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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:37:56 UTC

Update Date

2022-03-07 02:52:37 UTC

HMDB ID

HMDB0030610

Secondary Accession Numbers

HMDB30610

Metabolite Identification

Common Name

Desmethylxanthohumol

Description

Desmethylxanthohumol, also known as xanthohumol, belongs to the class of organic compounds known as 3-prenylated chalcones. These are chalcones featuring a C5-isoprenoid unit at the 3-position. Desmethylxanthohumol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Desmethylxanthohumol.

Structure

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

HMDB0030610
     RDKit          3D
Desmethylxanthohumol
 45 46  0  0  0  0  0  0  0  0999 V2000
   -6.5301   -0.2123   -0.0874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6570    0.9482    0.2238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2113    2.2967   -0.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4568    0.8648    0.7565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7607   -0.3843    1.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4624   -0.4845    0.4093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4959   -0.8778   -0.9356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7028   -1.1575   -1.5300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3310   -0.9823   -1.6514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1047   -0.7045   -1.0696 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9992   -0.8410   -1.8766 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0253   -0.3154    0.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2271   -0.0107    0.9054 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1749    0.3378    2.1252 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5118   -0.0704    0.2951 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6084    0.2369    1.0109 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9440    0.2050    0.4803 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1944   -0.1449   -0.8024 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5148   -0.1574   -1.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5421    0.1876   -0.4139 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8741    0.1905   -0.8311 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2907    0.5442    0.8918 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9889    0.5506    1.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2388   -0.2178    0.9529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1162    0.1756    2.2652 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6072    0.0578    0.0161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3738   -1.0769    0.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3433   -0.5541   -1.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4122    3.0351   -0.3346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7750    2.7181    0.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8573    2.2270   -1.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8693    1.7797    0.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3897   -1.2871    0.9551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5766   -0.3694    2.2208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7305   -1.4392   -2.4931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3810   -1.2930   -2.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9148   -1.1237   -2.8230 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7316   -0.3434   -0.7154 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4505    0.5233    2.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4663   -0.4289   -1.5445 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7735   -0.4271   -2.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1784   -0.0499   -1.7528 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1094    0.8088    1.5376 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7947    0.8330    2.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8807    0.2912    2.8724 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 12 24  2  0
 24 25  1  0
 24  6  1  0
 23 17  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  8 35  1  0
  9 36  1  0
 11 37  1  0
 15 38  1  0
 16 39  1  0
 18 40  1  0
 19 41  1  0
 21 42  1  0
 22 43  1  0
 23 44  1  0
 25 45  1  0
M  END


  Mrv0541 05061305232D          

 25 26  0  0  0  0            999 V2000
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  4  1  0  0  0  0
  8  5  2  0  0  0  0
  9  3  1  0  0  0  0
 10  6  2  0  0  0  0
 12  1  1  0  0  0  0
 12  2  1  0  0  0  0
 12  3  2  0  0  0  0
 13  4  2  0  0  0  0
 13  5  1  0  0  0  0
 13  6  1  0  0  0  0
 14  7  2  0  0  0  0
 14  8  1  0  0  0  0
 15  9  1  0  0  0  0
 16 10  1  0  0  0  0
 17 11  2  0  0  0  0
 17 15  1  0  0  0  0
 18 11  1  0  0  0  0
 19 16  1  0  0  0  0
 19 18  2  0  0  0  0
 20 15  2  0  0  0  0
 20 19  1  0  0  0  0
 21 14  1  0  0  0  0
 22 16  2  0  0  0  0
 23 17  1  0  0  0  0
 24 18  1  0  0  0  0
 25 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030610

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC1=C(O)C(C(=O)\C=C\C2=CC=C(O)C=C2)=C(O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H20O5/c1-12(2)3-9-15-17(23)11-18(24)19(20(15)25)16(22)10-6-13-4-7-14(21)8-5-13/h3-8,10-11,21,23-25H,9H2,1-2H3/b10-6+

> <INCHI_KEY>
FUSADYLVRMROPL-UXBLZVDNSA-N

> <FORMULA>
C20H20O5

> <MOLECULAR_WEIGHT>
340.3698

> <EXACT_MASS>
340.13107375

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
36.789705685530066

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-3-(4-hydroxyphenyl)-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-en-1-one

> <ALOGPS_LOGP>
3.53

> <JCHEM_LOGP>
5.704631021666667

> <ALOGPS_LOGS>
-4.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.62830977434329

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.613358303148392

> <JCHEM_PKA_STRONGEST_BASIC>
-5.6197614617885

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
99.04339999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.08e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
desmethylxanthohumol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030610
     RDKit          3D
Desmethylxanthohumol
 45 46  0  0  0  0  0  0  0  0999 V2000
   -6.5301   -0.2123   -0.0874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6570    0.9482    0.2238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2113    2.2967   -0.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4568    0.8648    0.7565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7607   -0.3843    1.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4624   -0.4845    0.4093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4959   -0.8778   -0.9356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7028   -1.1575   -1.5300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3310   -0.9823   -1.6514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1047   -0.7045   -1.0696 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9992   -0.8410   -1.8766 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0253   -0.3154    0.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2271   -0.0107    0.9054 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1749    0.3378    2.1252 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5118   -0.0704    0.2951 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6084    0.2369    1.0109 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9440    0.2050    0.4803 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1944   -0.1449   -0.8024 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5148   -0.1574   -1.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5421    0.1876   -0.4139 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8741    0.1905   -0.8311 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2907    0.5442    0.8918 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9889    0.5506    1.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2388   -0.2178    0.9529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1162    0.1756    2.2652 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6072    0.0578    0.0161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3738   -1.0769    0.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3433   -0.5541   -1.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4122    3.0351   -0.3346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7750    2.7181    0.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8573    2.2270   -1.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8693    1.7797    0.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3897   -1.2871    0.9551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5766   -0.3694    2.2208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7305   -1.4392   -2.4931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3810   -1.2930   -2.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9148   -1.1237   -2.8230 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7316   -0.3434   -0.7154 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4505    0.5233    2.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4663   -0.4289   -1.5445 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7735   -0.4271   -2.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1784   -0.0499   -1.7528 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1094    0.8088    1.5376 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7947    0.8330    2.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8807    0.2912    2.8724 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 12 24  2  0
 24 25  1  0
 24  6  1  0
 23 17  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  8 35  1  0
  9 36  1  0
 11 37  1  0
 15 38  1  0
 16 39  1  0
 18 40  1  0
 19 41  1  0
 21 42  1  0
 22 43  1  0
 23 44  1  0
 25 45  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.336  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.667  10.780   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -6.668   3.850   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   12                                                            
CONECT    3    9   12                                                       
CONECT    4    7   13                                                       
CONECT    5    8   13                                                       
CONECT    6   10   13                                                       
CONECT    7    4   14                                                       
CONECT    8    5   14                                                       
CONECT    9    3   15                                                       
CONECT   10    6   16                                                       
CONECT   11   17   18                                                       
CONECT   12    1    2    3                                                  
CONECT   13    4    5    6                                                  
CONECT   14    7    8   21                                                  
CONECT   15    9   17   20                                                  
CONECT   16   10   19   22                                                  
CONECT   17   11   15   23                                                  
CONECT   18   11   19   24                                                  
CONECT   19   16   18   20                                                  
CONECT   20   15   19   25                                                  
CONECT   21   14                                                            
CONECT   22   16                                                            
CONECT   23   17                                                            
CONECT   24   18                                                            
CONECT   25   20                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

COMPND    HMDB0030610
HETATM    1  C1  UNL     1      -6.530  -0.212  -0.087  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.657   0.948   0.224  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.211   2.297  -0.104  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.457   0.865   0.757  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.761  -0.384   1.140  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.462  -0.484   0.409  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.496  -0.878  -0.936  1.00  0.00           C  
HETATM    8  O1  UNL     1      -3.703  -1.158  -1.530  1.00  0.00           O  
HETATM    9  C8  UNL     1      -1.331  -0.982  -1.651  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.105  -0.705  -1.070  1.00  0.00           C  
HETATM   11  O2  UNL     1       0.999  -0.841  -1.877  1.00  0.00           O  
HETATM   12  C10 UNL     1      -0.025  -0.315   0.246  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.227  -0.011   0.905  1.00  0.00           C  
HETATM   14  O3  UNL     1       1.175   0.338   2.125  1.00  0.00           O  
HETATM   15  C12 UNL     1       2.512  -0.070   0.295  1.00  0.00           C  
HETATM   16  C13 UNL     1       3.608   0.237   1.011  1.00  0.00           C  
HETATM   17  C14 UNL     1       4.944   0.205   0.480  1.00  0.00           C  
HETATM   18  C15 UNL     1       5.194  -0.145  -0.802  1.00  0.00           C  
HETATM   19  C16 UNL     1       6.515  -0.157  -1.269  1.00  0.00           C  
HETATM   20  C17 UNL     1       7.542   0.188  -0.414  1.00  0.00           C  
HETATM   21  O4  UNL     1       8.874   0.190  -0.831  1.00  0.00           O  
HETATM   22  C18 UNL     1       7.291   0.544   0.892  1.00  0.00           C  
HETATM   23  C19 UNL     1       5.989   0.551   1.332  1.00  0.00           C  
HETATM   24  C20 UNL     1      -1.239  -0.218   0.953  1.00  0.00           C  
HETATM   25  O5  UNL     1      -1.116   0.176   2.265  1.00  0.00           O  
HETATM   26  H1  UNL     1      -7.607   0.058   0.016  1.00  0.00           H  
HETATM   27  H2  UNL     1      -6.374  -1.077   0.582  1.00  0.00           H  
HETATM   28  H3  UNL     1      -6.343  -0.554  -1.124  1.00  0.00           H  
HETATM   29  H4  UNL     1      -5.412   3.035  -0.335  1.00  0.00           H  
HETATM   30  H5  UNL     1      -6.775   2.718   0.763  1.00  0.00           H  
HETATM   31  H6  UNL     1      -6.857   2.227  -1.012  1.00  0.00           H  
HETATM   32  H7  UNL     1      -3.869   1.780   0.958  1.00  0.00           H  
HETATM   33  H8  UNL     1      -4.390  -1.287   0.955  1.00  0.00           H  
HETATM   34  H9  UNL     1      -3.577  -0.369   2.221  1.00  0.00           H  
HETATM   35  H10 UNL     1      -3.731  -1.439  -2.493  1.00  0.00           H  
HETATM   36  H11 UNL     1      -1.381  -1.293  -2.706  1.00  0.00           H  
HETATM   37  H12 UNL     1       0.915  -1.124  -2.823  1.00  0.00           H  
HETATM   38  H13 UNL     1       2.732  -0.343  -0.715  1.00  0.00           H  
HETATM   39  H14 UNL     1       3.450   0.523   2.052  1.00  0.00           H  
HETATM   40  H15 UNL     1       4.466  -0.429  -1.544  1.00  0.00           H  
HETATM   41  H16 UNL     1       6.774  -0.427  -2.278  1.00  0.00           H  
HETATM   42  H17 UNL     1       9.178  -0.050  -1.753  1.00  0.00           H  
HETATM   43  H18 UNL     1       8.109   0.809   1.538  1.00  0.00           H  
HETATM   44  H19 UNL     1       5.795   0.833   2.364  1.00  0.00           H  
HETATM   45  H20 UNL     1      -1.881   0.291   2.872  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3    4    4
CONECT    3   29   30   31
CONECT    4    5   32
CONECT    5    6   33   34
CONECT    6    7    7   24
CONECT    7    8    9
CONECT    8   35
CONECT    9   10   10   36
CONECT   10   11   12
CONECT   11   37
CONECT   12   13   24   24
CONECT   13   14   14   15
CONECT   15   16   16   38
CONECT   16   17   39
CONECT   17   18   18   23
CONECT   18   19   40
CONECT   19   20   20   41
CONECT   20   21   22
CONECT   21   42
CONECT   22   23   23   43
CONECT   23   44
CONECT   24   25
CONECT   25   45
END

HMDB0030610
     RDKit          3D
Desmethylxanthohumol
 45 46  0  0  0  0  0  0  0  0999 V2000
   -6.5301   -0.2123   -0.0874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6570    0.9482    0.2238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2113    2.2967   -0.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4568    0.8648    0.7565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7607   -0.3843    1.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4624   -0.4845    0.4093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4959   -0.8778   -0.9356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7028   -1.1575   -1.5300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3310   -0.9823   -1.6514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1047   -0.7045   -1.0696 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9992   -0.8410   -1.8766 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0253   -0.3154    0.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2271   -0.0107    0.9054 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1749    0.3378    2.1252 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5118   -0.0704    0.2951 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6084    0.2369    1.0109 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9440    0.2050    0.4803 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1944   -0.1449   -0.8024 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5148   -0.1574   -1.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5421    0.1876   -0.4139 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8741    0.1905   -0.8311 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2907    0.5442    0.8918 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9889    0.5506    1.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2388   -0.2178    0.9529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1162    0.1756    2.2652 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6072    0.0578    0.0161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3738   -1.0769    0.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3433   -0.5541   -1.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4122    3.0351   -0.3346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7750    2.7181    0.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8573    2.2270   -1.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8693    1.7797    0.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3897   -1.2871    0.9551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5766   -0.3694    2.2208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7305   -1.4392   -2.4931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3810   -1.2930   -2.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9148   -1.1237   -2.8230 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7316   -0.3434   -0.7154 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4505    0.5233    2.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4663   -0.4289   -1.5445 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7735   -0.4271   -2.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1784   -0.0499   -1.7528 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1094    0.8088    1.5376 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7947    0.8330    2.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8807    0.2912    2.8724 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 12 24  2  0
 24 25  1  0
 24  6  1  0
 23 17  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  8 35  1  0
  9 36  1  0
 11 37  1  0
 15 38  1  0
 16 39  1  0
 18 40  1  0
 19 41  1  0
 21 42  1  0
 22 43  1  0
 23 44  1  0
 25 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-(4-Hydroxyphenyl)-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propen-1-one	HMDB
1-(2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl)-3-(4-hydroxyphenyl)-2-propen-1-one	HMDB
Xanthohumol	HMDB

Chemical Formula

C₂₀H₂₀O₅

Average Molecular Weight

340.3698

Monoisotopic Molecular Weight

340.13107375

IUPAC Name

(2E)-3-(4-hydroxyphenyl)-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-en-1-one

Traditional Name

desmethylxanthohumol

CAS Registry Number

115063-39-3

SMILES

CC(C)=CCC1=C(O)C(C(=O)\C=C\C2=CC=C(O)C=C2)=C(O)C=C1O

InChI Identifier

InChI=1S/C20H20O5/c1-12(2)3-9-15-17(23)11-18(24)19(20(15)25)16(22)10-6-13-4-7-14(21)8-5-13/h3-8,10-11,21,23-25H,9H2,1-2H3/b10-6+

InChI Key

FUSADYLVRMROPL-UXBLZVDNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-prenylated chalcones. These are chalcones featuring a C5-isoprenoid unit at the 3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

3-prenylated chalcones

Alternative Parents

Substituents

3-prenylated chalcone
2'-hydroxychalcone
Cinnamylphenol
Hydroxycinnamic acid or derivatives
Acylphloroglucinol derivative
Benzenetriol
Phloroglucinol derivative
Benzoyl
Aryl ketone
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Acryloyl-group
Vinylogous acid
Enone
Alpha,beta-unsaturated ketone
Ketone
Polyol
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

benzenetriol (CHEBI:80489 )
chalcones (CHEBI:80489 )
chalcones (C16416 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030610)
Cell membrane (HMDB: HMDB0030610)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030610)

Source

Endogenous

Endogenous (HMDB: HMDB0030610)

Plant

Plant (HMDB: HMDB0030610)

Exogenous

Food

Food (HMDB: HMDB0030610)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Exogenous (HMDB: HMDB0030610)

Process

Not Available

Role

Not Available

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	0.41 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	0.011 g/L	ALOGPS
logP	3.53	ALOGPS
logP	5.7	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	7.61	ChemAxon
pKa (Strongest Basic)	-5.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	99.04 m³·mol⁻¹	ChemAxon
Polarizability	36.79 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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
DeepCCS	[M+H]+	177.035	30932474
DeepCCS	[M-H]-	174.677	30932474
DeepCCS	[M-2H]-	208.879	30932474
DeepCCS	[M+Na]+	184.107	30932474
AllCCS	[M+H]+	183.8	32859911
AllCCS	[M+H-H2O]+	180.5	32859911
AllCCS	[M+NH4]+	186.9	32859911
AllCCS	[M+Na]+	187.8	32859911
AllCCS	[M-H]-	181.5	32859911
AllCCS	[M+Na-2H]-	181.4	32859911
AllCCS	[M+HCOO]-	181.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	8.89 minutes	32390414
Predicted by Siyang on May 30, 2022	14.9481 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.26 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2989.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	319.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	180.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	166.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	322.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	797.0 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	747.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	71.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1410.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	642.1 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	1458.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	496.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	520.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	328.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	166.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	14.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Desmethylxanthohumol	CC(C)=CCC1=C(O)C(C(=O)\C=C\C2=CC=C(O)C=C2)=C(O)C=C1O	5141.0	Standard polar	33892256
Desmethylxanthohumol	CC(C)=CCC1=C(O)C(C(=O)\C=C\C2=CC=C(O)C=C2)=C(O)C=C1O	3016.6	Standard non polar	33892256
Desmethylxanthohumol	CC(C)=CCC1=C(O)C(C(=O)\C=C\C2=CC=C(O)C=C2)=C(O)C=C1O	3351.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Desmethylxanthohumol,1TMS,isomer #1	CC(C)=CCC1=C(O)C=C(O)C(C(=O)/C=C/C2=CC=C(O)C=C2)=C1O[Si](C)(C)C	3244.1	Semi standard non polar	33892256
Desmethylxanthohumol,1TMS,isomer #2	CC(C)=CCC1=C(O)C=C(O)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)=C1O	3222.5	Semi standard non polar	33892256
Desmethylxanthohumol,1TMS,isomer #3	CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C)C(C(=O)/C=C/C2=CC=C(O)C=C2)=C1O	3255.1	Semi standard non polar	33892256
Desmethylxanthohumol,1TMS,isomer #4	CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O)C(C(=O)/C=C/C2=CC=C(O)C=C2)=C1O	3219.4	Semi standard non polar	33892256
Desmethylxanthohumol,2TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O)C(C(=O)/C=C/C2=CC=C(O)C=C2)=C1O[Si](C)(C)C	3131.5	Semi standard non polar	33892256
Desmethylxanthohumol,2TMS,isomer #2	CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C)C(C(=O)/C=C/C2=CC=C(O)C=C2)=C1O[Si](C)(C)C	3177.9	Semi standard non polar	33892256
Desmethylxanthohumol,2TMS,isomer #3	CC(C)=CCC1=C(O)C=C(O)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)=C1O[Si](C)(C)C	3138.0	Semi standard non polar	33892256
Desmethylxanthohumol,2TMS,isomer #4	CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)=C1O	3135.4	Semi standard non polar	33892256
Desmethylxanthohumol,2TMS,isomer #5	CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)=C1O	3152.5	Semi standard non polar	33892256
Desmethylxanthohumol,2TMS,isomer #6	CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C(C(=O)/C=C/C2=CC=C(O)C=C2)=C1O	3126.0	Semi standard non polar	33892256
Desmethylxanthohumol,3TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C(C(=O)/C=C/C2=CC=C(O)C=C2)=C1O[Si](C)(C)C	3129.4	Semi standard non polar	33892256
Desmethylxanthohumol,3TMS,isomer #2	CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)=C1O[Si](C)(C)C	3127.3	Semi standard non polar	33892256
Desmethylxanthohumol,3TMS,isomer #3	CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)=C1O[Si](C)(C)C	3131.7	Semi standard non polar	33892256
Desmethylxanthohumol,3TMS,isomer #4	CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)=C1O	3130.3	Semi standard non polar	33892256
Desmethylxanthohumol,4TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)=C1O[Si](C)(C)C	3185.1	Semi standard non polar	33892256
Desmethylxanthohumol,1TBDMS,isomer #1	CC(C)=CCC1=C(O)C=C(O)C(C(=O)/C=C/C2=CC=C(O)C=C2)=C1O[Si](C)(C)C(C)(C)C	3512.2	Semi standard non polar	33892256
Desmethylxanthohumol,1TBDMS,isomer #2	CC(C)=CCC1=C(O)C=C(O)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=C1O	3494.2	Semi standard non polar	33892256
Desmethylxanthohumol,1TBDMS,isomer #3	CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C(C)(C)C)C(C(=O)/C=C/C2=CC=C(O)C=C2)=C1O	3504.0	Semi standard non polar	33892256
Desmethylxanthohumol,1TBDMS,isomer #4	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O)C(C(=O)/C=C/C2=CC=C(O)C=C2)=C1O	3480.0	Semi standard non polar	33892256
Desmethylxanthohumol,2TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O)C(C(=O)/C=C/C2=CC=C(O)C=C2)=C1O[Si](C)(C)C(C)(C)C	3679.8	Semi standard non polar	33892256
Desmethylxanthohumol,2TBDMS,isomer #2	CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C(C)(C)C)C(C(=O)/C=C/C2=CC=C(O)C=C2)=C1O[Si](C)(C)C(C)(C)C	3730.3	Semi standard non polar	33892256
Desmethylxanthohumol,2TBDMS,isomer #3	CC(C)=CCC1=C(O)C=C(O)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=C1O[Si](C)(C)C(C)(C)C	3700.6	Semi standard non polar	33892256
Desmethylxanthohumol,2TBDMS,isomer #4	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=C1O	3677.5	Semi standard non polar	33892256
Desmethylxanthohumol,2TBDMS,isomer #5	CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C(C)(C)C)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=C1O	3695.8	Semi standard non polar	33892256
Desmethylxanthohumol,2TBDMS,isomer #6	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C(C(=O)/C=C/C2=CC=C(O)C=C2)=C1O	3661.3	Semi standard non polar	33892256
Desmethylxanthohumol,3TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C(C(=O)/C=C/C2=CC=C(O)C=C2)=C1O[Si](C)(C)C(C)(C)C	3873.7	Semi standard non polar	33892256
Desmethylxanthohumol,3TBDMS,isomer #2	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=C1O[Si](C)(C)C(C)(C)C	3885.2	Semi standard non polar	33892256
Desmethylxanthohumol,3TBDMS,isomer #3	CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C(C)(C)C)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=C1O[Si](C)(C)C(C)(C)C	3905.1	Semi standard non polar	33892256
Desmethylxanthohumol,3TBDMS,isomer #4	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=C1O	3924.3	Semi standard non polar	33892256
Desmethylxanthohumol,4TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=C1O[Si](C)(C)C(C)(C)C	4101.2	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 - Desmethylxanthohumol GC-MS (Non-derivatized) - 70eV, Positive	splash10-006y-6798000000-1e76382a365bf3f7c624	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Desmethylxanthohumol GC-MS (4 TMS) - 70eV, Positive	splash10-03di-1000149000-a01a843a795485388633	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Desmethylxanthohumol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Desmethylxanthohumol 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Desmethylxanthohumol ESI-TOF , Negative-QTOF	splash10-0a4i-0529000000-a613547802dab4125d68	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Desmethylxanthohumol ESI-TOF 30V, Negative-QTOF	splash10-014i-0940000000-46dc70d70ca70dcf01b4	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Desmethylxanthohumol ESI-TOF , Negative-QTOF	splash10-000i-0009000000-6bfe956898b4539e080e	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Desmethylxanthohumol ESI-TOF 30V, Negative-QTOF	splash10-014i-0940000000-46dc70d70ca70dcf01b4	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Desmethylxanthohumol LC-ESI-TOF , negative-QTOF	splash10-014i-0940000000-46dc70d70ca70dcf01b4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Desmethylxanthohumol 30V, Positive-QTOF	splash10-014i-0940000000-46dc70d70ca70dcf01b4	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desmethylxanthohumol 10V, Positive-QTOF	splash10-0006-0239000000-5e5c002fdcabfcbc6bae	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desmethylxanthohumol 20V, Positive-QTOF	splash10-01bd-2594000000-e9108b3cd9cd75dc4b1f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desmethylxanthohumol 40V, Positive-QTOF	splash10-014i-5910000000-6747ff567422dfd30543	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desmethylxanthohumol 10V, Negative-QTOF	splash10-000i-0219000000-d86fdac27264b9a82f13	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desmethylxanthohumol 20V, Negative-QTOF	splash10-000f-0913000000-816feeed45ed4bd0b7ab	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desmethylxanthohumol 40V, Negative-QTOF	splash10-05fv-1900000000-6f3df54145550d6b335a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desmethylxanthohumol 10V, Negative-QTOF	splash10-000i-0009000000-fc98ca305e8f3c59dd80	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desmethylxanthohumol 20V, Negative-QTOF	splash10-000i-0439000000-633c01b2dd2c49a297d1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desmethylxanthohumol 40V, Negative-QTOF	splash10-014i-1910000000-7089c6e0dc73f5e33b70	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desmethylxanthohumol 10V, Positive-QTOF	splash10-000i-0592000000-5afd7f9975d02869f94f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desmethylxanthohumol 20V, Positive-QTOF	splash10-014i-0910000000-2665370e26d3729c14b3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desmethylxanthohumol 40V, Positive-QTOF	splash10-014i-1920000000-1fe40f99db5a2292008c	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Xanthohumol

METLIN ID

Not Available

PubChem Compound

6443339

PDB ID

Not Available

ChEBI ID

80489

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1821391

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Desmethylxanthohumol (HMDB0030610)

MOL for HMDB0030610 (Desmethylxanthohumol)

3D MOL for HMDB0030610 (Desmethylxanthohumol)

3D SDF for HMDB0030610 (Desmethylxanthohumol)

3D-SDF for HMDB0030610 (Desmethylxanthohumol)

PDB for HMDB0030610 (Desmethylxanthohumol)

3D PDB for HMDB0030610 (Desmethylxanthohumol)

SMILES for HMDB0030610 (Desmethylxanthohumol)

INCHI for HMDB0030610 (Desmethylxanthohumol)

Structure for HMDB0030610 (Desmethylxanthohumol)

3D Structure for HMDB0030610 (Desmethylxanthohumol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra