NP-MRD: Showing NP-Card for 4'-O-Methylxanthohumol (NP0054792)

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Record Information

Version

2.0

Created at

2022-04-28 01:01:55 UTC

Updated at

2022-04-28 01:01:55 UTC

NP-MRD ID

NP0054792

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4'-O-Methylxanthohumol

Description

2',4-Dihydroxy-4',6'-dimethoxy-3'-prenylchalcone, also known as 4'-methylxanthohumol or 3'-(isoprenyl)-2',4-dihydroxy-4',6'-dimethoxychalcone, 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, 2',4-dihydroxy-4',6'-dimethoxy-3'-prenylchalcone is considered to be a flavonoid lipid molecule. 2',4-Dihydroxy-4',6'-dimethoxy-3'-prenylchalcone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 2',4-Dihydroxy-4',6'-dimethoxy-3'-prenylchalcone has been detected, but not quantified in, alcoholic beverages. 4'-O-Methylxanthohumol is found in Humulus lupulus . 4'-O-Methylxanthohumol was first documented in 2000 (PMID: 10783982). This could make 2',4-dihydroxy-4',6'-dimethoxy-3'-prenylchalcone a potential biomarker for the consumption of these foods (PMID: 26162028).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061310402D          

 27 28  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
   -5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    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
   -2.1434   -0.4125    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
  9  6  1  0  0  0  0
 10  7  2  0  0  0  0
 11  5  1  0  0  0  0
 12  8  2  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  5  2  0  0  0  0
 15  6  2  0  0  0  0
 15  7  1  0  0  0  0
 15  8  1  0  0  0  0
 16  9  2  0  0  0  0
 16 10  1  0  0  0  0
 17 11  1  0  0  0  0
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 19 13  2  0  0  0  0
 19 17  1  0  0  0  0
 20 13  1  0  0  0  0
 21 18  1  0  0  0  0
 21 20  2  0  0  0  0
 22 17  2  0  0  0  0
 22 21  1  0  0  0  0
 23 16  1  0  0  0  0
 24 18  2  0  0  0  0
 25 22  1  0  0  0  0
 26  3  1  0  0  0  0
 26 19  1  0  0  0  0
 27  4  1  0  0  0  0
 27 20  1  0  0  0  0
M  END

     RDKit          3D

 51 52  0  0  0  0  0  0  0  0999 V2000
   -3.7011   -0.6962    2.5322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6243   -0.6337    1.1191 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3657   -0.5459    0.5589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2117   -0.5165    1.2819 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0367   -0.4266    0.6573 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1340   -0.4039    1.4675 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0312   -0.4671    2.8623 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1705   -0.3633   -0.6963 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3803   -0.2662   -1.4435 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1600   -0.2162   -2.7650 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.2470    0.0988   -0.4763 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.6941   -0.0351   -1.5048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0628   -0.3959   -1.4329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9413   -0.3301   -2.8104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2794   -0.4846   -0.8158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5313   -0.5102   -1.6295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2214    0.7848   -1.6743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4481    1.0202   -1.2568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3322   -0.0175   -0.6653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0254    2.3981   -1.3656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2376    0.2444    2.9109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0164   -1.5165    2.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2632   -0.5640    2.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3683    0.3665    3.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6173   -1.4665    3.1468 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0147   -0.3443    3.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3705   -0.1262   -2.1690 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1614   -0.2864    0.8159 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2734   -0.2263    1.7800 H   0  0  0  0  0  0  0  0  0  0  0  0
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    9.6356    1.0476   -0.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5979    0.1161   -2.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1899   -0.0135   -2.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7095   -0.3311   -3.4203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1649   -1.2943   -1.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3051   -0.9661   -2.5968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6482    1.6154   -2.0959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4066    0.2470   -0.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2226   -0.0913    0.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1920   -1.0087   -1.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2533    3.1782   -1.2447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3974    2.4946   -2.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8157    2.5701   -0.6198 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
  8 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  2  3
 25 26  1  0
 25 27  1  0
 22  3  1  0
 19 13  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  7 32  1  0
  7 33  1  0
  7 34  1  0
 11 35  1  0
 12 36  1  0
 14 37  1  0
 15 38  1  0
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 18 40  1  0
 19 41  1  0
 21 42  1  0
 23 43  1  0
 23 44  1  0
 24 45  1  0
 26 46  1  0
 26 47  1  0
 26 48  1  0
 27 49  1  0
 27 50  1  0
 27 51  1  0
M  END


  Mrv0541 05061310402D          

 27 28  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
   -5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    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
   -2.1434   -0.4125    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
  9  6  1  0  0  0  0
 10  7  2  0  0  0  0
 11  5  1  0  0  0  0
 12  8  2  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  5  2  0  0  0  0
 15  6  2  0  0  0  0
 15  7  1  0  0  0  0
 15  8  1  0  0  0  0
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 17 11  1  0  0  0  0
 18 12  1  0  0  0  0
 19 13  2  0  0  0  0
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 20 13  1  0  0  0  0
 21 18  1  0  0  0  0
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 26  3  1  0  0  0  0
 26 19  1  0  0  0  0
 27  4  1  0  0  0  0
 27 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054792

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(OC)=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=C1CC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C22H24O5/c1-14(2)5-11-17-19(26-3)13-20(27-4)21(22(17)25)18(24)12-8-15-6-9-16(23)10-7-15/h5-10,12-13,23,25H,11H2,1-4H3/b12-8+

> <INCHI_KEY>
UVBDKJHYMQEAQV-XYOKQWHBSA-N

> <FORMULA>
C22H24O5

> <MOLECULAR_WEIGHT>
368.423

> <EXACT_MASS>
368.162373878

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
40.94928960386925

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.84

> <JCHEM_LOGP>
5.346419133666666

> <ALOGPS_LOGS>
-5.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.074017945822584

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.967821636175678

> <JCHEM_PKA_STRONGEST_BASIC>
-4.581513469344819

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
108.00799999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.26e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4'-O-methylxanthohumol

> <JCHEM_VEBER_RULE>
0

$$$$

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      -9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.667  10.780   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -2.667   1.540   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
HETATM   26  O   UNK     0      -9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -6.668   3.850   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3   26                                                            
CONECT    4   27                                                            
CONECT    5   11   14                                                       
CONECT    6    9   15                                                       
CONECT    7   10   15                                                       
CONECT    8   12   15                                                       
CONECT    9    6   16                                                       
CONECT   10    7   16                                                       
CONECT   11    5   17                                                       
CONECT   12    8   18                                                       
CONECT   13   19   20                                                       
CONECT   14    1    2    5                                                  
CONECT   15    6    7    8                                                  
CONECT   16    9   10   23                                                  
CONECT   17   11   19   22                                                  
CONECT   18   12   21   24                                                  
CONECT   19   13   17   26                                                  
CONECT   20   13   21   27                                                  
CONECT   21   18   20   22                                                  
CONECT   22   17   21   25                                                  
CONECT   23   16                                                            
CONECT   24   18                                                            
CONECT   25   22                                                            
CONECT   26    3   19                                                       
CONECT   27    4   20                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

View in JSmol

Synonyms

Value	Source
3'-(Isoprenyl)-2',4-dihydroxy-4',6'-dimethoxychalcone	ChEBI
4'-Methylxanthohumol	ChEBI
4'-O-Methylxanthohumol	HMDB

Chemical Formula

C₂₂H₂₄O₅

Average Mass

368.4230 Da

Monoisotopic Mass

368.16237 Da

IUPAC Name

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

Traditional Name

4'-O-methylxanthohumol

CAS Registry Number

Not Available

SMILES

COC1=CC(OC)=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=C1CC=C(C)C

InChI Identifier

InChI=1S/C22H24O5/c1-14(2)5-11-17-19(26-3)13-20(27-4)21(22(17)25)18(24)12-8-15-6-9-16(23)10-7-15/h5-10,12-13,23,25H,11H2,1-4H3/b12-8+

InChI Key

UVBDKJHYMQEAQV-XYOKQWHBSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Humulus lupulus	Plant	KNApSAcK

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
Methoxyphenol
Dimethoxybenzene
M-dimethoxybenzene
Anisole
Methoxybenzene
Benzoyl
Aryl ketone
Phenoxy compound
Phenol ether
Styrene
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Acryloyl-group
Enone
Alpha,beta-unsaturated ketone
Vinylogous acid
Ketone
Ether
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Chalcones and dihydrochalcones (LMPK12120318 )

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	3.84	ALOGPS
logP	5.35	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	7.97	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	108.01 m³·mol⁻¹	ChemAxon
Polarizability	40.95 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

HMDB0038815

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018241

KNApSAcK ID

C00007100

Chemspider ID

9134771

KEGG Compound ID

Not Available

BioCyc ID

CPD-7122

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10959555

PDB ID

Not Available

ChEBI ID

136828

Good Scents ID

Not Available

References

General References

Stevens JF, Taylor AW, Nickerson GB, Ivancic M, Henning J, Haunold A, Deinzer ML: Prenylflavonoid variation in Humulus lupulus: distribution and taxonomic significance of xanthogalenol and 4'-O-methylxanthohumol. Phytochemistry. 2000 Apr;53(7):759-75. doi: 10.1016/s0031-9422(00)00005-4. [PubMed:10783982 ]
Kim DW, Woo HS, Kim JY, Ryuk JA, Park KH, Ko BS: Phenols displaying tyrosinase inhibition from Humulus lupulus. J Enzyme Inhib Med Chem. 2016 Oct;31(5):742-7. doi: 10.3109/14756366.2015.1063621. Epub 2015 Jul 10. [PubMed:26162028 ]

Showing NP-Card for 4'-O-Methylxanthohumol (NP0054792)

MOL for NP0054792 (4'-O-Methylxanthohumol)

3D MOL for NP0054792 (4'-O-Methylxanthohumol)

3D SDF for NP0054792 (4'-O-Methylxanthohumol)

3D-SDF for NP0054792 (4'-O-Methylxanthohumol)

PDB for NP0054792 (4'-O-Methylxanthohumol)

3D PDB for NP0054792 (4'-O-Methylxanthohumol)

SMILES for NP0054792 (4'-O-Methylxanthohumol)

INCHI for NP0054792 (4'-O-Methylxanthohumol)

Structure for NP0054792 (4'-O-Methylxanthohumol)

3D Structure for NP0054792 (4'-O-Methylxanthohumol)