NP-MRD: Showing NP-Card for dihydroxanthohumol (NP0027943)

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Record Information

Version

2.0

Created at

2021-06-19 19:57:41 UTC

Updated at

2021-06-29 23:54:24 UTC

NP-MRD ID

NP0027943

Secondary Accession Numbers

None

Natural Product Identification

Common Name

dihydroxanthohumol

Provided By

JEOL Database JEOL Logo

Description

Alpha,beta-Dihydroxanthohumol, also known as α,β-dihydroxanthohumol, belongs to the class of organic compounds known as 2'-hydroxy-dihydrochalcones. These are organic compounds containing dihydrochalcone skeleton that carries a hydroxyl group at the 2'-position. Thus, alpha,beta-dihydroxanthohumol is considered to be a flavonoid. Alpha,beta-Dihydroxanthohumol is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. dihydroxanthohumol is found in Humulus lupulus. dihydroxanthohumol was first documented in 2013 (PMID: 23434138). Based on a literature review a significant number of articles have been published on alpha,beta-Dihydroxanthohumol (PMID: 32627931) (PMID: 30471194) (PMID: 30423918) (PMID: 30126093) (PMID: 28754033).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192121573D          

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M  END

     RDKit          3D

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  Mrv1652306192121573D          

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   -3.7461   -2.9427   -0.9590 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5535    2.4146    0.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1455    2.5337    1.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5903    1.2800    3.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 18  1  0  0  0  0
  5  7  1  0  0  0  0
 18 19  1  0  0  0  0
  7  8  1  0  0  0  0
 16 17  2  0  0  0  0
 13 15  1  0  0  0  0
 19 20  1  0  0  0  0
  8  9  1  0  0  0  0
  5  6  1  0  0  0  0
 13 14  1  0  0  0  0
  9 10  2  3  0  0  0
  3  2  1  0  0  0  0
 15  3  2  0  0  0  0
  2  1  1  0  0  0  0
 10 11  1  0  0  0  0
 20 21  2  0  0  0  0
  7 13  2  0  0  0  0
 21 22  1  0  0  0  0
 10 12  1  0  0  0  0
 22 23  2  0  0  0  0
  3  4  1  0  0  0  0
 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
 18 43  1  0  0  0  0
 19 44  1  0  0  0  0
 19 45  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 46  1  0  0  0  0
 22 47  1  0  0  0  0
 25 49  1  0  0  0  0
 26 50  1  0  0  0  0
 24 48  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0027943

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C(=O)C1=C(OC([H])([H])[H])C([H])=C(O[H])C(=C1O[H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H24O5/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/h4-6,8-9,12,22,24-25H,7,10-11H2,1-3H3

> <INCHI_KEY>
SVTCZHIDEDUTBH-UHFFFAOYSA-N

> <FORMULA>
C21H24O5

> <MOLECULAR_WEIGHT>
356.4123

> <EXACT_MASS>
356.162373878

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
39.19381073783281

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.63

> <JCHEM_LOGP>
5.120001588

> <ALOGPS_LOGS>
-4.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.305433683181484

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.732440714690221

> <JCHEM_PKA_STRONGEST_BASIC>
-4.711882010884502

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
102.43239999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.70e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α,β-dihydroxanthohumol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 50 51  0  0  0  0  0  0  0  0999 V2000
   -3.7461   -2.9427   -0.9590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2015   -2.0492    0.0059 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7850   -0.8193   -0.4318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8108   -0.4105   -1.7666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3995    0.8766   -2.1240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4066    1.1483   -3.4649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0104    1.8210   -1.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5970    3.2261   -1.5487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1783    3.2700   -2.0561 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2849    3.7677   -3.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5463    4.4340   -4.2811 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7554    3.6933   -3.5458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9952    1.4080    0.1745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6409    2.3385    1.1242 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3268    0.0861    0.5371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1422   -0.3100    1.9568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4611    0.4987    2.8322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4381   -1.6148    2.2809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1396   -1.3521    3.0460 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8736   -0.6025    2.2102 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5492   -1.2420    1.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4330   -0.5271    0.3511 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6443    0.8254    0.5874 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5042    1.4902   -0.2364 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9930    1.4761    1.6290 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1108    0.7602    2.4409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6338   -2.5160   -1.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0557   -3.8513   -0.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9921   -3.2279   -1.6998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1298   -1.0723   -2.5655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7898    1.8818   -3.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3192    3.6111   -2.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6768    3.9049   -0.6917 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5410    2.8299   -1.3621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4959    3.8600   -5.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5996    4.5329   -4.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1673    5.4426   -4.4771 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1653    4.6996   -3.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9095    3.1275   -4.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3333    3.2017   -2.7560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9094    1.9887    2.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1221   -2.2195    2.8865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2119   -2.1848    1.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3013   -2.3071    3.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3463   -0.7973    3.9697 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3842   -2.2980    0.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9499   -1.0226   -0.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5535    2.4146    0.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1455    2.5337    1.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5903    1.2800    3.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 18  1  0
  5  7  1  0
 18 19  1  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
 18 43  1  0
 19 44  1  0
 19 45  1  0
  6 31  1  0
 14 41  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
 21 46  1  0
 22 47  1  0
 25 49  1  0
 26 50  1  0
 24 48  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      -3.746  -2.943  -0.959  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.201  -2.049   0.006  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.785  -0.819  -0.432  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.811  -0.411  -1.767  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.400   0.877  -2.124  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.407   1.148  -3.465  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.010   1.821  -1.166  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.597   3.226  -1.549  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.178   3.270  -2.056  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.285   3.768  -3.220  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.546   4.434  -4.281  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.755   3.693  -3.546  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.995   1.408   0.175  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.641   2.338   1.124  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.327   0.086   0.537  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.142  -0.310   1.957  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.461   0.499   2.832  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.438  -1.615   2.281  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.140  -1.352   3.046  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.874  -0.603   2.210  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.549  -1.242   1.161  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.433  -0.527   0.351  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.644   0.825   0.587  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.504   1.490  -0.236  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.993   1.476   1.629  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.111   0.760   2.441  0.00  0.00           C+0
HETATM   27  H   UNK     0      -4.634  -2.516  -1.437  0.00  0.00           H+0
HETATM   28  H   UNK     0      -4.056  -3.851  -0.434  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.992  -3.228  -1.700  0.00  0.00           H+0
HETATM   30  H   UNK     0      -3.130  -1.072  -2.566  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.790   1.882  -3.632  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.319   3.611  -2.275  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.677   3.905  -0.692  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.541   2.830  -1.362  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.496   3.860  -5.212  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.600   4.533  -4.012  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.167   5.443  -4.477  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.165   4.700  -3.680  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.910   3.127  -4.471  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.333   3.202  -2.756  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.909   1.989   2.003  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.122  -2.220   2.886  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.212  -2.185   1.376  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.301  -2.307   3.358  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.346  -0.797   3.970  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.384  -2.298   0.961  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.950  -1.023  -0.466  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.554   2.415   0.058  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.146   2.534   1.819  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.590   1.280   3.243  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   43                                             
CONECT   19   18   20   44   45                                             
CONECT   20   19   21   26                                                  
CONECT   21   20   22   46                                                  
CONECT   22   21   23   47                                                  
CONECT   23   22   25   24                                                  
CONECT   24   23   48                                                       
CONECT   25   23   26   49                                                  
CONECT   26   25   20   50                                                  
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   18                                                            
CONECT   44   19                                                            
CONECT   45   19                                                            
CONECT   46   21                                                            
CONECT   47   22                                                            
CONECT   48   24                                                            
CONECT   49   25                                                            
CONECT   50   26                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  102    0
END

RDKit          3D

50 51  0  0  0  0  0  0  0  0999 V2000
   -3.7461   -2.9427   -0.9590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2015   -2.0492    0.0059 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7850   -0.8193   -0.4318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8108   -0.4105   -1.7666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3995    0.8766   -2.1240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4066    1.1483   -3.4649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0104    1.8210   -1.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5970    3.2261   -1.5487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1783    3.2700   -2.0561 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2849    3.7677   -3.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5463    4.4340   -4.2811 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7554    3.6933   -3.5458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9952    1.4080    0.1745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6409    2.3385    1.1242 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3268    0.0861    0.5371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1422   -0.3100    1.9568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4611    0.4987    2.8322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4381   -1.6148    2.2809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1396   -1.3521    3.0460 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8736   -0.6025    2.2102 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5492   -1.2420    1.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4330   -0.5271    0.3511 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6443    0.8254    0.5874 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5042    1.4902   -0.2364 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9930    1.4761    1.6290 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1108    0.7602    2.4409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6338   -2.5160   -1.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0557   -3.8513   -0.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9921   -3.2279   -1.6998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1298   -1.0723   -2.5655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7898    1.8818   -3.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3192    3.6111   -2.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6768    3.9049   -0.6917 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5410    2.8299   -1.3621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4959    3.8600   -5.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5996    4.5329   -4.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1673    5.4426   -4.4771 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1653    4.6996   -3.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9095    3.1275   -4.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3333    3.2017   -2.7560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9094    1.9887    2.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1221   -2.2195    2.8865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2119   -2.1848    1.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3013   -2.3071    3.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3463   -0.7973    3.9697 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3842   -2.2980    0.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9499   -1.0226   -0.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5535    2.4146    0.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1455    2.5337    1.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5903    1.2800    3.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 18  1  0
  5  7  1  0
 18 19  1  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
 18 43  1  0
 19 44  1  0
 19 45  1  0
  6 31  1  0
 14 41  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
 21 46  1  0
 22 47  1  0
 25 49  1  0
 26 50  1  0
 24 48  1  0
M  END

View in JSmol

Synonyms

Value	Source
4,2',4'-Trihydroxy-6'-methoxy-3'-prenyldihydrochalcone	ChEBI
a,b-Dihydroxanthohumol	Generator
Α,β-dihydroxanthohumol	Generator
2',4,4'-Trihydroxy-6'-methoxy-3'-prenyldihydrochalcone	HMDB

Chemical Formula

C₂₁H₂₄O₅

Average Mass

356.4123 Da

Monoisotopic Mass

356.16237 Da

IUPAC Name

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

Traditional Name

α,β-dihydroxanthohumol

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C(=O)C1=C(OC([H])([H])[H])C([H])=C(O[H])C(=C1O[H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C21H24O5/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/h4-6,8-9,12,22,24-25H,7,10-11H2,1-3H3

InChI Key

SVTCZHIDEDUTBH-UHFFFAOYSA-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, 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)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2'-hydroxy-dihydrochalcones. These are organic compounds containing dihydrochalcone skeleton that carries a hydroxyl group at the 2'-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

2'-Hydroxy-dihydrochalcones

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	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.63	ALOGPS
logP	5.12	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	7.73	ChemAxon
pKa (Strongest Basic)	-4.7	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	7	ChemAxon
Refractivity	102.43 m³·mol⁻¹	ChemAxon
Polarizability	39.19 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

HMDB0035440

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014123

KNApSAcK ID

C00014615

Chemspider ID

8626337

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10450920

PDB ID

Not Available

ChEBI ID

66332

Good Scents ID

rw1849861

References

General References

Paraiso IL, Revel JS, Choi J, Miranda CL, Lak P, Kioussi C, Bobe G, Gombart AF, Raber J, Maier CS, Stevens JF: Targeting the Liver-Brain Axis with Hop-Derived Flavonoids Improves Lipid Metabolism and Cognitive Performance in Mice. Mol Nutr Food Res. 2020 Aug;64(15):e2000341. doi: 10.1002/mnfr.202000341. Epub 2020 Jul 6. [PubMed:32627931 ]
Paraiso IL, Plagmann LS, Yang L, Zielke R, Gombart AF, Maier CS, Sikora AE, Blakemore PR, Stevens JF: Reductive Metabolism of Xanthohumol and 8-Prenylnaringenin by the Intestinal Bacterium Eubacterium ramulus. Mol Nutr Food Res. 2019 Jan;63(2):e1800923. doi: 10.1002/mnfr.201800923. Epub 2018 Dec 3. [PubMed:30471194 ]
Bartmanska A, Tronina T, Poplonski J, Milczarek M, Filip-Psurska B, Wietrzyk J: Highly Cancer Selective Antiproliferative Activity of Natural Prenylated Flavonoids. Molecules. 2018 Nov 9;23(11). pii: molecules23112922. doi: 10.3390/molecules23112922. [PubMed:30423918 ]
Bartmanska A, Walecka-Zacharska E, Tronina T, Poplonski J, Sordon S, Brzezowska E, Bania J, Huszcza E: Antimicrobial Properties of Spent Hops Extracts, Flavonoids Isolated Therefrom, and Their Derivatives. Molecules. 2018 Aug 17;23(8). pii: molecules23082059. doi: 10.3390/molecules23082059. [PubMed:30126093 ]
Tronina T, Strugala P, Poplonski J, Wloch A, Sordon S, Bartmanska A, Huszcza E: The Influence of Glycosylation of Natural and Synthetic Prenylated Flavonoids on Binding to Human Serum Albumin and Inhibition of Cyclooxygenases COX-1 and COX-2. Molecules. 2017 Jul 21;22(7). pii: molecules22071230. doi: 10.3390/molecules22071230. [PubMed:28754033 ]
Tronina T, Bartmanska A, Filip-Psurska B, Wietrzyk J, Poplonski J, Huszcza E: Fungal metabolites of xanthohumol with potent antiproliferative activity on human cancer cell lines in vitro. Bioorg Med Chem. 2013 Apr 1;21(7):2001-6. doi: 10.1016/j.bmc.2013.01.026. Epub 2013 Feb 4. [PubMed:23434138 ]
Zhao, F., et al. (2005). Zhao, F., et al, J. Nat. Prod. 68, 43 (2005). J. Nat. Prod..

Showing NP-Card for dihydroxanthohumol (NP0027943)

MOL for NP0027943 (dihydroxanthohumol )

3D MOL for NP0027943 (dihydroxanthohumol )

3D SDF for NP0027943 (dihydroxanthohumol )

3D-SDF for NP0027943 (dihydroxanthohumol )

PDB for NP0027943 (dihydroxanthohumol )

3D PDB for NP0027943 (dihydroxanthohumol )

SMILES for NP0027943 (dihydroxanthohumol )

INCHI for NP0027943 (dihydroxanthohumol )

Structure for NP0027943 (dihydroxanthohumol )

3D Structure for NP0027943 (dihydroxanthohumol )