NP-MRD: Showing NP-Card for 3'-Prenyl-4,2',6'-trihydroxy-4'-methoxychalcone (NP0060671)

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Record Information

Version

2.0

Created at

2022-04-28 05:40:57 UTC

Updated at

2022-04-28 05:40:58 UTC

NP-MRD ID

NP0060671

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3'-Prenyl-4,2',6'-trihydroxy-4'-methoxychalcone

Description

Xanthogalenol 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, xanthogalenol is considered to be a flavonoid lipid molecule. Xanthogalenol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Xanthogalenol has been detected, but not quantified in, alcoholic beverages. 3'-Prenyl-4,2',6'-trihydroxy-4'-methoxychalcone is found in Angelika keiskei, Humulus lupulus and Neocheiropteris fortunei. 3'-Prenyl-4,2',6'-trihydroxy-4'-methoxychalcone was first documented in 2000 (PMID: 10783982). This could make xanthogalenol a potential biomarker for the consumption of these foods (PMID: 18343123) (PMID: 21377852) (PMID: 27238957).

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv0541 05061308112D          

 26 27  0  0  0  0            999 V2000
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -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
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    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
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    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
    1.4289   -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
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    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
    2.1434   -2.8875    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
    3.5724   -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
    3.5724   -2.8875    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
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  4  1  0  0  0  0
 11  7  2  0  0  0  0
 13  1  1  0  0  0  0
 13  2  1  0  0  0  0
 13  4  2  0  0  0  0
 14  5  2  0  0  0  0
 14  6  1  0  0  0  0
 14  7  1  0  0  0  0
 15  8  2  0  0  0  0
 15  9  1  0  0  0  0
 16 10  1  0  0  0  0
 17 11  1  0  0  0  0
 18 12  2  0  0  0  0
 19 12  1  0  0  0  0
 19 16  2  0  0  0  0
 20 17  1  0  0  0  0
 20 18  1  0  0  0  0
 21 16  1  0  0  0  0
 21 20  2  0  0  0  0
 22 15  1  0  0  0  0
 23 17  2  0  0  0  0
 24 18  1  0  0  0  0
 25 21  1  0  0  0  0
 26  3  1  0  0  0  0
 26 19  1  0  0  0  0
M  END

     RDKit          3D

 48 49  0  0  0  0  0  0  0  0999 V2000
   -3.3379    3.9627    0.3702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4690    2.6335   -0.0470 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383    1.8367   -0.1867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1010    2.3526    0.0836 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0354    1.5263   -0.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2368    2.0975    0.2189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0368    0.2202   -0.4698 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0650   -0.6728   -0.6469 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6467   -1.8881   -1.0641 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4645   -0.6949   -0.5252 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3919    0.1261   -0.1800 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8374   -0.2254   -0.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3402   -1.4361   -0.5018 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7290   -1.6935   -0.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6157   -0.7243   -0.0599 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9923   -0.9457   -0.0022 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1108    0.5100    0.2903 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7483    0.7576    0.2426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3272   -0.3110   -0.7495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5861   -1.5468   -1.1505 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4345    0.5328   -0.5930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7968    0.0119   -0.8799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5360   -0.2472    0.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9845   -1.4656    0.6217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7309   -1.6846    1.9176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8140   -2.6230   -0.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3581    4.4164    0.3486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9776    4.0591    1.4303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6517    4.4791   -0.3429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9710    3.3613    0.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3419    3.0428    0.5166 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9126   -1.7140   -0.8067 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1334    1.1255    0.1156 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6863   -2.2348   -0.8205 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0917   -2.6656   -0.7338 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4286   -1.2941    0.8448 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8181    1.2705    0.6011 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3674    1.7204    0.5174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4189   -2.4119   -1.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7819   -0.8727   -1.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4077    0.7802   -1.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7004    0.5486    1.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2471   -0.7587    2.1980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0509   -2.0472    2.7026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5134   -2.4703    1.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1786   -2.3092   -1.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4702   -3.4565    0.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7736   -2.9780   -0.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  2  3
 24 25  1  0
 24 26  1  0
 21 19  1  0
 19 20  1  0
 19  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
  7  5  1  0
  5  6  1  0
  5  4  2  0
  4  3  1  0
 18 12  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
 22 40  1  0
 22 41  1  0
 23 42  1  0
 25 43  1  0
 25 44  1  0
 25 45  1  0
 26 46  1  0
 26 47  1  0
 26 48  1  0
 20 39  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 14 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
  6 31  1  0
  4 30  1  0
M  END

  Mrv0541 05061308112D          

 26 27  0  0  0  0            999 V2000
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -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
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    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
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    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
    1.4289   -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
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    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
    2.1434   -2.8875    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
    3.5724   -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
    3.5724   -2.8875    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
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  4  1  0  0  0  0
 11  7  2  0  0  0  0
 13  1  1  0  0  0  0
 13  2  1  0  0  0  0
 13  4  2  0  0  0  0
 14  5  2  0  0  0  0
 14  6  1  0  0  0  0
 14  7  1  0  0  0  0
 15  8  2  0  0  0  0
 15  9  1  0  0  0  0
 16 10  1  0  0  0  0
 17 11  1  0  0  0  0
 18 12  2  0  0  0  0
 19 12  1  0  0  0  0
 19 16  2  0  0  0  0
 20 17  1  0  0  0  0
 20 18  1  0  0  0  0
 21 16  1  0  0  0  0
 21 20  2  0  0  0  0
 22 15  1  0  0  0  0
 23 17  2  0  0  0  0
 24 18  1  0  0  0  0
 25 21  1  0  0  0  0
 26  3  1  0  0  0  0
 26 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0060671

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(CC=C(C)C)C(O)=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O5/c1-13(2)4-10-16-19(26-3)12-18(24)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>
ALGFNVZQNNGHPA-YRNVUSSQSA-N

> <FORMULA>
C21H22O5

> <MOLECULAR_WEIGHT>
354.3964

> <EXACT_MASS>
354.146723814

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
38.85067021880515

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
3.93

> <JCHEM_LOGP>
5.850525077666667

> <ALOGPS_LOGS>
-4.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.820043791179547

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.817824577787964

> <JCHEM_PKA_STRONGEST_BASIC>
-4.868078789256216

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
103.52569999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.75e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
xanthogalenol

> <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      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   13                                                            
CONECT    3   26                                                            
CONECT    4   10   13                                                       
CONECT    5    8   14                                                       
CONECT    6    9   14                                                       
CONECT    7   11   14                                                       
CONECT    8    5   15                                                       
CONECT    9    6   15                                                       
CONECT   10    4   16                                                       
CONECT   11    7   17                                                       
CONECT   12   18   19                                                       
CONECT   13    1    2    4                                                  
CONECT   14    5    6    7                                                  
CONECT   15    8    9   22                                                  
CONECT   16   10   19   21                                                  
CONECT   17   11   20   23                                                  
CONECT   18   12   20   24                                                  
CONECT   19   12   16   26                                                  
CONECT   20   17   18   21                                                  
CONECT   21   16   20   25                                                  
CONECT   22   15                                                            
CONECT   23   17                                                            
CONECT   24   18                                                            
CONECT   25   21                                                            
CONECT   26    3   19                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

View in JSmol

Synonyms

Value	Source
3' Prenyl-4' O-methylchalconaringenin	ChEBI
3'-Prenyl-4,2',6'-trihydroxy-4'-methoxychalcone	ChEBI
2',4,6'-Trihydroxy-4'-methoxy-3'-prenylchalcone	HMDB

Chemical Formula

C₂₁H₂₂O₅

Average Mass

354.3964 Da

Monoisotopic Mass

354.14672 Da

IUPAC Name

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

Traditional Name

xanthogalenol

CAS Registry Number

Not Available

SMILES

COC1=C(CC=C(C)C)C(O)=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=C1

InChI Identifier

InChI=1S/C21H22O5/c1-13(2)4-10-16-19(26-3)12-18(24)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

ALGFNVZQNNGHPA-YRNVUSSQSA-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
Angelika keiskei	-	KNApSAcK
Humulus lupulus	Plant	KNApSAcK
Neocheiropteris fortunei	LOTUS Database	35616633

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Chalcones and dihydrochalcones (LMPK12120307 )

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	3.93	ALOGPS
logP	5.85	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	7.82	ChemAxon
pKa (Strongest Basic)	-4.9	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	6	ChemAxon
Refractivity	103.53 m³·mol⁻¹	ChemAxon
Polarizability	38.85 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

External Links

HMDB ID

HMDB0035002

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013606

KNApSAcK ID

C00014475

Chemspider ID

24692988

KEGG Compound ID

Not Available

BioCyc ID

CPD-7121

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14309735

PDB ID

Not Available

ChEBI ID

136826

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 ]
Vogel S, Ohmayer S, Brunner G, Heilmann J: Natural and non-natural prenylated chalcones: synthesis, cytotoxicity and anti-oxidative activity. Bioorg Med Chem. 2008 Apr 15;16(8):4286-93. doi: 10.1016/j.bmc.2008.02.079. Epub 2008 Feb 29. [PubMed:18343123 ]
Wang X, Zhen L, Zhang G, Wong MS, Qin L, Yao X: Osteogenic effects of flavonoid aglycones from an osteoprotective fraction of Drynaria fortunei--an in vitro efficacy study. Phytomedicine. 2011 Jul 15;18(10):868-72. doi: 10.1016/j.phymed.2011.01.022. Epub 2011 Mar 5. [PubMed:21377852 ]
Venturelli S, Burkard M, Biendl M, Lauer UM, Frank J, Busch C: Prenylated chalcones and flavonoids for the prevention and treatment of cancer. Nutrition. 2016 Nov-Dec;32(11-12):1171-8. doi: 10.1016/j.nut.2016.03.020. Epub 2016 Apr 8. [PubMed:27238957 ]

Showing NP-Card for 3'-Prenyl-4,2',6'-trihydroxy-4'-methoxychalcone (NP0060671)

MOL for NP0060671 (3'-Prenyl-4,2',6'-trihydroxy-4'-methoxychalcone)

3D MOL for NP0060671 (3'-Prenyl-4,2',6'-trihydroxy-4'-methoxychalcone)

3D SDF for NP0060671 (3'-Prenyl-4,2',6'-trihydroxy-4'-methoxychalcone)

3D-SDF for NP0060671 (3'-Prenyl-4,2',6'-trihydroxy-4'-methoxychalcone)

PDB for NP0060671 (3'-Prenyl-4,2',6'-trihydroxy-4'-methoxychalcone)

3D PDB for NP0060671 (3'-Prenyl-4,2',6'-trihydroxy-4'-methoxychalcone)

SMILES for NP0060671 (3'-Prenyl-4,2',6'-trihydroxy-4'-methoxychalcone)

INCHI for NP0060671 (3'-Prenyl-4,2',6'-trihydroxy-4'-methoxychalcone)

Structure for NP0060671 (3'-Prenyl-4,2',6'-trihydroxy-4'-methoxychalcone)

3D Structure for NP0060671 (3'-Prenyl-4,2',6'-trihydroxy-4'-methoxychalcone)