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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:56:53 UTC

Update Date

2022-03-07 02:55:27 UTC

HMDB ID

HMDB0037686

Secondary Accession Numbers

HMDB37686

Metabolite Identification

Common Name

7-Hydroxy-5-methoxyflavan

Description

7-Hydroxy-5-methoxyflavan belongs to the class of organic compounds known as 5-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C5 atom of the flavonoid backbone. Based on a literature review very few articles have been published on 7-Hydroxy-5-methoxyflavan.

Structure

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

HMDB0037686
     RDKit          3D
7-Hydroxy-5-methoxyflavan
 35 37  0  0  0  0  0  0  0  0999 V2000
   -4.9803    1.2900   -0.2025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5802    1.2169   -0.2052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8750    0.0319   -0.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5018   -1.1783    0.1262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7993   -2.3487    0.2821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4469   -3.5708    0.4575 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4153   -2.2346    0.2536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7621   -1.0341    0.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4901    0.1259   -0.0731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8301    1.4583   -0.2640 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5617    1.3391    0.3073 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2291    0.1819   -0.4453 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6830    0.2158   -0.2971 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3315   -0.1554    0.8735 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6885   -0.0923    0.9253 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4500    0.3270   -0.1415 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8260    0.7018   -1.3183 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4499    0.6351   -1.3631 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6466   -1.0007    0.0636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2725    2.1999   -0.7951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3788    0.4275   -0.7677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4203    1.3759    0.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5747   -1.2212    0.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9651   -4.4360    0.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8713   -3.1700    0.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4180    2.2782    0.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6970    1.6256   -1.3686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1488    2.2609    0.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4432    0.9919    1.3671 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9612    0.2759   -1.5018 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7079   -0.4779    1.6877 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2107   -0.3835    1.8457 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5303    0.3715   -0.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4293    1.0321   -2.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9812    0.9401   -2.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 12 19  1  0
  9  3  1  0
 18 13  1  0
 19  8  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
M  END


  Mrv0541 05061309572D          

 19 21  0  0  0  0            999 V2000
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    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
    0.7145    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
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    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
    0.7145    2.0625    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
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    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    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  8  7  1  0  0  0  0
 11  5  2  0  0  0  0
 11  6  1  0  0  0  0
 12  9  2  0  0  0  0
 12 10  1  0  0  0  0
 13  7  1  0  0  0  0
 14  8  1  0  0  0  0
 14 11  1  0  0  0  0
 15  9  1  0  0  0  0
 15 13  2  0  0  0  0
 16 10  2  0  0  0  0
 16 13  1  0  0  0  0
 17 12  1  0  0  0  0
 18  1  1  0  0  0  0
 18 15  1  0  0  0  0
 19 14  1  0  0  0  0
 19 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037686

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C2CCC(OC2=CC(O)=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O3/c1-18-15-9-12(17)10-16-13(15)7-8-14(19-16)11-5-3-2-4-6-11/h2-6,9-10,14,17H,7-8H2,1H3

> <INCHI_KEY>
UNCVBXFEZHBZKN-UHFFFAOYSA-N

> <FORMULA>
C16H16O3

> <MOLECULAR_WEIGHT>
256.2964

> <EXACT_MASS>
256.109944378

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.216782746524945

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-methoxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-7-ol

> <ALOGPS_LOGP>
3.47

> <JCHEM_LOGP>
3.623035321666666

> <ALOGPS_LOGS>
-4.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.854652759614286

> <JCHEM_PKA_STRONGEST_BASIC>
-4.571336160108634

> <JCHEM_POLAR_SURFACE_AREA>
38.69

> <JCHEM_REFRACTIVITY>
73.15870000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.47e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-methoxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-7-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0037686
     RDKit          3D
7-Hydroxy-5-methoxyflavan
 35 37  0  0  0  0  0  0  0  0999 V2000
   -4.9803    1.2900   -0.2025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5802    1.2169   -0.2052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8750    0.0319   -0.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5018   -1.1783    0.1262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7993   -2.3487    0.2821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4469   -3.5708    0.4575 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4153   -2.2346    0.2536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7621   -1.0341    0.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4901    0.1259   -0.0731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8301    1.4583   -0.2640 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5617    1.3391    0.3073 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2291    0.1819   -0.4453 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6830    0.2158   -0.2971 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3315   -0.1554    0.8735 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6885   -0.0923    0.9253 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4500    0.3270   -0.1415 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8260    0.7018   -1.3183 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4499    0.6351   -1.3631 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6466   -1.0007    0.0636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2725    2.1999   -0.7951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3788    0.4275   -0.7677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4203    1.3759    0.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5747   -1.2212    0.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9651   -4.4360    0.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8713   -3.1700    0.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4180    2.2782    0.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6970    1.6256   -1.3686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1488    2.2609    0.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4432    0.9919    1.3671 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9612    0.2759   -1.5018 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7079   -0.4779    1.6877 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2107   -0.3835    1.8457 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5303    0.3715   -0.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4293    1.0321   -2.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9812    0.9401   -2.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 12 19  1  0
  9  3  1  0
 18 13  1  0
 19  8  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  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       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   3.850   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  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.002   4.620   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   4.620   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3   11                                                       
CONECT    6    4   11                                                       
CONECT    7    8   13                                                       
CONECT    8    7   14                                                       
CONECT    9   12   15                                                       
CONECT   10   12   16                                                       
CONECT   11    5    6   14                                                  
CONECT   12    9   10   17                                                  
CONECT   13    7   15   16                                                  
CONECT   14    8   11   19                                                  
CONECT   15    9   13   18                                                  
CONECT   16   10   13   19                                                  
CONECT   17   12                                                            
CONECT   18    1   15                                                       
CONECT   19   14   16                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0037686
HETATM    1  C1  UNL     1      -4.980   1.290  -0.203  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.580   1.217  -0.205  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.875   0.032  -0.047  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.502  -1.178   0.126  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.799  -2.349   0.282  1.00  0.00           C  
HETATM    6  O2  UNL     1      -3.447  -3.571   0.458  1.00  0.00           O  
HETATM    7  C5  UNL     1      -1.415  -2.235   0.254  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.762  -1.034   0.081  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.490   0.126  -0.073  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.830   1.458  -0.264  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.562   1.339   0.307  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.229   0.182  -0.445  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.683   0.216  -0.297  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.332  -0.155   0.874  1.00  0.00           C  
HETATM   15  C13 UNL     1       4.689  -0.092   0.925  1.00  0.00           C  
HETATM   16  C14 UNL     1       5.450   0.327  -0.142  1.00  0.00           C  
HETATM   17  C15 UNL     1       4.826   0.702  -1.318  1.00  0.00           C  
HETATM   18  C16 UNL     1       3.450   0.635  -1.363  1.00  0.00           C  
HETATM   19  O3  UNL     1       0.647  -1.001   0.064  1.00  0.00           O  
HETATM   20  H1  UNL     1      -5.272   2.200  -0.795  1.00  0.00           H  
HETATM   21  H2  UNL     1      -5.379   0.428  -0.768  1.00  0.00           H  
HETATM   22  H3  UNL     1      -5.420   1.376   0.811  1.00  0.00           H  
HETATM   23  H4  UNL     1      -4.575  -1.221   0.142  1.00  0.00           H  
HETATM   24  H5  UNL     1      -2.965  -4.436   0.573  1.00  0.00           H  
HETATM   25  H6  UNL     1      -0.871  -3.170   0.378  1.00  0.00           H  
HETATM   26  H7  UNL     1      -1.418   2.278   0.183  1.00  0.00           H  
HETATM   27  H8  UNL     1      -0.697   1.626  -1.369  1.00  0.00           H  
HETATM   28  H9  UNL     1       1.149   2.261   0.238  1.00  0.00           H  
HETATM   29  H10 UNL     1       0.443   0.992   1.367  1.00  0.00           H  
HETATM   30  H11 UNL     1       0.961   0.276  -1.502  1.00  0.00           H  
HETATM   31  H12 UNL     1       2.708  -0.478   1.688  1.00  0.00           H  
HETATM   32  H13 UNL     1       5.211  -0.383   1.846  1.00  0.00           H  
HETATM   33  H14 UNL     1       6.530   0.372  -0.084  1.00  0.00           H  
HETATM   34  H15 UNL     1       5.429   1.032  -2.158  1.00  0.00           H  
HETATM   35  H16 UNL     1       2.981   0.940  -2.314  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3
CONECT    3    4    4    9
CONECT    4    5   23
CONECT    5    6    7    7
CONECT    6   24
CONECT    7    8   25
CONECT    8    9    9   19
CONECT    9   10
CONECT   10   11   26   27
CONECT   11   12   28   29
CONECT   12   13   19   30
CONECT   13   14   14   18
CONECT   14   15   31
CONECT   15   16   16   32
CONECT   16   17   33
CONECT   17   18   18   34
CONECT   18   35
END

HMDB0037686
     RDKit          3D
7-Hydroxy-5-methoxyflavan
 35 37  0  0  0  0  0  0  0  0999 V2000
   -4.9803    1.2900   -0.2025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5802    1.2169   -0.2052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8750    0.0319   -0.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5018   -1.1783    0.1262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7993   -2.3487    0.2821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4469   -3.5708    0.4575 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4153   -2.2346    0.2536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7621   -1.0341    0.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4901    0.1259   -0.0731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8301    1.4583   -0.2640 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5617    1.3391    0.3073 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2291    0.1819   -0.4453 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6830    0.2158   -0.2971 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3315   -0.1554    0.8735 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6885   -0.0923    0.9253 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4500    0.3270   -0.1415 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8260    0.7018   -1.3183 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4499    0.6351   -1.3631 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6466   -1.0007    0.0636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2725    2.1999   -0.7951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3788    0.4275   -0.7677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4203    1.3759    0.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5747   -1.2212    0.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9651   -4.4360    0.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8713   -3.1700    0.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4180    2.2782    0.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6970    1.6256   -1.3686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1488    2.2609    0.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4432    0.9919    1.3671 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9612    0.2759   -1.5018 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7079   -0.4779    1.6877 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2107   -0.3835    1.8457 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5303    0.3715   -0.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4293    1.0321   -2.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9812    0.9401   -2.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 12 19  1  0
  9  3  1  0
 18 13  1  0
 19  8  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2S)-5-Methoxy flavan-7-ol	HMDB
3,4-dihydro-5-Methoxy-2-phenyl-2H-1-benzopyran-7-ol	HMDB

Chemical Formula

C₁₆H₁₆O₃

Average Molecular Weight

256.2964

Monoisotopic Molecular Weight

256.109944378

IUPAC Name

5-methoxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-7-ol

Traditional Name

5-methoxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-7-ol

CAS Registry Number

35290-20-1

SMILES

COC1=C2CCC(OC2=CC(O)=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H16O3/c1-18-15-9-12(17)10-16-13(15)7-8-14(19-16)11-5-3-2-4-6-11/h2-6,9-10,14,17H,7-8H2,1H3

InChI Key

UNCVBXFEZHBZKN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 5-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C5 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

5-O-methylated flavonoids

Alternative Parents

Substituents

5-methoxyflavonoid-skeleton
7-hydroxyflavonoid
Hydroxyflavonoid
Flavan
Chromane
1-benzopyran
Benzopyran
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Organoheterocyclic compound
Oxacycle
Ether
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0037686)
Cell membrane (HMDB: HMDB0037686)

Source

Exogenous

Exogenous (HMDB: HMDB0037686)

Food

Food (HMDB: HMDB0037686)

Endogenous

Plant

Plant (HMDB: HMDB0037686)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0037686)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	96 - 97 °C	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	0.025 g/L	ALOGPS
logP	3.47	ALOGPS
logP	3.62	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	9.85	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.69 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	73.16 m³·mol⁻¹	ChemAxon
Polarizability	28.22 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	160.341	31661259
DarkChem	[M-H]-	162.412	31661259
DeepCCS	[M+H]+	161.643	30932474
DeepCCS	[M-H]-	159.285	30932474
DeepCCS	[M-2H]-	192.217	30932474
DeepCCS	[M+Na]+	167.737	30932474
AllCCS	[M+H]+	160.9	32859911
AllCCS	[M+H-H2O]+	156.9	32859911
AllCCS	[M+NH4]+	164.6	32859911
AllCCS	[M+Na]+	165.6	32859911
AllCCS	[M-H]-	164.6	32859911
AllCCS	[M+Na-2H]-	164.1	32859911
AllCCS	[M+HCOO]-	163.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	8.4 minutes	32390414
Predicted by Siyang on May 30, 2022	16.4059 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.59 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2441.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	498.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	213.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	271.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	393.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	775.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	744.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	106.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1521.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	557.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1499.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	463.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	447.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	386.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	365.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	13.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
7-Hydroxy-5-methoxyflavan	COC1=C2CCC(OC2=CC(O)=C1)C1=CC=CC=C1	3054.4	Standard polar	33892256
7-Hydroxy-5-methoxyflavan	COC1=C2CCC(OC2=CC(O)=C1)C1=CC=CC=C1	2280.6	Standard non polar	33892256
7-Hydroxy-5-methoxyflavan	COC1=C2CCC(OC2=CC(O)=C1)C1=CC=CC=C1	2441.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
7-Hydroxy-5-methoxyflavan,1TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=CC2=C1CCC(C1=CC=CC=C1)O2	2352.2	Semi standard non polar	33892256
7-Hydroxy-5-methoxyflavan,1TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC2=C1CCC(C1=CC=CC=C1)O2	2630.6	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 - 7-Hydroxy-5-methoxyflavan GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-1390000000-09548eab422135c63a51	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Hydroxy-5-methoxyflavan GC-MS (1 TMS) - 70eV, Positive	splash10-03k9-5196000000-04bfff5a3eec66056be5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Hydroxy-5-methoxyflavan 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 - 7-Hydroxy-5-methoxyflavan 10V, Positive-QTOF	splash10-0a4i-0590000000-198e1d97180febb31f5a	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-5-methoxyflavan 20V, Positive-QTOF	splash10-0udi-0910000000-7ba32e2e03d34f6dbcec	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-5-methoxyflavan 40V, Positive-QTOF	splash10-00kr-2900000000-6159628675051d7d5c0a	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-5-methoxyflavan 10V, Negative-QTOF	splash10-0a4i-0090000000-7eb0c67dec09e48fad84	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-5-methoxyflavan 20V, Negative-QTOF	splash10-0pb9-1590000000-19b577607591f1c7234e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-5-methoxyflavan 40V, Negative-QTOF	splash10-056r-8920000000-29e8306ebf7a7e0cc222	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-5-methoxyflavan 10V, Positive-QTOF	splash10-0a4i-0090000000-1764cfa47ef5606fd849	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-5-methoxyflavan 20V, Positive-QTOF	splash10-0a4i-0290000000-3efac985f0b9f9b05768	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-5-methoxyflavan 40V, Positive-QTOF	splash10-052f-4930000000-3fb9dee0698d95017f11	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-5-methoxyflavan 10V, Negative-QTOF	splash10-0a4i-0090000000-e382f8a0b4d1e3b6f408	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-5-methoxyflavan 20V, Negative-QTOF	splash10-0pb9-0190000000-2fde94cf84223e8a9ab9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-5-methoxyflavan 40V, Negative-QTOF	splash10-0umi-2980000000-aeb2bdb8f250e81a17d1	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

FDB016813

KNApSAcK ID

C00008750

Chemspider ID

303396

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

342294

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 7-Hydroxy-5-methoxyflavan (HMDB0037686)

MOL for HMDB0037686 (7-Hydroxy-5-methoxyflavan)

3D MOL for HMDB0037686 (7-Hydroxy-5-methoxyflavan)

3D SDF for HMDB0037686 (7-Hydroxy-5-methoxyflavan)

3D-SDF for HMDB0037686 (7-Hydroxy-5-methoxyflavan)

PDB for HMDB0037686 (7-Hydroxy-5-methoxyflavan)

3D PDB for HMDB0037686 (7-Hydroxy-5-methoxyflavan)

SMILES for HMDB0037686 (7-Hydroxy-5-methoxyflavan)

INCHI for HMDB0037686 (7-Hydroxy-5-methoxyflavan)

Structure for HMDB0037686 (7-Hydroxy-5-methoxyflavan)

3D Structure for HMDB0037686 (7-Hydroxy-5-methoxyflavan)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra