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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-13 22:38:47 UTC

Update Date

2021-10-13 04:43:55 UTC

HMDB ID

HMDB0004629

Secondary Accession Numbers

HMDB04629

Metabolite Identification

Common Name

O-Desmethylangolensin

Description

O-Desmethylangolensin (ODMA) is a metabolite of the soy isoflavone daidzein by intestinal bacteria in approximately 80-90% of persons. Studies suggest beneficial health effects associated with daidzein-metabolizing phenotypes, and there is some small association between ODMA production and some phenotypes. Few dietary factors are associated with daidzein-metabolizing phenotypes. However, it remains unclear why some, but not all, persons harbor ODMA-producing bacteria. ODMA production is inversely associated with age, height, weight, and body mass index. In addition, Asians are less likely than whites to be ODMA producers, and former smokers were more likely than never smokers to be ODMA producers. Investigators have attempted to identify the bacteria involved in ODMA production, and several candidate bacteria were associated, but not definitely identified. ODMA production is correlated with the abundance of methanogens, indicating that the metabolic fate of daidzein may be related to intestinal H(2) metabolism. (PMID: 18326607 , 17506823 ).

Structure

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

HMDB0004629
     RDKit          3D
O-Desmethylangolensin
 33 34  0  0  0  0  0  0  0  0999 V2000
   -0.7337   -2.7155    0.2606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0580   -1.5732   -0.6401 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0246   -1.1445   -1.5309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1190   -1.3802   -2.7820 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2545   -0.4799   -1.1830 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1710   -0.1313   -2.1838 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3580    0.5088   -1.9267 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6431    0.8144   -0.6155 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8433    1.4618   -0.3560 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7689    0.4898    0.4057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5843   -0.1538    0.1112 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7644   -0.4452    1.1873 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7294   -0.4177    0.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4726   -0.5719    1.1943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0765    0.5057    1.7894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9355    1.7569    1.2428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5475    2.8763    1.8384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1975    1.9721    0.1001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6059    0.8666   -0.4691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9199   -2.5326    1.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3731   -2.9300    0.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2694   -3.6653   -0.0506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8942   -1.9686   -1.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9799   -0.3572   -3.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0538    0.7706   -2.7103 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1381    1.7271    0.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9845    0.7246    1.4277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9788   -0.2197    2.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6123   -1.5199    1.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6769    0.4257    2.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9770    3.3628    2.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0903    2.9733   -0.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0049    0.9700   -1.3801 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
  2 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 11  5  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  6 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 12 28  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
M  END


  Mrv1652310011709302D          

 19 20  0  0  0  0            999 V2000
   19.2481  -16.0110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5335  -17.2486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6770  -12.7110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9625  -19.7236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6770  -16.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6770  -15.1860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9625  -16.4236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3915  -16.4236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9625  -17.2486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9625  -14.7735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3915  -14.7735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2481  -17.6611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6770  -17.6611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9625  -13.9485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3915  -13.9485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6770  -13.5360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2481  -18.4861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6770  -18.4861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9625  -18.8985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  2  0  0  0  0
  2 12  1  0  0  0  0
  3 16  1  0  0  0  0
  4 19  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  6 10  2  0  0  0  0
  6 11  1  0  0  0  0
  7  9  1  0  0  0  0
  9 12  2  0  0  0  0
  9 13  1  0  0  0  0
 10 14  1  0  0  0  0
 11 15  2  0  0  0  0
 12 17  1  0  0  0  0
 13 18  2  0  0  0  0
 14 16  2  0  0  0  0
 15 16  1  0  0  0  0
 17 19  2  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004629

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C(=O)C1=C(O)C=C(O)C=C1)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O4/c1-9(10-2-4-11(16)5-3-10)15(19)13-7-6-12(17)8-14(13)18/h2-9,16-18H,1H3

> <INCHI_KEY>
JDJPNKPFDDUBFV-UHFFFAOYSA-N

> <FORMULA>
C15H14O4

> <MOLECULAR_WEIGHT>
258.2693

> <EXACT_MASS>
258.089208936

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
26.376559364739467

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(2,4-dihydroxyphenyl)-2-(4-hydroxyphenyl)propan-1-one

> <ALOGPS_LOGP>
2.98

> <JCHEM_LOGP>
3.647523467666667

> <ALOGPS_LOGS>
-3.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.333559153112283

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.832218337443113

> <JCHEM_PKA_STRONGEST_BASIC>
-4.912202076859793

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
71.69990000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.39e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
O-desmethylangolensin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004629
     RDKit          3D
O-Desmethylangolensin
 33 34  0  0  0  0  0  0  0  0999 V2000
   -0.7337   -2.7155    0.2606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0580   -1.5732   -0.6401 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0246   -1.1445   -1.5309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1190   -1.3802   -2.7820 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2545   -0.4799   -1.1830 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1710   -0.1313   -2.1838 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3580    0.5088   -1.9267 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6431    0.8144   -0.6155 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8433    1.4618   -0.3560 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7689    0.4898    0.4057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5843   -0.1538    0.1112 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7644   -0.4452    1.1873 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7294   -0.4177    0.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4726   -0.5719    1.1943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0765    0.5057    1.7894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9355    1.7569    1.2428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5475    2.8763    1.8384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1975    1.9721    0.1001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6059    0.8666   -0.4691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9199   -2.5326    1.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3731   -2.9300    0.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2694   -3.6653   -0.0506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8942   -1.9686   -1.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9799   -0.3572   -3.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0538    0.7706   -2.7103 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1381    1.7271    0.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9845    0.7246    1.4277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9788   -0.2197    2.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6123   -1.5199    1.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6769    0.4257    2.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9770    3.3628    2.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0903    2.9733   -0.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0049    0.9700   -1.3801 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
  2 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 11  5  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  6 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 12 28  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
M  END

HEADER    PROTEIN                                 01-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-OCT-17         0                                  
HETATM    1  O   UNK     0      35.930 -29.887   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      34.596 -32.197   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      38.597 -23.727   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      37.263 -36.817   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      38.597 -29.887   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      38.597 -28.347   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      37.263 -30.657   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      39.931 -30.657   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      37.263 -32.197   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      37.263 -27.577   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      39.931 -27.577   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      35.930 -32.967   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      38.597 -32.967   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      37.263 -26.037   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      39.931 -26.037   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      38.597 -25.267   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      35.930 -34.507   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      38.597 -34.507   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      37.263 -35.277   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2   12                                                            
CONECT    3   16                                                            
CONECT    4   19                                                            
CONECT    5    6    7    8                                                  
CONECT    6    5   10   11                                                  
CONECT    7    1    5    9                                                  
CONECT    8    5                                                            
CONECT    9    7   12   13                                                  
CONECT   10    6   14                                                       
CONECT   11    6   15                                                       
CONECT   12    2    9   17                                                  
CONECT   13    9   18                                                       
CONECT   14   10   16                                                       
CONECT   15   11   16                                                       
CONECT   16    3   14   15                                                  
CONECT   17   12   19                                                       
CONECT   18   13   19                                                       
CONECT   19    4   17   18                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0004629
HETATM    1  C1  UNL     1      -0.734  -2.715   0.261  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.058  -1.573  -0.640  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.025  -1.144  -1.531  1.00  0.00           C  
HETATM    4  O1  UNL     1      -0.119  -1.380  -2.782  1.00  0.00           O  
HETATM    5  C4  UNL     1       1.254  -0.480  -1.183  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.171  -0.131  -2.184  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.358   0.509  -1.927  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.643   0.814  -0.615  1.00  0.00           C  
HETATM    9  O2  UNL     1       4.843   1.462  -0.356  1.00  0.00           O  
HETATM   10  C8  UNL     1       2.769   0.490   0.406  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.584  -0.154   0.111  1.00  0.00           C  
HETATM   12  O3  UNL     1       0.764  -0.445   1.187  1.00  0.00           O  
HETATM   13  C10 UNL     1      -1.729  -0.418   0.061  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.473  -0.572   1.194  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.076   0.506   1.789  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.935   1.757   1.243  1.00  0.00           C  
HETATM   17  O4  UNL     1      -3.547   2.876   1.838  1.00  0.00           O  
HETATM   18  C14 UNL     1      -2.197   1.972   0.100  1.00  0.00           C  
HETATM   19  C15 UNL     1      -1.606   0.867  -0.469  1.00  0.00           C  
HETATM   20  H1  UNL     1      -0.920  -2.533   1.325  1.00  0.00           H  
HETATM   21  H2  UNL     1       0.373  -2.930   0.164  1.00  0.00           H  
HETATM   22  H3  UNL     1      -1.269  -3.665  -0.051  1.00  0.00           H  
HETATM   23  H4  UNL     1      -1.894  -1.969  -1.319  1.00  0.00           H  
HETATM   24  H5  UNL     1       1.980  -0.357  -3.236  1.00  0.00           H  
HETATM   25  H6  UNL     1       4.054   0.771  -2.710  1.00  0.00           H  
HETATM   26  H7  UNL     1       5.138   1.727   0.583  1.00  0.00           H  
HETATM   27  H8  UNL     1       2.984   0.725   1.428  1.00  0.00           H  
HETATM   28  H9  UNL     1       0.979  -0.220   2.140  1.00  0.00           H  
HETATM   29  H10 UNL     1      -2.612  -1.520   1.649  1.00  0.00           H  
HETATM   30  H11 UNL     1      -3.677   0.426   2.693  1.00  0.00           H  
HETATM   31  H12 UNL     1      -2.977   3.363   2.540  1.00  0.00           H  
HETATM   32  H13 UNL     1      -2.090   2.973  -0.329  1.00  0.00           H  
HETATM   33  H14 UNL     1      -1.005   0.970  -1.380  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   13   23
CONECT    3    4    4    5
CONECT    5    6    6   11
CONECT    6    7   24
CONECT    7    8    8   25
CONECT    8    9   10
CONECT    9   26
CONECT   10   11   11   27
CONECT   11   12
CONECT   12   28
CONECT   13   14   14   19
CONECT   14   15   29
CONECT   15   16   16   30
CONECT   16   17   18
CONECT   17   31
CONECT   18   19   19   32
CONECT   19   33
END

HMDB0004629
     RDKit          3D
O-Desmethylangolensin
 33 34  0  0  0  0  0  0  0  0999 V2000
   -0.7337   -2.7155    0.2606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0580   -1.5732   -0.6401 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0246   -1.1445   -1.5309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1190   -1.3802   -2.7820 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2545   -0.4799   -1.1830 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1710   -0.1313   -2.1838 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3580    0.5088   -1.9267 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6431    0.8144   -0.6155 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8433    1.4618   -0.3560 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7689    0.4898    0.4057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5843   -0.1538    0.1112 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7644   -0.4452    1.1873 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7294   -0.4177    0.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4726   -0.5719    1.1943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0765    0.5057    1.7894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9355    1.7569    1.2428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5475    2.8763    1.8384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1975    1.9721    0.1001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6059    0.8666   -0.4691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9199   -2.5326    1.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3731   -2.9300    0.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2694   -3.6653   -0.0506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8942   -1.9686   -1.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9799   -0.3572   -3.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0538    0.7706   -2.7103 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1381    1.7271    0.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9845    0.7246    1.4277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9788   -0.2197    2.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6123   -1.5199    1.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6769    0.4257    2.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9770    3.3628    2.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0903    2.9733   -0.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0049    0.9700   -1.3801 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
  2 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 11  5  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  6 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 12 28  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2',4'-Dihydroxy-2-(P-hydroxyphenyl)-propiophenone	HMDB
2,4-Dihydroxyphenyl P-hydroxyphenethyl ketone	HMDB
O-Demethylangolensin	HMDB
O-Demethylangolesin	HMDB
O-Desmethylangolensin	MeSH

Chemical Formula

C₁₅H₁₄O₄

Average Molecular Weight

258.2693

Monoisotopic Molecular Weight

258.089208936

IUPAC Name

1-(2,4-dihydroxyphenyl)-2-(4-hydroxyphenyl)propan-1-one

Traditional Name

O-desmethylangolensin

CAS Registry Number

21255-69-6

SMILES

CC(C(=O)C1=C(O)C=C(O)C=C1)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C15H14O4/c1-9(10-2-4-11(16)5-3-10)15(19)13-7-6-12(17)8-14(13)18/h2-9,16-18H,1H3

InChI Key

JDJPNKPFDDUBFV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha-methyldeoxybenzoin flavonoids. These are flavonoids with a structure based on a 1,2-diphenyl-2-propan-2-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Alpha-methyldeoxybenzoin flavonoids

Sub Class

Not Available

Direct Parent

Alpha-methyldeoxybenzoin flavonoids

Alternative Parents

Substituents

Alpha-methyldeoxybenzoin flavonoid
Stilbene
Alkyl-phenylketone
Phenylketone
Phenylpropane
Benzoyl
Aryl alkyl ketone
Aryl ketone
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Health effect

Digestive system disorder

Gastrointestinal disorder

Lower gastrointestinal disorder

Ileostomy (HMDB: HMDB0004629)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 17449595)

Cellular substructure

Membrane (HMDB: HMDB0004629)
Cell membrane (HMDB: HMDB0004629)

Excreta

Biofluid or Excreta

Urine (PMID: 17413104)

Source

Endogenous

Endogenous (HMDB: HMDB0004629)

Plant

Plant (HMDB: HMDB0004629)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Fruits Consumption (MarkerDB: MDB00000451)
Vegetables Consumption (MarkerDB: MDB00000451)
Soy Foods Consumption (MarkerDB: MDB00000451)
Fats Consumption (MarkerDB: MDB00000451)
Dietary Fibre Consumption (MarkerDB: MDB00000451)
O-Desmethylangolensin Exposure (MarkerDB: MDB00000451)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	169.9 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.084 g/L	ALOGPS
logP	2.98	ALOGPS
logP	3.65	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	7.83	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	71.7 m³·mol⁻¹	ChemAxon
Polarizability	26.38 Å³	ChemAxon
Number of Rings	2	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]+	161.079	31661259
DarkChem	[M-H]-	162.664	31661259
DeepCCS	[M+H]+	163.12	30932474
DeepCCS	[M-H]-	160.746	30932474
DeepCCS	[M-2H]-	193.632	30932474
DeepCCS	[M+Na]+	169.197	30932474
AllCCS	[M+H]+	159.5	32859911
AllCCS	[M+H-H2O]+	155.5	32859911
AllCCS	[M+NH4]+	163.2	32859911
AllCCS	[M+Na]+	164.2	32859911
AllCCS	[M-H]-	160.7	32859911
AllCCS	[M+Na-2H]-	160.4	32859911
AllCCS	[M+HCOO]-	160.1	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.	6.34 minutes	32390414
Predicted by Siyang on May 30, 2022	12.469 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.11 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	23.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1965.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	309.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	149.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	176.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	337.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	641.8 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	546.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	83.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1082.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	439.4 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	1352.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	390.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	371.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	383.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	186.4 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	122.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
O-Desmethylangolensin	CC(C(=O)C1=C(O)C=C(O)C=C1)C1=CC=C(O)C=C1	3690.4	Standard polar	33892256
O-Desmethylangolensin	CC(C(=O)C1=C(O)C=C(O)C=C1)C1=CC=C(O)C=C1	2508.5	Standard non polar	33892256
O-Desmethylangolensin	CC(C(=O)C1=C(O)C=C(O)C=C1)C1=CC=C(O)C=C1	2616.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
O-Desmethylangolensin,1TMS,isomer #1	CC(C(=O)C1=CC=C(O)C=C1O[Si](C)(C)C)C1=CC=C(O)C=C1	2505.1	Semi standard non polar	33892256
O-Desmethylangolensin,1TMS,isomer #2	CC(C(=O)C1=CC=C(O[Si](C)(C)C)C=C1O)C1=CC=C(O)C=C1	2496.1	Semi standard non polar	33892256
O-Desmethylangolensin,1TMS,isomer #3	CC(C(=O)C1=CC=C(O)C=C1O)C1=CC=C(O[Si](C)(C)C)C=C1	2485.5	Semi standard non polar	33892256
O-Desmethylangolensin,2TMS,isomer #1	CC(C(=O)C1=CC=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C)C1=CC=C(O)C=C1	2469.6	Semi standard non polar	33892256
O-Desmethylangolensin,2TMS,isomer #2	CC(C(=O)C1=CC=C(O)C=C1O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C=C1	2475.8	Semi standard non polar	33892256
O-Desmethylangolensin,2TMS,isomer #3	CC(C(=O)C1=CC=C(O[Si](C)(C)C)C=C1O)C1=CC=C(O[Si](C)(C)C)C=C1	2466.9	Semi standard non polar	33892256
O-Desmethylangolensin,3TMS,isomer #1	CC(C(=O)C1=CC=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C=C1	2516.9	Semi standard non polar	33892256
O-Desmethylangolensin,1TBDMS,isomer #1	CC(C(=O)C1=CC=C(O)C=C1O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C=C1	2797.3	Semi standard non polar	33892256
O-Desmethylangolensin,1TBDMS,isomer #2	CC(C(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O)C1=CC=C(O)C=C1	2790.4	Semi standard non polar	33892256
O-Desmethylangolensin,1TBDMS,isomer #3	CC(C(=O)C1=CC=C(O)C=C1O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	2782.6	Semi standard non polar	33892256
O-Desmethylangolensin,2TBDMS,isomer #1	CC(C(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C=C1	2972.2	Semi standard non polar	33892256
O-Desmethylangolensin,2TBDMS,isomer #2	CC(C(=O)C1=CC=C(O)C=C1O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	3002.8	Semi standard non polar	33892256
O-Desmethylangolensin,2TBDMS,isomer #3	CC(C(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	3041.2	Semi standard non polar	33892256
O-Desmethylangolensin,3TBDMS,isomer #1	CC(C(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	3268.8	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 - O-Desmethylangolensin GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-1900000000-39495ea1c0376894fddf	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-Desmethylangolensin GC-MS (3 TMS) - 70eV, Positive	splash10-0a4i-4430900000-0e7b58ddbbc19e665858	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-Desmethylangolensin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-Desmethylangolensin 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 - O-Desmethylangolensin 10V, Positive-QTOF	splash10-0a4i-0390000000-95a81edd733d13d61677	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylangolensin 20V, Positive-QTOF	splash10-000b-1930000000-6a844b2d3f64f75db87b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylangolensin 40V, Positive-QTOF	splash10-0002-4900000000-3c4808d490aaff85f058	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylangolensin 10V, Negative-QTOF	splash10-0a4i-0190000000-1b486ce055fb4c745e83	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylangolensin 20V, Negative-QTOF	splash10-0a4i-0490000000-f6b7ddbf92a2c481414b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylangolensin 40V, Negative-QTOF	splash10-0aou-6910000000-ef3d7901fc4103baf88d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylangolensin 10V, Negative-QTOF	splash10-0a4i-0090000000-c2a50a42dfada53572a9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylangolensin 20V, Negative-QTOF	splash10-0a4i-2590000000-ff1a68dd0b89bc03287c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylangolensin 40V, Negative-QTOF	splash10-00kf-6900000000-8f8d3654f73a1a919a16	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylangolensin 10V, Positive-QTOF	splash10-0a4i-0390000000-1ca6275f205a504ebd5c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylangolensin 20V, Positive-QTOF	splash10-00di-1910000000-a1d96f103a978278101f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylangolensin 40V, Positive-QTOF	splash10-00fu-8900000000-a6ac1b1337f1eee505a2	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 879	20164315	details
Blood	Detected and Quantified	0.0002 uM	Adult (>18 years old)	Female	Normal	9796633	details
Blood	Detected and Quantified	0.0005 uM	Adult (>18 years old)	Female	Normal	9796633	details
Blood	Detected and Quantified	0.0006195 - 0.000658 uM	Adult (>18 years old)	Both	Normal	17449595	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 879	7722188	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 879	17499260	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 879	7662591	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 879	10509897	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 879	14698210	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 879	10527518	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 879	15506819	details
Blood	Detected and Quantified	0.00058 uM	Adult (>18 years old)	Female	Normal	17449595	details
Blood	Detected and Quantified	0.00066 +/- 0.00002 uM	Adult (>18 years old)	Male	Normal	17449595	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 879	18469255	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 879	8017326	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 879	10798213	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 879	10952094	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 879	15113171	details
Urine	Detected and Quantified	0.0100 +/- 0.0133 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	10744130	details
Urine	Detected and Quantified	0.00733 +/- 0.00600 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	10744130	details
Urine	Detected and Quantified	0.220 +/- 0.427 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	10778038	details
Urine	Detected and Quantified	0.0389 +/- 0.0913 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	18791925	details
Urine	Detected and Quantified	0.0409 +/- 0.102 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	18791925	details
Urine	Detected and Quantified	0.0928 +/- 0.234 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	9681530	details
Urine	Detected and Quantified	0.000503 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	19167951	details
Urine	Detected and Quantified	0.000876 umol/mmol creatinine	Children (1 - 13 years old)	Both	Normal	17976571	details
Urine	Detected and Quantified	0.0380 +/- 0.175 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	10744130	details
Urine	Detected and Quantified	0.000774 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	15159299	details
Urine	Detected and Quantified	0.00221 umol/mmol creatinine	Children (1 - 13 years old)	Female	Normal	17366830	details
Urine	Detected and Quantified	0.113 umol/mmol creatinine	Children (1-13 years old)	Female	Normal	20385037	details
Urine	Detected and Quantified	0.172 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	22493748	details
Urine	Detected and Quantified	0.215 umol/mmol creatinine	Children (1-13 years old)	Female	Normal	20385037	details
Urine	Detected and Quantified	0.0176 +/- 0.0464 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	9681530	details
Urine	Detected and Quantified	0.0224 +/- 0.0544 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	9681530	details
Urine	Detected and Quantified	0.0256 +/- 0.0512 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	9681530	details
Urine	Detected and Quantified	0.0256 +/- 0.104 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	9681530	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 879	14698210	details
Urine	Detected and Quantified	0.008 +/- 0.002 (0.006 -0.012) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	17413104	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 879	14698210	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 879	18469255	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 879	8017326	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 879	10798213	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 879	10952094	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 879	15506819	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 879	15113171	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 879	10527518	details
Urine	Detected and Quantified	0.14 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	10778038	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 879	10509897	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 879	20164315	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 879	7662591	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 879	17499260	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 879	7722188	details
Urine	Detected and Quantified	0.00198 (0.00172-0.00235) umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	National Health a...	details
Urine	Detected and Quantified	0.00403 (0.00293-0.00560) umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	National Health a...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	23657156	details
Urine	Detected and Quantified	0.0733 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	10778038	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	0 - 0.057 umol/mmol creatinine	Adult (>18 years old)	Both	Soy consumption (ileostomies)	17413104	details

Associated Disorders and Diseases

Disease References

Ileostomy
Walsh KR, Haak SJ, Bohn T, Tian Q, Schwartz SJ, Failla ML: Isoflavonoid glucosides are deconjugated and absorbed in the small intestine of human subjects with ileostomies. Am J Clin Nutr. 2007 Apr;85(4):1050-6. [PubMed:17413104 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023387

KNApSAcK ID

Not Available

Chemspider ID

80750

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

O-Desmethylangolensin

METLIN ID

Not Available

PubChem Compound

89472

PDB ID

Not Available

ChEBI ID

88902

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000451

Good Scents ID

rw1198411

References

Synthesis Reference

Salakka, A.; Wahala, K. Synthesis of a-methyldeoxybenzoins. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1999), (18), 2601-2604.

Material Safety Data Sheet (MSDS)

Not Available

General References

Atkinson C, Newton KM, Bowles EJ, Yong M, Lampe JW: Demographic, anthropometric, and lifestyle factors and dietary intakes in relation to daidzein-metabolizing phenotypes among premenopausal women in the United States. Am J Clin Nutr. 2008 Mar;87(3):679-87. [PubMed:18326607 ]
Possemiers S, Bolca S, Eeckhaut E, Depypere H, Verstraete W: Metabolism of isoflavones, lignans and prenylflavonoids by intestinal bacteria: producer phenotyping and relation with intestinal community. FEMS Microbiol Ecol. 2007 Aug;61(2):372-83. Epub 2007 May 16. [PubMed:17506823 ]

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

O-Desmethylangolensin → 6-{4-[1-(2,4-dihydroxyphenyl)-1-oxopropan-2-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details
O-Desmethylangolensin → 3,4,5-trihydroxy-6-{3-hydroxy-4-[2-(4-hydroxyphenyl)propanoyl]phenoxy}oxane-2-carboxylic acid	details
O-Desmethylangolensin → 3,4,5-trihydroxy-6-{5-hydroxy-2-[2-(4-hydroxyphenyl)propanoyl]phenoxy}oxane-2-carboxylic acid	details

Enzyme Details

2. Sulfotransferase 1A3

General function:: sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:: SULT1A3
Uniprot ID:: P0DMM9
Molecular weight:: 34195.96

Reactions

O-Desmethylangolensin → {4-[1-(2,4-dihydroxyphenyl)-1-oxopropan-2-yl]phenyl}oxidanesulfonic acid	details

Showing metabocard for O-Desmethylangolensin (HMDB0004629)

MOL for HMDB0004629 (O-Desmethylangolensin)

3D MOL for HMDB0004629 (O-Desmethylangolensin)

3D SDF for HMDB0004629 (O-Desmethylangolensin)

3D-SDF for HMDB0004629 (O-Desmethylangolensin)

PDB for HMDB0004629 (O-Desmethylangolensin)

3D PDB for HMDB0004629 (O-Desmethylangolensin)

SMILES for HMDB0004629 (O-Desmethylangolensin)

INCHI for HMDB0004629 (O-Desmethylangolensin)

Structure for HMDB0004629 (O-Desmethylangolensin)

3D Structure for HMDB0004629 (O-Desmethylangolensin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions