NP-MRD: Showing NP-Card for Desmethylisoxanthohumol (NP0054773)

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Record Information

Version

2.0

Created at

2022-04-28 01:01:07 UTC

Updated at

2022-04-28 01:01:07 UTC

NP-MRD ID

NP0054773

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Desmethylisoxanthohumol

Description

(2E)-3-phenyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-en-1-one, also known as 2,4',6'-trihydroxy-3'-prenylchalcone, 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, (2E)-3-phenyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-en-1-one is considered to be a flavonoid lipid molecule (2E)-3-phenyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-en-1-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Desmethylisoxanthohumol is found in Helichrysum athrixiifolium, Helichrysum cymosum, Helichrysum dregeanum, Helichrysum felinum, Helichrysum melanacme, Helichrysum revolutum, Helichrysum tenuifolium, Metalasia cymbifolia, Pleiotaxis rugosa and Pleiotaxis spp.. It is generated by Dehydroxylase enzyme via a -4p-dehydroxylation-of-substituted-benzene reaction.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652308211910542D          

 26 27  0  0  0  0            999 V2000
    0.7145   11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   11.1375    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
   -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
   -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
    1.4289    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   10.7250    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
    0.7145    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    6.1875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    5.7750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
 10  8  1  0  0  0  0
 11  9  2  0  0  0  0
 13  1  1  0  0  0  0
 13  2  1  0  0  0  0
 13  8  2  0  0  0  0
 14  6  2  0  0  0  0
 14  7  1  0  0  0  0
 14  9  1  0  0  0  0
 15 10  1  0  0  0  0
 16 11  1  0  0  0  0
 17 12  2  0  0  0  0
 17 15  1  0  0  0  0
 18 12  1  0  0  0  0
 19 16  1  0  0  0  0
 19 18  2  0  0  0  0
 20 15  2  0  0  0  0
 20 19  1  0  0  0  0
 21 16  2  0  0  0  0
 22 17  1  0  0  0  0
 23 18  1  0  0  0  0
 24 20  1  0  0  0  0
 25  9  1  0  0  0  0
 26 11  1  0  0  0  0
M  END

     RDKit          3D

 44 45  0  0  0  0  0  0  0  0999 V2000
   -6.2903   -0.6444    0.1434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4639    0.5559    0.4378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0168    1.6180    1.3336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2668    0.6924   -0.0730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5689   -0.2587   -0.9711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2508   -0.6163   -0.3442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2209   -1.5306    0.6896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4054   -2.1121    1.1287 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0029   -1.8307    1.2479 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1764   -1.2525    0.8111 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3874   -1.6076    1.4296 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1778   -0.3435   -0.2111 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3567    0.3170   -0.7374 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1831    1.1434   -1.7001 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7079    0.1390   -0.2875 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7271    0.8051   -0.8495 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1097    0.6533   -0.4232 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5271   -0.1736    0.5857 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8796   -0.2635    0.9382 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7999    0.4989    0.2503 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4180    1.3417   -0.7699 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0871    1.4059   -1.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0873   -0.0416   -0.7796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0858    0.8781   -1.8122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1598   -0.9842   -0.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0189   -1.4246    0.8824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3784   -0.3886    0.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0886    1.4071    1.5497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8537    2.6210    0.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4839    1.4918    2.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6825    1.6037    0.1703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1731   -1.1928   -1.1224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4484    0.1595   -1.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4433   -2.7822    1.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9429   -2.5409    2.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4261   -2.2622    2.1729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9803   -0.5192    0.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4766    1.4777   -1.6536 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8126   -0.7815    1.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1837   -0.9324    1.7481 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8681    0.4581    0.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1314    1.9497   -1.3221 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7655    2.0548   -1.8803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8489    1.2117   -2.3167 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 15 13  1  0
 13 14  2  0
 13 12  1  0
 12 10  2  0
 10 11  1  0
 10  9  1  0
  9  7  2  0
  7  8  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  2  3
  2  1  1  0
  2  3  1  0
  6 23  2  0
 23 24  1  0
 22 17  1  0
 23 12  1  0
 15 37  1  0
 16 38  1  0
 18 39  1  0
 19 40  1  0
 20 41  1  0
 21 42  1  0
 22 43  1  0
 11 36  1  0
  9 35  1  0
  8 34  1  0
  5 32  1  0
  5 33  1  0
  4 31  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
 24 44  1  0
M  END

  Mrv1652308211910542D          

 26 27  0  0  0  0            999 V2000
    0.7145   11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   11.1375    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
   -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
   -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
    1.4289    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   10.7250    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
    0.7145    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    6.1875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    5.7750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
 10  8  1  0  0  0  0
 11  9  2  0  0  0  0
 13  1  1  0  0  0  0
 13  2  1  0  0  0  0
 13  8  2  0  0  0  0
 14  6  2  0  0  0  0
 14  7  1  0  0  0  0
 14  9  1  0  0  0  0
 15 10  1  0  0  0  0
 16 11  1  0  0  0  0
 17 12  2  0  0  0  0
 17 15  1  0  0  0  0
 18 12  1  0  0  0  0
 19 16  1  0  0  0  0
 19 18  2  0  0  0  0
 20 15  2  0  0  0  0
 20 19  1  0  0  0  0
 21 16  2  0  0  0  0
 22 17  1  0  0  0  0
 23 18  1  0  0  0  0
 24 20  1  0  0  0  0
 25  9  1  0  0  0  0
 26 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054773

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(=C(\[H])C1=CC=CC=C1)C(=O)C1=C(O)C=C(O)C(CC=C(C)C)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H20O4/c1-13(2)8-10-15-17(22)12-18(23)19(20(15)24)16(21)11-9-14-6-4-3-5-7-14/h3-9,11-12,22-24H,10H2,1-2H3/b11-9+

> <INCHI_KEY>
HDFDQMFITYCMDM-PKNBQFBNSA-N

> <FORMULA>
C20H20O4

> <MOLECULAR_WEIGHT>
324.376

> <EXACT_MASS>
324.136159124

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
35.698309715552

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
4.05

> <JCHEM_LOGP>
6.008196343333333

> <ALOGPS_LOGS>
-4.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.125158820182602

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.878515959352493

> <JCHEM_PKA_STRONGEST_BASIC>
-6.379079447194511

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
97.06249999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.64e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
desmethylisoxanthohumol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 21-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-AUG-19         0                                  
HETATM    1  C   UNK     0       1.334  20.790   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  20.790   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  18.480   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667  10.780   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  17.710   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334  11.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  13.860   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  20.020   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  16.170   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334  13.090   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  15.400   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334  13.090   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000  13.860   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000  15.400   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.667  13.860   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.001  16.170   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.334  11.550   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -1.334  16.170   0.000  0.00  0.00           O+0
HETATM   25  H   UNK     0      -4.001  11.550   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.000  10.780   0.000  0.00  0.00           H+0
CONECT    1   13                                                            
CONECT    2   13                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4   14                                                       
CONECT    7    5   14                                                       
CONECT    8   10   13                                                       
CONECT    9   11   14   25                                                  
CONECT   10    8   15                                                       
CONECT   11    9   16   26                                                  
CONECT   12   17   18                                                       
CONECT   13    1    2    8                                                  
CONECT   14    6    7    9                                                  
CONECT   15   10   17   20                                                  
CONECT   16   11   19   21                                                  
CONECT   17   12   15   22                                                  
CONECT   18   12   19   23                                                  
CONECT   19   16   18   20                                                  
CONECT   20   15   19   24                                                  
CONECT   21   16                                                            
CONECT   22   17                                                            
CONECT   23   18                                                            
CONECT   24   20                                                            
CONECT   25    9                                                            
CONECT   26   11                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

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Synonyms

Value	Source
2,4',6'-Trihydroxy-3'-prenylchalcone	HMDB

Chemical Formula

C₂₀H₂₀O₄

Average Mass

324.3760 Da

Monoisotopic Mass

324.13616 Da

IUPAC Name

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

Traditional Name

desmethylisoxanthohumol

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\[H])C1=CC=CC=C1)C(=O)C1=C(O)C=C(O)C(CC=C(C)C)=C1O

InChI Identifier

InChI=1S/C20H20O4/c1-13(2)8-10-15-17(22)12-18(23)19(20(15)24)16(21)11-9-14-6-4-3-5-7-14/h3-9,11-12,22-24H,10H2,1-2H3/b11-9+

InChI Key

HDFDQMFITYCMDM-PKNBQFBNSA-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
Helichrysum athrixiifolium	Plant	KNApSAcK
Helichrysum cymosum	LOTUS Database	35616633
Helichrysum dregeanum	Plant	KNApSAcK
Helichrysum felinum	Plant	KNApSAcK
Helichrysum melanacme	LOTUS Database	35616633
Helichrysum revolutum	Plant	KNApSAcK
Helichrysum tenuifolium	Plant	KNApSAcK
Metalasia cymbifolia	Plant	KNApSAcK
Pleiotaxis rugosa	LOTUS Database	35616633
Pleiotaxis spp.	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
Cinnamic acid or derivatives
Acylphloroglucinol derivative
Benzenetriol
Phloroglucinol derivative
Benzoyl
Styrene
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Enone
Acryloyl-group
Alpha,beta-unsaturated ketone
Ketone
Polyol
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Chalcones and dihydrochalcones (LMPK12120213 )

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	4.05	ALOGPS
logP	6.01	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	6.88	ChemAxon
pKa (Strongest Basic)	-6.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	97.06 m³·mol⁻¹	ChemAxon
Polarizability	35.7 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

HMDB0129257

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10164615

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11992148

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Desmethylisoxanthohumol (NP0054773)

MOL for NP0054773 (Desmethylisoxanthohumol)

3D MOL for NP0054773 (Desmethylisoxanthohumol)

3D SDF for NP0054773 (Desmethylisoxanthohumol)

3D-SDF for NP0054773 (Desmethylisoxanthohumol)

PDB for NP0054773 (Desmethylisoxanthohumol)

3D PDB for NP0054773 (Desmethylisoxanthohumol)

SMILES for NP0054773 (Desmethylisoxanthohumol)

INCHI for NP0054773 (Desmethylisoxanthohumol)

Structure for NP0054773 (Desmethylisoxanthohumol)

3D Structure for NP0054773 (Desmethylisoxanthohumol)