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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 03:34:43 UTC

Update Date

2022-03-07 02:57:07 UTC

HMDB ID

HMDB0041660

Secondary Accession Numbers

HMDB41660

Metabolite Identification

Common Name

3'-O-Methylequol

Description

3'-O-Methylequol belongs to the class of organic compounds known as 3'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C3' atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one. Based on a literature review very few articles have been published on 3'-O-Methylequol.

Structure

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

HMDB0041660
     RDKit          3D
3'-O-Methylequol
 36 38  0  0  0  0  0  0  0  0999 V2000
   -3.5201    2.4648   -0.2935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0840    1.2941    0.2002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3875    0.1110    0.4032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0429    0.0885    0.0960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2549   -1.0340    0.2589 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2032   -1.0101   -0.0892 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3090   -0.7409   -1.5455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4426   -0.0382   -1.9436 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4922    0.2771   -1.1203 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7140    0.5765   -1.6799 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7806    0.8960   -0.8626 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9964    1.1925   -1.4526 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5772    0.9027    0.4980 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3426    0.5999    1.0592 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2697    0.2786    0.2402 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9511   -0.0472    0.7834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8652   -2.1795    0.7557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2094   -2.1733    1.0678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9575   -1.0300    0.8891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3110   -0.9990    1.1958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8757    2.2505   -1.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3459    3.1040   -0.6804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9176    3.0323    0.4394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5405    0.9852   -0.2986 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6033   -2.0300    0.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2546   -1.7268   -2.0832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5925   -0.1723   -1.8903 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8432    0.5626   -2.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6718    0.4569   -1.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4113    1.1530    1.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2331    0.6183    2.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1201   -0.5678    1.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3842    0.8758    1.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2622   -3.0619    0.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6770   -3.0897    1.4604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7563   -1.8201    1.5537 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  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
  5 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19  3  1  0
 16  6  1  0
 15  9  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  6
  7 26  1  0
  7 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 20 36  1  0
M  END


  Mrv0541 02271201302D          

 20 22  0  0  0  0            999 V2000
    0.9336   -1.1020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6481   -1.5145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3625   -1.1020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3625   -0.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6481    0.1355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9336   -0.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2191    0.1355    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2191    0.9605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4954    1.3730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2098    0.9605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9243    1.3730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6388    0.9605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6388    0.1355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9243   -0.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2098    0.1355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4954   -0.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0770   -1.5145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3532    1.3730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0770    0.1355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0770    0.9605    0.0000 C   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 17  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  7  8  1  0  0  0  0
  7 16  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
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 18  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
  7  6  1  6  0  0  0
  4 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041660

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(=CC=C1O)[C@H]1COC2=CC(O)=CC=C2C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O4/c1-19-16-7-10(3-5-14(16)18)12-6-11-2-4-13(17)8-15(11)20-9-12/h2-5,7-8,12,17-18H,6,9H2,1H3/t12-/m1/s1

> <INCHI_KEY>
BMADVHDZKAZTNF-GFCCVEGCSA-N

> <FORMULA>
C16H16O4

> <MOLECULAR_WEIGHT>
272.2958

> <EXACT_MASS>
272.104859

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.08439993512036

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.97

> <JCHEM_LOGP>
3.0340066116666664

> <ALOGPS_LOGS>
-3.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.298070019479178

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.626404427026676

> <JCHEM_PKA_STRONGEST_BASIC>
-4.572248850864139

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
75.42340000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.66e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041660
     RDKit          3D
3'-O-Methylequol
 36 38  0  0  0  0  0  0  0  0999 V2000
   -3.5201    2.4648   -0.2935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0840    1.2941    0.2002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3875    0.1110    0.4032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0429    0.0885    0.0960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2549   -1.0340    0.2589 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2032   -1.0101   -0.0892 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3090   -0.7409   -1.5455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4426   -0.0382   -1.9436 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4922    0.2771   -1.1203 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7140    0.5765   -1.6799 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7806    0.8960   -0.8626 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9964    1.1925   -1.4526 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5772    0.9027    0.4980 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3426    0.5999    1.0592 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2697    0.2786    0.2402 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9511   -0.0472    0.7834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8652   -2.1795    0.7557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2094   -2.1733    1.0678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9575   -1.0300    0.8891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3110   -0.9990    1.1958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8757    2.2505   -1.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3459    3.1040   -0.6804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9176    3.0323    0.4394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5405    0.9852   -0.2986 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6033   -2.0300    0.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2546   -1.7268   -2.0832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5925   -0.1723   -1.8903 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8432    0.5626   -2.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6718    0.4569   -1.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4113    1.1530    1.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2331    0.6183    2.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1201   -0.5678    1.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3842    0.8758    1.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2622   -3.0619    0.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6770   -3.0897    1.4604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7563   -1.8201    1.5537 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  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
  5 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19  3  1  0
 16  6  1  0
 15  9  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  6
  7 26  1  0
  7 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 20 36  1  0
M  END

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  C   UNK     0       1.743  -2.057   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.076  -2.827   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.410  -2.057   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.410  -0.517   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.076   0.253   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.743  -0.517   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.409   0.253   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.409   1.793   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.925   2.563   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.258   1.793   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.592   2.563   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.926   1.793   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.926   0.253   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.592  -0.517   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.258   0.253   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.925  -0.517   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.744  -2.827   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -6.259   2.563   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.744   0.253   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.744   1.793   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    5   19                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    8   16    6                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   10   14   16                                                  
CONECT   16    7   15                                                       
CONECT   17    3                                                            
CONECT   18   12                                                            
CONECT   19    4   20                                                       
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0041660
HETATM    1  C1  UNL     1      -3.520   2.465  -0.294  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.084   1.294   0.200  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.388   0.111   0.403  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.043   0.089   0.096  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.255  -1.034   0.259  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.203  -1.010  -0.089  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.309  -0.741  -1.546  1.00  0.00           C  
HETATM    8  O2  UNL     1       1.443  -0.038  -1.944  1.00  0.00           O  
HETATM    9  C7  UNL     1       2.492   0.277  -1.120  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.714   0.576  -1.680  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.781   0.896  -0.863  1.00  0.00           C  
HETATM   12  O3  UNL     1       5.996   1.193  -1.453  1.00  0.00           O  
HETATM   13  C10 UNL     1       4.577   0.903   0.498  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.343   0.600   1.059  1.00  0.00           C  
HETATM   15  C12 UNL     1       2.270   0.279   0.240  1.00  0.00           C  
HETATM   16  C13 UNL     1       0.951  -0.047   0.783  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.865  -2.180   0.756  1.00  0.00           C  
HETATM   18  C15 UNL     1      -3.209  -2.173   1.068  1.00  0.00           C  
HETATM   19  C16 UNL     1      -3.957  -1.030   0.889  1.00  0.00           C  
HETATM   20  O4  UNL     1      -5.311  -0.999   1.196  1.00  0.00           O  
HETATM   21  H1  UNL     1      -2.876   2.251  -1.180  1.00  0.00           H  
HETATM   22  H2  UNL     1      -4.346   3.104  -0.680  1.00  0.00           H  
HETATM   23  H3  UNL     1      -2.918   3.032   0.439  1.00  0.00           H  
HETATM   24  H4  UNL     1      -1.541   0.985  -0.299  1.00  0.00           H  
HETATM   25  H5  UNL     1       0.603  -2.030   0.133  1.00  0.00           H  
HETATM   26  H6  UNL     1       0.255  -1.727  -2.083  1.00  0.00           H  
HETATM   27  H7  UNL     1      -0.592  -0.172  -1.890  1.00  0.00           H  
HETATM   28  H8  UNL     1       3.843   0.563  -2.762  1.00  0.00           H  
HETATM   29  H9  UNL     1       6.672   0.457  -1.634  1.00  0.00           H  
HETATM   30  H10 UNL     1       5.411   1.153   1.148  1.00  0.00           H  
HETATM   31  H11 UNL     1       3.233   0.618   2.124  1.00  0.00           H  
HETATM   32  H12 UNL     1       1.120  -0.568   1.770  1.00  0.00           H  
HETATM   33  H13 UNL     1       0.384   0.876   1.016  1.00  0.00           H  
HETATM   34  H14 UNL     1      -1.262  -3.062   0.888  1.00  0.00           H  
HETATM   35  H15 UNL     1      -3.677  -3.090   1.460  1.00  0.00           H  
HETATM   36  H16 UNL     1      -5.756  -1.820   1.554  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3
CONECT    3    4    4   19
CONECT    4    5   24
CONECT    5    6   17   17
CONECT    6    7   16   25
CONECT    7    8   26   27
CONECT    8    9
CONECT    9   10   10   15
CONECT   10   11   28
CONECT   11   12   13   13
CONECT   12   29
CONECT   13   14   30
CONECT   14   15   15   31
CONECT   15   16
CONECT   16   32   33
CONECT   17   18   34
CONECT   18   19   19   35
CONECT   19   20
CONECT   20   36
END

HMDB0041660
     RDKit          3D
3'-O-Methylequol
 36 38  0  0  0  0  0  0  0  0999 V2000
   -3.5201    2.4648   -0.2935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0840    1.2941    0.2002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3875    0.1110    0.4032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0429    0.0885    0.0960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2549   -1.0340    0.2589 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2032   -1.0101   -0.0892 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3090   -0.7409   -1.5455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4426   -0.0382   -1.9436 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4922    0.2771   -1.1203 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7140    0.5765   -1.6799 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7806    0.8960   -0.8626 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9964    1.1925   -1.4526 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5772    0.9027    0.4980 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3426    0.5999    1.0592 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2697    0.2786    0.2402 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9511   -0.0472    0.7834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8652   -2.1795    0.7557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2094   -2.1733    1.0678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9575   -1.0300    0.8891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3110   -0.9990    1.1958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8757    2.2505   -1.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3459    3.1040   -0.6804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9176    3.0323    0.4394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5405    0.9852   -0.2986 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6033   -2.0300    0.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2546   -1.7268   -2.0832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5925   -0.1723   -1.8903 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8432    0.5626   -2.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6718    0.4569   -1.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4113    1.1530    1.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2331    0.6183    2.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1201   -0.5678    1.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3842    0.8758    1.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2622   -3.0619    0.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6770   -3.0897    1.4604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7563   -1.8201    1.5537 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  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
  5 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19  3  1  0
 16  6  1  0
 15  9  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  6
  7 26  1  0
  7 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 20 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₆H₁₆O₄

Average Molecular Weight

272.2958

Monoisotopic Molecular Weight

272.104859

IUPAC Name

(3S)-3-(4-hydroxy-3-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol

Traditional Name

(3S)-3-(4-hydroxy-3-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)[C@H]1COC2=CC(O)=CC=C2C1

InChI Identifier

InChI=1S/C16H16O4/c1-19-16-7-10(3-5-14(16)18)12-6-11-2-4-13(17)8-15(11)20-9-12/h2-5,7-8,12,17-18H,6,9H2,1H3/t12-/m1/s1

InChI Key

BMADVHDZKAZTNF-GFCCVEGCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C3' 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

3'-O-methylated isoflavonoids

Alternative Parents

Substituents

3p-methoxyisoflavonoid-skeleton
Hydroxyisoflavonoid
Isoflavanol
Isoflavan
Chromane
Benzopyran
Methoxyphenol
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Oxacycle
Ether
Organoheterocyclic compound
Organooxygen compound
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

Membrane (HMDB: HMDB0041660)
Cell membrane (HMDB: HMDB0041660)

Excreta

Biofluid or Excreta

Urine (PMID: 14698210)

Source

Exogenous

Exogenous (HMDB: HMDB0041660)

Food

Food (HMDB: HMDB0041660)

Endogenous

Plant

Plant (HMDB: HMDB0041660)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0041660)

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	0.047 g/L	ALOGPS
logP	2.97	ALOGPS
logP	3.03	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	9.63	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	75.42 m³·mol⁻¹	ChemAxon
Polarizability	29.08 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]+	165.025	31661259
DarkChem	[M-H]-	167.335	31661259
DeepCCS	[M+H]+	160.584	30932474
DeepCCS	[M-H]-	158.226	30932474
DeepCCS	[M-2H]-	191.404	30932474
DeepCCS	[M+Na]+	166.677	30932474
AllCCS	[M+H]+	163.6	32859911
AllCCS	[M+H-H2O]+	159.8	32859911
AllCCS	[M+NH4]+	167.2	32859911
AllCCS	[M+Na]+	168.2	32859911
AllCCS	[M-H]-	167.4	32859911
AllCCS	[M+Na-2H]-	166.9	32859911
AllCCS	[M+HCOO]-	166.5	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.	5.92 minutes	32390414
Predicted by Siyang on May 30, 2022	12.0988 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.86 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1795.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	291.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	164.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	173.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	229.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	610.2 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	433.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	118.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1140.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	441.2 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	1241.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	363.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	369.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	345.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	242.6 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	48.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3'-O-Methylequol	COC1=CC(=CC=C1O)[C@H]1COC2=CC(O)=CC=C2C1	3569.6	Standard polar	33892256
3'-O-Methylequol	COC1=CC(=CC=C1O)[C@H]1COC2=CC(O)=CC=C2C1	2566.6	Standard non polar	33892256
3'-O-Methylequol	COC1=CC(=CC=C1O)[C@H]1COC2=CC(O)=CC=C2C1	2723.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3'-O-Methylequol,1TMS,isomer #1	COC1=CC([C@H]2COC3=CC(O)=CC=C3C2)=CC=C1O[Si](C)(C)C	2644.8	Semi standard non polar	33892256
3'-O-Methylequol,1TMS,isomer #2	COC1=CC([C@H]2COC3=CC(O[Si](C)(C)C)=CC=C3C2)=CC=C1O	2631.2	Semi standard non polar	33892256
3'-O-Methylequol,2TMS,isomer #1	COC1=CC([C@H]2COC3=CC(O[Si](C)(C)C)=CC=C3C2)=CC=C1O[Si](C)(C)C	2617.1	Semi standard non polar	33892256
3'-O-Methylequol,1TBDMS,isomer #1	COC1=CC([C@H]2COC3=CC(O)=CC=C3C2)=CC=C1O[Si](C)(C)C(C)(C)C	2931.2	Semi standard non polar	33892256
3'-O-Methylequol,1TBDMS,isomer #2	COC1=CC([C@H]2COC3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3C2)=CC=C1O	2904.6	Semi standard non polar	33892256
3'-O-Methylequol,2TBDMS,isomer #1	COC1=CC([C@H]2COC3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3C2)=CC=C1O[Si](C)(C)C(C)(C)C	3097.7	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 - 3'-O-Methylequol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dr-0970000000-315d76031d585b3ebbd7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3'-O-Methylequol GC-MS (2 TMS) - 70eV, Positive	splash10-0ukc-6847900000-21ea77ded24a3a273671	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3'-O-Methylequol 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 - 3'-O-Methylequol 10V, Positive-QTOF	splash10-00di-0960000000-d51b7c6d2e123e35e372	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-O-Methylequol 20V, Positive-QTOF	splash10-00di-0930000000-9f3237b51e09dd3c8b79	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-O-Methylequol 40V, Positive-QTOF	splash10-0aba-4900000000-e326d1e3a4ee1c927add	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-O-Methylequol 10V, Negative-QTOF	splash10-00di-0290000000-a1122cc5c82bdf519566	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-O-Methylequol 20V, Negative-QTOF	splash10-00di-0490000000-f53bf4327eda66d2601f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-O-Methylequol 40V, Negative-QTOF	splash10-05fr-1930000000-f424827a35ab832f3cc7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-O-Methylequol 10V, Negative-QTOF	splash10-00di-0090000000-fa0ebf6f807322562116	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-O-Methylequol 20V, Negative-QTOF	splash10-00dr-0190000000-ee07e165ee2d8c56b614	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-O-Methylequol 40V, Negative-QTOF	splash10-00kb-1940000000-d2d6c88b4ab705c21117	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-O-Methylequol 10V, Positive-QTOF	splash10-00di-0390000000-786ff42f716a29cfcede	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-O-Methylequol 20V, Positive-QTOF	splash10-00dm-0590000000-fdf62b2d81ad55714da4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-O-Methylequol 40V, Positive-QTOF	splash10-0ki7-1950000000-892fc8984719cdb31aa3	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 901	14698210	details

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

901

FooDB ID

FDB029818

KNApSAcK ID

Not Available

Chemspider ID

30777592

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131753179

PDB ID

Not Available

ChEBI ID

174585

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

Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8. [PubMed:20428313 ]

Showing metabocard for 3'-O-Methylequol (HMDB0041660)

MOL for HMDB0041660 (3'-O-Methylequol)

3D MOL for HMDB0041660 (3'-O-Methylequol)

3D SDF for HMDB0041660 (3'-O-Methylequol)

3D-SDF for HMDB0041660 (3'-O-Methylequol)

PDB for HMDB0041660 (3'-O-Methylequol)

3D PDB for HMDB0041660 (3'-O-Methylequol)

SMILES for HMDB0041660 (3'-O-Methylequol)

INCHI for HMDB0041660 (3'-O-Methylequol)

Structure for HMDB0041660 (3'-O-Methylequol)

3D Structure for HMDB0041660 (3'-O-Methylequol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra