NP-MRD: Showing NP-Card for xanthohumol (NP0027941)

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Record Information

Version

1.0

Created at

2021-06-19 19:57:36 UTC

Updated at

2021-08-20 00:00:11 UTC

NP-MRD ID

NP0027941

Secondary Accession Numbers

None

Natural Product Identification

Common Name

xanthohumol

Provided By

JEOL Database JEOL Logo

Description

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. Thus, xanthohumol is considered to be a flavonoid. Xanthohumol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. xanthohumol is found in Humulus lupulus and Taxus yunnanensis. It was first documented in 2004 (PMID: 14670594). Based on a literature review a significant number of articles have been published on Xanthohumol (PMID: 15679315) (PMID: 15550272) (PMID: 15723722) (PMID: 19634869).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192121573D          

 48 49  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306192121573D          

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 23 25  1  0  0  0  0
 15 16  1  0  0  0  0
 25 26  2  0  0  0  0
 26 20  1  0  0  0  0
  4  5  2  0  0  0  0
 23 24  1  0  0  0  0
  4 30  1  0  0  0  0
  8 32  1  0  0  0  0
  8 33  1  0  0  0  0
  9 34  1  0  0  0  0
 11 35  1  0  0  0  0
 11 36  1  0  0  0  0
 11 37  1  0  0  0  0
 12 38  1  0  0  0  0
 12 39  1  0  0  0  0
 12 40  1  0  0  0  0
 18 42  1  0  0  0  0
 19 43  1  0  0  0  0
  6 31  1  0  0  0  0
 14 41  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
 21 44  1  0  0  0  0
 22 45  1  0  0  0  0
 25 47  1  0  0  0  0
 26 48  1  0  0  0  0
 24 46  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0027941

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(\C([H])=C(/[H])C(=O)C2=C(OC([H])([H])[H])C([H])=C(O[H])C(=C2O[H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O5/c1-13(2)4-10-16-18(24)12-19(26-3)20(21(16)25)17(23)11-7-14-5-8-15(22)9-6-14/h4-9,11-12,22,24-25H,10H2,1-3H3/b11-7+

> <INCHI_KEY>
ORXQGKIUCDPEAJ-YRNVUSSQSA-N

> <FORMULA>
C21H22O5

> <MOLECULAR_WEIGHT>
354.3964

> <EXACT_MASS>
354.146723814

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
38.5242701785884

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.91

> <JCHEM_LOGP>
5.200525077666667

> <ALOGPS_LOGS>
-4.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.483703818528035

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.010896021528515

> <JCHEM_PKA_STRONGEST_BASIC>
-4.896190778259284

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
103.5257

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.56e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
xanthohumol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 48 49  0  0  0  0  0  0  0  0999 V2000
    0.8193   -3.1384   -1.7791 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4987   -1.7567   -1.8986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2281   -1.1765   -0.8920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7386   -1.8834    0.2003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4211   -1.2216    1.2240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8509   -2.0147    2.2524 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6312    0.1619    1.1961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3948    0.8773    2.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5634    1.0740    3.5328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8370    0.6954    4.7976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0836   -0.0127    5.2521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8601    0.9906    5.9079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1023    0.8709    0.1048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2585    2.2386    0.1101 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4373    0.2132   -0.9554 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0346    1.0452   -2.0948 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4261    2.1902   -1.8683 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0919    0.5178   -3.4789 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4442    1.1992   -4.5028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3594    0.7661   -5.9034 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4649   -0.5806   -6.2779 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4060   -0.9485   -7.6244 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2527    0.0284   -8.5998 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2002   -0.3751   -9.9007 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1623    1.3716   -8.2527 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2220    1.7379   -6.9047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0849   -3.7550   -1.8083 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4357   -3.4123   -2.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4058   -3.3325   -0.8751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6130   -2.9569    0.3003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9985   -1.4560    3.0346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3156    0.3182    2.4841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7374    1.8614    1.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6305    1.6093    3.3456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8263   -0.9885    5.6772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8054   -0.1838    4.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5902    0.5765    6.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5379    0.0594    6.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3284    1.6272    6.6657 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0364    1.5065    5.5484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6416    2.6227   -0.5541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6429   -0.4025   -3.6262 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9639    2.1393   -4.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6067   -1.3573   -5.5307 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4860   -1.9934   -7.9100 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0957    0.4091  -10.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0480    2.1432   -9.0072 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1517    2.7913   -6.6409 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 18  1  0
  5  7  1  0
 18 19  2  0
  7  8  1  0
 16 17  2  0
 13 15  1  0
 19 20  1  0
  8  9  1  0
  5  6  1  0
 13 14  1  0
  9 10  2  3
  3  2  1  0
 15  3  2  0
  2  1  1  0
 10 11  1  0
 20 21  2  0
  7 13  2  0
 21 22  1  0
 10 12  1  0
 22 23  2  0
  3  4  1  0
 23 25  1  0
 15 16  1  0
 25 26  2  0
 26 20  1  0
  4  5  2  0
 23 24  1  0
  4 30  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 11 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 12 40  1  0
 18 42  1  0
 19 43  1  0
  6 31  1  0
 14 41  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
 21 44  1  0
 22 45  1  0
 25 47  1  0
 26 48  1  0
 24 46  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       0.819  -3.138  -1.779  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.499  -1.757  -1.899  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.228  -1.177  -0.892  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.739  -1.883   0.200  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.421  -1.222   1.224  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.851  -2.015   2.252  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.631   0.162   1.196  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.395   0.877   2.292  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.563   1.074   3.533  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.837   0.695   4.798  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.084  -0.013   5.252  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.860   0.991   5.908  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.102   0.871   0.105  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.258   2.239   0.110  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.437   0.213  -0.955  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.035   1.045  -2.095  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.426   2.190  -1.868  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.092   0.518  -3.479  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.444   1.199  -4.503  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.359   0.766  -5.903  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.465  -0.581  -6.278  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.406  -0.949  -7.624  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.253   0.028  -8.600  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.200  -0.375  -9.901  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.162   1.372  -8.253  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.222   1.738  -6.905  0.00  0.00           C+0
HETATM   27  H   UNK     0      -0.085  -3.755  -1.808  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.436  -3.412  -2.641  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.406  -3.333  -0.875  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.613  -2.957   0.300  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.999  -1.456   3.035  0.00  0.00           H+0
HETATM   32  H   UNK     0      -3.316   0.318   2.484  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.737   1.861   1.951  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.631   1.609   3.346  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.826  -0.989   5.677  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.805  -0.184   4.451  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.590   0.577   6.024  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.538   0.059   6.385  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.328   1.627   6.666  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.036   1.506   5.548  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.642   2.623  -0.554  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.643  -0.403  -3.626  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.964   2.139  -4.325  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.607  -1.357  -5.531  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.486  -1.993  -7.910  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.096   0.409 -10.464  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.048   2.143  -9.007  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.152   2.791  -6.641  0.00  0.00           H+0
CONECT    1    2   27   28   29                                             
CONECT    2    3    1                                                       
CONECT    3    2   15    4                                                  
CONECT    4    3    5   30                                                  
CONECT    5    7    6    4                                                  
CONECT    6    5   31                                                       
CONECT    7    5    8   13                                                  
CONECT    8    7    9   32   33                                             
CONECT    9    8   10   34                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10   35   36   37                                             
CONECT   12   10   38   39   40                                             
CONECT   13   15   14    7                                                  
CONECT   14   13   41                                                       
CONECT   15   13    3   16                                                  
CONECT   16   18   17   15                                                  
CONECT   17   16                                                            
CONECT   18   16   19   42                                                  
CONECT   19   18   20   43                                                  
CONECT   20   19   21   26                                                  
CONECT   21   20   22   44                                                  
CONECT   22   21   23   45                                                  
CONECT   23   22   25   24                                                  
CONECT   24   23   46                                                       
CONECT   25   23   26   47                                                  
CONECT   26   25   20   48                                                  
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    4                                                            
CONECT   31    6                                                            
CONECT   32    8                                                            
CONECT   33    8                                                            
CONECT   34    9                                                            
CONECT   35   11                                                            
CONECT   36   11                                                            
CONECT   37   11                                                            
CONECT   38   12                                                            
CONECT   39   12                                                            
CONECT   40   12                                                            
CONECT   41   14                                                            
CONECT   42   18                                                            
CONECT   43   19                                                            
CONECT   44   21                                                            
CONECT   45   22                                                            
CONECT   46   24                                                            
CONECT   47   25                                                            
CONECT   48   26                                                            
MASTER        0    0    0    0    0    0    0    0   48    0   98    0
END

RDKit          3D

48 49  0  0  0  0  0  0  0  0999 V2000
    0.8193   -3.1384   -1.7791 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4987   -1.7567   -1.8986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2281   -1.1765   -0.8920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7386   -1.8834    0.2003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4211   -1.2216    1.2240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8509   -2.0147    2.2524 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6312    0.1619    1.1961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3948    0.8773    2.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5634    1.0740    3.5328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8370    0.6954    4.7976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0836   -0.0127    5.2521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8601    0.9906    5.9079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1023    0.8709    0.1048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2585    2.2386    0.1101 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4373    0.2132   -0.9554 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0346    1.0452   -2.0948 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4261    2.1902   -1.8683 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0919    0.5178   -3.4789 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4442    1.1992   -4.5028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3594    0.7661   -5.9034 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4649   -0.5806   -6.2779 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4060   -0.9485   -7.6244 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2527    0.0284   -8.5998 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2002   -0.3751   -9.9007 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1623    1.3716   -8.2527 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2220    1.7379   -6.9047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0849   -3.7550   -1.8083 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4357   -3.4123   -2.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4058   -3.3325   -0.8751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6130   -2.9569    0.3003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9985   -1.4560    3.0346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3156    0.3182    2.4841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7374    1.8614    1.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6305    1.6093    3.3456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8263   -0.9885    5.6772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8054   -0.1838    4.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5902    0.5765    6.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5379    0.0594    6.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3284    1.6272    6.6657 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0364    1.5065    5.5484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6416    2.6227   -0.5541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6429   -0.4025   -3.6262 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9639    2.1393   -4.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6067   -1.3573   -5.5307 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4860   -1.9934   -7.9100 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0957    0.4091  -10.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0480    2.1432   -9.0072 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1517    2.7913   -6.6409 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 18  1  0
  5  7  1  0
 18 19  2  0
  7  8  1  0
 16 17  2  0
 13 15  1  0
 19 20  1  0
  8  9  1  0
  5  6  1  0
 13 14  1  0
  9 10  2  3
  3  2  1  0
 15  3  2  0
  2  1  1  0
 10 11  1  0
 20 21  2  0
  7 13  2  0
 21 22  1  0
 10 12  1  0
 22 23  2  0
  3  4  1  0
 23 25  1  0
 15 16  1  0
 25 26  2  0
 26 20  1  0
  4  5  2  0
 23 24  1  0
  4 30  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 11 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 12 40  1  0
 18 42  1  0
 19 43  1  0
  6 31  1  0
 14 41  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
 21 44  1  0
 22 45  1  0
 25 47  1  0
 26 48  1  0
 24 46  1  0
M  END

View in JSmol

Synonyms

Value	Source
2',4,4'-Trihydroxy-6'-methoxy-3'-prenylchalcone	ChEBI
(2E)-1-[2,4-Dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one	Kegg
Desmethylxanthohumol	HMDB
1-(2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl)-3-(4-hydroxyphenyl)-2-propen-1-one	HMDB

Chemical Formula

C₂₁H₂₂O₅

Average Mass

354.3964 Da

Monoisotopic Mass

354.14672 Da

IUPAC Name

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

Traditional Name

xanthohumol

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(\C([H])=C(/[H])C(=O)C2=C(OC([H])([H])[H])C([H])=C(O[H])C(=C2O[H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])C([H])=C1[H]

InChI Identifier

InChI=1S/C21H22O5/c1-13(2)4-10-16-18(24)12-19(26-3)20(21(16)25)17(23)11-7-14-5-8-15(22)9-6-14/h4-9,11-12,22,24-25H,10H2,1-3H3/b11-7+

InChI Key

ORXQGKIUCDPEAJ-YRNVUSSQSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Humulus lupulus	JEOL database	Zhao, F., et al, J. Nat. Prod. 68, 43 (2005)
Medicago sativa	KNApSAcK Database	22123792
Sophora angustifolia	KNApSAcK Database	22123792
Sophora flavescens	KNApSAcK Database	22123792
Taxus chinensis	KNApSAcK Database	22123792
Taxus fuana	KNApSAcK Database	22123792
Taxus wallichiana var. yunnanensis	Plant	KNApSAcK
Taxus yunnanensis	KNApSAcK Database	22123792

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

Not Available

Substituents

Not Available

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	576.00 to 577.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.51 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	5.172 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	3.91	ALOGPS
logP	5.2	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	7.01	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	103.53 m³·mol⁻¹	ChemAxon
Polarizability	38.52 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0037479

DrugBank ID

Not Available

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Xanthohumol

METLIN ID

Not Available

PubChem Compound

639665

PDB ID

Not Available

ChEBI ID

66331

Good Scents ID

rw1500861

References

General References

Zhao F, Watanabe Y, Nozawa H, Daikonnya A, Kondo K, Kitanaka S: Prenylflavonoids and phloroglucinol derivatives from hops (Humulus lupulus). J Nat Prod. 2005 Jan;68(1):43-9. doi: 10.1021/np0499113. [PubMed:15679315 ]
Buckwold VE, Wilson RJ, Nalca A, Beer BB, Voss TG, Turpin JA, Buckheit RW 3rd, Wei J, Wenzel-Mathers M, Walton EM, Smith RJ, Pallansch M, Ward P, Wells J, Chuvala L, Sloane S, Paulman R, Russell J, Hartman T, Ptak R: Antiviral activity of hop constituents against a series of DNA and RNA viruses. Antiviral Res. 2004 Jan;61(1):57-62. doi: 10.1016/s0166-3542(03)00155-4. [PubMed:14670594 ]
Wang Q, Ding ZH, Liu JK, Zheng YT: Xanthohumol, a novel anti-HIV-1 agent purified from Hops Humulus lupulus. Antiviral Res. 2004 Dec;64(3):189-94. doi: 10.1016/j.antiviral.2004.08.005. [PubMed:15550272 ]
Goto K, Asai T, Hara S, Namatame I, Tomoda H, Ikemoto M, Oku N: Enhanced antitumor activity of xanthohumol, a diacylglycerol acyltransferase inhibitor, under hypoxia. Cancer Lett. 2005 Mar 10;219(2):215-22. doi: 10.1016/j.canlet.2004.07.034. [PubMed:15723722 ]
Lupinacci E, Meijerink J, Vincken JP, Gabriele B, Gruppen H, Witkamp RF: Xanthohumol from hop (Humulus lupulus L.) is an efficient inhibitor of monocyte chemoattractant protein-1 and tumor necrosis factor-alpha release in LPS-stimulated RAW 264.7 mouse macrophages and U937 human monocytes. J Agric Food Chem. 2009 Aug 26;57(16):7274-81. doi: 10.1021/jf901244k. [PubMed:19634869 ]
Zhao, F., et al. (2005). Zhao, F., et al, J. Nat. Prod. 68, 43 (2005). J. Nat. Prod..

Showing NP-Card for xanthohumol (NP0027941)

MOL for NP0027941 (xanthohumol )

3D MOL for NP0027941 (xanthohumol )

3D SDF for NP0027941 (xanthohumol )

3D-SDF for NP0027941 (xanthohumol )

PDB for NP0027941 (xanthohumol )

3D PDB for NP0027941 (xanthohumol )

SMILES for NP0027941 (xanthohumol )

INCHI for NP0027941 (xanthohumol )

Structure for NP0027941 (xanthohumol )

3D Structure for NP0027941 (xanthohumol )