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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 12:29:38 UTC

Update Date

2021-09-26 23:07:05 UTC

HMDB ID

HMDB0253690

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Isosakuranetin

Description

5,7-dihydroxy-2-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one belongs to the class of organic compounds known as 4'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C4' atom of the flavonoid backbone. 5,7-dihydroxy-2-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 5,7-dihydroxy-2-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one has been detected, but not quantified in, sweet oranges. This could make 5,7-dihydroxy-2-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one a potential biomarker for the consumption of these foods. This compound has been identified in human blood as reported by (PMID: 31557052 ). Isosakuranetin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Isosakuranetin 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

HMDB0253690
     RDKit          3D
Isosakuranetin
 35 37  0  0  0  0  0  0  0  0999 V2000
    5.9848    0.2396   -1.1176 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4358    0.6772    0.1125 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0603    0.5207    0.2978 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4364    0.9178    1.4640 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0764    0.7525    1.6226 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2696    0.1946    0.6532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1902    0.0366    0.8685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5899   -1.3363    1.2614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8464   -1.7426    0.5872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1742   -2.9685    0.4809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7793   -0.7894    0.0077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1261   -0.9781   -0.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7144   -2.1289    0.3661 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9017    0.0346   -0.6817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3699    1.2084   -1.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1394    2.1951   -1.7331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9921    1.3630   -1.0358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2088    0.3891   -0.4660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8321    0.4649   -0.3066 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8944   -0.2013   -0.5106 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2541   -0.0377   -0.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4205    0.8032   -1.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7845   -0.8461   -1.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0572    0.4098   -1.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0556    1.3621    2.2452 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5846    1.0697    2.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4692    0.7232    1.7158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8087   -1.4070    2.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1885   -2.1055    1.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3434   -2.9179    0.8038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9775   -0.1369   -0.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5682    2.9533   -1.2551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5417    2.2689   -1.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3082   -0.6419   -1.2964 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7625   -0.3463   -1.5890 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
  6 20  1  0
 20 21  2  0
 21  3  1  0
 19  7  1  0
 18 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 17 33  1  0
 20 34  1  0
 21 35  1  0
M  END

  Mrv1652309171718142D          

 21 23  0  0  0  0            999 V2000
    7.8592   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    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
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   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
    4.2868    0.0000    0.0000 C   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
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   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
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  9  2  2  0  0  0  0
  9  3  1  0  0  0  0
 10  6  2  0  0  0  0
 10  7  1  0  0  0  0
 11  4  2  0  0  0  0
 11  5  1  0  0  0  0
 12  6  1  0  0  0  0
 13  8  1  0  0  0  0
 14  8  1  0  0  0  0
 14  9  1  0  0  0  0
 15  7  2  0  0  0  0
 16 12  2  0  0  0  0
 16 13  1  0  0  0  0
 16 15  1  0  0  0  0
 17 10  1  0  0  0  0
 18 12  1  0  0  0  0
 19 13  2  0  0  0  0
 20  1  1  0  0  0  0
 20 11  1  0  0  0  0
 21 14  1  0  0  0  0
 21 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253690

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C(C=C1)C1CC(=O)C2=C(O)C=C(O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O5/c1-20-11-4-2-9(3-5-11)14-8-13(19)16-12(18)6-10(17)7-15(16)21-14/h2-7,14,17-18H,8H2,1H3

> <INCHI_KEY>
HMUJXQRRKBLVOO-UHFFFAOYSA-N

> <FORMULA>
C16H14O5

> <MOLECULAR_WEIGHT>
286.283

> <EXACT_MASS>
286.084123551

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
29.415916351185615

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-2-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
2.95

> <JCHEM_LOGP>
2.9810021063333334

> <ALOGPS_LOGS>
-3.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.50821189558811

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.866811862762185

> <JCHEM_PKA_STRONGEST_BASIC>
-4.582032172551624

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
75.77210000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.79e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isosakuranetin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0253690
     RDKit          3D
Isosakuranetin
 35 37  0  0  0  0  0  0  0  0999 V2000
    5.9848    0.2396   -1.1176 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4358    0.6772    0.1125 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0603    0.5207    0.2978 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4364    0.9178    1.4640 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0764    0.7525    1.6226 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2696    0.1946    0.6532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1902    0.0366    0.8685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5899   -1.3363    1.2614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8464   -1.7426    0.5872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1742   -2.9685    0.4809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7793   -0.7894    0.0077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1261   -0.9781   -0.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7144   -2.1289    0.3661 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9017    0.0346   -0.6817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3699    1.2084   -1.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1394    2.1951   -1.7331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9921    1.3630   -1.0358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2088    0.3891   -0.4660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8321    0.4649   -0.3066 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8944   -0.2013   -0.5106 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2541   -0.0377   -0.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4205    0.8032   -1.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7845   -0.8461   -1.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0572    0.4098   -1.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0556    1.3621    2.2452 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5846    1.0697    2.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4692    0.7232    1.7158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8087   -1.4070    2.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1885   -2.1055    1.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3434   -2.9179    0.8038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9775   -0.1369   -0.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5682    2.9533   -1.2551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5417    2.2689   -1.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3082   -0.6419   -1.2964 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7625   -0.3463   -1.5890 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
  6 20  1  0
 20 21  2  0
 21  3  1  0
 19  7  1  0
 18 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 17 33  1  0
 20 34  1  0
 21 35  1  0
M  END

HEADER    PROTEIN                                 17-SEP-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-SEP-17         0                                  
HETATM    1  C   UNK     0      14.670  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2    4    9                                                       
CONECT    3    5    9                                                       
CONECT    4    2   11                                                       
CONECT    5    3   11                                                       
CONECT    6   10   12                                                       
CONECT    7   10   15                                                       
CONECT    8   13   14                                                       
CONECT    9    2    3   14                                                  
CONECT   10    6    7   17                                                  
CONECT   11    4    5   20                                                  
CONECT   12    6   16   18                                                  
CONECT   13    8   16   19                                                  
CONECT   14    8    9   21                                                  
CONECT   15    7   16   21                                                  
CONECT   16   12   13   15                                                  
CONECT   17   10                                                            
CONECT   18   12                                                            
CONECT   19   13                                                            
CONECT   20    1   11                                                       
CONECT   21   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0253690
HETATM    1  C1  UNL     1       5.985   0.240  -1.118  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.436   0.677   0.113  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.060   0.521   0.298  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.436   0.918   1.464  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.076   0.752   1.623  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.270   0.195   0.653  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.190   0.037   0.868  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.590  -1.336   1.261  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.846  -1.743   0.587  1.00  0.00           C  
HETATM   10  O2  UNL     1      -2.174  -2.969   0.481  1.00  0.00           O  
HETATM   11  C9  UNL     1      -2.779  -0.789   0.008  1.00  0.00           C  
HETATM   12  C10 UNL     1      -4.126  -0.978  -0.094  1.00  0.00           C  
HETATM   13  O3  UNL     1      -4.714  -2.129   0.366  1.00  0.00           O  
HETATM   14  C11 UNL     1      -4.902   0.035  -0.682  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.370   1.208  -1.159  1.00  0.00           C  
HETATM   16  O4  UNL     1      -5.139   2.195  -1.733  1.00  0.00           O  
HETATM   17  C13 UNL     1      -2.992   1.363  -1.036  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.209   0.389  -0.466  1.00  0.00           C  
HETATM   19  O5  UNL     1      -0.832   0.465  -0.307  1.00  0.00           O  
HETATM   20  C15 UNL     1       1.894  -0.201  -0.511  1.00  0.00           C  
HETATM   21  C16 UNL     1       3.254  -0.038  -0.673  1.00  0.00           C  
HETATM   22  H1  UNL     1       5.421   0.803  -1.915  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.785  -0.846  -1.290  1.00  0.00           H  
HETATM   24  H3  UNL     1       7.057   0.410  -1.194  1.00  0.00           H  
HETATM   25  H4  UNL     1       4.056   1.362   2.245  1.00  0.00           H  
HETATM   26  H5  UNL     1       1.585   1.070   2.552  1.00  0.00           H  
HETATM   27  H6  UNL     1      -0.469   0.723   1.716  1.00  0.00           H  
HETATM   28  H7  UNL     1      -0.809  -1.407   2.368  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.188  -2.105   1.062  1.00  0.00           H  
HETATM   30  H9  UNL     1      -4.343  -2.918   0.804  1.00  0.00           H  
HETATM   31  H10 UNL     1      -5.978  -0.137  -0.754  1.00  0.00           H  
HETATM   32  H11 UNL     1      -5.568   2.953  -1.255  1.00  0.00           H  
HETATM   33  H12 UNL     1      -2.542   2.269  -1.398  1.00  0.00           H  
HETATM   34  H13 UNL     1       1.308  -0.642  -1.296  1.00  0.00           H  
HETATM   35  H14 UNL     1       3.762  -0.346  -1.589  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5   25
CONECT    5    6    6   26
CONECT    6    7   20
CONECT    7    8   19   27
CONECT    8    9   28   29
CONECT    9   10   10   11
CONECT   11   12   12   18
CONECT   12   13   14
CONECT   13   30
CONECT   14   15   15   31
CONECT   15   16   17
CONECT   16   32
CONECT   17   18   18   33
CONECT   18   19
CONECT   20   21   21   34
CONECT   21   35
END

HMDB0253690
     RDKit          3D
Isosakuranetin
 35 37  0  0  0  0  0  0  0  0999 V2000
    5.9848    0.2396   -1.1176 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4358    0.6772    0.1125 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0603    0.5207    0.2978 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4364    0.9178    1.4640 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0764    0.7525    1.6226 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2696    0.1946    0.6532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1902    0.0366    0.8685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5899   -1.3363    1.2614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8464   -1.7426    0.5872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1742   -2.9685    0.4809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7793   -0.7894    0.0077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1261   -0.9781   -0.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7144   -2.1289    0.3661 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9017    0.0346   -0.6817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3699    1.2084   -1.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1394    2.1951   -1.7331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9921    1.3630   -1.0358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2088    0.3891   -0.4660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8321    0.4649   -0.3066 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8944   -0.2013   -0.5106 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2541   -0.0377   -0.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4205    0.8032   -1.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7845   -0.8461   -1.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0572    0.4098   -1.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0556    1.3621    2.2452 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5846    1.0697    2.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4692    0.7232    1.7158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8087   -1.4070    2.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1885   -2.1055    1.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3434   -2.9179    0.8038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9775   -0.1369   -0.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5682    2.9533   -1.2551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5417    2.2689   -1.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3082   -0.6419   -1.2964 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7625   -0.3463   -1.5890 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
  6 20  1  0
 20 21  2  0
 21  3  1  0
 19  7  1  0
 18 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 17 33  1  0
 20 34  1  0
 21 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₆H₁₄O₅

Average Molecular Weight

286.283

Monoisotopic Molecular Weight

286.084123551

IUPAC Name

5,7-dihydroxy-2-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

isosakuranetin

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1)C1CC(=O)C2=C(O)C=C(O)C=C2O1

InChI Identifier

InChI=1S/C16H14O5/c1-20-11-4-2-9(3-5-11)14-8-13(19)16-12(18)6-10(17)7-15(16)21-14/h2-7,14,17-18H,8H2,1H3

InChI Key

HMUJXQRRKBLVOO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C4' atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

4'-O-methylated flavonoids

Alternative Parents

Substituents

4p-methoxyflavonoid-skeleton
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Flavan
Chromone
Benzopyran
Chromane
1-benzopyran
Phenoxy compound
Methoxybenzene
Anisole
Phenol ether
Aryl ketone
Aryl alkyl ketone
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Endogenous (HMDB: HMDB0132458)

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	2.95	ALOGPS
logP	2.98	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	7.87	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	75.77 m³·mol⁻¹	ChemAxon
Polarizability	29.42 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+H]+	168.774	30932474
DeepCCS	[M-H]-	166.416	30932474
DeepCCS	[M-2H]-	199.302	30932474
DeepCCS	[M+Na]+	174.867	30932474
AllCCS	[M+H]+	167.2	32859911
AllCCS	[M+H-H2O]+	163.5	32859911
AllCCS	[M+NH4]+	170.7	32859911
AllCCS	[M+Na]+	171.7	32859911
AllCCS	[M-H]-	168.3	32859911
AllCCS	[M+Na-2H]-	167.8	32859911
AllCCS	[M+HCOO]-	167.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isosakuranetin	COC1=CC=C(C=C1)C1CC(=O)C2=C(O)C=C(O)C=C2O1	3918.9	Standard polar	33892256
Isosakuranetin	COC1=CC=C(C=C1)C1CC(=O)C2=C(O)C=C(O)C=C2O1	2823.2	Standard non polar	33892256
Isosakuranetin	COC1=CC=C(C=C1)C1CC(=O)C2=C(O)C=C(O)C=C2O1	2799.7	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 - 5,7-dihydroxy-2-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0abl-0490000000-4aa7394d5873ec15130e	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,7-dihydroxy-2-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one GC-MS (2 TMS) - 70eV, Positive	splash10-0829-4958700000-4169fb8dfbd23cbf53a3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,7-dihydroxy-2-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,7-dihydroxy-2-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,7-dihydroxy-2-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,7-dihydroxy-2-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,7-dihydroxy-2-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,7-dihydroxy-2-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,7-dihydroxy-2-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isosakuranetin 6V, Positive-QTOF	splash10-000i-0590000000-91aead682b79cce39cb6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isosakuranetin 6V, Positive-QTOF	splash10-000i-0090000000-e9190c54f2562a1eb8f8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isosakuranetin 6V, Positive-QTOF	splash10-0aor-1900000000-4c869af1dc39dae04326	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isosakuranetin 6V, Positive-QTOF	splash10-0aor-2900000000-7140a81f584286218305	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isosakuranetin 6V, Positive-QTOF	splash10-0aor-2900000000-9597465030fdb2ac6670	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isosakuranetin 6V, Positive-QTOF	splash10-000i-0090000000-f767dc9443fa072c3745	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isosakuranetin 6V, Positive-QTOF	splash10-000i-0490000000-80d7b061d7a943a29549	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isosakuranetin 6V, Positive-QTOF	splash10-06ri-0910000000-6db82f25ee36cf25c5e0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isosakuranetin 6V, Positive-QTOF	splash10-000i-0490000000-2ee94020fb60c21ea308	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isosakuranetin 6V, Positive-QTOF	splash10-0btr-0910000000-2741bbb00026a2dc9a85	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isosakuranetin 6V, Positive-QTOF	splash10-000i-0090000000-2020ab326fb386fa974f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isosakuranetin 6V, Positive-QTOF	splash10-06ri-0910000000-0c2920386c42597e90a6	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosakuranetin 10V, Positive-QTOF	splash10-000i-0290000000-fe1c7c0d2e22bd7083b8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosakuranetin 20V, Positive-QTOF	splash10-000i-0890000000-3e37218616b6bccbd80f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosakuranetin 40V, Positive-QTOF	splash10-0udr-2910000000-b21ee8cf7212f9dd644c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosakuranetin 10V, Negative-QTOF	splash10-000i-0090000000-febd3853bfa7cd36f868	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosakuranetin 20V, Negative-QTOF	splash10-000i-0390000000-85ed2a469702ad1af360	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosakuranetin 40V, Negative-QTOF	splash10-0le9-4940000000-3140d79369cf072de9dc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosakuranetin 10V, Positive-QTOF	splash10-000i-0590000000-ce3fbd9ea37b829bce1f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosakuranetin 20V, Positive-QTOF	splash10-0f9i-0960000000-4d174c4f4e9ea1510d23	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosakuranetin 40V, Positive-QTOF	splash10-0udi-0900000000-abe911f3d4cbd54a3029	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosakuranetin 10V, Negative-QTOF	splash10-000i-0090000000-72ed1dce05f182779977	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosakuranetin 20V, Negative-QTOF	splash10-000i-0390000000-4a0dd0200380f840cec5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosakuranetin 40V, Negative-QTOF	splash10-03xr-3900000000-c2b8d6cdd284442e365d	2021-09-24	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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000610

KNApSAcK ID

Not Available

Chemspider ID

4293046

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Isosakuranetin

METLIN ID

Not Available

PubChem Compound

5118250

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

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 Isosakuranetin (HMDB0253690)

MOL for HMDB0253690 (Isosakuranetin)

3D MOL for HMDB0253690 (Isosakuranetin)

3D SDF for HMDB0253690 (Isosakuranetin)

3D-SDF for HMDB0253690 (Isosakuranetin)

PDB for HMDB0253690 (Isosakuranetin)

3D PDB for HMDB0253690 (Isosakuranetin)

SMILES for HMDB0253690 (Isosakuranetin)

INCHI for HMDB0253690 (Isosakuranetin)

Structure for HMDB0253690 (Isosakuranetin)

3D Structure for HMDB0253690 (Isosakuranetin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra