NP-MRD: Showing NP-Card for cis-(-)-7,2’-dihydroxy-4’-methoxyisoflavanol (NP0001546)

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Record Information

Version

1.0

Created at

2020-09-13 04:33:45 UTC

Updated at

2021-08-10 02:55:09 UTC

NP-MRD ID

NP0001546

Secondary Accession Numbers

None

Natural Product Identification

Common Name

cis-(-)-7,2’-dihydroxy-4’-methoxyisoflavanol

Description

(3R,4R)-7,2'-dihydroxy-4'-methoxyisoflavanol, also known as DMI or (3R,4R)-4'-methoxyisoflavan-2',4,7-triol, belongs to the class of organic compounds known as 4'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C4' atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one (3R,4R)-7,2'-dihydroxy-4'-methoxyisoflavanol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on (3R,4R)-7,2'-dihydroxy-4'-methoxyisoflavanol.

Structure

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

NP0001546
     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
   -6.0783   -0.3782    0.4003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2586   -0.8124   -0.6557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9223   -0.4361   -0.6421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1307   -0.8699   -1.6851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7871   -0.5189   -1.7153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1998    0.2554   -0.7348 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2396    0.6129   -0.7970 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8509    0.0053   -2.0308 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2168    0.3191   -2.1383 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0298    0.1599   -1.0357 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4092    0.0481   -1.1943 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2118   -0.1105   -0.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5966   -0.2242   -0.2270 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6259   -0.1542    1.1492 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2579   -0.0431    1.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4416    0.1157    0.2099 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9821    0.2286    0.4540 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5434   -0.9658    0.9974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0026    0.6844    0.3054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4645    1.4668    1.3205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3534    0.3353    0.3418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8686   -0.9204    1.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9691    0.7129    0.6036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1618   -0.5561    0.1530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5773   -1.4891   -2.4793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1902   -0.8790   -2.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2858    1.7179   -0.9219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3348    0.4340   -2.9094 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7660   -1.1106   -2.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7901    0.0919   -2.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1526    0.6382   -0.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2901   -0.2815    2.0151 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8483   -0.0842    2.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8328    1.0256    1.2246 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2950   -1.4615    1.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0577    1.7774    2.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9787    0.6665    1.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
  6 19  1  0
 19 20  1  0
 19 21  2  0
 21  3  1  0
 17  7  1  0
 16 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  6
  8 28  1  0
  8 29  1  0
 11 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 17 34  1  1
 18 35  1  0
 20 36  1  0
 21 37  1  0
M  END


  Mrv1652309132006332D          

 21 23  0  0  1  0            999 V2000
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   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
   -1.4289   -1.6500    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   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  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
    1.4289    0.0000    0.0000 O   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
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   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   -1.6500    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
    1.4289   -1.6500    0.0000 C   0  0  2  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
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
  7 17  1  0  0  0  0
 17 18  1  6  0  0  0
  6 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
  3 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001546

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C([C@@H]2COC3=CC(O)=CC=C3[C@@H]2O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O5/c1-20-10-3-5-11(14(18)7-10)13-8-21-15-6-9(17)2-4-12(15)16(13)19/h2-7,13,16-19H,8H2,1H3/t13-,16-/m0/s1

> <INCHI_KEY>
YZBBUYKPTHDZHF-BBRMVZONSA-N

> <FORMULA>
C16H16O5

> <MOLECULAR_WEIGHT>
288.299

> <EXACT_MASS>
288.099773615

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
29.300510245405537

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,4R)-3-(2-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4,7-diol

> <ALOGPS_LOGP>
1.54

> <JCHEM_LOGP>
1.8447522716666658

> <ALOGPS_LOGS>
-3.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.830822938435615

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.207069703169386

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3241203778102824

> <JCHEM_POLAR_SURFACE_AREA>
79.15

> <JCHEM_REFRACTIVITY>
76.8401

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.72e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4R)-3-(2-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4,7-diol

> <JCHEM_VEBER_RULE>
0

$$$$

NP0001546
     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
   -6.0783   -0.3782    0.4003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2586   -0.8124   -0.6557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9223   -0.4361   -0.6421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1307   -0.8699   -1.6851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7871   -0.5189   -1.7153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1998    0.2554   -0.7348 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2396    0.6129   -0.7970 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8509    0.0053   -2.0308 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2168    0.3191   -2.1383 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0298    0.1599   -1.0357 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4092    0.0481   -1.1943 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2118   -0.1105   -0.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5966   -0.2242   -0.2270 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6259   -0.1542    1.1492 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2579   -0.0431    1.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4416    0.1157    0.2099 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9821    0.2286    0.4540 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5434   -0.9658    0.9974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0026    0.6844    0.3054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4645    1.4668    1.3205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3534    0.3353    0.3418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8686   -0.9204    1.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9691    0.7129    0.6036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1618   -0.5561    0.1530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5773   -1.4891   -2.4793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1902   -0.8790   -2.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2858    1.7179   -0.9219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3348    0.4340   -2.9094 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7660   -1.1106   -2.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7901    0.0919   -2.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1526    0.6382   -0.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2901   -0.2815    2.0151 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8483   -0.0842    2.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8328    1.0256    1.2246 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2950   -1.4615    1.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0577    1.7774    2.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9787    0.6665    1.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
  6 19  1  0
 19 20  1  0
 19 21  2  0
 21  3  1  0
 17  7  1  0
 16 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  6
  8 28  1  0
  8 29  1  0
 11 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 17 34  1  1
 18 35  1  0
 20 36  1  0
 21 37  1  0
M  END

HEADER    PROTEIN                                 13-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-20         0                                  
HETATM    1  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   19                                                  
CONECT    7    6    8   17                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   10   17                                                  
CONECT   17   16    7   18                                                  
CONECT   18   17                                                            
CONECT   19    6   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    3                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    NP0001546
HETATM    1  C1  UNL     1      -6.078  -0.378   0.400  1.00  0.00           C  
HETATM    2  O1  UNL     1      -5.259  -0.812  -0.656  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.922  -0.436  -0.642  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.131  -0.870  -1.685  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.787  -0.519  -1.715  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.200   0.255  -0.735  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.240   0.613  -0.797  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.851   0.005  -2.031  1.00  0.00           C  
HETATM    9  O2  UNL     1       2.217   0.319  -2.138  1.00  0.00           O  
HETATM   10  C8  UNL     1       3.030   0.160  -1.036  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.409   0.048  -1.194  1.00  0.00           C  
HETATM   12  C10 UNL     1       5.212  -0.110  -0.087  1.00  0.00           C  
HETATM   13  O3  UNL     1       6.597  -0.224  -0.227  1.00  0.00           O  
HETATM   14  C11 UNL     1       4.626  -0.154   1.149  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.258  -0.043   1.304  1.00  0.00           C  
HETATM   16  C13 UNL     1       2.442   0.116   0.210  1.00  0.00           C  
HETATM   17  C14 UNL     1       0.982   0.229   0.454  1.00  0.00           C  
HETATM   18  O4  UNL     1       0.543  -0.966   0.997  1.00  0.00           O  
HETATM   19  C15 UNL     1      -2.003   0.684   0.305  1.00  0.00           C  
HETATM   20  O5  UNL     1      -1.464   1.467   1.320  1.00  0.00           O  
HETATM   21  C16 UNL     1      -3.353   0.335   0.342  1.00  0.00           C  
HETATM   22  H1  UNL     1      -5.869  -0.920   1.345  1.00  0.00           H  
HETATM   23  H2  UNL     1      -5.969   0.713   0.604  1.00  0.00           H  
HETATM   24  H3  UNL     1      -7.162  -0.556   0.153  1.00  0.00           H  
HETATM   25  H4  UNL     1      -3.577  -1.489  -2.479  1.00  0.00           H  
HETATM   26  H5  UNL     1      -1.190  -0.879  -2.555  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.286   1.718  -0.922  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.335   0.434  -2.909  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.766  -1.111  -2.025  1.00  0.00           H  
HETATM   30  H9  UNL     1       4.790   0.092  -2.191  1.00  0.00           H  
HETATM   31  H10 UNL     1       7.153   0.638  -0.205  1.00  0.00           H  
HETATM   32  H11 UNL     1       5.290  -0.282   2.015  1.00  0.00           H  
HETATM   33  H12 UNL     1       2.848  -0.084   2.304  1.00  0.00           H  
HETATM   34  H13 UNL     1       0.833   1.026   1.225  1.00  0.00           H  
HETATM   35  H14 UNL     1       1.295  -1.461   1.411  1.00  0.00           H  
HETATM   36  H15 UNL     1      -2.058   1.777   2.079  1.00  0.00           H  
HETATM   37  H16 UNL     1      -3.979   0.667   1.147  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5   25
CONECT    5    6    6   26
CONECT    6    7   19
CONECT    7    8   17   27
CONECT    8    9   28   29
CONECT    9   10
CONECT   10   11   11   16
CONECT   11   12   30
CONECT   12   13   14   14
CONECT   13   31
CONECT   14   15   32
CONECT   15   16   16   33
CONECT   16   17
CONECT   17   18   34
CONECT   18   35
CONECT   19   20   21   21
CONECT   20   36
CONECT   21   37
END

NP0001546
     RDKit          3D

37 39  0  0  0  0  0  0  0  0999 V2000
   -6.0783   -0.3782    0.4003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2586   -0.8124   -0.6557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9223   -0.4361   -0.6421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1307   -0.8699   -1.6851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7871   -0.5189   -1.7153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1998    0.2554   -0.7348 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2396    0.6129   -0.7970 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8509    0.0053   -2.0308 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2168    0.3191   -2.1383 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0298    0.1599   -1.0357 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4092    0.0481   -1.1943 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2118   -0.1105   -0.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5966   -0.2242   -0.2270 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6259   -0.1542    1.1492 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2579   -0.0431    1.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4416    0.1157    0.2099 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9821    0.2286    0.4540 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5434   -0.9658    0.9974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0026    0.6844    0.3054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4645    1.4668    1.3205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3534    0.3353    0.3418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8686   -0.9204    1.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9691    0.7129    0.6036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1618   -0.5561    0.1530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5773   -1.4891   -2.4793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1902   -0.8790   -2.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2858    1.7179   -0.9219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3348    0.4340   -2.9094 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7660   -1.1106   -2.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7901    0.0919   -2.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1526    0.6382   -0.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2901   -0.2815    2.0151 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8483   -0.0842    2.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8328    1.0256    1.2246 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2950   -1.4615    1.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0577    1.7774    2.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9787    0.6665    1.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
  6 19  1  0
 19 20  1  0
 19 21  2  0
 21  3  1  0
 17  7  1  0
 16 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  6
  8 28  1  0
  8 29  1  0
 11 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 17 34  1  1
 18 35  1  0
 20 36  1  0
 21 37  1  0
M  END

View in JSmol

Synonyms

Value	Source
DMI	Kegg
(3R,4R)-4'-Methoxyisoflavan-2',4,7-triol	Kegg

Chemical Formula

C₁₆H₁₆O₅

Average Mass

288.2990 Da

Monoisotopic Mass

288.09977 Da

IUPAC Name

(3R,4R)-3-(2-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4,7-diol

Traditional Name

(3R,4R)-3-(2-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4,7-diol

CAS Registry Number

Not Available

SMILES

COC1=CC=C([C@@H]2COC3=CC(O)=CC=C3[C@@H]2O)C(O)=C1

InChI Identifier

InChI=1S/C16H16O5/c1-20-10-3-5-11(14(18)7-10)13-8-21-15-6-9(17)2-4-12(15)16(13)19/h2-7,13,16-19H,8H2,1H3/t13-,16-/m0/s1

InChI Key

YZBBUYKPTHDZHF-BBRMVZONSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C] NMR Spectrum (2D, 600Mz, Methanol, simulated)	john.cort@pnnl.gov	Not Available	Not Available	2020-09-13	View Spectrum

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C4' atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

4'-O-methylated isoflavonoids

Alternative Parents

Substituents

4p-methoxyisoflavonoid
Isoflavanol
Hydroxyisoflavonoid
Isoflavan
Chromane
Benzopyran
Methoxyphenol
1-benzopyran
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Secondary alcohol
Oxacycle
Ether
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

7,2'-dihydroxy-4'-methoxyisoflavanol (CHEBI:72646 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	1.54	ALOGPS
logP	1.84	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	79.15 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	76.84 m³·mol⁻¹	ChemAxon
Polarizability	29.3 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28639081

KEGG Compound ID

C16187

BioCyc ID

CPD-3441

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

72646

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for cis-(-)-7,2’-dihydroxy-4’-methoxyisoflavanol (NP0001546)

MOL for NP0001546 (cis-(-)-7,2’-dihydroxy-4’-methoxyisoflavanol)

3D MOL for NP0001546 (cis-(-)-7,2’-dihydroxy-4’-methoxyisoflavanol)

3D SDF for NP0001546 (cis-(-)-7,2’-dihydroxy-4’-methoxyisoflavanol)

3D-SDF for NP0001546 (cis-(-)-7,2’-dihydroxy-4’-methoxyisoflavanol)

PDB for NP0001546 (cis-(-)-7,2’-dihydroxy-4’-methoxyisoflavanol)

3D PDB for NP0001546 (cis-(-)-7,2’-dihydroxy-4’-methoxyisoflavanol)

SMILES for NP0001546 (cis-(-)-7,2’-dihydroxy-4’-methoxyisoflavanol)

INCHI for NP0001546 (cis-(-)-7,2’-dihydroxy-4’-methoxyisoflavanol)

Structure for NP0001546 (cis-(-)-7,2’-dihydroxy-4’-methoxyisoflavanol)

3D Structure for NP0001546 (cis-(-)-7,2’-dihydroxy-4’-methoxyisoflavanol)