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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:25:06 UTC

Update Date

2022-03-07 02:56:45 UTC

HMDB ID

HMDB0040828

Secondary Accession Numbers

HMDB40828

Metabolite Identification

Common Name

(2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan

Description

(2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan 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,3S,4R)-3,4,4',7-Tetrahydroxyflavan has been detected, but not quantified in, fruits. This could make (2S,3S,4R)-3,4,4',7-tetrahydroxyflavan a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan.

Structure

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

HMDB0040828
     RDKit          3D
(2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan
 34 36  0  0  0  0  0  0  0  0999 V2000
   -5.7853    1.6957   -0.0189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4720    1.2570   -0.1805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0439    0.7226   -1.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7385    0.2862   -1.5399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8207    0.3664   -0.5208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4372   -0.1148   -0.7466 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4328    0.8567   -0.2061 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7662    0.5575   -0.0775 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7737    1.4844   -0.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0918    1.0927   -0.0313 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0676    2.0736   -0.1396 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4617   -0.2152    0.2110 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4393   -1.1372    0.3066 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1074   -0.7571    0.1643 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0990   -1.8241    0.2854 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6268   -2.9660   -0.3386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2519   -1.4775   -0.1826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2283   -1.6669    0.8230 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2409    0.8995    0.6803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5461    1.3350    0.8394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0575    2.0769    0.8641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7238    0.6387   -2.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4660   -0.1263   -2.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2598   -0.1130   -1.8413 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4930    2.5145   -0.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4789    2.2871   -1.0582 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5060   -0.4898    0.3186 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7356   -2.1615    0.4968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0370   -2.0909    1.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6257   -3.7537    0.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5445   -2.2135   -0.9890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7231   -1.7691    1.6670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5349    0.9787    1.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8679    1.7532    1.7883 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  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
  5 19  1  0
 19 20  2  0
 20  2  1  0
 17  6  1  0
 14  8  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
M  END


  Mrv0541 02241210282D          

 20 22  0  0  0  0            999 V2000
    1.8144   -1.8558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0721   -1.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0721   -0.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8144   -0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4744   -0.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4744   -1.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2169   -1.8558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4744    0.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8144    1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721    0.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3296    1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3296    1.8558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0721    1.0308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3296    0.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3296   -0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3296   -0.6183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721   -0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8144   -0.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4744   -0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2169   -0.6183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3 15  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  9  1  0  0  0  0
  8 19  2  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 17  1  0  0  0  0
 11 12  1  0  0  0  0
 11 14  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040828

> <DATABASE_NAME>
hmdb

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

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

> <INCHI_KEY>
NTLUSUFJOUMRLA-UHFFFAOYSA-N

> <FORMULA>
C15H14O5

> <MOLECULAR_WEIGHT>
274.2687

> <EXACT_MASS>
274.084123558

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
27.52740731244312

> <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-3,4,7-triol

> <ALOGPS_LOGP>
1.05

> <JCHEM_LOGP>
1.4832415116666668

> <ALOGPS_LOGS>
-2.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.738987737853373

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.134618961218838

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5993488556195237

> <JCHEM_POLAR_SURFACE_AREA>
90.15

> <JCHEM_REFRACTIVITY>
71.24539999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.44e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040828
     RDKit          3D
(2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan
 34 36  0  0  0  0  0  0  0  0999 V2000
   -5.7853    1.6957   -0.0189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4720    1.2570   -0.1805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0439    0.7226   -1.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7385    0.2862   -1.5399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8207    0.3664   -0.5208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4372   -0.1148   -0.7466 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4328    0.8567   -0.2061 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7662    0.5575   -0.0775 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7737    1.4844   -0.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0918    1.0927   -0.0313 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0676    2.0736   -0.1396 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4617   -0.2152    0.2110 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4393   -1.1372    0.3066 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1074   -0.7571    0.1643 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0990   -1.8241    0.2854 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6268   -2.9660   -0.3386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2519   -1.4775   -0.1826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2283   -1.6669    0.8230 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2409    0.8995    0.6803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5461    1.3350    0.8394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0575    2.0769    0.8641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7238    0.6387   -2.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4660   -0.1263   -2.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2598   -0.1130   -1.8413 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4930    2.5145   -0.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4789    2.2871   -1.0582 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5060   -0.4898    0.3186 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7356   -2.1615    0.4968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0370   -2.0909    1.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6257   -3.7537    0.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5445   -2.2135   -0.9890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7231   -1.7691    1.6670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5349    0.9787    1.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8679    1.7532    1.7883 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  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
  5 19  1  0
 19 20  2  0
 20  2  1  0
 17  6  1  0
 14  8  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       3.387  -3.464   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.001  -2.694   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.001  -1.154   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.387  -0.384   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.619  -1.154   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.619  -2.694   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.005  -3.464   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -4.619   1.154   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.387   1.924   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.001   1.154   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.615   1.924   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.615   3.464   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.001   1.924   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.615   1.154   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.615  -0.384   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.615  -1.154   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.001  -0.384   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.387  -1.154   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.619  -0.384   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -6.005  -1.154   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6                                                            
CONECT    8    9   19                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12   14                                                  
CONECT   12   11                                                            
CONECT   13   14                                                            
CONECT   14   11   13   15                                                  
CONECT   15    3   14   16                                                  
CONECT   16   15   17                                                       
CONECT   17   10   16   18                                                  
CONECT   18   17   19                                                       
CONECT   19    8   18   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0040828
HETATM    1  O1  UNL     1      -5.785   1.696  -0.019  1.00  0.00           O  
HETATM    2  C1  UNL     1      -4.472   1.257  -0.180  1.00  0.00           C  
HETATM    3  C2  UNL     1      -4.044   0.723  -1.379  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.738   0.286  -1.540  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.821   0.366  -0.521  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.437  -0.115  -0.747  1.00  0.00           C  
HETATM    7  O2  UNL     1       0.433   0.857  -0.206  1.00  0.00           O  
HETATM    8  C6  UNL     1       1.766   0.558  -0.077  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.774   1.484  -0.175  1.00  0.00           C  
HETATM   10  C8  UNL     1       4.092   1.093  -0.031  1.00  0.00           C  
HETATM   11  O3  UNL     1       5.068   2.074  -0.140  1.00  0.00           O  
HETATM   12  C9  UNL     1       4.462  -0.215   0.211  1.00  0.00           C  
HETATM   13  C10 UNL     1       3.439  -1.137   0.307  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.107  -0.757   0.164  1.00  0.00           C  
HETATM   15  C12 UNL     1       1.099  -1.824   0.285  1.00  0.00           C  
HETATM   16  O4  UNL     1       1.627  -2.966  -0.339  1.00  0.00           O  
HETATM   17  C13 UNL     1      -0.252  -1.478  -0.183  1.00  0.00           C  
HETATM   18  O5  UNL     1      -1.228  -1.667   0.823  1.00  0.00           O  
HETATM   19  C14 UNL     1      -2.241   0.899   0.680  1.00  0.00           C  
HETATM   20  C15 UNL     1      -3.546   1.335   0.839  1.00  0.00           C  
HETATM   21  H1  UNL     1      -6.057   2.077   0.864  1.00  0.00           H  
HETATM   22  H2  UNL     1      -4.724   0.639  -2.205  1.00  0.00           H  
HETATM   23  H3  UNL     1      -2.466  -0.126  -2.514  1.00  0.00           H  
HETATM   24  H4  UNL     1      -0.260  -0.113  -1.841  1.00  0.00           H  
HETATM   25  H5  UNL     1       2.493   2.515  -0.365  1.00  0.00           H  
HETATM   26  H6  UNL     1       5.479   2.287  -1.058  1.00  0.00           H  
HETATM   27  H7  UNL     1       5.506  -0.490   0.319  1.00  0.00           H  
HETATM   28  H8  UNL     1       3.736  -2.162   0.497  1.00  0.00           H  
HETATM   29  H9  UNL     1       1.037  -2.091   1.378  1.00  0.00           H  
HETATM   30  H10 UNL     1       1.626  -3.754   0.236  1.00  0.00           H  
HETATM   31  H11 UNL     1      -0.544  -2.214  -0.989  1.00  0.00           H  
HETATM   32  H12 UNL     1      -0.723  -1.769   1.667  1.00  0.00           H  
HETATM   33  H13 UNL     1      -1.535   0.979   1.516  1.00  0.00           H  
HETATM   34  H14 UNL     1      -3.868   1.753   1.788  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   17   24
CONECT    7    8
CONECT    8    9    9   14
CONECT    9   10   25
CONECT   10   11   12   12
CONECT   11   26
CONECT   12   13   27
CONECT   13   14   14   28
CONECT   14   15
CONECT   15   16   17   29
CONECT   16   30
CONECT   17   18   31
CONECT   18   32
CONECT   19   20   20   33
CONECT   20   34
END

HMDB0040828
     RDKit          3D
(2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan
 34 36  0  0  0  0  0  0  0  0999 V2000
   -5.7853    1.6957   -0.0189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4720    1.2570   -0.1805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0439    0.7226   -1.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7385    0.2862   -1.5399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8207    0.3664   -0.5208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4372   -0.1148   -0.7466 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4328    0.8567   -0.2061 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7662    0.5575   -0.0775 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7737    1.4844   -0.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0918    1.0927   -0.0313 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0676    2.0736   -0.1396 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4617   -0.2152    0.2110 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4393   -1.1372    0.3066 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1074   -0.7571    0.1643 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0990   -1.8241    0.2854 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6268   -2.9660   -0.3386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2519   -1.4775   -0.1826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2283   -1.6669    0.8230 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2409    0.8995    0.6803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5461    1.3350    0.8394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0575    2.0769    0.8641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7238    0.6387   -2.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4660   -0.1263   -2.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2598   -0.1130   -1.8413 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4930    2.5145   -0.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4789    2.2871   -1.0582 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5060   -0.4898    0.3186 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7356   -2.1615    0.4968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0370   -2.0909    1.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6257   -3.7537    0.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5445   -2.2135   -0.9890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7231   -1.7691    1.6670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5349    0.9787    1.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8679    1.7532    1.7883 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  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
  5 19  1  0
 19 20  2  0
 20  2  1  0
 17  6  1  0
 14  8  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 18 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-3,4,7-triol

Traditional Name

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

CAS Registry Number

149820-44-0

SMILES

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

InChI Identifier

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

InChI Key

NTLUSUFJOUMRLA-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
7-hydroxyflavonoid
Hydroxyflavonoid
Chromane
Benzopyran
1-benzopyran
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
1,2-diol
Secondary alcohol
Organoheterocyclic compound
Ether
Oxacycle
Polyol
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: HMDB0040828)
Cytoplasm (HMDB: HMDB0040828)

Cytoplasm (HMDB: HMDB0040828)
Extracellular (HMDB: HMDB0040828)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040828)

Source

Exogenous

Food

Food (HMDB: HMDB0040828)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0040828)

Not Available

Nutrient (HMDB: HMDB0040828)

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	1.44 g/L	ALOGPS
logP	1.05	ALOGPS
logP	1.48	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	9.13	ChemAxon
pKa (Strongest Basic)	-3.6	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	71.25 m³·mol⁻¹	ChemAxon
Polarizability	27.53 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]+	164.141	31661259
DarkChem	[M-H]-	162.69	31661259
DeepCCS	[M+H]+	164.714	30932474
DeepCCS	[M-H]-	162.356	30932474
DeepCCS	[M-2H]-	195.242	30932474
DeepCCS	[M+Na]+	170.807	30932474
AllCCS	[M+H]+	165.5	32859911
AllCCS	[M+H-H2O]+	161.7	32859911
AllCCS	[M+NH4]+	169.1	32859911
AllCCS	[M+Na]+	170.1	32859911
AllCCS	[M-H]-	164.7	32859911
AllCCS	[M+Na-2H]-	164.3	32859911
AllCCS	[M+HCOO]-	163.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan	OC1C(O)C2=CC=C(O)C=C2OC1C1=CC=C(O)C=C1	4371.5	Standard polar	33892256
(2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan	OC1C(O)C2=CC=C(O)C=C2OC1C1=CC=C(O)C=C1	2835.7	Standard non polar	33892256
(2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan	OC1C(O)C2=CC=C(O)C=C2OC1C1=CC=C(O)C=C1	2851.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan,1TMS,isomer #1	C[Si](C)(C)OC1C(O)C2=CC=C(O)C=C2OC1C1=CC=C(O)C=C1	2777.8	Semi standard non polar	33892256
(2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan,1TMS,isomer #2	C[Si](C)(C)OC1C2=CC=C(O)C=C2OC(C2=CC=C(O)C=C2)C1O	2825.0	Semi standard non polar	33892256
(2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan,1TMS,isomer #3	C[Si](C)(C)OC1=CC=C2C(=C1)OC(C1=CC=C(O)C=C1)C(O)C2O	2880.7	Semi standard non polar	33892256
(2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan,1TMS,isomer #4	C[Si](C)(C)OC1=CC=C(C2OC3=CC(O)=CC=C3C(O)C2O)C=C1	2876.6	Semi standard non polar	33892256
(2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan,2TMS,isomer #1	C[Si](C)(C)OC1C2=CC=C(O)C=C2OC(C2=CC=C(O)C=C2)C1O[Si](C)(C)C	2769.0	Semi standard non polar	33892256
(2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C2C(=C1)OC(C1=CC=C(O)C=C1)C(O[Si](C)(C)C)C2O	2771.7	Semi standard non polar	33892256
(2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan,2TMS,isomer #3	C[Si](C)(C)OC1=CC=C(C2OC3=CC(O)=CC=C3C(O)C2O[Si](C)(C)C)C=C1	2755.9	Semi standard non polar	33892256
(2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan,2TMS,isomer #4	C[Si](C)(C)OC1=CC=C2C(=C1)OC(C1=CC=C(O)C=C1)C(O)C2O[Si](C)(C)C	2827.5	Semi standard non polar	33892256
(2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan,2TMS,isomer #5	C[Si](C)(C)OC1=CC=C(C2OC3=CC(O)=CC=C3C(O[Si](C)(C)C)C2O)C=C1	2803.2	Semi standard non polar	33892256
(2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan,2TMS,isomer #6	C[Si](C)(C)OC1=CC=C(C2OC3=CC(O[Si](C)(C)C)=CC=C3C(O)C2O)C=C1	2879.8	Semi standard non polar	33892256
(2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C(=C1)OC(C1=CC=C(O)C=C1)C(O[Si](C)(C)C)C2O[Si](C)(C)C	2688.2	Semi standard non polar	33892256
(2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C2OC3=CC(O)=CC=C3C(O[Si](C)(C)C)C2O[Si](C)(C)C)C=C1	2681.3	Semi standard non polar	33892256
(2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan,3TMS,isomer #3	C[Si](C)(C)OC1=CC=C(C2OC3=CC(O[Si](C)(C)C)=CC=C3C(O)C2O[Si](C)(C)C)C=C1	2697.0	Semi standard non polar	33892256
(2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan,3TMS,isomer #4	C[Si](C)(C)OC1=CC=C(C2OC3=CC(O[Si](C)(C)C)=CC=C3C(O[Si](C)(C)C)C2O)C=C1	2773.9	Semi standard non polar	33892256
(2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan,4TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2OC3=CC(O[Si](C)(C)C)=CC=C3C(O[Si](C)(C)C)C2O[Si](C)(C)C)C=C1	2677.4	Semi standard non polar	33892256
(2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C(O)C2=CC=C(O)C=C2OC1C1=CC=C(O)C=C1	3064.9	Semi standard non polar	33892256
(2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1C2=CC=C(O)C=C2OC(C2=CC=C(O)C=C2)C1O	3091.4	Semi standard non polar	33892256
(2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OC(C1=CC=C(O)C=C1)C(O)C2O	3110.7	Semi standard non polar	33892256
(2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(C2OC3=CC(O)=CC=C3C(O)C2O)C=C1	3124.1	Semi standard non polar	33892256
(2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C2=CC=C(O)C=C2OC(C2=CC=C(O)C=C2)C1O[Si](C)(C)C(C)(C)C	3343.3	Semi standard non polar	33892256
(2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OC(C1=CC=C(O)C=C1)C(O[Si](C)(C)C(C)(C)C)C2O	3301.2	Semi standard non polar	33892256
(2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(C2OC3=CC(O)=CC=C3C(O)C2O[Si](C)(C)C(C)(C)C)C=C1	3319.5	Semi standard non polar	33892256
(2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OC(C1=CC=C(O)C=C1)C(O)C2O[Si](C)(C)C(C)(C)C	3346.6	Semi standard non polar	33892256
(2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC=C(C2OC3=CC(O)=CC=C3C(O[Si](C)(C)C(C)(C)C)C2O)C=C1	3361.6	Semi standard non polar	33892256
(2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC=C(C2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3C(O)C2O)C=C1	3376.8	Semi standard non polar	33892256
(2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OC(C1=CC=C(O)C=C1)C(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C	3394.4	Semi standard non polar	33892256
(2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(C2OC3=CC(O)=CC=C3C(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C)C=C1	3424.1	Semi standard non polar	33892256
(2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(C2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3C(O)C2O[Si](C)(C)C(C)(C)C)C=C1	3434.3	Semi standard non polar	33892256
(2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(C2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3C(O[Si](C)(C)C(C)(C)C)C2O)C=C1	3503.6	Semi standard non polar	33892256
(2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3C(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C)C=C1	3561.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-0980000000-9c4015aa1b03d8a57b28	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan GC-MS (4 TMS) - 70eV, Positive	splash10-0002-2120790000-8c2fb8d6cb91c953d3b2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2S,3S,4R)-3,4,4',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 - (2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan 10V, Positive-QTOF	splash10-004i-0190000000-df10d7bae35e01546fb7	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan 20V, Positive-QTOF	splash10-05bs-0960000000-b6eaae301a6c4bbbee0c	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan 40V, Positive-QTOF	splash10-00di-5900000000-7d8cfd7b25f020db0c23	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan 10V, Negative-QTOF	splash10-00di-0290000000-bbcb8c8e6270dfaede88	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan 20V, Negative-QTOF	splash10-00dr-1890000000-9c1aeabfa42f8535aaad	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan 40V, Negative-QTOF	splash10-052f-7920000000-96896b4de8803084b22c	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan 10V, Positive-QTOF	splash10-004i-0090000000-9e8a575c60b3968ddaf0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan 20V, Positive-QTOF	splash10-0a4r-0910000000-273e98e25b599305e1a2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan 40V, Positive-QTOF	splash10-0a4i-3910000000-026bfd88d3b892dc0816	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan 10V, Negative-QTOF	splash10-00di-0090000000-d21e0432f5b087005e99	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan 20V, Negative-QTOF	splash10-05fr-1980000000-9e50d74e0b5948f596ee	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan 40V, Negative-QTOF	splash10-0079-1920000000-e1c6c21477f22ac8f7dd	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

FDB020648

KNApSAcK ID

Not Available

Chemspider ID

28710997

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13886894

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 (2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan (HMDB0040828)

MOL for HMDB0040828 ((2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan)

3D MOL for HMDB0040828 ((2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan)

3D SDF for HMDB0040828 ((2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan)

3D-SDF for HMDB0040828 ((2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan)

PDB for HMDB0040828 ((2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan)

3D PDB for HMDB0040828 ((2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan)

SMILES for HMDB0040828 ((2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan)

INCHI for HMDB0040828 ((2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan)

Structure for HMDB0040828 ((2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan)

3D Structure for HMDB0040828 ((2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra