NP-MRD: Showing NP-Card for Glycitein (NP0043886)

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Record Information

Version

2.0

Created at

2021-06-22 17:27:33 UTC

Updated at

2021-08-20 00:00:47 UTC

NP-MRD ID

NP0043886

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Glycitein

Description

Glycitein belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom. Thus, glycitein is considered to be a flavonoid. Glycitein is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Glycitein is found in Ammopiptanthus mongolicus, Psoralea corylifolia , Acca sellowiana, Ophiocordyceps sinensis, Pueraria montana, Sarcolobus globosus, Trifolium repens and Wisteria brachybotrys. Glycitein was first documented in 2002 (PMID: 12011578). Based on a literature review very few articles have been published on Glycitein (PMID: 16248547).

Structure

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

NP0043886
     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
   -4.8036   -1.2415   -1.3478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8435   -0.2071   -0.3890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6536    0.3014    0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4520   -0.1855   -0.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2744    0.3633    0.1457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0585   -0.1176   -0.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0237   -1.0380   -1.1510 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1334    0.3999    0.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4158   -0.1056   -0.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4260   -0.3763    0.6137 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6594   -0.8562    0.2269 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9335   -1.0885   -1.1039 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1807   -1.5759   -1.5160 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9296   -0.8216   -2.0153 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7022   -0.3420   -1.6109 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0257    1.4134    1.1229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1482    1.8633    1.5380 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2823    1.3748    1.0833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5112    1.8668    1.5372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6717    1.3138    1.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9018    1.7927    1.4644 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8315   -1.7000   -1.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1171   -2.0202   -0.9835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5613   -0.8690   -2.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3681   -0.9766   -1.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2312   -0.2008    1.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4438   -1.0645    0.9409 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8711   -1.7519   -0.8144 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1551   -1.0092   -3.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9598   -0.1534   -2.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9412    1.8432    1.5229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5560    2.6464    2.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9975    2.5224    2.1407 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
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
  8 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20  3  1  0
 18  5  2  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
 10 26  1  0
 11 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 19 32  1  0
 21 33  1  0
M  END


  Mrv1652306222119272D          

 21 23  0  0  0  0            999 V2000
   -2.1434   -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
   -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   -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
    0.7145   -0.4125    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
    1.4289   -0.0000    0.0000 C   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
    2.1434   -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
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -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
    5.0013    1.2375    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
  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
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  6 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 17 20  1  0  0  0  0
  4 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043886

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C2OC=C(C(=O)C2=C1)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O5/c1-20-15-6-11-14(7-13(15)18)21-8-12(16(11)19)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3

> <INCHI_KEY>
DXYUAIFZCFRPTH-UHFFFAOYSA-N

> <FORMULA>
C16H12O5

> <MOLECULAR_WEIGHT>
284.267

> <EXACT_MASS>
284.068473486

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
28.808298653213832

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
3.35

> <JCHEM_LOGP>
2.5727664456666663

> <ALOGPS_LOGS>
-3.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.967081247143751

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.919338975199671

> <JCHEM_PKA_STRONGEST_BASIC>
-4.75168191145487

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
76.1652

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.56e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
glycitein

> <JCHEM_VEBER_RULE>
0

$$$$

NP0043886
     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
   -4.8036   -1.2415   -1.3478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8435   -0.2071   -0.3890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6536    0.3014    0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4520   -0.1855   -0.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2744    0.3633    0.1457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0585   -0.1176   -0.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0237   -1.0380   -1.1510 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1334    0.3999    0.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4158   -0.1056   -0.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4260   -0.3763    0.6137 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6594   -0.8562    0.2269 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9335   -1.0885   -1.1039 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1807   -1.5759   -1.5160 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9296   -0.8216   -2.0153 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7022   -0.3420   -1.6109 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0257    1.4134    1.1229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1482    1.8633    1.5380 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2823    1.3748    1.0833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5112    1.8668    1.5372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6717    1.3138    1.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9018    1.7927    1.4644 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8315   -1.7000   -1.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1171   -2.0202   -0.9835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5613   -0.8690   -2.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3681   -0.9766   -1.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2312   -0.2008    1.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4438   -1.0645    0.9409 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8711   -1.7519   -0.8144 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1551   -1.0092   -3.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9598   -0.1534   -2.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9412    1.8432    1.5229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5560    2.6464    2.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9975    2.5224    2.1407 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
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
  8 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20  3  1  0
 18  5  2  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
 10 26  1  0
 11 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 19 32  1  0
 21 33  1  0
M  END

HEADER    PROTEIN                                 22-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-21         0                                  
HETATM    1  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5   21                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    3                                                       
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12    6                                                       
CONECT   14   11   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20   17                                                            
CONECT   21    4                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    NP0043886
HETATM    1  C1  UNL     1      -4.804  -1.242  -1.348  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.843  -0.207  -0.389  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.654   0.301   0.084  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.452  -0.186  -0.365  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.274   0.363   0.146  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.058  -0.118  -0.298  1.00  0.00           C  
HETATM    7  O2  UNL     1       0.024  -1.038  -1.151  1.00  0.00           O  
HETATM    8  C6  UNL     1       1.133   0.400   0.184  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.416  -0.106  -0.283  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.426  -0.376   0.614  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.659  -0.856   0.227  1.00  0.00           C  
HETATM   12  C10 UNL     1       4.933  -1.088  -1.104  1.00  0.00           C  
HETATM   13  O3  UNL     1       6.181  -1.576  -1.516  1.00  0.00           O  
HETATM   14  C11 UNL     1       3.930  -0.822  -2.015  1.00  0.00           C  
HETATM   15  C12 UNL     1       2.702  -0.342  -1.611  1.00  0.00           C  
HETATM   16  C13 UNL     1       1.026   1.413   1.123  1.00  0.00           C  
HETATM   17  O4  UNL     1      -0.148   1.863   1.538  1.00  0.00           O  
HETATM   18  C14 UNL     1      -1.282   1.375   1.083  1.00  0.00           C  
HETATM   19  C15 UNL     1      -2.511   1.867   1.537  1.00  0.00           C  
HETATM   20  C16 UNL     1      -3.672   1.314   1.023  1.00  0.00           C  
HETATM   21  O5  UNL     1      -4.902   1.793   1.464  1.00  0.00           O  
HETATM   22  H1  UNL     1      -5.832  -1.700  -1.345  1.00  0.00           H  
HETATM   23  H2  UNL     1      -4.117  -2.020  -0.983  1.00  0.00           H  
HETATM   24  H3  UNL     1      -4.561  -0.869  -2.364  1.00  0.00           H  
HETATM   25  H4  UNL     1      -2.368  -0.977  -1.098  1.00  0.00           H  
HETATM   26  H5  UNL     1       3.231  -0.201   1.663  1.00  0.00           H  
HETATM   27  H6  UNL     1       5.444  -1.065   0.941  1.00  0.00           H  
HETATM   28  H7  UNL     1       6.871  -1.752  -0.814  1.00  0.00           H  
HETATM   29  H8  UNL     1       4.155  -1.009  -3.075  1.00  0.00           H  
HETATM   30  H9  UNL     1       1.960  -0.153  -2.372  1.00  0.00           H  
HETATM   31  H10 UNL     1       1.941   1.843   1.523  1.00  0.00           H  
HETATM   32  H11 UNL     1      -2.556   2.646   2.260  1.00  0.00           H  
HETATM   33  H12 UNL     1      -4.997   2.522   2.141  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   20
CONECT    4    5   25
CONECT    5    6   18   18
CONECT    6    7    7    8
CONECT    8    9   16   16
CONECT    9   10   10   15
CONECT   10   11   26
CONECT   11   12   12   27
CONECT   12   13   14
CONECT   13   28
CONECT   14   15   15   29
CONECT   15   30
CONECT   16   17   31
CONECT   17   18
CONECT   18   19
CONECT   19   20   20   32
CONECT   20   21
CONECT   21   33
END

NP0043886
     RDKit          3D

33 35  0  0  0  0  0  0  0  0999 V2000
   -4.8036   -1.2415   -1.3478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8435   -0.2071   -0.3890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6536    0.3014    0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4520   -0.1855   -0.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2744    0.3633    0.1457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0585   -0.1176   -0.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0237   -1.0380   -1.1510 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1334    0.3999    0.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4158   -0.1056   -0.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4260   -0.3763    0.6137 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6594   -0.8562    0.2269 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9335   -1.0885   -1.1039 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1807   -1.5759   -1.5160 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9296   -0.8216   -2.0153 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7022   -0.3420   -1.6109 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0257    1.4134    1.1229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1482    1.8633    1.5380 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2823    1.3748    1.0833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5112    1.8668    1.5372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6717    1.3138    1.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9018    1.7927    1.4644 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8315   -1.7000   -1.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1171   -2.0202   -0.9835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5613   -0.8690   -2.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3681   -0.9766   -1.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2312   -0.2008    1.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4438   -1.0645    0.9409 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8711   -1.7519   -0.8144 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1551   -1.0092   -3.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9598   -0.1534   -2.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9412    1.8432    1.5229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5560    2.6464    2.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9975    2.5224    2.1407 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
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
  8 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20  3  1  0
 18  5  2  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
 10 26  1  0
 11 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 19 32  1  0
 21 33  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
7,4'-Dihydroxy-6-methoxyisoflavone	ChEBI
7-Hydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-1-benzopyran-4-one	ChEBI

Chemical Formula

C₁₆H₁₂O₅

Average Mass

284.2670 Da

Monoisotopic Mass

284.06847 Da

IUPAC Name

7-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-chromen-4-one

Traditional Name

glycitein

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C2OC=C(C(=O)C2=C1)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C16H12O5/c1-20-15-6-11-14(7-13(15)18)21-8-12(16(11)19)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3

InChI Key

DXYUAIFZCFRPTH-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 50 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 150 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 250 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 175 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 75 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 225 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 125 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 25 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Acca sellowiana	KNApSAcK Database	22123792
Allium sativum	FooDB	USDA
Aloe vera	KNApSAcK Database	22123792
Ammopiptanthus mongolicus	LOTUS Database	35616633
Anacardium occidentale	FooDB	USDA
Arabidopsis thaliana	KNApSAcK Database	22123792
Arachis hypogaea	FooDB	USDA
Bos taurus	FooDB	USDA
Bupleurum scorzonerifolium	KNApSAcK Database	22123792
Castanea sativa	FooDB	USDA
Centrosema haitiense	KNApSAcK Database	22123792
Centrosema pubescens	KNApSAcK Database	22123792
Cicer arietinum	KNApSAcK Database	22123792
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	USDA
Coffea arabica L.	FooDB	USDA
Coffea canephora	FooDB	USDA
Corylus	FooDB	USDA
Cullen corylifolium	Plant	KNApSAcK
Dalbergia frutescens	KNApSAcK Database	22123792
Erycibe expansa	KNApSAcK Database	22123792
Erythroxylum ulei	KNApSAcK Database	22123792
Feijoa sellowiana	Plant	KNApSAcK
Glycine max	KNApSAcK Database	22123792
Glycyrrhiza glabra	KNApSAcK Database	22123792
Juglans regia	FooDB	USDA
Lens culinaris	FooDB	USDA
Linum usitatissimum	FooDB	USDA
Lupinus albus	FooDB	USDA
Maackia amurensis	KNApSAcK Database	22123792
Medicago sativa	KNApSAcK Database	22123792
Mildbraediodendron excelsum	KNApSAcK Database	22123792
Olea europaea	FooDB	USDA
Ophiocordyceps sinensis	LOTUS Database	35616633
Phaseolus coccineus	FooDB	USDA
Phaseolus vulgaris	KNApSAcK Database	22123792
Phoenix dactylifera	FooDB	USDA
Pistacia vera	FooDB	USDA
Pisum sativum	KNApSAcK Database	22123792
Prunus armeniaca	FooDB	USDA
Prunus dulcis	FooDB	USDA
Psoralea corylifolia	KNApSAcK Database	22123792
Pterocarpus marsupium	KNApSAcK Database	22123792
Pueraria lobata	KNApSAcK Database	22123792
Pueraria montana	LOTUS Database	35616633
Pueraria thunbergiana	KNApSAcK Database	22123792
Pueraria tuberosa	KNApSAcK Database	22123792
Ribes nigrum	FooDB	USDA
Sarcolobus globosus	-	KNApSAcK
Thunnus	FooDB	USDA
Thunnus alalunga	FooDB	USDA
Trifolium pratense	KNApSAcK Database	22123792
Trifolium repens	Plant	KNApSAcK
Vaccinium macrocarpon	FooDB	USDA
Vicia faba	FooDB	USDA
Vigna angularis	FooDB	USDA
Vigna mungo	FooDB	USDA
Vigna radiata	KNApSAcK Database	22123792
Vitis vinifera L.	FooDB	USDA
Wisteria brachybotrys	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflav-2-enes

Direct Parent

Isoflavones

Alternative Parents

Substituents

Hydroxyisoflavonoid
Isoflavone
Chromone
Benzopyran
1-benzopyran
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Oxacycle
Ether
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

methoxyisoflavone (CHEBI:34778 )
7-hydroxyisoflavone (CHEBI:34778 )
isoflavones (C14536 )
Isoflavonoids (C14536 )
Isoflavonoids (LMPK12050104 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	547.40 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	542.1 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.570 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	3.35	ALOGPS
logP	2.57	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	6.92	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	76.17 m³·mol⁻¹	ChemAxon
Polarizability	28.81 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

HMDB0005781

DrugBank ID

Not Available

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Glycitein

METLIN ID

Not Available

PubChem Compound

5317750

PDB ID

Not Available

ChEBI ID

34778

Good Scents ID

rw1679411

References

General References

Sirtori CR, Bosisio R, Pazzucconi F, Bondioli A, Gatti E, Lovati MR, Murphy P: Soy milk with a high glycitein content does not reduce low-density lipoprotein cholesterolemia in type II hypercholesterolemic patients. Ann Nutr Metab. 2002;46(2):88-92. doi: 10.1159/000057646. [PubMed:12011578 ]
Simons AL, Renouf M, Hendrich S, Murphy PA: Metabolism of glycitein (7,4'-dihydroxy-6-methoxy-isoflavone) by human gut microflora. J Agric Food Chem. 2005 Nov 2;53(22):8519-25. doi: 10.1021/jf051546d. [PubMed:16248547 ]

Showing NP-Card for Glycitein (NP0043886)

MOL for NP0043886 (Glycitein)

3D MOL for NP0043886 (Glycitein)

3D SDF for NP0043886 (Glycitein)

3D-SDF for NP0043886 (Glycitein)

PDB for NP0043886 (Glycitein)

3D PDB for NP0043886 (Glycitein)

SMILES for NP0043886 (Glycitein)

INCHI for NP0043886 (Glycitein)

Structure for NP0043886 (Glycitein)

3D Structure for NP0043886 (Glycitein)