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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 03:43:02 UTC

Update Date

2022-03-07 02:57:12 UTC

HMDB ID

HMDB0041790

Secondary Accession Numbers

HMDB41790

Metabolite Identification

Common Name

Violanone

Description

Violanone belongs to the class of organic compounds known as 2'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C2' atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one. Based on a literature review a small amount of articles have been published on Violanone.

Structure

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

HMDB0041790
     RDKit          3D
Violanone
 39 41  0  0  0  0  0  0  0  0999 V2000
   -1.7930   -0.9530    2.9257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6873    0.2478    2.1414 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9137    0.0953    0.7617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9271    0.0532   -0.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4289    0.4337    0.1266 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1725   -0.4372    1.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4004    0.3517    1.3896 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3147    0.3791    0.3460 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6632    0.4658    0.5532 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5275    0.4790   -0.4964 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8991    0.5622   -0.3142 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0135    0.4025   -1.7810 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6487    0.3174   -1.9991 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7489    0.3081   -0.9025 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3074    0.2167   -1.0929 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9361   -0.0342   -2.2275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3446   -0.1328   -1.4743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7517   -0.2697   -1.7670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6961   -0.2199   -0.8042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1534   -0.4717   -1.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9462    0.5444   -0.5898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2938   -0.0343    0.4903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2521    0.0322    1.4978 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3311   -0.8128    3.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2462   -1.7692    2.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7905   -1.2977    3.1678 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4923    1.4884    0.4286 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4357   -1.3875    0.7286 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7487   -0.3973    2.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0620    0.5563    1.5566 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3203    0.6004    0.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7367    0.4249   -2.6154 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2593    0.2323   -3.0023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7823   -0.1721   -2.3765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0196   -0.4206   -2.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4423   -1.4425   -0.7440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2714   -0.4159   -2.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5096    1.2785   -0.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9639    0.1720    2.4588 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  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  4 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  2  0
 22 23  1  0
 22  3  1  0
 15  5  1  0
 14  8  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 17 34  1  0
 18 35  1  0
 20 36  1  0
 20 37  1  0
 21 38  1  0
 23 39  1  0
M  END


  Mrv0541 02271201272D          

 23 25  0  0  0  0            999 V2000
    2.3298   -1.1658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6153   -0.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9009   -1.1658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1864   -0.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1864    0.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9009    0.4842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6153    0.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5281    0.4842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5281    1.3092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2426    1.7217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9570    1.3092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9570    0.4842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2426    0.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2426   -0.7533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6715    0.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3860    0.4842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3860    1.3092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6715    1.7217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1004    1.7217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5281   -1.1658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5281   -1.9908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9009   -1.9908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3298   -1.9908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  2  0  0  0  0
 12 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 11 18  1  0  0  0  0
 17 19  1  0  0  0  0
  4 20  1  0  0  0  0
 20 21  1  0  0  0  0
  3 22  1  0  0  0  0
  1 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041790

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(C=CC(CO)=C1O)C1COC2=C(C=CC(O)=C2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H16O6/c1-22-17-11(4-2-9(7-18)15(17)20)13-8-23-14-6-10(19)3-5-12(14)16(13)21/h2-6,13,18-20H,7-8H2,1H3

> <INCHI_KEY>
NAOWONDUKAFFFO-UHFFFAOYSA-N

> <FORMULA>
C17H16O6

> <MOLECULAR_WEIGHT>
316.3053

> <EXACT_MASS>
316.094688244

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
31.674344759848626

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroxy-3-[3-hydroxy-4-(hydroxymethyl)-2-methoxyphenyl]-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
1.91

> <JCHEM_LOGP>
1.456202402666666

> <ALOGPS_LOGS>
-3.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.282091813386947

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.781959652775316

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9552847849088586

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
82.97470000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.06e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-hydroxy-3-[3-hydroxy-4-(hydroxymethyl)-2-methoxyphenyl]-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041790
     RDKit          3D
Violanone
 39 41  0  0  0  0  0  0  0  0999 V2000
   -1.7930   -0.9530    2.9257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6873    0.2478    2.1414 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9137    0.0953    0.7617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9271    0.0532   -0.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4289    0.4337    0.1266 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1725   -0.4372    1.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4004    0.3517    1.3896 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3147    0.3791    0.3460 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6632    0.4658    0.5532 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5275    0.4790   -0.4964 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8991    0.5622   -0.3142 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0135    0.4025   -1.7810 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6487    0.3174   -1.9991 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7489    0.3081   -0.9025 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3074    0.2167   -1.0929 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9361   -0.0342   -2.2275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3446   -0.1328   -1.4743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7517   -0.2697   -1.7670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6961   -0.2199   -0.8042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1534   -0.4717   -1.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9462    0.5444   -0.5898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2938   -0.0343    0.4903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2521    0.0322    1.4978 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3311   -0.8128    3.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2462   -1.7692    2.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7905   -1.2977    3.1678 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4923    1.4884    0.4286 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4357   -1.3875    0.7286 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7487   -0.3973    2.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0620    0.5563    1.5566 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3203    0.6004    0.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7367    0.4249   -2.6154 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2593    0.2323   -3.0023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7823   -0.1721   -2.3765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0196   -0.4206   -2.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4423   -1.4425   -0.7440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2714   -0.4159   -2.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5096    1.2785   -0.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9639    0.1720    2.4588 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  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  4 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  2  0
 22 23  1  0
 22  3  1  0
 15  5  1  0
 14  8  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 17 34  1  0
 18 35  1  0
 20 36  1  0
 20 37  1  0
 21 38  1  0
 23 39  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       4.349  -2.176   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.015  -1.406   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.682  -2.176   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.348  -1.406   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.348   0.134   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.682   0.904   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.015   0.134   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.986   0.904   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.986   2.444   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.320   3.214   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -3.653   2.444   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.653   0.904   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.320   0.134   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.320  -1.406   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.987   0.134   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.321   0.904   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.321   2.444   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.987   3.214   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -7.654   3.214   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -0.986  -2.176   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.986  -3.716   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.682  -3.716   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.349  -3.716   0.000  0.00  0.00           O+0
CONECT    1    2   23                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4   22                                                  
CONECT    4    3    5   20                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8    5    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   18                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12    8   14                                                  
CONECT   14   13                                                            
CONECT   15   12   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17   11                                                       
CONECT   19   17                                                            
CONECT   20    4   21                                                       
CONECT   21   20                                                            
CONECT   22    3                                                            
CONECT   23    1                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0041790
HETATM    1  C1  UNL     1      -1.793  -0.953   2.926  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.687   0.248   2.141  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.914   0.095   0.762  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.927   0.053  -0.206  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.429   0.434   0.127  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.172  -0.437   1.125  1.00  0.00           C  
HETATM    7  O2  UNL     1       2.400   0.352   1.390  1.00  0.00           O  
HETATM    8  C6  UNL     1       3.315   0.379   0.346  1.00  0.00           C  
HETATM    9  C7  UNL     1       4.663   0.466   0.553  1.00  0.00           C  
HETATM   10  C8  UNL     1       5.528   0.479  -0.496  1.00  0.00           C  
HETATM   11  O3  UNL     1       6.899   0.562  -0.314  1.00  0.00           O  
HETATM   12  C9  UNL     1       5.013   0.402  -1.781  1.00  0.00           C  
HETATM   13  C10 UNL     1       3.649   0.317  -1.999  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.749   0.308  -0.902  1.00  0.00           C  
HETATM   15  C12 UNL     1       1.307   0.217  -1.093  1.00  0.00           C  
HETATM   16  O4  UNL     1       0.936  -0.034  -2.228  1.00  0.00           O  
HETATM   17  C13 UNL     1      -1.345  -0.133  -1.474  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.752  -0.270  -1.767  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.696  -0.220  -0.804  1.00  0.00           C  
HETATM   20  C16 UNL     1      -5.153  -0.472  -1.047  1.00  0.00           C  
HETATM   21  O5  UNL     1      -5.946   0.544  -0.590  1.00  0.00           O  
HETATM   22  C17 UNL     1      -3.294  -0.034   0.490  1.00  0.00           C  
HETATM   23  O6  UNL     1      -4.252   0.032   1.498  1.00  0.00           O  
HETATM   24  H1  UNL     1      -2.331  -0.813   3.865  1.00  0.00           H  
HETATM   25  H2  UNL     1      -2.246  -1.769   2.297  1.00  0.00           H  
HETATM   26  H3  UNL     1      -0.791  -1.298   3.168  1.00  0.00           H  
HETATM   27  H4  UNL     1       0.492   1.488   0.429  1.00  0.00           H  
HETATM   28  H5  UNL     1       1.436  -1.388   0.729  1.00  0.00           H  
HETATM   29  H6  UNL     1       0.749  -0.397   2.125  1.00  0.00           H  
HETATM   30  H7  UNL     1       5.062   0.556   1.557  1.00  0.00           H  
HETATM   31  H8  UNL     1       7.320   0.600   0.574  1.00  0.00           H  
HETATM   32  H9  UNL     1       5.737   0.425  -2.615  1.00  0.00           H  
HETATM   33  H10 UNL     1       3.259   0.232  -3.002  1.00  0.00           H  
HETATM   34  H11 UNL     1      -0.782  -0.172  -2.376  1.00  0.00           H  
HETATM   35  H12 UNL     1      -3.020  -0.421  -2.805  1.00  0.00           H  
HETATM   36  H13 UNL     1      -5.442  -1.442  -0.744  1.00  0.00           H  
HETATM   37  H14 UNL     1      -5.271  -0.416  -2.187  1.00  0.00           H  
HETATM   38  H15 UNL     1      -5.510   1.278  -0.125  1.00  0.00           H  
HETATM   39  H16 UNL     1      -3.964   0.172   2.459  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4   22
CONECT    4    5   17
CONECT    5    6   15   27
CONECT    6    7   28   29
CONECT    7    8
CONECT    8    9    9   14
CONECT    9   10   30
CONECT   10   11   12   12
CONECT   11   31
CONECT   12   13   32
CONECT   13   14   14   33
CONECT   14   15
CONECT   15   16   16
CONECT   17   18   18   34
CONECT   18   19   35
CONECT   19   20   22   22
CONECT   20   21   36   37
CONECT   21   38
CONECT   22   23
CONECT   23   39
END

HMDB0041790
     RDKit          3D
Violanone
 39 41  0  0  0  0  0  0  0  0999 V2000
   -1.7930   -0.9530    2.9257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6873    0.2478    2.1414 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9137    0.0953    0.7617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9271    0.0532   -0.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4289    0.4337    0.1266 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1725   -0.4372    1.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4004    0.3517    1.3896 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3147    0.3791    0.3460 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6632    0.4658    0.5532 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5275    0.4790   -0.4964 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8991    0.5622   -0.3142 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0135    0.4025   -1.7810 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6487    0.3174   -1.9991 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7489    0.3081   -0.9025 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3074    0.2167   -1.0929 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9361   -0.0342   -2.2275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3446   -0.1328   -1.4743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7517   -0.2697   -1.7670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6961   -0.2199   -0.8042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1534   -0.4717   -1.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9462    0.5444   -0.5898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2938   -0.0343    0.4903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2521    0.0322    1.4978 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3311   -0.8128    3.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2462   -1.7692    2.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7905   -1.2977    3.1678 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4923    1.4884    0.4286 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4357   -1.3875    0.7286 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7487   -0.3973    2.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0620    0.5563    1.5566 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3203    0.6004    0.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7367    0.4249   -2.6154 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2593    0.2323   -3.0023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7823   -0.1721   -2.3765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0196   -0.4206   -2.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4423   -1.4425   -0.7440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2714   -0.4159   -2.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5096    1.2785   -0.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9639    0.1720    2.4588 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  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  4 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  2  0
 22 23  1  0
 22  3  1  0
 15  5  1  0
 14  8  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 17 34  1  0
 18 35  1  0
 20 36  1  0
 20 37  1  0
 21 38  1  0
 23 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
7,3'-Dihydroxy-2',4'-dimethoxyisoflavone	HMDB

Chemical Formula

C₁₇H₁₆O₆

Average Molecular Weight

316.3053

Monoisotopic Molecular Weight

316.094688244

IUPAC Name

7-hydroxy-3-[3-hydroxy-4-(hydroxymethyl)-2-methoxyphenyl]-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

7-hydroxy-3-[3-hydroxy-4-(hydroxymethyl)-2-methoxyphenyl]-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

COC1=C(C=CC(CO)=C1O)C1COC2=C(C=CC(O)=C2)C1=O

InChI Identifier

InChI=1S/C17H16O6/c1-22-17-11(4-2-9(7-18)15(17)20)13-8-23-14-6-10(19)3-5-12(14)16(13)21/h2-6,13,18-20H,7-8H2,1H3

InChI Key

NAOWONDUKAFFFO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C2' atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

2'-O-methylated isoflavonoids

Alternative Parents

Substituents

2p-methoxyisoflavonoid-skeleton
Isoflavanol
Hydroxyisoflavonoid
Isoflavanone
Isoflavan
Chromone
Chromane
Benzopyran
Methoxyphenol
1-benzopyran
Phenoxy compound
Anisole
Benzyl alcohol
Methoxybenzene
Phenol ether
Aryl ketone
Aryl alkyl ketone
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Organooxygen compound
Organic oxygen compound
Organic oxide
Primary alcohol
Aromatic alcohol
Hydrocarbon derivative
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0041790)
Cytoplasm (HMDB: HMDB0041790)

Source

Exogenous

Food

Food (HMDB: HMDB0041790)

Endogenous

Plant

Plant (HMDB: HMDB0041790)

Not Available

Nutrient (HMDB: HMDB0041790)

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
Water Solubility	0.11 g/L	ALOGPS
logP	1.91	ALOGPS
logP	1.46	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	7.78	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	82.97 m³·mol⁻¹	ChemAxon
Polarizability	31.67 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]+	173.236	31661259
DarkChem	[M-H]-	171.946	31661259
DeepCCS	[M+H]+	177.724	30932474
DeepCCS	[M-H]-	175.366	30932474
DeepCCS	[M-2H]-	208.604	30932474
DeepCCS	[M+Na]+	184.345	30932474
AllCCS	[M+H]+	174.0	32859911
AllCCS	[M+H-H2O]+	170.5	32859911
AllCCS	[M+NH4]+	177.2	32859911
AllCCS	[M+Na]+	178.1	32859911
AllCCS	[M-H]-	175.9	32859911
AllCCS	[M+Na-2H]-	175.6	32859911
AllCCS	[M+HCOO]-	175.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Violanone	COC1=C(C=CC(CO)=C1O)C1COC2=C(C=CC(O)=C2)C1=O	4229.5	Standard polar	33892256
Violanone	COC1=C(C=CC(CO)=C1O)C1COC2=C(C=CC(O)=C2)C1=O	2944.7	Standard non polar	33892256
Violanone	COC1=C(C=CC(CO)=C1O)C1COC2=C(C=CC(O)=C2)C1=O	3165.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Violanone,1TMS,isomer #1	COC1=C(C2COC3=CC(O)=CC=C3C2=O)C=CC(CO[Si](C)(C)C)=C1O	3011.5	Semi standard non polar	33892256
Violanone,1TMS,isomer #2	COC1=C(C2COC3=CC(O)=CC=C3C2=O)C=CC(CO)=C1O[Si](C)(C)C	2939.0	Semi standard non polar	33892256
Violanone,1TMS,isomer #3	COC1=C(C2COC3=CC(O[Si](C)(C)C)=CC=C3C2=O)C=CC(CO)=C1O	2975.4	Semi standard non polar	33892256
Violanone,2TMS,isomer #1	COC1=C(C2COC3=CC(O[Si](C)(C)C)=CC=C3C2=O)C=CC(CO[Si](C)(C)C)=C1O	2919.6	Semi standard non polar	33892256
Violanone,2TMS,isomer #2	COC1=C(C2COC3=CC(O)=CC=C3C2=O)C=CC(CO[Si](C)(C)C)=C1O[Si](C)(C)C	2933.1	Semi standard non polar	33892256
Violanone,2TMS,isomer #3	COC1=C(C2COC3=CC(O[Si](C)(C)C)=CC=C3C2=O)C=CC(CO)=C1O[Si](C)(C)C	2878.4	Semi standard non polar	33892256
Violanone,3TMS,isomer #1	COC1=C(C2COC3=CC(O[Si](C)(C)C)=CC=C3C2=O)C=CC(CO[Si](C)(C)C)=C1O[Si](C)(C)C	2853.0	Semi standard non polar	33892256
Violanone,1TBDMS,isomer #1	COC1=C(C2COC3=CC(O)=CC=C3C2=O)C=CC(CO[Si](C)(C)C(C)(C)C)=C1O	3254.7	Semi standard non polar	33892256
Violanone,1TBDMS,isomer #2	COC1=C(C2COC3=CC(O)=CC=C3C2=O)C=CC(CO)=C1O[Si](C)(C)C(C)(C)C	3215.7	Semi standard non polar	33892256
Violanone,1TBDMS,isomer #3	COC1=C(C2COC3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3C2=O)C=CC(CO)=C1O	3244.4	Semi standard non polar	33892256
Violanone,2TBDMS,isomer #1	COC1=C(C2COC3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3C2=O)C=CC(CO[Si](C)(C)C(C)(C)C)=C1O	3406.0	Semi standard non polar	33892256
Violanone,2TBDMS,isomer #2	COC1=C(C2COC3=CC(O)=CC=C3C2=O)C=CC(CO[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	3392.5	Semi standard non polar	33892256
Violanone,2TBDMS,isomer #3	COC1=C(C2COC3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3C2=O)C=CC(CO)=C1O[Si](C)(C)C(C)(C)C	3371.5	Semi standard non polar	33892256
Violanone,3TBDMS,isomer #1	COC1=C(C2COC3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3C2=O)C=CC(CO[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	3512.3	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 - Violanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kr-0981000000-3eb9a65117069e371550	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Violanone GC-MS (3 TMS) - 70eV, Positive	splash10-01b9-1156590000-dd07609d229138432dd8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Violanone 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 - Violanone 10V, Positive-QTOF	splash10-00kb-0597000000-c2539b6a0bbbb5b55273	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Violanone 20V, Positive-QTOF	splash10-014s-0971000000-12a23aace07e281ec4f6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Violanone 40V, Positive-QTOF	splash10-0abi-2900000000-23433d1fb5bbcd4f11aa	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Violanone 10V, Negative-QTOF	splash10-014i-0139000000-fd4f879d110aa193b98a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Violanone 20V, Negative-QTOF	splash10-03y0-0972000000-fb0af7741dc673c711bf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Violanone 40V, Negative-QTOF	splash10-00di-1960000000-fd5474d096f6f889d644	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Violanone 10V, Positive-QTOF	splash10-02ti-0569000000-a8bf21dbdb03f1f6bb84	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Violanone 20V, Positive-QTOF	splash10-000j-0961000000-6a07cc9312fd6e87828b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Violanone 40V, Positive-QTOF	splash10-000i-0920000000-3830945a99a95014d257	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Violanone 10V, Negative-QTOF	splash10-02t9-0409000000-06591f8fadb3ad15aa8b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Violanone 20V, Negative-QTOF	splash10-0292-0390000000-cb5bf2587e43d0fba852	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Violanone 40V, Negative-QTOF	splash10-01p9-0972000000-27c0a12a21753b5c4606	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB029966

KNApSAcK ID

C00009542

Chemspider ID

35015230

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131753209

PDB ID

Not Available

ChEBI ID

Not Available

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

Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8. [PubMed:20428313 ]

Showing metabocard for Violanone (HMDB0041790)

MOL for HMDB0041790 (Violanone)

3D MOL for HMDB0041790 (Violanone)

3D SDF for HMDB0041790 (Violanone)

3D-SDF for HMDB0041790 (Violanone)

PDB for HMDB0041790 (Violanone)

3D PDB for HMDB0041790 (Violanone)

SMILES for HMDB0041790 (Violanone)

INCHI for HMDB0041790 (Violanone)

Structure for HMDB0041790 (Violanone)

3D Structure for HMDB0041790 (Violanone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra