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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 03:36:20 UTC

Update Date

2022-03-07 02:57:08 UTC

HMDB ID

HMDB0041686

Secondary Accession Numbers

HMDB41686

Metabolite Identification

Common Name

5'-Methoxy-O-desmethylangolensin

Description

5'-Methoxy-O-desmethylangolensin 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. Based on a literature review very few articles have been published on 5'-Methoxy-O-desmethylangolensin.

Structure

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

HMDB0041686
     RDKit          3D
5'-Methoxy-O-desmethylangolensin
 37 38  0  0  0  0  0  0  0  0999 V2000
    4.8341   -0.9962    1.6202 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5286    0.3648    1.3954 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3341    0.6722    0.7706 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4476   -0.3102    0.3681 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2460   -0.0631   -0.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3914   -1.1709   -0.6280 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8687   -2.3245   -0.3365 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8988   -1.1525   -1.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3455   -2.6134   -1.5184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0334   -0.5461   -0.5904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2192   -0.5147    0.7721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3504    0.0713    1.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3335    0.6426    0.5037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4776    1.2340    1.0449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1468    0.6118   -0.8803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0241    0.0308   -1.3982 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9154    1.2680   -0.4936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2760    1.5902   -1.1190 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7863    2.2591   -0.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9901    1.9865    0.5286 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8454    3.0254    0.9123 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0407   -1.5232    2.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7647   -1.0860    2.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9260   -1.5126    0.6264 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7781   -1.3258    0.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7925   -0.7541   -2.3198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9419   -2.9823   -0.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9518   -2.6848   -2.4286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4599   -3.2772   -1.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4456   -0.9633    1.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4524    0.0715    2.3668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3842    2.2401    1.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9195    1.0613   -1.5018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9242    0.0319   -2.4864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5129    2.5446   -1.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4819    3.2970   -0.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7113    2.7975    1.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
  5 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 20  3  1  0
 16 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
 11 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 18 35  1  0
 19 36  1  0
 21 37  1  0
M  END

  Mrv0541 02271201282D          

 21 22  0  0  0  0            999 V2000
    1.5990   -0.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5990   -1.4236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3135   -1.8361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0280   -1.4236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7425   -1.8361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7425   -2.6611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4569   -3.0736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0280   -3.0736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3135   -2.6611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8846   -1.8361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8846   -2.6611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1701   -1.4236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5444   -1.8361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5444   -2.6611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2588   -1.4236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2588   -0.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9733   -0.1861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5444   -0.1861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1701   -0.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5444    0.6389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1700    1.0514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  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
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041686

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(C(=O)C(C)C2=CC=C(O)C=C2)=C(O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O5/c1-9(10-3-5-11(17)6-4-10)16(20)12-7-15(21-2)14(19)8-13(12)18/h3-9,17-19H,1-2H3

> <INCHI_KEY>
NAIOQCWMMFVXSV-UHFFFAOYSA-N

> <FORMULA>
C16H16O5

> <MOLECULAR_WEIGHT>
288.2952

> <EXACT_MASS>
288.099773622

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
28.842797847672518

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(2,4-dihydroxy-5-methoxyphenyl)-2-(4-hydroxyphenyl)propan-1-one

> <ALOGPS_LOGP>
3.10

> <JCHEM_LOGP>
3.4898522019999993

> <ALOGPS_LOGS>
-3.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.51457523794382

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.281226862136938

> <JCHEM_PKA_STRONGEST_BASIC>
-3.841032501420874

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
78.16310000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.18e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(2,4-dihydroxy-5-methoxyphenyl)-2-(4-hydroxyphenyl)propan-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041686
     RDKit          3D
5'-Methoxy-O-desmethylangolensin
 37 38  0  0  0  0  0  0  0  0999 V2000
    4.8341   -0.9962    1.6202 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5286    0.3648    1.3954 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3341    0.6722    0.7706 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4476   -0.3102    0.3681 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2460   -0.0631   -0.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3914   -1.1709   -0.6280 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8687   -2.3245   -0.3365 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8988   -1.1525   -1.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3455   -2.6134   -1.5184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0334   -0.5461   -0.5904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2192   -0.5147    0.7721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3504    0.0713    1.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3335    0.6426    0.5037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4776    1.2340    1.0449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1468    0.6118   -0.8803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0241    0.0308   -1.3982 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9154    1.2680   -0.4936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2760    1.5902   -1.1190 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7863    2.2591   -0.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9901    1.9865    0.5286 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8454    3.0254    0.9123 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0407   -1.5232    2.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7647   -1.0860    2.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9260   -1.5126    0.6264 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7781   -1.3258    0.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7925   -0.7541   -2.3198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9419   -2.9823   -0.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9518   -2.6848   -2.4286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4599   -3.2772   -1.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4456   -0.9633    1.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4524    0.0715    2.3668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3842    2.2401    1.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9195    1.0613   -1.5018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9242    0.0319   -2.4864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5129    2.5446   -1.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4819    3.2970   -0.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7113    2.7975    1.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
  5 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 20  3  1  0
 16 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
 11 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 18 35  1  0
 19 36  1  0
 21 37  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       2.985  -1.117   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.985  -2.657   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.319  -3.427   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.652  -2.657   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.986  -3.427   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.986  -4.967   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.320  -5.737   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.652  -5.737   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.319  -4.967   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.651  -3.427   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.651  -4.967   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.318  -2.657   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.016  -3.427   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.016  -4.967   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.350  -2.657   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.350  -1.117   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.683  -0.347   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.016  -0.347   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.318  -1.117   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.016   1.193   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.317   1.963   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   20                                                  
CONECT   19   18   12                                                       
CONECT   20   18   21                                                       
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0041686
HETATM    1  C1  UNL     1       4.834  -0.996   1.620  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.529   0.365   1.395  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.334   0.672   0.771  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.448  -0.310   0.368  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.246  -0.063  -0.257  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.391  -1.171  -0.628  1.00  0.00           C  
HETATM    7  O2  UNL     1       0.869  -2.324  -0.336  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.899  -1.152  -1.268  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.345  -2.613  -1.518  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.033  -0.546  -0.590  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.219  -0.515   0.772  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.350   0.071   1.283  1.00  0.00           C  
HETATM   13  C11 UNL     1      -4.334   0.643   0.504  1.00  0.00           C  
HETATM   14  O3  UNL     1      -5.478   1.234   1.045  1.00  0.00           O  
HETATM   15  C12 UNL     1      -4.147   0.612  -0.880  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.024   0.031  -1.398  1.00  0.00           C  
HETATM   17  C14 UNL     1       0.915   1.268  -0.494  1.00  0.00           C  
HETATM   18  O4  UNL     1      -0.276   1.590  -1.119  1.00  0.00           O  
HETATM   19  C15 UNL     1       1.786   2.259  -0.099  1.00  0.00           C  
HETATM   20  C16 UNL     1       2.990   1.987   0.529  1.00  0.00           C  
HETATM   21  O5  UNL     1       3.845   3.025   0.912  1.00  0.00           O  
HETATM   22  H1  UNL     1       4.041  -1.523   2.190  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.765  -1.086   2.213  1.00  0.00           H  
HETATM   24  H3  UNL     1       4.926  -1.513   0.626  1.00  0.00           H  
HETATM   25  H4  UNL     1       2.778  -1.326   0.588  1.00  0.00           H  
HETATM   26  H5  UNL     1      -0.792  -0.754  -2.320  1.00  0.00           H  
HETATM   27  H6  UNL     1      -1.942  -2.982  -0.654  1.00  0.00           H  
HETATM   28  H7  UNL     1      -1.952  -2.685  -2.429  1.00  0.00           H  
HETATM   29  H8  UNL     1      -0.460  -3.277  -1.594  1.00  0.00           H  
HETATM   30  H9  UNL     1      -1.446  -0.963   1.368  1.00  0.00           H  
HETATM   31  H10 UNL     1      -3.452   0.072   2.367  1.00  0.00           H  
HETATM   32  H11 UNL     1      -5.384   2.240   1.253  1.00  0.00           H  
HETATM   33  H12 UNL     1      -4.920   1.061  -1.502  1.00  0.00           H  
HETATM   34  H13 UNL     1      -2.924   0.032  -2.486  1.00  0.00           H  
HETATM   35  H14 UNL     1      -0.513   2.545  -1.288  1.00  0.00           H  
HETATM   36  H15 UNL     1       1.482   3.297  -0.307  1.00  0.00           H  
HETATM   37  H16 UNL     1       4.711   2.798   1.366  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   20
CONECT    4    5   25
CONECT    5    6   17   17
CONECT    6    7    7    8
CONECT    8    9   10   26
CONECT    9   27   28   29
CONECT   10   11   11   16
CONECT   11   12   30
CONECT   12   13   13   31
CONECT   13   14   15
CONECT   14   32
CONECT   15   16   16   33
CONECT   16   34
CONECT   17   18   19
CONECT   18   35
CONECT   19   20   20   36
CONECT   20   21
CONECT   21   37
END

HMDB0041686
     RDKit          3D
5'-Methoxy-O-desmethylangolensin
 37 38  0  0  0  0  0  0  0  0999 V2000
    4.8341   -0.9962    1.6202 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5286    0.3648    1.3954 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3341    0.6722    0.7706 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4476   -0.3102    0.3681 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2460   -0.0631   -0.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3914   -1.1709   -0.6280 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8687   -2.3245   -0.3365 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8988   -1.1525   -1.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3455   -2.6134   -1.5184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0334   -0.5461   -0.5904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2192   -0.5147    0.7721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3504    0.0713    1.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3335    0.6426    0.5037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4776    1.2340    1.0449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1468    0.6118   -0.8803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0241    0.0308   -1.3982 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9154    1.2680   -0.4936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2760    1.5902   -1.1190 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7863    2.2591   -0.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9901    1.9865    0.5286 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8454    3.0254    0.9123 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0407   -1.5232    2.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7647   -1.0860    2.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9260   -1.5126    0.6264 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7781   -1.3258    0.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7925   -0.7541   -2.3198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9419   -2.9823   -0.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9518   -2.6848   -2.4286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4599   -3.2772   -1.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4456   -0.9633    1.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4524    0.0715    2.3668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3842    2.2401    1.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9195    1.0613   -1.5018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9242    0.0319   -2.4864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5129    2.5446   -1.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4819    3.2970   -0.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7113    2.7975    1.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
  5 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 20  3  1  0
 16 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
 11 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 18 35  1  0
 19 36  1  0
 21 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₆H₁₆O₅

Average Molecular Weight

288.2952

Monoisotopic Molecular Weight

288.099773622

IUPAC Name

1-(2,4-dihydroxy-5-methoxyphenyl)-2-(4-hydroxyphenyl)propan-1-one

Traditional Name

1-(2,4-dihydroxy-5-methoxyphenyl)-2-(4-hydroxyphenyl)propan-1-one

CAS Registry Number

Not Available

SMILES

COC1=CC(C(=O)C(C)C2=CC=C(O)C=C2)=C(O)C=C1O

InChI Identifier

InChI=1S/C16H16O5/c1-9(10-3-5-11(17)6-4-10)16(20)12-7-15(21-2)14(19)8-13(12)18/h3-9,17-19H,1-2H3

InChI Key

NAIOQCWMMFVXSV-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
Methoxyphenol
Phenylpropane
4-alkoxyphenol
Phenylketone
Anisole
Benzoyl
Phenol ether
Resorcinol
Phenoxy compound
Aryl ketone
Aryl alkyl ketone
Methoxybenzene
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Ether
Organic oxide
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0041686)
Cell membrane (HMDB: HMDB0041686)

Excreta

Biofluid or Excreta

Urine (PMID: 14698210)

Source

Exogenous

Exogenous (HMDB: HMDB0041686)

Food

Food (HMDB: HMDB0041686)

Endogenous

Plant

Plant (HMDB: HMDB0041686)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0041686)

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	0.062 g/L	ALOGPS
logP	3.1	ALOGPS
logP	3.49	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	8.28	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	78.16 m³·mol⁻¹	ChemAxon
Polarizability	28.84 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]+	168.924	31661259
DarkChem	[M-H]-	169.115	31661259
DeepCCS	[M+H]+	166.965	30932474
DeepCCS	[M-H]-	164.607	30932474
DeepCCS	[M-2H]-	198.183	30932474
DeepCCS	[M+Na]+	173.41	30932474
AllCCS	[M+H]+	167.0	32859911
AllCCS	[M+H-H2O]+	163.3	32859911
AllCCS	[M+NH4]+	170.5	32859911
AllCCS	[M+Na]+	171.5	32859911
AllCCS	[M-H]-	168.6	32859911
AllCCS	[M+Na-2H]-	168.3	32859911
AllCCS	[M+HCOO]-	168.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5'-Methoxy-O-desmethylangolensin	COC1=CC(C(=O)C(C)C2=CC=C(O)C=C2)=C(O)C=C1O	3853.4	Standard polar	33892256
5'-Methoxy-O-desmethylangolensin	COC1=CC(C(=O)C(C)C2=CC=C(O)C=C2)=C(O)C=C1O	2661.0	Standard non polar	33892256
5'-Methoxy-O-desmethylangolensin	COC1=CC(C(=O)C(C)C2=CC=C(O)C=C2)=C(O)C=C1O	2631.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5'-Methoxy-O-desmethylangolensin,1TMS,isomer #1	COC1=CC(C(=O)C(C)C2=CC=C(O[Si](C)(C)C)C=C2)=C(O)C=C1O	2578.1	Semi standard non polar	33892256
5'-Methoxy-O-desmethylangolensin,1TMS,isomer #2	COC1=CC(C(=O)C(C)C2=CC=C(O)C=C2)=C(O[Si](C)(C)C)C=C1O	2603.6	Semi standard non polar	33892256
5'-Methoxy-O-desmethylangolensin,1TMS,isomer #3	COC1=CC(C(=O)C(C)C2=CC=C(O)C=C2)=C(O)C=C1O[Si](C)(C)C	2590.6	Semi standard non polar	33892256
5'-Methoxy-O-desmethylangolensin,2TMS,isomer #1	COC1=CC(C(=O)C(C)C2=CC=C(O[Si](C)(C)C)C=C2)=C(O[Si](C)(C)C)C=C1O	2589.3	Semi standard non polar	33892256
5'-Methoxy-O-desmethylangolensin,2TMS,isomer #2	COC1=CC(C(=O)C(C)C2=CC=C(O[Si](C)(C)C)C=C2)=C(O)C=C1O[Si](C)(C)C	2562.6	Semi standard non polar	33892256
5'-Methoxy-O-desmethylangolensin,2TMS,isomer #3	COC1=CC(C(=O)C(C)C2=CC=C(O)C=C2)=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C	2555.4	Semi standard non polar	33892256
5'-Methoxy-O-desmethylangolensin,3TMS,isomer #1	COC1=CC(C(=O)C(C)C2=CC=C(O[Si](C)(C)C)C=C2)=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C	2609.1	Semi standard non polar	33892256
5'-Methoxy-O-desmethylangolensin,1TBDMS,isomer #1	COC1=CC(C(=O)C(C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=C(O)C=C1O	2885.2	Semi standard non polar	33892256
5'-Methoxy-O-desmethylangolensin,1TBDMS,isomer #2	COC1=CC(C(=O)C(C)C2=CC=C(O)C=C2)=C(O[Si](C)(C)C(C)(C)C)C=C1O	2887.0	Semi standard non polar	33892256
5'-Methoxy-O-desmethylangolensin,1TBDMS,isomer #3	COC1=CC(C(=O)C(C)C2=CC=C(O)C=C2)=C(O)C=C1O[Si](C)(C)C(C)(C)C	2876.5	Semi standard non polar	33892256
5'-Methoxy-O-desmethylangolensin,2TBDMS,isomer #1	COC1=CC(C(=O)C(C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=C(O[Si](C)(C)C(C)(C)C)C=C1O	3131.0	Semi standard non polar	33892256
5'-Methoxy-O-desmethylangolensin,2TBDMS,isomer #2	COC1=CC(C(=O)C(C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=C(O)C=C1O[Si](C)(C)C(C)(C)C	3111.8	Semi standard non polar	33892256
5'-Methoxy-O-desmethylangolensin,2TBDMS,isomer #3	COC1=CC(C(=O)C(C)C2=CC=C(O)C=C2)=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	3066.2	Semi standard non polar	33892256
5'-Methoxy-O-desmethylangolensin,3TBDMS,isomer #1	COC1=CC(C(=O)C(C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	3363.4	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 - 5'-Methoxy-O-desmethylangolensin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-2900000000-18c17ef960b1eec846ea	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5'-Methoxy-O-desmethylangolensin GC-MS (3 TMS) - 70eV, Positive	splash10-000l-4311900000-0526680862b657b16009	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5'-Methoxy-O-desmethylangolensin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5'-Methoxy-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 - 5'-Methoxy-O-desmethylangolensin 10V, Positive-QTOF	splash10-000i-0490000000-a1260b0d6b43af2f4d55	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Methoxy-O-desmethylangolensin 20V, Positive-QTOF	splash10-0002-1930000000-069f9f65fc891479f145	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Methoxy-O-desmethylangolensin 40V, Positive-QTOF	splash10-00r2-1900000000-0651a879af49b4388ce3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Methoxy-O-desmethylangolensin 10V, Negative-QTOF	splash10-000i-0190000000-13cb2745d0b2d5191757	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Methoxy-O-desmethylangolensin 20V, Negative-QTOF	splash10-000i-0390000000-f536b0f56981828e3d98	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Methoxy-O-desmethylangolensin 40V, Negative-QTOF	splash10-006x-5940000000-ce05e7e563e46326caed	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Methoxy-O-desmethylangolensin 10V, Negative-QTOF	splash10-000i-0090000000-1b01e1b5bd30ed06ec25	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Methoxy-O-desmethylangolensin 20V, Negative-QTOF	splash10-000i-2980000000-185fe59357826ec78f1d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Methoxy-O-desmethylangolensin 40V, Negative-QTOF	splash10-014u-4940000000-58748e128b29d499b80a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Methoxy-O-desmethylangolensin 10V, Positive-QTOF	splash10-000i-0290000000-ac63346bf8a0c174e78c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Methoxy-O-desmethylangolensin 20V, Positive-QTOF	splash10-00di-0910000000-79225587f32a93748347	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Methoxy-O-desmethylangolensin 40V, Positive-QTOF	splash10-00di-4900000000-c3217dd1b0fc66b68282	2021-09-22	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 844	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

Not Available

FooDB ID

FDB029847

KNApSAcK ID

Not Available

Chemspider ID

28554480

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71367568

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 ]

Showing metabocard for 5'-Methoxy-O-desmethylangolensin (HMDB0041686)

MOL for HMDB0041686 (5'-Methoxy-O-desmethylangolensin)

3D MOL for HMDB0041686 (5'-Methoxy-O-desmethylangolensin)

3D SDF for HMDB0041686 (5'-Methoxy-O-desmethylangolensin)

3D-SDF for HMDB0041686 (5'-Methoxy-O-desmethylangolensin)

PDB for HMDB0041686 (5'-Methoxy-O-desmethylangolensin)

3D PDB for HMDB0041686 (5'-Methoxy-O-desmethylangolensin)

SMILES for HMDB0041686 (5'-Methoxy-O-desmethylangolensin)

INCHI for HMDB0041686 (5'-Methoxy-O-desmethylangolensin)

Structure for HMDB0041686 (5'-Methoxy-O-desmethylangolensin)

3D Structure for HMDB0041686 (5'-Methoxy-O-desmethylangolensin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra