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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 03:33:59 UTC

Update Date

2022-03-07 02:57:06 UTC

HMDB ID

HMDB0041647

Secondary Accession Numbers

HMDB41647

Metabolite Identification

Common Name

2-Dehydro-O-desmethylangolensin

Description

2-Dehydro-O-desmethylangolensin belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Based on a literature review very few articles have been published on 2-Dehydro-O-desmethylangolensin.

Structure

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

HMDB0041647
     RDKit          3D
2-Dehydro-O-desmethylangolensin
 31 32  0  0  0  0  0  0  0  0999 V2000
    0.6560   -1.2729   -1.6431 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6762   -0.4841   -0.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4405    0.0085    0.1079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0483    0.7723    1.1261 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8593   -0.1290   -0.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5858   -0.8225   -0.9351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9755   -0.8925   -0.9722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6883   -0.2261   -0.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0680   -0.2932   -0.0603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0348    0.4850    0.9222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6574    0.5446    0.9457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0869    1.2899    1.9450 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0718   -0.1133   -0.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3922    1.1315    0.2916 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7065    1.3939    0.7144 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6867    0.4350    0.6747 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0010    0.7075    1.1005 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3565   -0.8132    0.2049 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0639   -1.0687   -0.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6622   -1.5501   -2.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1684   -1.6912   -2.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0804   -1.3547   -1.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4482   -1.4757   -1.7530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6439    0.3742   -0.5794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6439    1.0058    1.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6484    1.7676    2.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6688    1.9101    0.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9612    2.3783    1.0835 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2088    1.6342    1.4395 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1233   -1.5666    0.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8426   -2.0842   -0.5712 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  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
  6 22  1  0
  7 23  1  0
  9 24  1  0
 10 25  1  0
 12 26  1  0
 14 27  1  0
 15 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  0
M  END

  Mrv0541 02271201282D          

 19 20  0  0  0  0            999 V2000
    1.4289   -0.3039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.1289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.5414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.1289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5723   -1.5414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5723   -2.3664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.7789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.7789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.3664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.5414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.3664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.1289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.5414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.3664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.1289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.3039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.1086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.3039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 12 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041647

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C(C=C1)C(=C)C(=O)C1=C(O)C=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O4/c1-9(10-2-4-11(16)5-3-10)15(19)13-7-6-12(17)8-14(13)18/h2-8,16-18H,1H2

> <INCHI_KEY>
MPNKZWIUITZJCR-UHFFFAOYSA-N

> <FORMULA>
C15H12O4

> <MOLECULAR_WEIGHT>
256.2534

> <EXACT_MASS>
256.073558872

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
25.812361794423367

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.98

> <JCHEM_LOGP>
3.694578172

> <ALOGPS_LOGS>
-2.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.810108014477263

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.716540156433847

> <JCHEM_PKA_STRONGEST_BASIC>
-5.922553552955372

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
71.50330000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.18e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(2,4-dihydroxyphenyl)-2-(4-hydroxyphenyl)prop-2-en-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041647
     RDKit          3D
2-Dehydro-O-desmethylangolensin
 31 32  0  0  0  0  0  0  0  0999 V2000
    0.6560   -1.2729   -1.6431 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6762   -0.4841   -0.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4405    0.0085    0.1079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0483    0.7723    1.1261 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8593   -0.1290   -0.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5858   -0.8225   -0.9351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9755   -0.8925   -0.9722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6883   -0.2261   -0.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0680   -0.2932   -0.0603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0348    0.4850    0.9222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6574    0.5446    0.9457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0869    1.2899    1.9450 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0718   -0.1133   -0.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3922    1.1315    0.2916 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7065    1.3939    0.7144 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6867    0.4350    0.6747 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0010    0.7075    1.1005 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3565   -0.8132    0.2049 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0639   -1.0687   -0.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6622   -1.5501   -2.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1684   -1.6912   -2.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0804   -1.3547   -1.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4482   -1.4757   -1.7530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6439    0.3742   -0.5794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6439    1.0058    1.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6484    1.7676    2.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6688    1.9101    0.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9612    2.3783    1.0835 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2088    1.6342    1.4395 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1233   -1.5666    0.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8426   -2.0842   -0.5712 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  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
  6 22  1  0
  7 23  1  0
  9 24  1  0
 10 25  1  0
 12 26  1  0
 14 27  1  0
 15 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  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       2.667  -0.567   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -2.107   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -2.877   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -2.107   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -2.877   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -4.417   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.002  -5.187   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.335  -5.187   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -4.417   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.877   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.334  -4.417   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.000  -2.107   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334  -2.877   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.334  -4.417   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.667  -2.107   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667  -0.567   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.001   0.203   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.334   0.203   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000  -0.567   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8    3                                                       
CONECT   10    2   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   19                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   12                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0041647
HETATM    1  C1  UNL     1       0.656  -1.273  -1.643  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.676  -0.484  -0.612  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.440   0.008   0.108  1.00  0.00           C  
HETATM    4  O1  UNL     1      -0.048   0.772   1.126  1.00  0.00           O  
HETATM    5  C4  UNL     1      -1.859  -0.129  -0.013  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.586  -0.823  -0.935  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.976  -0.893  -0.972  1.00  0.00           C  
HETATM    8  C7  UNL     1      -4.688  -0.226  -0.027  1.00  0.00           C  
HETATM    9  O2  UNL     1      -6.068  -0.293  -0.060  1.00  0.00           O  
HETATM   10  C8  UNL     1      -4.035   0.485   0.922  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.657   0.545   0.946  1.00  0.00           C  
HETATM   12  O3  UNL     1      -2.087   1.290   1.945  1.00  0.00           O  
HETATM   13  C10 UNL     1       2.072  -0.113  -0.174  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.392   1.131   0.292  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.707   1.394   0.714  1.00  0.00           C  
HETATM   16  C13 UNL     1       4.687   0.435   0.675  1.00  0.00           C  
HETATM   17  O4  UNL     1       6.001   0.707   1.101  1.00  0.00           O  
HETATM   18  C14 UNL     1       4.356  -0.813   0.205  1.00  0.00           C  
HETATM   19  C15 UNL     1       3.064  -1.069  -0.210  1.00  0.00           C  
HETATM   20  H1  UNL     1       1.662  -1.550  -2.076  1.00  0.00           H  
HETATM   21  H2  UNL     1      -0.168  -1.691  -2.128  1.00  0.00           H  
HETATM   22  H3  UNL     1      -2.080  -1.355  -1.693  1.00  0.00           H  
HETATM   23  H4  UNL     1      -4.448  -1.476  -1.753  1.00  0.00           H  
HETATM   24  H5  UNL     1      -6.644   0.374  -0.579  1.00  0.00           H  
HETATM   25  H6  UNL     1      -4.644   1.006   1.663  1.00  0.00           H  
HETATM   26  H7  UNL     1      -2.648   1.768   2.625  1.00  0.00           H  
HETATM   27  H8  UNL     1       1.669   1.910   0.325  1.00  0.00           H  
HETATM   28  H9  UNL     1       3.961   2.378   1.084  1.00  0.00           H  
HETATM   29  H10 UNL     1       6.209   1.634   1.440  1.00  0.00           H  
HETATM   30  H11 UNL     1       5.123  -1.567   0.172  1.00  0.00           H  
HETATM   31  H12 UNL     1       2.843  -2.084  -0.571  1.00  0.00           H  
CONECT    1    2    2   20   21
CONECT    2    3   13
CONECT    3    4    4    5
CONECT    5    6    6   11
CONECT    6    7   22
CONECT    7    8    8   23
CONECT    8    9   10
CONECT    9   24
CONECT   10   11   11   25
CONECT   11   12
CONECT   12   26
CONECT   13   14   14   19
CONECT   14   15   27
CONECT   15   16   16   28
CONECT   16   17   18
CONECT   17   29
CONECT   18   19   19   30
CONECT   19   31
END

HMDB0041647
     RDKit          3D
2-Dehydro-O-desmethylangolensin
 31 32  0  0  0  0  0  0  0  0999 V2000
    0.6560   -1.2729   -1.6431 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6762   -0.4841   -0.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4405    0.0085    0.1079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0483    0.7723    1.1261 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8593   -0.1290   -0.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5858   -0.8225   -0.9351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9755   -0.8925   -0.9722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6883   -0.2261   -0.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0680   -0.2932   -0.0603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0348    0.4850    0.9222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6574    0.5446    0.9457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0869    1.2899    1.9450 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0718   -0.1133   -0.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3922    1.1315    0.2916 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7065    1.3939    0.7144 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6867    0.4350    0.6747 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0010    0.7075    1.1005 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3565   -0.8132    0.2049 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0639   -1.0687   -0.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6622   -1.5501   -2.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1684   -1.6912   -2.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0804   -1.3547   -1.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4482   -1.4757   -1.7530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6439    0.3742   -0.5794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6439    1.0058    1.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6484    1.7676    2.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6688    1.9101    0.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9612    2.3783    1.0835 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2088    1.6342    1.4395 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1233   -1.5666    0.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8426   -2.0842   -0.5712 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  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
  6 22  1  0
  7 23  1  0
  9 24  1  0
 10 25  1  0
 12 26  1  0
 14 27  1  0
 15 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₁₂O₄

Average Molecular Weight

256.2534

Monoisotopic Molecular Weight

256.073558872

IUPAC Name

1-(2,4-dihydroxyphenyl)-2-(4-hydroxyphenyl)prop-2-en-1-one

Traditional Name

1-(2,4-dihydroxyphenyl)-2-(4-hydroxyphenyl)prop-2-en-1-one

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1)C(=C)C(=O)C1=C(O)C=C(O)C=C1

InChI Identifier

InChI=1S/C15H12O4/c1-9(10-2-4-11(16)5-3-10)15(19)13-7-6-12(17)8-14(13)18/h2-8,16-18H,1H2

InChI Key

MPNKZWIUITZJCR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
Benzoyl
Resorcinol
Aryl ketone
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Alpha-branched alpha,beta-unsaturated-ketone
Benzenoid
Acryloyl-group
Enone
Vinylogous acid
Alpha,beta-unsaturated ketone
Ketone
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0041647)
Cell membrane (HMDB: HMDB0041647)

Excreta

Biofluid or Excreta

Urine (PMID: 10527518)

Source

Exogenous

Exogenous (HMDB: HMDB0041647)

Food

Food (HMDB: HMDB0041647)

Endogenous

Plant

Plant (HMDB: HMDB0041647)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0041647)

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	0.32 g/L	ALOGPS
logP	2.98	ALOGPS
logP	3.69	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	7.72	ChemAxon
pKa (Strongest Basic)	-5.9	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	71.5 m³·mol⁻¹	ChemAxon
Polarizability	25.81 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]+	161.341	31661259
DarkChem	[M-H]-	161.651	31661259
DeepCCS	[M+H]+	165.14	30932474
DeepCCS	[M-H]-	162.782	30932474
DeepCCS	[M-2H]-	195.668	30932474
DeepCCS	[M+Na]+	171.233	30932474
AllCCS	[M+H]+	158.4	32859911
AllCCS	[M+H-H2O]+	154.4	32859911
AllCCS	[M+NH4]+	162.2	32859911
AllCCS	[M+Na]+	163.2	32859911
AllCCS	[M-H]-	158.0	32859911
AllCCS	[M+Na-2H]-	157.5	32859911
AllCCS	[M+HCOO]-	157.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Dehydro-O-desmethylangolensin	OC1=CC=C(C=C1)C(=C)C(=O)C1=C(O)C=C(O)C=C1	4242.3	Standard polar	33892256
2-Dehydro-O-desmethylangolensin	OC1=CC=C(C=C1)C(=C)C(=O)C1=C(O)C=C(O)C=C1	2451.5	Standard non polar	33892256
2-Dehydro-O-desmethylangolensin	OC1=CC=C(C=C1)C(=C)C(=O)C1=C(O)C=C(O)C=C1	2776.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Dehydro-O-desmethylangolensin,1TMS,isomer #1	C=C(C(=O)C1=CC=C(O)C=C1O)C1=CC=C(O[Si](C)(C)C)C=C1	2570.6	Semi standard non polar	33892256
2-Dehydro-O-desmethylangolensin,1TMS,isomer #2	C=C(C(=O)C1=CC=C(O)C=C1O[Si](C)(C)C)C1=CC=C(O)C=C1	2568.9	Semi standard non polar	33892256
2-Dehydro-O-desmethylangolensin,1TMS,isomer #3	C=C(C(=O)C1=CC=C(O[Si](C)(C)C)C=C1O)C1=CC=C(O)C=C1	2587.3	Semi standard non polar	33892256
2-Dehydro-O-desmethylangolensin,2TMS,isomer #1	C=C(C(=O)C1=CC=C(O[Si](C)(C)C)C=C1O)C1=CC=C(O[Si](C)(C)C)C=C1	2579.1	Semi standard non polar	33892256
2-Dehydro-O-desmethylangolensin,2TMS,isomer #2	C=C(C(=O)C1=CC=C(O)C=C1O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C=C1	2544.0	Semi standard non polar	33892256
2-Dehydro-O-desmethylangolensin,2TMS,isomer #3	C=C(C(=O)C1=CC=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C)C1=CC=C(O)C=C1	2554.4	Semi standard non polar	33892256
2-Dehydro-O-desmethylangolensin,3TMS,isomer #1	C=C(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	2615.5	Semi standard non polar	33892256
2-Dehydro-O-desmethylangolensin,1TBDMS,isomer #1	C=C(C(=O)C1=CC=C(O)C=C1O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	2863.0	Semi standard non polar	33892256
2-Dehydro-O-desmethylangolensin,1TBDMS,isomer #2	C=C(C(=O)C1=CC=C(O)C=C1O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C=C1	2878.8	Semi standard non polar	33892256
2-Dehydro-O-desmethylangolensin,1TBDMS,isomer #3	C=C(C(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O)C1=CC=C(O)C=C1	2877.9	Semi standard non polar	33892256
2-Dehydro-O-desmethylangolensin,2TBDMS,isomer #1	C=C(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	3133.4	Semi standard non polar	33892256
2-Dehydro-O-desmethylangolensin,2TBDMS,isomer #2	C=C(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	3099.9	Semi standard non polar	33892256
2-Dehydro-O-desmethylangolensin,2TBDMS,isomer #3	C=C(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	3092.3	Semi standard non polar	33892256
2-Dehydro-O-desmethylangolensin,3TBDMS,isomer #1	C=C(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	3379.8	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 - 2-Dehydro-O-desmethylangolensin GC-MS (Non-derivatized) - 70eV, Positive	splash10-014r-5930000000-61e0a06d5028cd69d819	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Dehydro-O-desmethylangolensin GC-MS (3 TMS) - 70eV, Positive	splash10-0ab9-5413900000-b940d94fbc562b19d3fe	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Dehydro-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 - 2-Dehydro-O-desmethylangolensin 10V, Positive-QTOF	splash10-0a4i-0390000000-8dd26699daaf59809aa0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Dehydro-O-desmethylangolensin 20V, Positive-QTOF	splash10-000b-1930000000-84edc7ed490a9c314414	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Dehydro-O-desmethylangolensin 40V, Positive-QTOF	splash10-014i-3900000000-a49f5e11700e329c23a4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Dehydro-O-desmethylangolensin 10V, Negative-QTOF	splash10-0a4i-0190000000-870ea4f7f70c26afdf42	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Dehydro-O-desmethylangolensin 20V, Negative-QTOF	splash10-0a4i-0390000000-f0cb33dbf2aa4f601e2f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Dehydro-O-desmethylangolensin 40V, Negative-QTOF	splash10-0aor-7900000000-33263f5dadb41e9bf42d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Dehydro-O-desmethylangolensin 10V, Negative-QTOF	splash10-0a4i-0190000000-838a14b5d4c546b0c337	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Dehydro-O-desmethylangolensin 20V, Negative-QTOF	splash10-0ap0-0940000000-4825b3dae808a4b2a5a5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Dehydro-O-desmethylangolensin 40V, Negative-QTOF	splash10-014i-9400000000-6cc94137def3608423d7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Dehydro-O-desmethylangolensin 10V, Positive-QTOF	splash10-0a4i-0290000000-99086cfea20d711030d2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Dehydro-O-desmethylangolensin 20V, Positive-QTOF	splash10-014r-0900000000-d81b7b4a231fdb21d0fa	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Dehydro-O-desmethylangolensin 40V, Positive-QTOF	splash10-0fvl-9600000000-c6b777fc3a0af7a126e2	2021-09-24	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 826	10527518	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 826	7662591	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

Not Available

FooDB ID

FDB029802

KNApSAcK ID

Not Available

Chemspider ID

8396211

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10220719

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]

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

2-Dehydro-O-desmethylangolensin → 6-{4-[3-(2,4-dihydroxyphenyl)-3-oxoprop-1-en-2-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details
2-Dehydro-O-desmethylangolensin → 3,4,5-trihydroxy-6-{3-hydroxy-4-[2-(4-hydroxyphenyl)prop-2-enoyl]phenoxy}oxane-2-carboxylic acid	details
2-Dehydro-O-desmethylangolensin → 3,4,5-trihydroxy-6-{5-hydroxy-2-[2-(4-hydroxyphenyl)prop-2-enoyl]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

2-Dehydro-O-desmethylangolensin → {4-[3-(2,4-dihydroxyphenyl)-3-oxoprop-1-en-2-yl]phenyl}oxidanesulfonic acid	details

Showing metabocard for 2-Dehydro-O-desmethylangolensin (HMDB0041647)

MOL for HMDB0041647 (2-Dehydro-O-desmethylangolensin)

3D MOL for HMDB0041647 (2-Dehydro-O-desmethylangolensin)

3D SDF for HMDB0041647 (2-Dehydro-O-desmethylangolensin)

3D-SDF for HMDB0041647 (2-Dehydro-O-desmethylangolensin)

PDB for HMDB0041647 (2-Dehydro-O-desmethylangolensin)

3D PDB for HMDB0041647 (2-Dehydro-O-desmethylangolensin)

SMILES for HMDB0041647 (2-Dehydro-O-desmethylangolensin)

INCHI for HMDB0041647 (2-Dehydro-O-desmethylangolensin)

Structure for HMDB0041647 (2-Dehydro-O-desmethylangolensin)

3D Structure for HMDB0041647 (2-Dehydro-O-desmethylangolensin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions