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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:28:24 UTC

Update Date

2022-03-07 02:55:14 UTC

HMDB ID

HMDB0037232

Secondary Accession Numbers

HMDB37232

Metabolite Identification

Common Name

(2xi,4xi)-4,4',5,7-Tetrahydroxyflavan

Description

(2xi,4xi)-4,4',5,7-Tetrahydroxyflavan belongs to the class of organic compounds known as flavan-4-ols. These are flavans that bear and hydroxyl group at position 4 (B ring), but not at the 3-position. Thus, (2XI,4XI)-4,4',5,7-tetrahydroxyflavan is considered to be a flavonoid (2xi,4xi)-4,4',5,7-Tetrahydroxyflavan has been detected, but not quantified in, breakfast cereal and cereals and cereal products. This could make (2XI,4XI)-4,4',5,7-tetrahydroxyflavan a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (2xi,4xi)-4,4',5,7-Tetrahydroxyflavan.

Structure

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

HMDB0037232
     RDKit          3D
(2xi,4xi)-4,4',5,7-Tetrahydroxyflavan
 34 36  0  0  0  0  0  0  0  0999 V2000
   -6.1082    0.2202   -1.0615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7723    0.2520   -0.6855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2503   -0.7992    0.0329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9130   -0.8335    0.4448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0780    0.2158    0.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6488    0.2911    0.5072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1397   -0.9903    1.1242 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2223   -0.6176    1.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7326   -1.6358    2.5025 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0816   -0.2268    0.6040 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4478   -0.4852    0.5986 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9541   -1.1373    1.7247 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2491   -0.1166   -0.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7184    0.5268   -1.5581 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5471    0.8878   -2.6109 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3652    0.7810   -1.5492 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5301    0.4150   -0.4837 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1691    0.7090   -0.5525 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6029    1.2613   -0.5892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9261    1.2967   -0.9976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8595    0.5997   -0.4825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8857   -1.6363    0.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5085   -1.6494    1.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5336    1.0761    1.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0172   -1.8069    0.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7685   -1.2689    1.9904 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0206    0.2883    2.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0725   -1.2619    3.3504 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9591   -1.3343    1.7349 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3183   -0.3381   -0.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0076    1.7993   -2.6255 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9465    1.2890   -2.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9740    2.1158   -0.8632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3557    2.1132   -1.5627 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
  5 19  1  0
 19 20  2  0
 20  2  1  0
 18  6  1  0
 17 10  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 19 33  1  0
 20 34  1  0
M  END


  Mrv0541 05061309392D          

 20 22  0  0  0  0            999 V2000
    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
    6.4302   -1.2375    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
    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
    7.1447   -1.6500    0.0000 O   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
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  8  1  2  0  0  0  0
  8  2  1  0  0  0  0
  9  3  2  0  0  0  0
  9  4  1  0  0  0  0
 10  5  2  0  0  0  0
 10  6  1  0  0  0  0
 11  5  1  0  0  0  0
 12  7  1  0  0  0  0
 13  7  1  0  0  0  0
 13  8  1  0  0  0  0
 14  6  2  0  0  0  0
 15 11  2  0  0  0  0
 15 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16  9  1  0  0  0  0
 17 10  1  0  0  0  0
 18 11  1  0  0  0  0
 19 12  1  0  0  0  0
 20 13  1  0  0  0  0
 20 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037232

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1CC(OC2=CC(O)=CC(O)=C12)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-6,12-13,16-19H,7H2

> <INCHI_KEY>
RPKUCYSGAXIESU-UHFFFAOYSA-N

> <FORMULA>
C15H14O5

> <MOLECULAR_WEIGHT>
274.2687

> <EXACT_MASS>
274.084123558

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
27.635665026387194

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4,5,7-triol

> <ALOGPS_LOGP>
1.25

> <JCHEM_LOGP>
1.8699708709999998

> <ALOGPS_LOGS>
-2.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.683866437531549

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.084501797198937

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2747909609911545

> <JCHEM_POLAR_SURFACE_AREA>
90.15

> <JCHEM_REFRACTIVITY>
72.12920000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.15e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
apiferol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037232
     RDKit          3D
(2xi,4xi)-4,4',5,7-Tetrahydroxyflavan
 34 36  0  0  0  0  0  0  0  0999 V2000
   -6.1082    0.2202   -1.0615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7723    0.2520   -0.6855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2503   -0.7992    0.0329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9130   -0.8335    0.4448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0780    0.2158    0.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6488    0.2911    0.5072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1397   -0.9903    1.1242 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2223   -0.6176    1.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7326   -1.6358    2.5025 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0816   -0.2268    0.6040 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4478   -0.4852    0.5986 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9541   -1.1373    1.7247 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2491   -0.1166   -0.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7184    0.5268   -1.5581 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5471    0.8878   -2.6109 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3652    0.7810   -1.5492 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5301    0.4150   -0.4837 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1691    0.7090   -0.5525 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6029    1.2613   -0.5892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9261    1.2967   -0.9976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8595    0.5997   -0.4825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8857   -1.6363    0.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5085   -1.6494    1.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5336    1.0761    1.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0172   -1.8069    0.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7685   -1.2689    1.9904 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0206    0.2883    2.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0725   -1.2619    3.3504 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9591   -1.3343    1.7349 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3183   -0.3381   -0.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0076    1.7993   -2.6255 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9465    1.2890   -2.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9740    2.1158   -0.8632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3557    2.1132   -1.5627 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
  5 19  1  0
 19 20  2  0
 20  2  1  0
 18  6  1  0
 17 10  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 19 33  1  0
 20 34  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.003  -2.310   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       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+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       6.668  -0.770   0.000  0.00  0.00           O+0
CONECT    1    3    8                                                       
CONECT    2    4    8                                                       
CONECT    3    1    9                                                       
CONECT    4    2    9                                                       
CONECT    5   10   11                                                       
CONECT    6   10   14                                                       
CONECT    7   12   13                                                       
CONECT    8    1    2   13                                                  
CONECT    9    3    4   16                                                  
CONECT   10    5    6   17                                                  
CONECT   11    5   15   18                                                  
CONECT   12    7   15   19                                                  
CONECT   13    7    8   20                                                  
CONECT   14    6   15   20                                                  
CONECT   15   11   12   14                                                  
CONECT   16    9                                                            
CONECT   17   10                                                            
CONECT   18   11                                                            
CONECT   19   12                                                            
CONECT   20   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0037232
HETATM    1  O1  UNL     1      -6.108   0.220  -1.062  1.00  0.00           O  
HETATM    2  C1  UNL     1      -4.772   0.252  -0.685  1.00  0.00           C  
HETATM    3  C2  UNL     1      -4.250  -0.799   0.033  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.913  -0.833   0.445  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.078   0.216   0.127  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.649   0.291   0.507  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.140  -0.990   1.124  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.222  -0.618   1.729  1.00  0.00           C  
HETATM    9  O2  UNL     1       1.733  -1.636   2.503  1.00  0.00           O  
HETATM   10  C8  UNL     1       2.082  -0.227   0.604  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.448  -0.485   0.599  1.00  0.00           C  
HETATM   12  O3  UNL     1       3.954  -1.137   1.725  1.00  0.00           O  
HETATM   13  C10 UNL     1       4.249  -0.117  -0.459  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.718   0.527  -1.558  1.00  0.00           C  
HETATM   15  O4  UNL     1       4.547   0.888  -2.611  1.00  0.00           O  
HETATM   16  C12 UNL     1       2.365   0.781  -1.549  1.00  0.00           C  
HETATM   17  C13 UNL     1       1.530   0.415  -0.484  1.00  0.00           C  
HETATM   18  O5  UNL     1       0.169   0.709  -0.552  1.00  0.00           O  
HETATM   19  C14 UNL     1      -2.603   1.261  -0.589  1.00  0.00           C  
HETATM   20  C15 UNL     1      -3.926   1.297  -0.998  1.00  0.00           C  
HETATM   21  H1  UNL     1      -6.860   0.600  -0.482  1.00  0.00           H  
HETATM   22  H2  UNL     1      -4.886  -1.636   0.296  1.00  0.00           H  
HETATM   23  H3  UNL     1      -2.509  -1.649   1.002  1.00  0.00           H  
HETATM   24  H4  UNL     1      -0.534   1.076   1.312  1.00  0.00           H  
HETATM   25  H5  UNL     1      -0.017  -1.807   0.385  1.00  0.00           H  
HETATM   26  H6  UNL     1      -0.769  -1.269   1.990  1.00  0.00           H  
HETATM   27  H7  UNL     1       1.021   0.288   2.361  1.00  0.00           H  
HETATM   28  H8  UNL     1       2.073  -1.262   3.350  1.00  0.00           H  
HETATM   29  H9  UNL     1       4.959  -1.334   1.735  1.00  0.00           H  
HETATM   30  H10 UNL     1       5.318  -0.338  -0.424  1.00  0.00           H  
HETATM   31  H11 UNL     1       5.008   1.799  -2.625  1.00  0.00           H  
HETATM   32  H12 UNL     1       1.946   1.289  -2.417  1.00  0.00           H  
HETATM   33  H13 UNL     1      -1.974   2.116  -0.863  1.00  0.00           H  
HETATM   34  H14 UNL     1      -4.356   2.113  -1.563  1.00  0.00           H  
CONECT    1    2   21
CONECT    2    3    3   20
CONECT    3    4   22
CONECT    4    5    5   23
CONECT    5    6   19
CONECT    6    7   18   24
CONECT    7    8   25   26
CONECT    8    9   10   27
CONECT    9   28
CONECT   10   11   11   17
CONECT   11   12   13
CONECT   12   29
CONECT   13   14   14   30
CONECT   14   15   16
CONECT   15   31
CONECT   16   17   17   32
CONECT   17   18
CONECT   19   20   20   33
CONECT   20   34
END

HMDB0037232
     RDKit          3D
(2xi,4xi)-4,4',5,7-Tetrahydroxyflavan
 34 36  0  0  0  0  0  0  0  0999 V2000
   -6.1082    0.2202   -1.0615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7723    0.2520   -0.6855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2503   -0.7992    0.0329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9130   -0.8335    0.4448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0780    0.2158    0.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6488    0.2911    0.5072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1397   -0.9903    1.1242 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2223   -0.6176    1.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7326   -1.6358    2.5025 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0816   -0.2268    0.6040 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4478   -0.4852    0.5986 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9541   -1.1373    1.7247 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2491   -0.1166   -0.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7184    0.5268   -1.5581 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5471    0.8878   -2.6109 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3652    0.7810   -1.5492 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5301    0.4150   -0.4837 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1691    0.7090   -0.5525 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6029    1.2613   -0.5892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9261    1.2967   -0.9976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8595    0.5997   -0.4825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8857   -1.6363    0.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5085   -1.6494    1.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5336    1.0761    1.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0172   -1.8069    0.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7685   -1.2689    1.9904 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0206    0.2883    2.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0725   -1.2619    3.3504 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9591   -1.3343    1.7349 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3183   -0.3381   -0.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0076    1.7993   -2.6255 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9465    1.2890   -2.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9740    2.1158   -0.8632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3557    2.1132   -1.5627 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
  5 19  1  0
 19 20  2  0
 20  2  1  0
 18  6  1  0
 17 10  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 19 33  1  0
 20 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₁₄O₅

Average Molecular Weight

274.2687

Monoisotopic Molecular Weight

274.084123558

IUPAC Name

2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4,5,7-triol

Traditional Name

apiferol

CAS Registry Number

Not Available

SMILES

OC1CC(OC2=CC(O)=CC(O)=C12)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C15H14O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-6,12-13,16-19H,7H2

InChI Key

RPKUCYSGAXIESU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavan-4-ols. These are flavans that bear and hydroxyl group at position 4 (B ring), but not at the 3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavan-4-ols

Alternative Parents

Substituents

4'-hydroxyflavonoid
4-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavan-4-ol
Hydroxyflavonoid
1-benzopyran
Chromane
Benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Polyol
Organoheterocyclic compound
Oxacycle
Ether
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavans, Flavanols and Leucoanthocyanidins (LMPK12020166 )
a small molecule (CPD-11940 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0037232)
Cytoplasm (HMDB: HMDB0037232)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037232)

Source

Exogenous

Food

Food (HMDB: HMDB0037232)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Endogenous

Plant

Plant (HMDB: HMDB0037232)
Poaceae (HMDB: HMDB0037232)

Not Available

Nutrient (HMDB: HMDB0037232)

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	0.42 g/L	ALOGPS
logP	1.25	ALOGPS
logP	1.87	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	9.08	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	90.15 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	72.13 m³·mol⁻¹	ChemAxon
Polarizability	27.64 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]+	164.727	31661259
DarkChem	[M-H]-	165.483	31661259
DeepCCS	[M-2H]-	195.039	30932474
DeepCCS	[M+Na]+	170.605	30932474
AllCCS	[M+H]+	164.7	32859911
AllCCS	[M+H-H2O]+	160.9	32859911
AllCCS	[M+NH4]+	168.3	32859911
AllCCS	[M+Na]+	169.3	32859911
AllCCS	[M-H]-	164.8	32859911
AllCCS	[M+Na-2H]-	164.3	32859911
AllCCS	[M+HCOO]-	164.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(2xi,4xi)-4,4',5,7-Tetrahydroxyflavan	OC1CC(OC2=CC(O)=CC(O)=C12)C1=CC=C(O)C=C1	3835.6	Standard polar	33892256
(2xi,4xi)-4,4',5,7-Tetrahydroxyflavan	OC1CC(OC2=CC(O)=CC(O)=C12)C1=CC=C(O)C=C1	2972.5	Standard non polar	33892256
(2xi,4xi)-4,4',5,7-Tetrahydroxyflavan	OC1CC(OC2=CC(O)=CC(O)=C12)C1=CC=C(O)C=C1	3018.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(2xi,4xi)-4,4',5,7-Tetrahydroxyflavan,1TMS,isomer #1	C[Si](C)(C)OC1CC(C2=CC=C(O)C=C2)OC2=CC(O)=CC(O)=C21	2841.6	Semi standard non polar	33892256
(2xi,4xi)-4,4',5,7-Tetrahydroxyflavan,1TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=C2C(=C1)OC(C1=CC=C(O)C=C1)CC2O	2854.5	Semi standard non polar	33892256
(2xi,4xi)-4,4',5,7-Tetrahydroxyflavan,1TMS,isomer #3	C[Si](C)(C)OC1=CC(O)=CC2=C1C(O)CC(C1=CC=C(O)C=C1)O2	2829.3	Semi standard non polar	33892256
(2xi,4xi)-4,4',5,7-Tetrahydroxyflavan,1TMS,isomer #4	C[Si](C)(C)OC1=CC=C(C2CC(O)C3=C(O)C=C(O)C=C3O2)C=C1	2868.4	Semi standard non polar	33892256
(2xi,4xi)-4,4',5,7-Tetrahydroxyflavan,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2CC(O[Si](C)(C)C)C3=C(O)C=C(O)C=C3O2)C=C1	2908.1	Semi standard non polar	33892256
(2xi,4xi)-4,4',5,7-Tetrahydroxyflavan,2TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=C2C(=C1)OC(C1=CC=C(O)C=C1)CC2O[Si](C)(C)C	2903.1	Semi standard non polar	33892256
(2xi,4xi)-4,4',5,7-Tetrahydroxyflavan,2TMS,isomer #3	C[Si](C)(C)OC1=CC(O)=CC2=C1C(O[Si](C)(C)C)CC(C1=CC=C(O)C=C1)O2	2891.2	Semi standard non polar	33892256
(2xi,4xi)-4,4',5,7-Tetrahydroxyflavan,2TMS,isomer #4	C[Si](C)(C)OC1=CC2=C(C(O[Si](C)(C)C)=C1)C(O)CC(C1=CC=C(O)C=C1)O2	2923.2	Semi standard non polar	33892256
(2xi,4xi)-4,4',5,7-Tetrahydroxyflavan,2TMS,isomer #5	C[Si](C)(C)OC1=CC=C(C2CC(O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)C=C1	2965.0	Semi standard non polar	33892256
(2xi,4xi)-4,4',5,7-Tetrahydroxyflavan,2TMS,isomer #6	C[Si](C)(C)OC1=CC=C(C2CC(O)C3=C(C=C(O)C=C3O[Si](C)(C)C)O2)C=C1	2926.1	Semi standard non polar	33892256
(2xi,4xi)-4,4',5,7-Tetrahydroxyflavan,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2CC(O[Si](C)(C)C)C3=C(C=C(O)C=C3O[Si](C)(C)C)O2)C=C1	2837.0	Semi standard non polar	33892256
(2xi,4xi)-4,4',5,7-Tetrahydroxyflavan,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C2CC(O[Si](C)(C)C)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)C=C1	2816.4	Semi standard non polar	33892256
(2xi,4xi)-4,4',5,7-Tetrahydroxyflavan,3TMS,isomer #3	C[Si](C)(C)OC1=CC2=C(C(O[Si](C)(C)C)=C1)C(O[Si](C)(C)C)CC(C1=CC=C(O)C=C1)O2	2830.1	Semi standard non polar	33892256
(2xi,4xi)-4,4',5,7-Tetrahydroxyflavan,3TMS,isomer #4	C[Si](C)(C)OC1=CC=C(C2CC(O)C3=C(C=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)O2)C=C1	2892.6	Semi standard non polar	33892256
(2xi,4xi)-4,4',5,7-Tetrahydroxyflavan,4TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2CC(O[Si](C)(C)C)C3=C(C=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)O2)C=C1	2832.2	Semi standard non polar	33892256
(2xi,4xi)-4,4',5,7-Tetrahydroxyflavan,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CC(C2=CC=C(O)C=C2)OC2=CC(O)=CC(O)=C21	3120.8	Semi standard non polar	33892256
(2xi,4xi)-4,4',5,7-Tetrahydroxyflavan,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=C1)OC(C1=CC=C(O)C=C1)CC2O	3120.2	Semi standard non polar	33892256
(2xi,4xi)-4,4',5,7-Tetrahydroxyflavan,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C(O)CC(C1=CC=C(O)C=C1)O2	3102.8	Semi standard non polar	33892256
(2xi,4xi)-4,4',5,7-Tetrahydroxyflavan,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(O)C3=C(O)C=C(O)C=C3O2)C=C1	3127.3	Semi standard non polar	33892256
(2xi,4xi)-4,4',5,7-Tetrahydroxyflavan,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(O[Si](C)(C)C(C)(C)C)C3=C(O)C=C(O)C=C3O2)C=C1	3434.3	Semi standard non polar	33892256
(2xi,4xi)-4,4',5,7-Tetrahydroxyflavan,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=C1)OC(C1=CC=C(O)C=C1)CC2O[Si](C)(C)C(C)(C)C	3419.9	Semi standard non polar	33892256
(2xi,4xi)-4,4',5,7-Tetrahydroxyflavan,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C(O[Si](C)(C)C(C)(C)C)CC(C1=CC=C(O)C=C1)O2	3414.0	Semi standard non polar	33892256
(2xi,4xi)-4,4',5,7-Tetrahydroxyflavan,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1)C(O)CC(C1=CC=C(O)C=C1)O2	3432.4	Semi standard non polar	33892256
(2xi,4xi)-4,4',5,7-Tetrahydroxyflavan,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C=C1	3457.5	Semi standard non polar	33892256
(2xi,4xi)-4,4',5,7-Tetrahydroxyflavan,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(O)C3=C(C=C(O)C=C3O[Si](C)(C)C(C)(C)C)O2)C=C1	3442.2	Semi standard non polar	33892256
(2xi,4xi)-4,4',5,7-Tetrahydroxyflavan,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(O[Si](C)(C)C(C)(C)C)C3=C(C=C(O)C=C3O[Si](C)(C)C(C)(C)C)O2)C=C1	3563.9	Semi standard non polar	33892256
(2xi,4xi)-4,4',5,7-Tetrahydroxyflavan,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(O[Si](C)(C)C(C)(C)C)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C=C1	3586.2	Semi standard non polar	33892256
(2xi,4xi)-4,4',5,7-Tetrahydroxyflavan,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1)C(O[Si](C)(C)C(C)(C)C)CC(C1=CC=C(O)C=C1)O2	3521.7	Semi standard non polar	33892256
(2xi,4xi)-4,4',5,7-Tetrahydroxyflavan,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(O)C3=C(C=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)O2)C=C1	3646.9	Semi standard non polar	33892256
(2xi,4xi)-4,4',5,7-Tetrahydroxyflavan,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(O[Si](C)(C)C(C)(C)C)C3=C(C=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)O2)C=C1	3694.0	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 - (2xi,4xi)-4,4',5,7-Tetrahydroxyflavan GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-0390000000-3c84149313679c186122	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2xi,4xi)-4,4',5,7-Tetrahydroxyflavan GC-MS (4 TMS) - 70eV, Positive	splash10-0002-1500980000-da6b653ea63e83122158	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2xi,4xi)-4,4',5,7-Tetrahydroxyflavan 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 - (2xi,4xi)-4,4',5,7-Tetrahydroxyflavan 10V, Positive-QTOF	splash10-0a6r-0390000000-46271437f44ecdd24254	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2xi,4xi)-4,4',5,7-Tetrahydroxyflavan 20V, Positive-QTOF	splash10-0a4i-0960000000-6da0556e752ccd28d873	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2xi,4xi)-4,4',5,7-Tetrahydroxyflavan 40V, Positive-QTOF	splash10-00ri-4900000000-c3c4966d2071dbfccdb4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2xi,4xi)-4,4',5,7-Tetrahydroxyflavan 10V, Negative-QTOF	splash10-00di-0290000000-60341a19c4e92686a9c6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2xi,4xi)-4,4',5,7-Tetrahydroxyflavan 20V, Negative-QTOF	splash10-0kmi-0980000000-cb770905091bebc94f52	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2xi,4xi)-4,4',5,7-Tetrahydroxyflavan 40V, Negative-QTOF	splash10-066u-5910000000-ae5c75751782fc9c920a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2xi,4xi)-4,4',5,7-Tetrahydroxyflavan 10V, Positive-QTOF	splash10-056r-0090000000-b2b185ad63b79a75b53f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2xi,4xi)-4,4',5,7-Tetrahydroxyflavan 20V, Positive-QTOF	splash10-0a6s-0970000000-243d7344099a4e1195f4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2xi,4xi)-4,4',5,7-Tetrahydroxyflavan 40V, Positive-QTOF	splash10-0adi-3910000000-3e9e48d1608d8c12d3ec	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2xi,4xi)-4,4',5,7-Tetrahydroxyflavan 10V, Negative-QTOF	splash10-00di-0090000000-7dbb1e549f6404042b70	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2xi,4xi)-4,4',5,7-Tetrahydroxyflavan 20V, Negative-QTOF	splash10-01di-1930000000-1a5d4e0078839ef38485	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2xi,4xi)-4,4',5,7-Tetrahydroxyflavan 40V, Negative-QTOF	splash10-014l-5930000000-05b60407940c6bb45a98	2021-09-22	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

FDB016239

KNApSAcK ID

Not Available

Chemspider ID

161511

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

185795

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for (2xi,4xi)-4,4',5,7-Tetrahydroxyflavan (HMDB0037232)

MOL for HMDB0037232 ((2xi,4xi)-4,4',5,7-Tetrahydroxyflavan)

3D MOL for HMDB0037232 ((2xi,4xi)-4,4',5,7-Tetrahydroxyflavan)

3D SDF for HMDB0037232 ((2xi,4xi)-4,4',5,7-Tetrahydroxyflavan)

3D-SDF for HMDB0037232 ((2xi,4xi)-4,4',5,7-Tetrahydroxyflavan)

PDB for HMDB0037232 ((2xi,4xi)-4,4',5,7-Tetrahydroxyflavan)

3D PDB for HMDB0037232 ((2xi,4xi)-4,4',5,7-Tetrahydroxyflavan)

SMILES for HMDB0037232 ((2xi,4xi)-4,4',5,7-Tetrahydroxyflavan)

INCHI for HMDB0037232 ((2xi,4xi)-4,4',5,7-Tetrahydroxyflavan)

Structure for HMDB0037232 ((2xi,4xi)-4,4',5,7-Tetrahydroxyflavan)

3D Structure for HMDB0037232 ((2xi,4xi)-4,4',5,7-Tetrahydroxyflavan)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra