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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:15:08 UTC

Update Date

2022-03-07 02:56:41 UTC

HMDB ID

HMDB0040679

Secondary Accession Numbers

HMDB40679

Metabolite Identification

Common Name

(2S,3R,4R)-3,4,4'-Trihydroxyflavan

Description

(2S,3R,4R)-3,4,4'-Trihydroxyflavan belongs to the class of organic compounds known as leucoanthocyanidins. These are flavonoids consisting of a flavan (3,4-dihydro-2-phenyl-2H-1-benzopyran) moiety that carries two hydroxy groups at the C3- and C4-positions (2S,3R,4R)-3,4,4'-Trihydroxyflavan has been detected, but not quantified in, fruits. This could make (2S,3R,4R)-3,4,4'-trihydroxyflavan a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (2S,3R,4R)-3,4,4'-Trihydroxyflavan.

Structure

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

HMDB0040679
     RDKit          3D
(2S,3R,4R)-3,4,4'-Trihydroxyflavan
 33 35  0  0  0  0  0  0  0  0999 V2000
    5.5401    0.3808    0.8802 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2112    0.1669    0.4990 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9767   -0.9771   -0.2681 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7003   -1.2774   -0.6943 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6735   -0.4294   -0.3478 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2923   -0.7420   -0.8012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3231    0.4238   -1.2998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6281    0.7956   -0.9985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3836    1.5900   -1.8568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6784    1.9536   -1.5484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1899    1.4947   -0.3522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4392    0.6987    0.5126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1505    0.3447    0.1915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3387   -0.4947    1.0886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1163   -1.2370    1.9627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4533   -1.4024    0.3034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2284   -2.4844   -0.1400 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9038    0.7001    0.4093 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1912    1.0052    0.8406 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1600    0.9104    0.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7626   -1.6532   -0.5504 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5355   -2.1781   -1.2946 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3187   -1.4659   -1.6666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9230    1.9155   -2.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2821    2.5749   -2.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2065    1.7504   -0.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8336    0.3343    1.4538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6810    0.1679    1.7205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6762   -1.3461    2.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2887   -1.8452    1.0196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5377   -2.9551    0.6879 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1168    1.3840    0.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3982    1.8966    1.4428 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  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
  5 18  1  0
 18 19  2  0
 19  2  1  0
 16  6  1  0
 13  8  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
M  END

  Mrv0541 05061312022D          

 19 21  0  0  0  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    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
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -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   -0.4125    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
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
 10  7  2  0  0  0  0
 10  8  1  0  0  0  0
 11  3  2  0  0  0  0
 12  4  2  0  0  0  0
 12 11  1  0  0  0  0
 13 11  1  0  0  0  0
 14 13  1  0  0  0  0
 15  9  1  0  0  0  0
 15 14  1  0  0  0  0
 16 10  1  0  0  0  0
 17 13  1  0  0  0  0
 18 14  1  0  0  0  0
 19 12  1  0  0  0  0
 19 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040679

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1C(O)C2=CC=CC=C2OC1C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O4/c16-10-7-5-9(6-8-10)15-14(18)13(17)11-3-1-2-4-12(11)19-15/h1-8,13-18H

> <INCHI_KEY>
HGNZPAIPVKRUKE-UHFFFAOYSA-N

> <FORMULA>
C15H14O4

> <MOLECULAR_WEIGHT>
258.2693

> <EXACT_MASS>
258.089208936

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
26.355846360272057

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4-diol

> <ALOGPS_LOGP>
1.20

> <JCHEM_LOGP>
1.786806833333333

> <ALOGPS_LOGS>
-2.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.77120196000584

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.469532784927305

> <JCHEM_PKA_STRONGEST_BASIC>
-3.604392147057019

> <JCHEM_POLAR_SURFACE_AREA>
69.92

> <JCHEM_REFRACTIVITY>
69.26450000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.56e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040679
     RDKit          3D
(2S,3R,4R)-3,4,4'-Trihydroxyflavan
 33 35  0  0  0  0  0  0  0  0999 V2000
    5.5401    0.3808    0.8802 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2112    0.1669    0.4990 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9767   -0.9771   -0.2681 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7003   -1.2774   -0.6943 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6735   -0.4294   -0.3478 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2923   -0.7420   -0.8012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3231    0.4238   -1.2998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6281    0.7956   -0.9985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3836    1.5900   -1.8568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6784    1.9536   -1.5484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1899    1.4947   -0.3522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4392    0.6987    0.5126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1505    0.3447    0.1915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3387   -0.4947    1.0886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1163   -1.2370    1.9627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4533   -1.4024    0.3034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2284   -2.4844   -0.1400 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9038    0.7001    0.4093 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1912    1.0052    0.8406 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1600    0.9104    0.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7626   -1.6532   -0.5504 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5355   -2.1781   -1.2946 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3187   -1.4659   -1.6666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9230    1.9155   -2.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2821    2.5749   -2.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2065    1.7504   -0.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8336    0.3343    1.4538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6810    0.1679    1.7205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6762   -1.3461    2.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2887   -1.8452    1.0196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5377   -2.9551    0.6879 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1168    1.3840    0.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3982    1.8966    1.4428 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  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
  5 18  1  0
 18 19  2  0
 19  2  1  0
 16  6  1  0
 13  8  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  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      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1   11                                                       
CONECT    4    2   12                                                       
CONECT    5    7    9                                                       
CONECT    6    8    9                                                       
CONECT    7    5   10                                                       
CONECT    8    6   10                                                       
CONECT    9    5    6   15                                                  
CONECT   10    7    8   16                                                  
CONECT   11    3   12   13                                                  
CONECT   12    4   11   19                                                  
CONECT   13   11   14   17                                                  
CONECT   14   13   15   18                                                  
CONECT   15    9   14   19                                                  
CONECT   16   10                                                            
CONECT   17   13                                                            
CONECT   18   14                                                            
CONECT   19   12   15                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0040679
HETATM    1  O1  UNL     1       5.540   0.381   0.880  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.211   0.167   0.499  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.977  -0.977  -0.268  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.700  -1.277  -0.694  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.673  -0.429  -0.348  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.292  -0.742  -0.801  1.00  0.00           C  
HETATM    7  O2  UNL     1      -0.323   0.424  -1.300  1.00  0.00           O  
HETATM    8  C6  UNL     1      -1.628   0.796  -0.999  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.384   1.590  -1.857  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.678   1.954  -1.548  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.190   1.495  -0.352  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.439   0.699   0.513  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.151   0.345   0.192  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.339  -0.495   1.089  1.00  0.00           C  
HETATM   15  O3  UNL     1      -2.116  -1.237   1.963  1.00  0.00           O  
HETATM   16  C13 UNL     1      -0.453  -1.402   0.303  1.00  0.00           C  
HETATM   17  O4  UNL     1      -1.228  -2.484  -0.140  1.00  0.00           O  
HETATM   18  C14 UNL     1       1.904   0.700   0.409  1.00  0.00           C  
HETATM   19  C15 UNL     1       3.191   1.005   0.841  1.00  0.00           C  
HETATM   20  H1  UNL     1       6.160   0.910   0.307  1.00  0.00           H  
HETATM   21  H2  UNL     1       4.763  -1.653  -0.550  1.00  0.00           H  
HETATM   22  H3  UNL     1       2.535  -2.178  -1.295  1.00  0.00           H  
HETATM   23  H4  UNL     1       0.319  -1.466  -1.667  1.00  0.00           H  
HETATM   24  H5  UNL     1      -1.923   1.915  -2.778  1.00  0.00           H  
HETATM   25  H6  UNL     1      -4.282   2.575  -2.210  1.00  0.00           H  
HETATM   26  H7  UNL     1      -5.206   1.750  -0.057  1.00  0.00           H  
HETATM   27  H8  UNL     1      -3.834   0.334   1.454  1.00  0.00           H  
HETATM   28  H9  UNL     1      -0.681   0.168   1.721  1.00  0.00           H  
HETATM   29  H10 UNL     1      -1.676  -1.346   2.847  1.00  0.00           H  
HETATM   30  H11 UNL     1       0.289  -1.845   1.020  1.00  0.00           H  
HETATM   31  H12 UNL     1      -1.538  -2.955   0.688  1.00  0.00           H  
HETATM   32  H13 UNL     1       1.117   1.384   0.696  1.00  0.00           H  
HETATM   33  H14 UNL     1       3.398   1.897   1.443  1.00  0.00           H  
CONECT    1    2   20
CONECT    2    3    3   19
CONECT    3    4   21
CONECT    4    5    5   22
CONECT    5    6   18
CONECT    6    7   16   23
CONECT    7    8
CONECT    8    9    9   13
CONECT    9   10   24
CONECT   10   11   11   25
CONECT   11   12   26
CONECT   12   13   13   27
CONECT   13   14
CONECT   14   15   16   28
CONECT   15   29
CONECT   16   17   30
CONECT   17   31
CONECT   18   19   19   32
CONECT   19   33
END

HMDB0040679
     RDKit          3D
(2S,3R,4R)-3,4,4'-Trihydroxyflavan
 33 35  0  0  0  0  0  0  0  0999 V2000
    5.5401    0.3808    0.8802 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2112    0.1669    0.4990 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9767   -0.9771   -0.2681 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7003   -1.2774   -0.6943 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6735   -0.4294   -0.3478 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2923   -0.7420   -0.8012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3231    0.4238   -1.2998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6281    0.7956   -0.9985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3836    1.5900   -1.8568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6784    1.9536   -1.5484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1899    1.4947   -0.3522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4392    0.6987    0.5126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1505    0.3447    0.1915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3387   -0.4947    1.0886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1163   -1.2370    1.9627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4533   -1.4024    0.3034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2284   -2.4844   -0.1400 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9038    0.7001    0.4093 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1912    1.0052    0.8406 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1600    0.9104    0.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7626   -1.6532   -0.5504 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5355   -2.1781   -1.2946 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3187   -1.4659   -1.6666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9230    1.9155   -2.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2821    2.5749   -2.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2065    1.7504   -0.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8336    0.3343    1.4538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6810    0.1679    1.7205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6762   -1.3461    2.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2887   -1.8452    1.0196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5377   -2.9551    0.6879 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1168    1.3840    0.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3982    1.8966    1.4428 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  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
  5 18  1  0
 18 19  2  0
 19  2  1  0
 16  6  1  0
 13  8  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Methylumbelliferyl-N,n'-diacetyl-beta-chitobiose	HMDB
4-Methylumbelliferyl-N,N-diacetylchitobioside	HMDB
4-Mudacb	HMDB
GUM	HMDB
Me-dinag	HMDB

Chemical Formula

C₁₅H₁₄O₄

Average Molecular Weight

258.2693

Monoisotopic Molecular Weight

258.089208936

IUPAC Name

2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4-diol

Traditional Name

2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4-diol

CAS Registry Number

149747-10-4

SMILES

OC1C(O)C2=CC=CC=C2OC1C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C15H14O4/c16-10-7-5-9(6-8-10)15-14(18)13(17)11-3-1-2-4-12(11)19-15/h1-8,13-18H

InChI Key

HGNZPAIPVKRUKE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as leucoanthocyanidins. These are flavonoids consisting of a flavan (3,4-dihydro-2-phenyl-2H-1-benzopyran) moiety that carries two hydroxy groups at the C3- and C4-positions.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Leucoanthocyanidins

Alternative Parents

Substituents

Leucoanthocyanidin-skeleton
3-hydroxyflavonoid
4'-hydroxyflavonoid
4-hydroxyflavonoid
Hydroxyflavonoid
Chromane
Benzopyran
1-benzopyran
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
1,2-diol
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0040679)
Cytoplasm (HMDB: HMDB0040679)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040679)

Source

Exogenous

Exogenous (HMDB: HMDB0040679)

Food

Food (HMDB: HMDB0040679)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0040679)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0040679)

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	1.56 g/L	ALOGPS
logP	1.2	ALOGPS
logP	1.79	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	9.47	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.92 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	69.26 m³·mol⁻¹	ChemAxon
Polarizability	26.36 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]+	159.68	31661259
DarkChem	[M-H]-	157.327	31661259
DeepCCS	[M+H]+	158.677	30932474
DeepCCS	[M-H]-	156.281	30932474
DeepCCS	[M-2H]-	189.166	30932474
DeepCCS	[M+Na]+	164.708	30932474
AllCCS	[M+H]+	162.2	32859911
AllCCS	[M+H-H2O]+	158.3	32859911
AllCCS	[M+NH4]+	165.9	32859911
AllCCS	[M+Na]+	166.9	32859911
AllCCS	[M-H]-	162.3	32859911
AllCCS	[M+Na-2H]-	161.9	32859911
AllCCS	[M+HCOO]-	161.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(2S,3R,4R)-3,4,4'-Trihydroxyflavan	OC1C(O)C2=CC=CC=C2OC1C1=CC=C(O)C=C1	3597.9	Standard polar	33892256
(2S,3R,4R)-3,4,4'-Trihydroxyflavan	OC1C(O)C2=CC=CC=C2OC1C1=CC=C(O)C=C1	2540.4	Standard non polar	33892256
(2S,3R,4R)-3,4,4'-Trihydroxyflavan	OC1C(O)C2=CC=CC=C2OC1C1=CC=C(O)C=C1	2545.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(2S,3R,4R)-3,4,4'-Trihydroxyflavan,1TMS,isomer #1	C[Si](C)(C)OC1C(O)C2=CC=CC=C2OC1C1=CC=C(O)C=C1	2493.1	Semi standard non polar	33892256
(2S,3R,4R)-3,4,4'-Trihydroxyflavan,1TMS,isomer #2	C[Si](C)(C)OC1C2=CC=CC=C2OC(C2=CC=C(O)C=C2)C1O	2524.6	Semi standard non polar	33892256
(2S,3R,4R)-3,4,4'-Trihydroxyflavan,1TMS,isomer #3	C[Si](C)(C)OC1=CC=C(C2OC3=CC=CC=C3C(O)C2O)C=C1	2543.4	Semi standard non polar	33892256
(2S,3R,4R)-3,4,4'-Trihydroxyflavan,2TMS,isomer #1	C[Si](C)(C)OC1C2=CC=CC=C2OC(C2=CC=C(O)C=C2)C1O[Si](C)(C)C	2434.4	Semi standard non polar	33892256
(2S,3R,4R)-3,4,4'-Trihydroxyflavan,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C2OC3=CC=CC=C3C(O)C2O[Si](C)(C)C)C=C1	2417.4	Semi standard non polar	33892256
(2S,3R,4R)-3,4,4'-Trihydroxyflavan,2TMS,isomer #3	C[Si](C)(C)OC1=CC=C(C2OC3=CC=CC=C3C(O[Si](C)(C)C)C2O)C=C1	2479.8	Semi standard non polar	33892256
(2S,3R,4R)-3,4,4'-Trihydroxyflavan,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2OC3=CC=CC=C3C(O[Si](C)(C)C)C2O[Si](C)(C)C)C=C1	2405.1	Semi standard non polar	33892256
(2S,3R,4R)-3,4,4'-Trihydroxyflavan,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C(O)C2=CC=CC=C2OC1C1=CC=C(O)C=C1	2773.1	Semi standard non polar	33892256
(2S,3R,4R)-3,4,4'-Trihydroxyflavan,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1C2=CC=CC=C2OC(C2=CC=C(O)C=C2)C1O	2795.2	Semi standard non polar	33892256
(2S,3R,4R)-3,4,4'-Trihydroxyflavan,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(C2OC3=CC=CC=C3C(O)C2O)C=C1	2831.6	Semi standard non polar	33892256
(2S,3R,4R)-3,4,4'-Trihydroxyflavan,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C2=CC=CC=C2OC(C2=CC=C(O)C=C2)C1O[Si](C)(C)C(C)(C)C	2921.5	Semi standard non polar	33892256
(2S,3R,4R)-3,4,4'-Trihydroxyflavan,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(C2OC3=CC=CC=C3C(O)C2O[Si](C)(C)C(C)(C)C)C=C1	2941.6	Semi standard non polar	33892256
(2S,3R,4R)-3,4,4'-Trihydroxyflavan,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(C2OC3=CC=CC=C3C(O[Si](C)(C)C(C)(C)C)C2O)C=C1	2986.4	Semi standard non polar	33892256
(2S,3R,4R)-3,4,4'-Trihydroxyflavan,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2OC3=CC=CC=C3C(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C)C=C1	3098.6	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 - (2S,3R,4R)-3,4,4'-Trihydroxyflavan GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-0930000000-549a8fc2e62ffda69a30	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2S,3R,4R)-3,4,4'-Trihydroxyflavan GC-MS (3 TMS) - 70eV, Positive	splash10-11b9-5425900000-6bed84fb61262afe7605	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2S,3R,4R)-3,4,4'-Trihydroxyflavan 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 - (2S,3R,4R)-3,4,4'-Trihydroxyflavan 10V, Positive-QTOF	splash10-0a4i-0190000000-d10d3bb12067fbddcd77	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3R,4R)-3,4,4'-Trihydroxyflavan 20V, Positive-QTOF	splash10-0ab9-1940000000-ab7a086c698c6a866a88	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3R,4R)-3,4,4'-Trihydroxyflavan 40V, Positive-QTOF	splash10-0a6r-9700000000-694e2686ae61bae74d76	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3R,4R)-3,4,4'-Trihydroxyflavan 10V, Negative-QTOF	splash10-0a4i-0190000000-ce7caccb44efb7ce8b01	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3R,4R)-3,4,4'-Trihydroxyflavan 20V, Negative-QTOF	splash10-0ab9-2970000000-b5351f379937670a13ab	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3R,4R)-3,4,4'-Trihydroxyflavan 40V, Negative-QTOF	splash10-054o-9600000000-3f6a211cc3dec3331622	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3R,4R)-3,4,4'-Trihydroxyflavan 10V, Positive-QTOF	splash10-0a4i-0090000000-7466f0ff4fc176d35adf	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3R,4R)-3,4,4'-Trihydroxyflavan 20V, Positive-QTOF	splash10-0a4i-0930000000-ee4dba855d471b8e6e1b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3R,4R)-3,4,4'-Trihydroxyflavan 40V, Positive-QTOF	splash10-0a4i-4900000000-6db2eb115d0f16420f17	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3R,4R)-3,4,4'-Trihydroxyflavan 10V, Negative-QTOF	splash10-0a4r-0090000000-e0a309d8eb88e252f016	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3R,4R)-3,4,4'-Trihydroxyflavan 20V, Negative-QTOF	splash10-0a4i-2960000000-0bf8678210a682cb61b6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3R,4R)-3,4,4'-Trihydroxyflavan 40V, Negative-QTOF	splash10-05mo-4900000000-2e452767f869fcc2f03e	2021-09-24	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

FDB020477

KNApSAcK ID

Not Available

Chemspider ID

32683377

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

85979126

PDB ID

Not Available

ChEBI ID

174379

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 (2S,3R,4R)-3,4,4'-Trihydroxyflavan (HMDB0040679)

MOL for HMDB0040679 ((2S,3R,4R)-3,4,4'-Trihydroxyflavan)

3D MOL for HMDB0040679 ((2S,3R,4R)-3,4,4'-Trihydroxyflavan)

3D SDF for HMDB0040679 ((2S,3R,4R)-3,4,4'-Trihydroxyflavan)

3D-SDF for HMDB0040679 ((2S,3R,4R)-3,4,4'-Trihydroxyflavan)

PDB for HMDB0040679 ((2S,3R,4R)-3,4,4'-Trihydroxyflavan)

3D PDB for HMDB0040679 ((2S,3R,4R)-3,4,4'-Trihydroxyflavan)

SMILES for HMDB0040679 ((2S,3R,4R)-3,4,4'-Trihydroxyflavan)

INCHI for HMDB0040679 ((2S,3R,4R)-3,4,4'-Trihydroxyflavan)

Structure for HMDB0040679 ((2S,3R,4R)-3,4,4'-Trihydroxyflavan)

3D Structure for HMDB0040679 ((2S,3R,4R)-3,4,4'-Trihydroxyflavan)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra