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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-09-18 00:55:15 UTC

Update Date

2020-09-15 23:50:25 UTC

HMDB ID

HMDB0134007

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Khrinone A

Description

Khrinone A belongs to the class of organic compounds known as 3'-hydroxy,4'-methoxyisoflavonoids. These are isoflavonoids carrying a methoxy group attached to the C4' atom, as well as a hydroxyl group at the C3'-position of the isoflavonoid backbone. BioTransformer predicts that khrinone A is a product of 2'-hydroxyformononetin metabolism via a hydroxylation-of-benzene-para-to-edg reaction catalyzed by CYP1A2, CYP2C9, and CYP2D6 enzymes (PMID: 30612223 ).

Structure

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

HMDB0134007
     RDKit          3D
Khrinone A
 34 36  0  0  0  0  0  0  0  0999 V2000
    6.1747   -0.6452    1.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9112   -0.5571    0.9754 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6505   -0.3959    0.8335 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9642    0.6887    1.4307 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6195    0.9019    1.3067 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0331    2.0039    1.9346 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8693    0.0141    0.5563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5430    0.1733    0.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3765    0.3651    1.5243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6676    0.4847    1.3861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3261    0.4456    0.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6884    0.5765    0.1864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3511    0.5311   -1.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7482    0.6633   -1.0830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5997    0.3464   -2.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2317    0.2141   -2.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5467    0.2569   -0.8944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1849    0.1261   -0.8033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5254   -0.0439   -1.8957 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5007   -1.0657   -0.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8395   -1.2593    0.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4342   -2.3661   -0.5436 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5992   -0.3652    2.1939 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8153    0.0497    0.5050 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6797   -1.6535    0.9335 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6107    1.3630    2.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6509    2.5918    2.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9690    0.4174    2.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2635    0.7260    1.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3327   -0.1861   -1.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1265    0.3135   -3.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6795    0.0764   -3.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9404   -1.7949   -0.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8672   -2.9966   -1.1022 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
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  7 20  1  0
 20 21  2  0
 21 22  1  0
 21  3  1  0
 18  8  1  0
 17 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  9 28  1  0
 12 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 20 33  1  0
 22 34  1  0
M  END


  Mrv1652309042020192D          

 22 24  0  0  0  0            999 V2000
 9999.3090 9998.9513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.0213 9998.5419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.878910000.1923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.455310001.4360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.8789 9998.5419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.5946 9998.9554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.882910001.4326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.168310001.0201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.168310000.1951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8828 9999.7826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1655 9999.7802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.451110000.1926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7365 9999.7801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7365 9998.9551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4510 9998.5426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1655 9998.9552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.309210001.4326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.594710001.0201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.594710000.1950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3092 9999.7826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.023710000.1950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.023710001.0201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  8  4  1  0  0  0  0
 11 12  2  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
 16 11  1  0  0  0  0
 14  2  1  0  0  0  0
 11  3  1  0  0  0  0
 16  5  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 18  1  0  0  0  0
 17 22  1  0  0  0  0
  1 20  2  0  0  0  0
 21 13  1  0  0  0  0
 18  7  2  0  0  0  0
 10 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0134007

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(O)=C(C=C1O)C1=COC2=CC(O)=CC=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O6/c1-21-15-6-12(18)10(5-13(15)19)11-7-22-14-4-8(17)2-3-9(14)16(11)20/h2-7,17-19H,1H3

> <INCHI_KEY>
MPBPGCHGTKVWMR-UHFFFAOYSA-N

> <FORMULA>
C16H12O6

> <MOLECULAR_WEIGHT>
300.266

> <EXACT_MASS>
300.063388106

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
29.63647927476882

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(2,5-dihydroxy-4-methoxyphenyl)-7-hydroxy-4H-chromen-4-one

> <ALOGPS_LOGP>
3.01

> <JCHEM_LOGP>
2.2692011239999994

> <ALOGPS_LOGS>
-3.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.993825795257496

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.471447399660221

> <JCHEM_PKA_STRONGEST_BASIC>
-4.77143354589211

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
78.1461

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.74e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
khrinone A

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0134007
     RDKit          3D
Khrinone A
 34 36  0  0  0  0  0  0  0  0999 V2000
    6.1747   -0.6452    1.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9112   -0.5571    0.9754 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6505   -0.3959    0.8335 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9642    0.6887    1.4307 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6195    0.9019    1.3067 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0331    2.0039    1.9346 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8693    0.0141    0.5563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5430    0.1733    0.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3765    0.3651    1.5243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6676    0.4847    1.3861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3261    0.4456    0.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6884    0.5765    0.1864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3511    0.5311   -1.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7482    0.6633   -1.0830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5997    0.3464   -2.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2317    0.2141   -2.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5467    0.2569   -0.8944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1849    0.1261   -0.8033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5254   -0.0439   -1.8957 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5007   -1.0657   -0.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8395   -1.2593    0.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4342   -2.3661   -0.5436 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5992   -0.3652    2.1939 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8153    0.0497    0.5050 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6797   -1.6535    0.9335 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6107    1.3630    2.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6509    2.5918    2.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9690    0.4174    2.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2635    0.7260    1.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3327   -0.1861   -1.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1265    0.3135   -3.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6795    0.0764   -3.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9404   -1.7949   -0.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8672   -2.9966   -1.1022 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
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  7 20  1  0
 20 21  2  0
 21 22  1  0
 21  3  1  0
 18  8  1  0
 17 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  9 28  1  0
 12 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 20 33  1  0
 22 34  1  0
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  O   UNK     0    8665.3778664.709   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8666.7068663.945   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8672.0418667.026   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8660.0508669.347   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8672.0418663.945   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8673.3778664.717   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8662.7158669.341   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8661.3818668.571   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8661.3818667.031   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8662.7158666.261   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8670.7098666.256   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8669.3758667.026   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8668.0418666.256   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8668.0418664.716   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8669.3758663.946   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8670.7098664.716   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0    8665.3778669.341   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0    8664.0438668.571   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8664.0438667.031   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8665.3778666.261   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8666.7118667.031   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8666.7118668.571   0.000  0.00  0.00           C+0
CONECT    1   20                                                            
CONECT    2   14                                                            
CONECT    3   11                                                            
CONECT    4    8                                                            
CONECT    5    6   16                                                       
CONECT    6    5                                                            
CONECT    7    8   18                                                       
CONECT    8    7    9    4                                                  
CONECT    9    8   10                                                       
CONECT   10    9   19                                                       
CONECT   11   12   16    3                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   21                                                  
CONECT   14   13   15    2                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11    5                                                  
CONECT   17   18   22                                                       
CONECT   18   19   17    7                                                  
CONECT   19   18   20   10                                                  
CONECT   20   19   21    1                                                  
CONECT   21   20   22   13                                                  
CONECT   22   21   17                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0134007
HETATM    1  C1  UNL     1       6.175  -0.645   1.167  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.911  -0.557   0.975  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.651  -0.396   0.833  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.964   0.689   1.431  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.620   0.902   1.307  1.00  0.00           C  
HETATM    6  O2  UNL     1       1.033   2.004   1.935  1.00  0.00           O  
HETATM    7  C5  UNL     1       0.869   0.014   0.556  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.543   0.173   0.407  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.376   0.365   1.524  1.00  0.00           C  
HETATM   10  O3  UNL     1      -2.668   0.485   1.386  1.00  0.00           O  
HETATM   11  C8  UNL     1      -3.326   0.446   0.261  1.00  0.00           C  
HETATM   12  C9  UNL     1      -4.688   0.576   0.186  1.00  0.00           C  
HETATM   13  C10 UNL     1      -5.351   0.531  -1.001  1.00  0.00           C  
HETATM   14  O4  UNL     1      -6.748   0.663  -1.083  1.00  0.00           O  
HETATM   15  C11 UNL     1      -4.600   0.346  -2.156  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.232   0.214  -2.088  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.547   0.257  -0.894  1.00  0.00           C  
HETATM   18  C14 UNL     1      -1.185   0.126  -0.803  1.00  0.00           C  
HETATM   19  O5  UNL     1      -0.525  -0.044  -1.896  1.00  0.00           O  
HETATM   20  C15 UNL     1       1.501  -1.066  -0.048  1.00  0.00           C  
HETATM   21  C16 UNL     1       2.840  -1.259   0.088  1.00  0.00           C  
HETATM   22  O6  UNL     1       3.434  -2.366  -0.544  1.00  0.00           O  
HETATM   23  H1  UNL     1       6.599  -0.365   2.194  1.00  0.00           H  
HETATM   24  H2  UNL     1       6.815   0.050   0.505  1.00  0.00           H  
HETATM   25  H3  UNL     1       6.680  -1.653   0.934  1.00  0.00           H  
HETATM   26  H4  UNL     1       3.611   1.363   2.016  1.00  0.00           H  
HETATM   27  H5  UNL     1       1.651   2.592   2.465  1.00  0.00           H  
HETATM   28  H6  UNL     1      -0.969   0.417   2.514  1.00  0.00           H  
HETATM   29  H7  UNL     1      -5.263   0.726   1.111  1.00  0.00           H  
HETATM   30  H8  UNL     1      -7.333  -0.186  -1.031  1.00  0.00           H  
HETATM   31  H9  UNL     1      -5.126   0.313  -3.100  1.00  0.00           H  
HETATM   32  H10 UNL     1      -2.680   0.076  -3.011  1.00  0.00           H  
HETATM   33  H11 UNL     1       0.940  -1.795  -0.642  1.00  0.00           H  
HETATM   34  H12 UNL     1       2.867  -2.997  -1.102  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5   26
CONECT    5    6    7    7
CONECT    6   27
CONECT    7    8   20
CONECT    8    9    9   18
CONECT    9   10   28
CONECT   10   11
CONECT   11   12   12   17
CONECT   12   13   29
CONECT   13   14   15   15
CONECT   14   30
CONECT   15   16   31
CONECT   16   17   17   32
CONECT   17   18
CONECT   18   19   19
CONECT   20   21   21   33
CONECT   21   22
CONECT   22   34
END

HMDB0134007
     RDKit          3D
Khrinone A
 34 36  0  0  0  0  0  0  0  0999 V2000
    6.1747   -0.6452    1.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9112   -0.5571    0.9754 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6505   -0.3959    0.8335 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9642    0.6887    1.4307 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6195    0.9019    1.3067 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0331    2.0039    1.9346 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8693    0.0141    0.5563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5430    0.1733    0.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3765    0.3651    1.5243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6676    0.4847    1.3861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3261    0.4456    0.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6884    0.5765    0.1864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3511    0.5311   -1.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7482    0.6633   -1.0830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5997    0.3464   -2.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2317    0.2141   -2.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5467    0.2569   -0.8944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1849    0.1261   -0.8033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5254   -0.0439   -1.8957 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5007   -1.0657   -0.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8395   -1.2593    0.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4342   -2.3661   -0.5436 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5992   -0.3652    2.1939 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8153    0.0497    0.5050 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6797   -1.6535    0.9335 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6107    1.3630    2.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6509    2.5918    2.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9690    0.4174    2.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2635    0.7260    1.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3327   -0.1861   -1.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1265    0.3135   -3.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6795    0.0764   -3.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9404   -1.7949   -0.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8672   -2.9966   -1.1022 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
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  7 20  1  0
 20 21  2  0
 21 22  1  0
 21  3  1  0
 18  8  1  0
 17 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  9 28  1  0
 12 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 20 33  1  0
 22 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-(2,5-Dihydroxy-4-methoxyphenyl)-7-hydroxy-4H-1-benzopyran-4-one	HMDB
Khrinone A	HMDB

Chemical Formula

C₁₆H₁₂O₆

Average Molecular Weight

300.266

Monoisotopic Molecular Weight

300.063388106

IUPAC Name

3-(2,5-dihydroxy-4-methoxyphenyl)-7-hydroxy-4H-chromen-4-one

Traditional Name

khrinone A

CAS Registry Number

1201493-77-7

SMILES

COC1=CC(O)=C(C=C1O)C1=COC2=CC(O)=CC=C2C1=O

InChI Identifier

InChI=1S/C16H12O6/c1-21-15-6-12(18)10(5-13(15)19)11-7-22-14-4-8(17)2-3-9(14)16(11)20/h2-7,17-19H,1H3

InChI Key

MPBPGCHGTKVWMR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3'-hydroxy,4'-methoxyisoflavonoids. These are isoflavonoids carrying a methoxy group attached to the C4' atom, as well as a hydroxyl group at the C3'-position of the isoflavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

3'-hydroxy,4'-methoxyisoflavonoids

Alternative Parents

Substituents

4p-o-methylisoflavone
3'-hydroxy,4'-methoxyisoflavonoid
Isoflavone
Hydroxyisoflavonoid
Chromone
Methoxyphenol
Benzopyran
1-benzopyran
Phenoxy compound
Hydroquinone
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Pyranone
Benzenoid
Monocyclic benzene moiety
Pyran
Heteroaromatic compound
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Not Available

Not Available

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	3.01	ALOGPS
logP	2.27	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	6.47	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	78.15 m³·mol⁻¹	ChemAxon
Polarizability	29.64 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]+	171.138	31661259
DarkChem	[M-H]-	172.886	31661259
DeepCCS	[M+H]+	167.236	30932474
DeepCCS	[M-H]-	164.878	30932474
DeepCCS	[M-2H]-	197.764	30932474
DeepCCS	[M+Na]+	173.329	30932474
AllCCS	[M+H]+	168.3	32859911
AllCCS	[M+H-H2O]+	164.7	32859911
AllCCS	[M+NH4]+	171.7	32859911
AllCCS	[M+Na]+	172.7	32859911
AllCCS	[M-H]-	169.0	32859911
AllCCS	[M+Na-2H]-	168.3	32859911
AllCCS	[M+HCOO]-	167.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Khrinone A	COC1=CC(O)=C(C=C1O)C1=COC2=CC(O)=CC=C2C1=O	4477.7	Standard polar	33892256
Khrinone A	COC1=CC(O)=C(C=C1O)C1=COC2=CC(O)=CC=C2C1=O	2824.1	Standard non polar	33892256
Khrinone A	COC1=CC(O)=C(C=C1O)C1=COC2=CC(O)=CC=C2C1=O	3157.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Khrinone A,1TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C(C2=COC3=CC(O)=CC=C3C2=O)C=C1O	3109.0	Semi standard non polar	33892256
Khrinone A,1TMS,isomer #2	COC1=CC(O)=C(C2=COC3=CC(O)=CC=C3C2=O)C=C1O[Si](C)(C)C	3084.4	Semi standard non polar	33892256
Khrinone A,1TMS,isomer #3	COC1=CC(O)=C(C2=COC3=CC(O[Si](C)(C)C)=CC=C3C2=O)C=C1O	3129.9	Semi standard non polar	33892256
Khrinone A,2TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C(C2=COC3=CC(O[Si](C)(C)C)=CC=C3C2=O)C=C1O	2985.0	Semi standard non polar	33892256
Khrinone A,2TMS,isomer #2	COC1=CC(O[Si](C)(C)C)=C(C2=COC3=CC(O)=CC=C3C2=O)C=C1O[Si](C)(C)C	2982.1	Semi standard non polar	33892256
Khrinone A,2TMS,isomer #3	COC1=CC(O)=C(C2=COC3=CC(O[Si](C)(C)C)=CC=C3C2=O)C=C1O[Si](C)(C)C	2958.6	Semi standard non polar	33892256
Khrinone A,3TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C(C2=COC3=CC(O[Si](C)(C)C)=CC=C3C2=O)C=C1O[Si](C)(C)C	2909.2	Semi standard non polar	33892256
Khrinone A,1TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C(C2=COC3=CC(O)=CC=C3C2=O)C=C1O	3349.1	Semi standard non polar	33892256
Khrinone A,1TBDMS,isomer #2	COC1=CC(O)=C(C2=COC3=CC(O)=CC=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C	3346.8	Semi standard non polar	33892256
Khrinone A,1TBDMS,isomer #3	COC1=CC(O)=C(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3C2=O)C=C1O	3362.4	Semi standard non polar	33892256
Khrinone A,2TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3C2=O)C=C1O	3473.8	Semi standard non polar	33892256
Khrinone A,2TBDMS,isomer #2	COC1=CC(O[Si](C)(C)C(C)(C)C)=C(C2=COC3=CC(O)=CC=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C	3487.9	Semi standard non polar	33892256
Khrinone A,2TBDMS,isomer #3	COC1=CC(O)=C(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C	3503.8	Semi standard non polar	33892256
Khrinone A,3TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C	3615.3	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 - Khrinone A GC-MS (3 TMS) - 70eV, Positive	splash10-0udl-2423970000-bc55978594c02682a802	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Khrinone A GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-0391000000-1c5f2ff6b1a0b17eda83	2017-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Khrinone A 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 - Khrinone A 10V, Positive-QTOF	splash10-0udi-0029000000-8e8af5c0b6e3af447087	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Khrinone A 20V, Positive-QTOF	splash10-0uki-0695000000-d6d4777e218a36a1a8d3	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Khrinone A 40V, Positive-QTOF	splash10-0c10-1960000000-d379898c260495ed1444	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Khrinone A 10V, Negative-QTOF	splash10-0002-0090000000-0010919c1d654c8ebcea	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Khrinone A 20V, Negative-QTOF	splash10-03dj-0790000000-c9452c22a7491bf3c1ce	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Khrinone A 40V, Negative-QTOF	splash10-0a4i-2690000000-244568f75f029ea8ba27	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Khrinone A 10V, Negative-QTOF	splash10-0002-0090000000-fb4a565723d52a1e4624	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Khrinone A 20V, Negative-QTOF	splash10-000t-0190000000-5368d9b8451b5f697233	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Khrinone A 40V, Negative-QTOF	splash10-000i-1940000000-9576e6f5735c29d7b5e9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Khrinone A 10V, Positive-QTOF	splash10-0udi-0009000000-545fc7c692e0abcd7966	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Khrinone A 20V, Positive-QTOF	splash10-0udi-0249000000-cdb012e5b16cb856f744	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Khrinone A 40V, Positive-QTOF	splash10-002r-0940000000-8e5c1b52092435b6e6ab	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB091028

KNApSAcK ID

Not Available

Chemspider ID

24660228

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44613666

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

Djoumbou-Feunang Y, Fiamoncini J, Gil-de-la-Fuente A, Greiner R, Manach C, Wishart DS: BioTransformer: a comprehensive computational tool for small molecule metabolism prediction and metabolite identification. J Cheminform. 2019 Jan 5;11(1):2. doi: 10.1186/s13321-018-0324-5. [PubMed:30612223 ]

Showing metabocard for Khrinone A (HMDB0134007)

MOL for HMDB0134007 (Khrinone A)

3D MOL for HMDB0134007 (Khrinone A)

3D SDF for HMDB0134007 (Khrinone A)

3D-SDF for HMDB0134007 (Khrinone A)

PDB for HMDB0134007 (Khrinone A)

3D PDB for HMDB0134007 (Khrinone A)

SMILES for HMDB0134007 (Khrinone A)

INCHI for HMDB0134007 (Khrinone A)

Structure for HMDB0134007 (Khrinone A)

3D Structure for HMDB0134007 (Khrinone A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra