NP-MRD: Showing NP-Card for xanthohumol D (NP0027942)

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Record Information

Version

1.0

Created at

2021-06-19 19:57:39 UTC

Updated at

2021-06-29 23:54:24 UTC

NP-MRD ID

NP0027942

Secondary Accession Numbers

None

Natural Product Identification

Common Name

xanthohumol D

Provided By

JEOL Database JEOL Logo

Description

xanthohumol D is found in Humulus lupulus. It was first documented in 2005 (Zhao, F., et al.). Based on a literature review very few articles have been published on ZINC14762532.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192121573D          

 49 50  0  0  0  0            999 V2000
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    0.4521    3.1757    3.4353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4822    3.6832    4.5031 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2759    1.7146    3.0579 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0615    0.9333    3.9755 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6966    1.3332    1.6266 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1818   -0.0361    1.2204 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7955   -1.2101    1.6679 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8267   -1.1953    2.5667 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3884   -2.4684    1.2229 C   0  0  0  0  0  0  0  0  0  0  0  0
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  5 34  1  0  0  0  0
M  END

     RDKit          3D

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    1.3515    4.0016    2.8719 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4521    3.1757    3.4353 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2759    1.7146    3.0579 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0615    0.9333    3.9755 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6966    1.3332    1.6266 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306192121573D          

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  2  1  2  3  0  0  0
 21 22  2  0  0  0  0
 11 10  2  0  0  0  0
 22 24  1  0  0  0  0
 14 15  1  0  0  0  0
 24 25  2  0  0  0  0
 25 19  1  0  0  0  0
 10  8  1  0  0  0  0
 22 23  1  0  0  0  0
 15 17  1  0  0  0  0
  4  5  1  0  0  0  0
 10 38  1  0  0  0  0
  6 35  1  0  0  0  0
  6 36  1  0  0  0  0
  4 33  1  6  0  0  0
  3 30  1  0  0  0  0
  3 31  1  0  0  0  0
  3 32  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
 17 42  1  0  0  0  0
 18 43  1  0  0  0  0
  9 37  1  0  0  0  0
 27 49  1  0  0  0  0
 13 39  1  0  0  0  0
 13 40  1  0  0  0  0
 13 41  1  0  0  0  0
 20 44  1  0  0  0  0
 21 45  1  0  0  0  0
 24 47  1  0  0  0  0
 25 48  1  0  0  0  0
 23 46  1  0  0  0  0
  5 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0027942

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(\C([H])=C(/[H])C(=O)C2=C(O[H])C(=C(O[H])C([H])=C2OC([H])([H])[H])C([H])([H])[C@@]([H])(O[H])C(=C([H])[H])C([H])([H])[H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O6/c1-12(2)17(24)10-15-18(25)11-19(27-3)20(21(15)26)16(23)9-6-13-4-7-14(22)8-5-13/h4-9,11,17,22,24-26H,1,10H2,2-3H3/b9-6+/t17-/m1/s1

> <INCHI_KEY>
IIWLGOCXDBSFCM-RCMYXZNBSA-N

> <FORMULA>
C21H22O6

> <MOLECULAR_WEIGHT>
370.401

> <EXACT_MASS>
370.141638428

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
40.269041869335446

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-1-{2,4-dihydroxy-3-[(2R)-2-hydroxy-3-methylbut-3-en-1-yl]-6-methoxyphenyl}-3-(4-hydroxyphenyl)prop-2-en-1-one

> <ALOGPS_LOGP>
2.85

> <JCHEM_LOGP>
4.027647680999999

> <ALOGPS_LOGS>
-3.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.648167101012223

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.354351776000019

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0490866005400292

> <JCHEM_POLAR_SURFACE_AREA>
107.22

> <JCHEM_REFRACTIVITY>
103.96870000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.62e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-1-{2,4-dihydroxy-3-[(2R)-2-hydroxy-3-methylbut-3-en-1-yl]-6-methoxyphenyl}-3-(4-hydroxyphenyl)prop-2-en-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 49 50  0  0  0  0  0  0  0  0999 V2000
    1.3515    4.0016    2.8719 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4521    3.1757    3.4353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4822    3.6832    4.5031 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2759    1.7146    3.0579 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0615    0.9333    3.9755 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6966    1.3332    1.6266 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1818   -0.0361    1.2204 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7955   -1.2101    1.6679 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8267   -1.1953    2.5667 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3884   -2.4684    1.2229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6918   -2.5973    0.3451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1124   -3.7985   -0.1642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2658   -4.9276    0.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3868   -1.4388   -0.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5928   -1.4803   -0.9189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7741   -0.5655   -1.7225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6002   -2.5537   -0.7111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6306   -2.6740   -1.5620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6820   -3.6907   -1.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4051   -5.0056   -1.0278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4282   -5.9549   -0.9406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7295   -5.5896   -1.2666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7575   -6.4820   -1.1966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0214   -4.2969   -1.6820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9981   -3.3503   -1.7698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9219   -0.1699    0.3652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5394    0.9894   -0.0454 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4321    5.0433    3.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0429    3.6696    2.1036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3099    4.7395    4.7354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5221    3.5816    4.1756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3522    3.1156    5.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7752    1.4355    3.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9684    1.3483    4.8515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7912    1.3193    1.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3472    2.0893    0.9138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7258   -0.3935    3.1283 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9356   -3.3288    1.5945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6898   -5.7597   -0.5456 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7423   -4.7399   -0.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2419   -5.2253    1.0778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4868   -3.2010    0.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7369   -1.9853   -2.3985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3881   -5.3088   -0.7909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1887   -6.9653   -0.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4060   -7.3379   -0.9019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0411   -4.0251   -1.9395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2408   -2.3421   -2.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1025    0.7763   -0.8247 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  2  0
 17 18  2  0
  7  6  1  0
 15 16  2  0
 26 14  2  0
 18 19  1  0
  6  4  1  0
  8  9  1  0
 26 27  1  0
  4  2  1  0
 11 12  1  0
 14 11  1  0
 12 13  1  0
  2  3  1  0
 19 20  2  0
  7 26  1  0
 20 21  1  0
  2  1  2  3
 21 22  2  0
 11 10  2  0
 22 24  1  0
 14 15  1  0
 24 25  2  0
 25 19  1  0
 10  8  1  0
 22 23  1  0
 15 17  1  0
  4  5  1  0
 10 38  1  0
  6 35  1  0
  6 36  1  0
  4 33  1  6
  3 30  1  0
  3 31  1  0
  3 32  1  0
  1 28  1  0
  1 29  1  0
 17 42  1  0
 18 43  1  0
  9 37  1  0
 27 49  1  0
 13 39  1  0
 13 40  1  0
 13 41  1  0
 20 44  1  0
 21 45  1  0
 24 47  1  0
 25 48  1  0
 23 46  1  0
  5 34  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       1.351   4.002   2.872  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.452   3.176   3.435  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.482   3.683   4.503  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.276   1.715   3.058  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.062   0.933   3.975  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.697   1.333   1.627  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.182  -0.036   1.220  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.796  -1.210   1.668  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.827  -1.195   2.567  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.388  -2.468   1.223  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.692  -2.597   0.345  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.112  -3.799  -0.164  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.266  -4.928   0.025  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.387  -1.439  -0.049  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.593  -1.480  -0.919  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.774  -0.566  -1.722  0.00  0.00           O+0
HETATM   17  C   UNK     0      -3.600  -2.554  -0.711  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.631  -2.674  -1.562  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.682  -3.691  -1.430  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.405  -5.006  -1.028  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.428  -5.955  -0.941  0.00  0.00           C+0
HETATM   22  C   UNK     0      -7.729  -5.590  -1.267  0.00  0.00           C+0
HETATM   23  O   UNK     0      -8.758  -6.482  -1.197  0.00  0.00           O+0
HETATM   24  C   UNK     0      -8.021  -4.297  -1.682  0.00  0.00           C+0
HETATM   25  C   UNK     0      -6.998  -3.350  -1.770  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.922  -0.170   0.365  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.539   0.989  -0.045  0.00  0.00           O+0
HETATM   28  H   UNK     0       1.432   5.043   3.170  0.00  0.00           H+0
HETATM   29  H   UNK     0       2.043   3.670   2.104  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.310   4.739   4.735  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.522   3.582   4.176  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.352   3.116   5.430  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.775   1.436   3.205  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.968   1.348   4.851  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.791   1.319   1.535  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.347   2.089   0.914  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.726  -0.394   3.128  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.936  -3.329   1.595  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.690  -5.760  -0.546  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.742  -4.740  -0.360  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.242  -5.225   1.078  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.487  -3.201   0.149  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.737  -1.985  -2.398  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.388  -5.309  -0.791  0.00  0.00           H+0
HETATM   45  H   UNK     0      -6.189  -6.965  -0.625  0.00  0.00           H+0
HETATM   46  H   UNK     0      -8.406  -7.338  -0.902  0.00  0.00           H+0
HETATM   47  H   UNK     0      -9.041  -4.025  -1.940  0.00  0.00           H+0
HETATM   48  H   UNK     0      -7.241  -2.342  -2.099  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.103   0.776  -0.825  0.00  0.00           H+0
CONECT    1    2   28   29                                                  
CONECT    2    4    3    1                                                  
CONECT    3    2   30   31   32                                             
CONECT    4    6    2    5   33                                             
CONECT    5    4   34                                                       
CONECT    6    7    4   35   36                                             
CONECT    7    8    6   26                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8   37                                                       
CONECT   10   11    8   38                                                  
CONECT   11   12   14   10                                                  
CONECT   12   11   13                                                       
CONECT   13   12   39   40   41                                             
CONECT   14   26   11   15                                                  
CONECT   15   16   14   17                                                  
CONECT   16   15                                                            
CONECT   17   18   15   42                                                  
CONECT   18   17   19   43                                                  
CONECT   19   18   20   25                                                  
CONECT   20   19   21   44                                                  
CONECT   21   20   22   45                                                  
CONECT   22   21   24   23                                                  
CONECT   23   22   46                                                       
CONECT   24   22   25   47                                                  
CONECT   25   24   19   48                                                  
CONECT   26   14   27    7                                                  
CONECT   27   26   49                                                       
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    3                                                            
CONECT   31    3                                                            
CONECT   32    3                                                            
CONECT   33    4                                                            
CONECT   34    5                                                            
CONECT   35    6                                                            
CONECT   36    6                                                            
CONECT   37    9                                                            
CONECT   38   10                                                            
CONECT   39   13                                                            
CONECT   40   13                                                            
CONECT   41   13                                                            
CONECT   42   17                                                            
CONECT   43   18                                                            
CONECT   44   20                                                            
CONECT   45   21                                                            
CONECT   46   23                                                            
CONECT   47   24                                                            
CONECT   48   25                                                            
CONECT   49   27                                                            
MASTER        0    0    0    0    0    0    0    0   49    0  100    0
END

RDKit          3D

49 50  0  0  0  0  0  0  0  0999 V2000
    1.3515    4.0016    2.8719 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4521    3.1757    3.4353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4822    3.6832    4.5031 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2759    1.7146    3.0579 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0615    0.9333    3.9755 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6966    1.3332    1.6266 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1818   -0.0361    1.2204 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7955   -1.2101    1.6679 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8267   -1.1953    2.5667 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3884   -2.4684    1.2229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6918   -2.5973    0.3451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1124   -3.7985   -0.1642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2658   -4.9276    0.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3868   -1.4388   -0.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5928   -1.4803   -0.9189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7741   -0.5655   -1.7225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6002   -2.5537   -0.7111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6306   -2.6740   -1.5620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6820   -3.6907   -1.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4051   -5.0056   -1.0278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4282   -5.9549   -0.9406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7295   -5.5896   -1.2666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7575   -6.4820   -1.1966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0214   -4.2969   -1.6820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9981   -3.3503   -1.7698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9219   -0.1699    0.3652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5394    0.9894   -0.0454 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4321    5.0433    3.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0429    3.6696    2.1036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3099    4.7395    4.7354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5221    3.5816    4.1756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3522    3.1156    5.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7752    1.4355    3.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9684    1.3483    4.8515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7912    1.3193    1.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3472    2.0893    0.9138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7258   -0.3935    3.1283 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9356   -3.3288    1.5945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6898   -5.7597   -0.5456 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7423   -4.7399   -0.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2419   -5.2253    1.0778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4868   -3.2010    0.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7369   -1.9853   -2.3985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3881   -5.3088   -0.7909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1887   -6.9653   -0.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4060   -7.3379   -0.9019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0411   -4.0251   -1.9395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2408   -2.3421   -2.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1025    0.7763   -0.8247 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  2  0
 17 18  2  0
  7  6  1  0
 15 16  2  0
 26 14  2  0
 18 19  1  0
  6  4  1  0
  8  9  1  0
 26 27  1  0
  4  2  1  0
 11 12  1  0
 14 11  1  0
 12 13  1  0
  2  3  1  0
 19 20  2  0
  7 26  1  0
 20 21  1  0
  2  1  2  3
 21 22  2  0
 11 10  2  0
 22 24  1  0
 14 15  1  0
 24 25  2  0
 25 19  1  0
 10  8  1  0
 22 23  1  0
 15 17  1  0
  4  5  1  0
 10 38  1  0
  6 35  1  0
  6 36  1  0
  4 33  1  6
  3 30  1  0
  3 31  1  0
  3 32  1  0
  1 28  1  0
  1 29  1  0
 17 42  1  0
 18 43  1  0
  9 37  1  0
 27 49  1  0
 13 39  1  0
 13 40  1  0
 13 41  1  0
 20 44  1  0
 21 45  1  0
 24 47  1  0
 25 48  1  0
 23 46  1  0
  5 34  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₂O₆

Average Mass

370.4010 Da

Monoisotopic Mass

370.14164 Da

IUPAC Name

(2E)-1-{2,4-dihydroxy-3-[(2R)-2-hydroxy-3-methylbut-3-en-1-yl]-6-methoxyphenyl}-3-(4-hydroxyphenyl)prop-2-en-1-one

Traditional Name

(2E)-1-{2,4-dihydroxy-3-[(2R)-2-hydroxy-3-methylbut-3-en-1-yl]-6-methoxyphenyl}-3-(4-hydroxyphenyl)prop-2-en-1-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(\C([H])=C(/[H])C(=O)C2=C(O[H])C(=C(O[H])C([H])=C2OC([H])([H])[H])C([H])([H])[C@@]([H])(O[H])C(=C([H])[H])C([H])([H])[H])C([H])=C1[H]

InChI Identifier

InChI=1S/C21H22O6/c1-12(2)17(24)10-15-18(25)11-19(27-3)20(21(15)26)16(23)9-6-13-4-7-14(22)8-5-13/h4-9,11,17,22,24-26H,1,10H2,2-3H3/b9-6+/t17-/m1/s1

InChI Key

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

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	2.85	ALOGPS
logP	4.03	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	7.35	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	103.97 m³·mol⁻¹	ChemAxon
Polarizability	40.27 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

92469725

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhao, F., et al. (2005). Zhao, F., et al, J. Nat. Prod. 68, 43 (2005). J. Nat. Prod..

Showing NP-Card for xanthohumol D (NP0027942)

MOL for NP0027942 (xanthohumol D)

3D MOL for NP0027942 (xanthohumol D)

3D SDF for NP0027942 (xanthohumol D)

3D-SDF for NP0027942 (xanthohumol D)

PDB for NP0027942 (xanthohumol D)

3D PDB for NP0027942 (xanthohumol D)

SMILES for NP0027942 (xanthohumol D)

INCHI for NP0027942 (xanthohumol D)

Structure for NP0027942 (xanthohumol D)

3D Structure for NP0027942 (xanthohumol D)