>
-3.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.883592055682298

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.12517164611968

> <JCHEM_PKA_STRONGEST_BASIC>
-4.900778860933335

> <JCHEM_POLAR_SURFACE_AREA>
75.99

> <JCHEM_REFRACTIVITY>
85.5263

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.83e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
melannin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041758
     RDKit          3D
Melanettin
 33 35  0  0  0  0  0  0  0  0999 V2000
   -5.4205   -0.6132    0.8755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1718   -0.5642    1.4911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9850   -0.3741    0.8147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9327   -0.2139   -0.5483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7260   -0.0245   -1.1992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7212    0.1239   -2.5198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5925    0.3022   -3.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5438    0.4475   -4.4189 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6036    0.3394   -2.4747 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6349    0.1876   -1.0865 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9326    0.2718   -0.3971 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9389   -0.5803   -0.8022 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1866   -0.5698   -0.2464 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4214    0.3488    0.7671 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6904    0.3891    1.3621 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4295    1.1985    1.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1885    1.1713    0.6060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5631    0.0008   -0.4404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5805   -0.1574    0.9263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7977   -0.3441    1.5450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8481   -0.5046    2.9101 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4090   -1.0685   -0.1315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8439    0.4313    0.8436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1627   -1.2175    1.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8513   -0.2333   -1.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5631    0.4856   -2.9709 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7536   -1.3083   -1.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9942   -1.2245   -0.5426 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4067   -0.2398    1.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6528    1.8978    1.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4077    1.8685    0.9403 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3552   -0.1462    1.5027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0099   -0.4859    3.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 10 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20  3  1  0
 18  5  2  0
 17 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  9 26  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 19 32  1  0
 21 33  1  0
M  END

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  C   UNK     0      -6.105   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.439   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.439   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.105  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.771   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.771   1.540   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.438   2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -3.438  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.104   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.104   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.438  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.771  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.771  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.438  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.104  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.104  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -8.772   2.310   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0     -10.106   1.540   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -8.772  -0.770   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -0.770   2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -3.438  -6.930   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   17                                                  
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    1    7    5                                                  
CONECT    7    6   10                                                       
CONECT    8    5    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    7    9   20                                                  
CONECT   11    8   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   11   15                                                       
CONECT   17    2   18                                                       
CONECT   18   17                                                            
CONECT   19    3                                                            
CONECT   20   10                                                            
CONECT   21   14                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0041758
HETATM    1  C1  UNL     1      -5.421  -0.613   0.875  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.172  -0.564   1.491  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.985  -0.374   0.815  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.933  -0.214  -0.548  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.726  -0.025  -1.199  1.00  0.00           C  
HETATM    6  O2  UNL     1      -1.721   0.124  -2.520  1.00  0.00           O  
HETATM    7  C5  UNL     1      -0.592   0.302  -3.159  1.00  0.00           C  
HETATM    8  O3  UNL     1      -0.544   0.447  -4.419  1.00  0.00           O  
HETATM    9  C6  UNL     1       0.604   0.339  -2.475  1.00  0.00           C  
HETATM   10  C7  UNL     1       0.635   0.188  -1.087  1.00  0.00           C  
HETATM   11  C8  UNL     1       1.933   0.272  -0.397  1.00  0.00           C  
HETATM   12  C9  UNL     1       2.939  -0.580  -0.802  1.00  0.00           C  
HETATM   13  C10 UNL     1       4.187  -0.570  -0.246  1.00  0.00           C  
HETATM   14  C11 UNL     1       4.421   0.349   0.767  1.00  0.00           C  
HETATM   15  O4  UNL     1       5.690   0.389   1.362  1.00  0.00           O  
HETATM   16  C12 UNL     1       3.430   1.198   1.176  1.00  0.00           C  
HETATM   17  C13 UNL     1       2.189   1.171   0.606  1.00  0.00           C  
HETATM   18  C14 UNL     1      -0.563   0.001  -0.440  1.00  0.00           C  
HETATM   19  C15 UNL     1      -0.581  -0.157   0.926  1.00  0.00           C  
HETATM   20  C16 UNL     1      -1.798  -0.344   1.545  1.00  0.00           C  
HETATM   21  O5  UNL     1      -1.848  -0.505   2.910  1.00  0.00           O  
HETATM   22  H1  UNL     1      -5.409  -1.068  -0.132  1.00  0.00           H  
HETATM   23  H2  UNL     1      -5.844   0.431   0.844  1.00  0.00           H  
HETATM   24  H3  UNL     1      -6.163  -1.218   1.464  1.00  0.00           H  
HETATM   25  H4  UNL     1      -3.851  -0.233  -1.148  1.00  0.00           H  
HETATM   26  H5  UNL     1       1.563   0.486  -2.971  1.00  0.00           H  
HETATM   27  H6  UNL     1       2.754  -1.308  -1.605  1.00  0.00           H  
HETATM   28  H7  UNL     1       4.994  -1.224  -0.543  1.00  0.00           H  
HETATM   29  H8  UNL     1       6.407  -0.240   1.052  1.00  0.00           H  
HETATM   30  H9  UNL     1       3.653   1.898   1.967  1.00  0.00           H  
HETATM   31  H10 UNL     1       1.408   1.869   0.940  1.00  0.00           H  
HETATM   32  H11 UNL     1       0.355  -0.146   1.503  1.00  0.00           H  
HETATM   33  H12 UNL     1      -1.010  -0.486   3.448  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   20
CONECT    4    5   25
CONECT    5    6   18   18
CONECT    6    7
CONECT    7    8    8    9
CONECT    9   10   10   26
CONECT   10   11   18
CONECT   11   12   12   17
CONECT   12   13   27
CONECT   13   14   14   28
CONECT   14   15   16
CONECT   15   29
CONECT   16   17   17   30
CONECT   17   31
CONECT   18   19
CONECT   19   20   20   32
CONECT   20   21
CONECT   21   33
END

HMDB0041758
     RDKit          3D
Melanettin
 33 35  0  0  0  0  0  0  0  0999 V2000
   -5.4205   -0.6132    0.8755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1718   -0.5642    1.4911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9850   -0.3741    0.8147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9327   -0.2139   -0.5483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7260   -0.0245   -1.1992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7212    0.1239   -2.5198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5925    0.3022   -3.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5438    0.4475   -4.4189 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6036    0.3394   -2.4747 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6349    0.1876   -1.0865 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9326    0.2718   -0.3971 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9389   -0.5803   -0.8022 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1866   -0.5698   -0.2464 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4214    0.3488    0.7671 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6904    0.3891    1.3621 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4295    1.1985    1.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1885    1.1713    0.6060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5631    0.0008   -0.4404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5805   -0.1574    0.9263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7977   -0.3441    1.5450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8481   -0.5046    2.9101 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4090   -1.0685   -0.1315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8439    0.4313    0.8436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1627   -1.2175    1.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8513   -0.2333   -1.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5631    0.4856   -2.9709 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7536   -1.3083   -1.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9942   -1.2245   -0.5426 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4067   -0.2398    1.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6528    1.8978    1.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4077    1.8685    0.9403 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3552   -0.1462    1.5027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0099   -0.4859    3.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 10 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20  3  1  0
 18  5  2  0
 17 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  9 26  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 19 32  1  0
 21 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6-Hydroxy-4-(4-hydroxyphenyl)-7-methoxycoumarin	HMDB
Melannin	HMDB

Chemical Formula

C₁₆H₁₂O₅

Average Molecular Weight

284.2635

Monoisotopic Molecular Weight

284.068473494

IUPAC Name

6-hydroxy-4-(4-hydroxyphenyl)-7-methoxy-2H-chromen-2-one

Traditional Name

melannin

CAS Registry Number

58115-08-5

SMILES

COC1=C(O)C=C2C(OC(=O)C=C2C2=CC=C(O)C=C2)=C1

InChI Identifier

InChI=1S/C16H12O5/c1-20-15-8-14-12(6-13(15)18)11(7-16(19)21-14)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3

InChI Key

HUGUGFBIYQBLCS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as neoflavones. These are neoflavonoids with a structure based on the 4-phenylcoumarin skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Neoflavonoids

Sub Class

Neoflavones

Direct Parent

Neoflavones

Alternative Parents

Substituents

4-phenylcoumarin
Hydroxycoumarin
Coumarin
Benzopyran
1-benzopyran
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Lactone
Ether
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

neoflavonoid (CHEBI:6728 )
Neoflavonoids (C10504 )
Neoflavonoids (LMPK12100004 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0041758)

Cellular substructure

Membrane (HMDB: HMDB0041758)

Source

Exogenous

Food

Food (HMDB: HMDB0041758)

Endogenous

Plant

Plant (HMDB: HMDB0041758)

Not Available

Nutrient (HMDB: HMDB0041758)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	233 - 234 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	4137 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	0.048 g/L	ALOGPS
logP	2.7	ALOGPS
logP	2.45	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	9.13	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	85.53 m³·mol⁻¹	ChemAxon
Polarizability	28.49 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
DarkChem	[M+H]+	167.133	31661259
DarkChem	[M-H]-	169.388	31661259
DeepCCS	[M+H]+	169.604	30932474
DeepCCS	[M-H]-	167.246	30932474
DeepCCS	[M-2H]-	200.133	30932474
DeepCCS	[M+Na]+	175.698	30932474
AllCCS	[M+H]+	164.3	32859911
AllCCS	[M+H-H2O]+	160.5	32859911
AllCCS	[M+NH4]+	167.8	32859911
AllCCS	[M+Na]+	168.8	32859911
AllCCS	[M-H]-	166.4	32859911
AllCCS	[M+Na-2H]-	165.7	32859911
AllCCS	[M+HCOO]-	164.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Melanettin	COC1=C(O)C=C2C(OC(=O)C=C2C2=CC=C(O)C=C2)=C1	4118.6	Standard polar	33892256
Melanettin	COC1=C(O)C=C2C(OC(=O)C=C2C2=CC=C(O)C=C2)=C1	2747.8	Standard non polar	33892256
Melanettin	COC1=C(O)C=C2C(OC(=O)C=C2C2=CC=C(O)C=C2)=C1	3094.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Melanettin,1TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)C(C1=CC=C(O)C=C1)=CC(=O)O2	3061.0	Semi standard non polar	33892256
Melanettin,1TMS,isomer #2	COC1=CC2=C(C=C1O)C(C1=CC=C(O[Si](C)(C)C)C=C1)=CC(=O)O2	3132.9	Semi standard non polar	33892256
Melanettin,2TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)C(C1=CC=C(O[Si](C)(C)C)C=C1)=CC(=O)O2	3072.5	Semi standard non polar	33892256
Melanettin,1TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C(C1=CC=C(O)C=C1)=CC(=O)O2	3281.7	Semi standard non polar	33892256
Melanettin,1TBDMS,isomer #2	COC1=CC2=C(C=C1O)C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)=CC(=O)O2	3361.7	Semi standard non polar	33892256
Melanettin,2TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)=CC(=O)O2	3547.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Melanettin GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-0290000000-d762404531d11004ccf8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Melanettin GC-MS (2 TMS) - 70eV, Positive	splash10-08mi-3119400000-5c442ffc492766ce3ba8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Melanettin 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 - Melanettin 10V, Positive-QTOF	splash10-000i-0090000000-d9818f34f1852858c724	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melanettin 20V, Positive-QTOF	splash10-052r-0090000000-c4019e46f2db63153421	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melanettin 40V, Positive-QTOF	splash10-02t9-0590000000-1f1e0da5447d4e14f625	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melanettin 10V, Negative-QTOF	splash10-001i-0090000000-fabdd6e71e950f3569d7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melanettin 20V, Negative-QTOF	splash10-001i-0090000000-cb46e122b941bc918982	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melanettin 40V, Negative-QTOF	splash10-01bj-0590000000-11596407c425ec6044d9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melanettin 10V, Positive-QTOF	splash10-000i-0090000000-edc9ea273e98ea6aa00a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melanettin 20V, Positive-QTOF	splash10-000i-0090000000-62045bada44abdb96ebe	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melanettin 40V, Positive-QTOF	splash10-0fdo-0390000000-71fd524aca9f38139e92	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melanettin 10V, Negative-QTOF	splash10-001i-0090000000-549f6b30f75977e8ff35	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melanettin 20V, Negative-QTOF	splash10-001i-0090000000-63f5d59760d4bd2731a1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melanettin 40V, Negative-QTOF	splash10-0170-1890000000-d1641319c591db3793a0	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442808

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1911301

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Melanettin (HMDB0041758)

MOL for HMDB0041758 (Melanettin)

3D MOL for HMDB0041758 (Melanettin)

3D SDF for HMDB0041758 (Melanettin)

3D-SDF for HMDB0041758 (Melanettin)

PDB for HMDB0041758 (Melanettin)

3D PDB for HMDB0041758 (Melanettin)

SMILES for HMDB0041758 (Melanettin)

INCHI for HMDB0041758 (Melanettin)

Structure for HMDB0041758 (Melanettin)

3D Structure for HMDB0041758 (Melanettin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra