NP-MRD: Showing NP-Card for oxygenated xanthohumol (NP0243868)

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Record Information

Version

2.0

Created at

2022-09-07 04:30:51 UTC

Updated at

2022-09-07 04:30:51 UTC

NP-MRD ID

NP0243868

Secondary Accession Numbers

None

Natural Product Identification

Common Name

oxygenated xanthohumol

Description

Oxygenated xanthohumol belongs to the class of organic compounds known as 3-prenylated chalcones. These are chalcones featuring a C5-isoprenoid unit at the 3-position. Oxygenated xanthohumol is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. oxygenated xanthohumol is found in Humulus lupulus. Based on a literature review very few articles have been published on oxygenated xanthohumol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072206302D          

 29 30  0  0  0  0            999 V2000
    2.1434   -1.2375    0.0000 C   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
    2.8579   -2.4750    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
    3.5724   -3.7125    0.0000 C   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   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7474   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    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   -4.1250    0.0000 O   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
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
  3 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 23 29  1  0  0  0  0
M  END

     RDKit          3D

 55 56  0  0  0  0  0  0  0  0999 V2000
    1.7398   -3.1804   -0.7794 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6791   -1.7890   -0.6785 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5159   -1.0512   -0.8220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6502   -1.7896   -1.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8359   -1.1336   -1.2346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9710   -1.9203   -1.5005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9204    0.1966   -1.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1593    0.9322   -1.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0237    1.2126   -0.1141 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1180    1.9466   -0.6822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6237    0.1685    0.7202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5077   -0.8191   -0.0505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5567   -0.6888    1.4307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3947    0.6257    1.7500 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4718    1.3885    1.5736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7618    0.9530   -0.8821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8978    2.2841   -0.8005 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4956    0.3167   -0.7162 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6548    1.1039   -0.4105 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3307    2.3951   -0.2908 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0407    0.9628   -0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9151    0.0186   -0.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3626    0.1647    0.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9055    1.3736    0.3863 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2734    1.5239    0.6641 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0967    0.4255    0.6332 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4586    0.5317    0.9038 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5258   -0.7936    0.3242 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1883   -0.9445    0.0520 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2965   -3.6087    0.1571 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2471   -3.5779   -1.6895 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8288   -3.4587   -0.7567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5882   -2.8851   -1.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9204   -2.9039   -1.5713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9243    1.9486   -1.7259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8356    0.4976   -2.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5864    1.9824    0.5985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8012    2.5735   -1.3694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1915   -1.8714    0.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4798   -0.6412   -1.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5665   -0.7767    0.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7472   -0.7239    2.5477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6025   -0.1517    1.3472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5708   -1.7310    1.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3628    2.3847    1.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8551    1.6453    2.6151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3741    0.8486    1.1479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4997    3.0927   -0.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5790    1.9619    0.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6232   -0.9650   -0.4334 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3592    2.2834    0.4337 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6704    2.5177    0.9043 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0986    0.7143    0.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1697   -1.6757    0.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7435   -1.8942   -0.1905 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
  5  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
 14 15  1  0
  7 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  2  0
 18  3  1  0
 29 23  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
  6 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  1
 10 38  1  0
 12 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 13 44  1  0
 15 45  1  0
 15 46  1  0
 15 47  1  0
 17 48  1  0
 21 49  1  0
 22 50  1  0
 24 51  1  0
 25 52  1  0
 27 53  1  0
 28 54  1  0
 29 55  1  0
M  END


  Mrv1652309072206302D          

 29 30  0  0  0  0            999 V2000
    2.1434   -1.2375    0.0000 C   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
    2.8579   -2.4750    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
    3.5724   -3.7125    0.0000 C   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   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7474   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    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   -4.1250    0.0000 O   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
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
  3 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 23 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0243868

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C(CC(O)C(C)(C)OC)C(O)=C1C(=O)\C=C\C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H26O7/c1-22(2,29-4)19(26)11-15-17(25)12-18(28-3)20(21(15)27)16(24)10-7-13-5-8-14(23)9-6-13/h5-10,12,19,23,25-27H,11H2,1-4H3/b10-7+

> <INCHI_KEY>
YXGBQKBRCDLZMP-JXMROGBWSA-N

> <FORMULA>
C22H26O7

> <MOLECULAR_WEIGHT>
402.443

> <EXACT_MASS>
402.167853177

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
42.72650959637511

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-1-[2,4-dihydroxy-3-(2-hydroxy-3-methoxy-3-methylbutyl)-6-methoxyphenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one

> <JCHEM_LOGP>
3.703212770666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.651855612655032

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.360217923022767

> <JCHEM_PKA_STRONGEST_BASIC>
-3.322662843276315

> <JCHEM_POLAR_SURFACE_AREA>
116.45

> <JCHEM_REFRACTIVITY>
110.62449999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-1-[2,4-dihydroxy-3-(2-hydroxy-3-methoxy-3-methylbutyl)-6-methoxyphenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.208 -11.550   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.128 -11.550   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.668 -13.090   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.002 -13.860   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   16                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   15                                                       
CONECT   15   14                                                            
CONECT   16    7   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    3   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   29                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   23                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   60    0
END

View in JSmol

Synonyms

Value	Source
rac-1-[2,4-Dihydroxy-3-(2-hydroxy-3-methoxy-3-methylbutyl)-6-methoxyphenyl]-3-(4-hydroxyphenyl)propenone	ChEBI

Chemical Formula

C₂₂H₂₆O₇

Average Mass

402.4430 Da

Monoisotopic Mass

402.16785 Da

IUPAC Name

(2E)-1-[2,4-dihydroxy-3-(2-hydroxy-3-methoxy-3-methylbutyl)-6-methoxyphenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one

Traditional Name

(2E)-1-[2,4-dihydroxy-3-(2-hydroxy-3-methoxy-3-methylbutyl)-6-methoxyphenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C(CC(O)C(C)(C)OC)C(O)=C1C(=O)\C=C\C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C22H26O7/c1-22(2,29-4)19(26)11-15-17(25)12-18(28-3)20(21(15)27)16(24)10-7-13-5-8-14(23)9-6-13/h5-10,12,19,23,25-27H,11H2,1-4H3/b10-7+

InChI Key

YXGBQKBRCDLZMP-JXMROGBWSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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	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
Phenol ether
Resorcinol
Phenoxy compound
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
Secondary alcohol
Ether
Dialkyl ether
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic ether (CHEBI:66333 )
secondary alcohol (CHEBI:66333 )
polyphenol (CHEBI:66333 )
chalcones (CHEBI:66333 )

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	3.7	ChemAxon
pKa (Strongest Acidic)	7.36	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	110.62 m³·mol⁻¹	ChemAxon
Polarizability	42.73 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

9433178

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11258152

PDB ID

Not Available

ChEBI ID

66333

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for oxygenated xanthohumol (NP0243868)

MOL for NP0243868 (oxygenated xanthohumol)

3D MOL for NP0243868 (oxygenated xanthohumol)

3D SDF for NP0243868 (oxygenated xanthohumol)

3D-SDF for NP0243868 (oxygenated xanthohumol)

PDB for NP0243868 (oxygenated xanthohumol)

3D PDB for NP0243868 (oxygenated xanthohumol)

SMILES for NP0243868 (oxygenated xanthohumol)

INCHI for NP0243868 (oxygenated xanthohumol)

Structure for NP0243868 (oxygenated xanthohumol)

3D Structure for NP0243868 (oxygenated xanthohumol)