NP-MRD: Showing NP-Card for 3',5'-Diprenyl-4,2',4'-trihydroxy-6-methoxychalcone (NP0060669)

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Record Information

Version

2.0

Created at

2022-04-28 05:40:54 UTC

Updated at

2022-04-28 05:40:54 UTC

NP-MRD ID

NP0060669

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3',5'-Diprenyl-4,2',4'-trihydroxy-6-methoxychalcone

Description

2',4,4'-Trihydroxy-6'-methoxy-3',5'-diprenylchalcone, also known as 1-(2-allyl-4-pentenoyl)-3-cyclohexyl-urea or 5'-prenylxanthohumol, belongs to the class of organic compounds known as 3-prenylated chalcones. These are chalcones featuring a C5-isoprenoid unit at the 3-position. Thus, 2',4,4'-trihydroxy-6'-methoxy-3',5'-diprenylchalcone is considered to be a flavonoid lipid molecule. 2',4,4'-Trihydroxy-6'-methoxy-3',5'-diprenylchalcone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 2',4,4'-Trihydroxy-6'-methoxy-3',5'-diprenylchalcone has been detected, but not quantified in, alcoholic beverages. 3',5'-Diprenyl-4,2',4'-trihydroxy-6-methoxychalcone is found in Humulus lupulus . This could make 2',4,4'-trihydroxy-6'-methoxy-3',5'-diprenylchalcone a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061308132D          

 31 32  0  0  0  0            999 V2000
   -7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    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
   -5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 11  8  1  0  0  0  0
 12  9  2  0  0  0  0
 13  6  1  0  0  0  0
 14  7  1  0  0  0  0
 15 10  2  0  0  0  0
 16  1  1  0  0  0  0
 16  2  1  0  0  0  0
 16  6  2  0  0  0  0
 17  3  1  0  0  0  0
 17  4  1  0  0  0  0
 17  7  2  0  0  0  0
 18  8  2  0  0  0  0
 18  9  1  0  0  0  0
 18 10  1  0  0  0  0
 19 11  2  0  0  0  0
 19 12  1  0  0  0  0
 20 13  1  0  0  0  0
 21 14  1  0  0  0  0
 22 15  1  0  0  0  0
 23 22  1  0  0  0  0
 24 20  2  0  0  0  0
 24 21  1  0  0  0  0
 25 20  1  0  0  0  0
 25 23  2  0  0  0  0
 26 21  2  0  0  0  0
 26 23  1  0  0  0  0
 27 19  1  0  0  0  0
 28 22  2  0  0  0  0
 29 24  1  0  0  0  0
 30 25  1  0  0  0  0
 31  5  1  0  0  0  0
 31 26  1  0  0  0  0
M  END

     RDKit          3D

 61 62  0  0  0  0  0  0  0  0999 V2000
   -0.1745   -3.4271    1.8306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3995   -2.7207    0.6053 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6983   -1.3509    0.6579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9709   -0.8758    0.7194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1175   -1.8356    0.6667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3828   -2.2512   -0.7382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4438   -3.5238   -1.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2598   -4.5717   -0.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7034   -3.9259   -2.4449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2433    0.4612    0.7784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5187    0.9447    0.8396 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2045    1.4008    0.7767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5194    2.8537    0.8364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9402    3.3015   -0.5063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0540    3.9247   -0.7643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3407    4.3129   -2.1873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0021    4.2613    0.3297 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0836    0.9146    0.7117 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0926    1.8547    0.7079 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3692   -0.4272    0.6518 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6954   -0.9582    0.5605 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8797   -2.2372    0.5044 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8996   -0.1701    0.5226 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0897   -0.7650    0.4364 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3470   -0.0278    0.3936 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5306   -0.7624    0.3069 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7401   -0.1225    0.2615 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8157    1.2585    0.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0432    1.8972    0.2535 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6433    1.9691    0.3854 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3902    1.3469    0.4338 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2148   -2.7576    2.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5433   -4.2805    1.6683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0852   -3.8966    2.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8372   -2.7356    1.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0064   -1.4242    1.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5274   -1.4929   -1.5217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6075   -5.5751   -0.3985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2118   -4.7277    0.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8649   -4.4158    0.8979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6062   -4.5654   -2.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8446   -3.0286   -3.0781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8139   -4.4678   -2.8822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3333    0.4096    0.8373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7612    3.4765    1.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4613    2.9505    1.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2369    3.0761   -1.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6252    5.0748   -2.5267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1745    3.3681   -2.7779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3887    4.6089   -2.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4814    4.6473    1.2302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6210    5.1125   -0.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6371    3.3774    0.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9753    2.8332    0.7389 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9050    0.9004    0.5600 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1055   -1.8449    0.3975 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4556   -1.8315    0.2779 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6540   -0.7182    0.1936 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4245    2.1471   -0.6403 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6935    3.0575    0.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.9741    0.5001 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  3
  7  8  1  0
  7  9  1  0
  4 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  3
 15 16  1  0
 15 17  1  0
 12 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 28 30  1  0
 30 31  2  0
 20  3  1  0
 31 25  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  0
  8 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  0
  9 42  1  0
  9 43  1  0
 11 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  0
 16 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
 17 52  1  0
 17 53  1  0
 19 54  1  0
 23 55  1  0
 24 56  1  0
 26 57  1  0
 27 58  1  0
 29 59  1  0
 30 60  1  0
 31 61  1  0
M  END


  Mrv0541 05061308132D          

 31 32  0  0  0  0            999 V2000
   -7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    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
   -5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 11  8  1  0  0  0  0
 12  9  2  0  0  0  0
 13  6  1  0  0  0  0
 14  7  1  0  0  0  0
 15 10  2  0  0  0  0
 16  1  1  0  0  0  0
 16  2  1  0  0  0  0
 16  6  2  0  0  0  0
 17  3  1  0  0  0  0
 17  4  1  0  0  0  0
 17  7  2  0  0  0  0
 18  8  2  0  0  0  0
 18  9  1  0  0  0  0
 18 10  1  0  0  0  0
 19 11  2  0  0  0  0
 19 12  1  0  0  0  0
 20 13  1  0  0  0  0
 21 14  1  0  0  0  0
 22 15  1  0  0  0  0
 23 22  1  0  0  0  0
 24 20  2  0  0  0  0
 24 21  1  0  0  0  0
 25 20  1  0  0  0  0
 25 23  2  0  0  0  0
 26 21  2  0  0  0  0
 26 23  1  0  0  0  0
 27 19  1  0  0  0  0
 28 22  2  0  0  0  0
 29 24  1  0  0  0  0
 30 25  1  0  0  0  0
 31  5  1  0  0  0  0
 31 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0060669

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C26H30O5/c1-16(2)6-13-20-24(29)21(14-7-17(3)4)26(31-5)23(25(20)30)22(28)15-10-18-8-11-19(27)12-9-18/h6-12,15,27,29-30H,13-14H2,1-5H3/b15-10+

> <INCHI_KEY>
HOTYOZVURUOVTK-XNTDXEJSSA-N

> <FORMULA>
C26H30O5

> <MOLECULAR_WEIGHT>
422.5134

> <EXACT_MASS>
422.20932407

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
48.568455865362985

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-1-[2,4-dihydroxy-6-methoxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one

> <ALOGPS_LOGP>
4.90

> <JCHEM_LOGP>
6.929092077000001

> <ALOGPS_LOGS>
-5.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.6687481695962

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.520047208464921

> <JCHEM_PKA_STRONGEST_BASIC>
-4.906696233683875

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
127.76849999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.58e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5'-prenylxanthohumol

> <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     -13.337   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -12.003   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.336  -5.390   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      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -10.669   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001   6.930   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      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -9.336   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -12.003   2.310   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      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.667  10.780   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -6.668   3.850   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
CONECT    1   16                                                            
CONECT    2   16                                                            
CONECT    3   17                                                            
CONECT    4   17                                                            
CONECT    5   31                                                            
CONECT    6   13   16                                                       
CONECT    7   14   17                                                       
CONECT    8   11   18                                                       
CONECT    9   12   18                                                       
CONECT   10   15   18                                                       
CONECT   11    8   19                                                       
CONECT   12    9   19                                                       
CONECT   13    6   20                                                       
CONECT   14    7   21                                                       
CONECT   15   10   22                                                       
CONECT   16    1    2    6                                                  
CONECT   17    3    4    7                                                  
CONECT   18    8    9   10                                                  
CONECT   19   11   12   27                                                  
CONECT   20   13   24   25                                                  
CONECT   21   14   24   26                                                  
CONECT   22   15   23   28                                                  
CONECT   23   22   25   26                                                  
CONECT   24   20   21   29                                                  
CONECT   25   20   23   30                                                  
CONECT   26   21   23   31                                                  
CONECT   27   19                                                            
CONECT   28   22                                                            
CONECT   29   24                                                            
CONECT   30   25                                                            
CONECT   31    5   26                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END

View in JSmol

Synonyms

Value	Source
5'-Prenylxanthohumol	HMDB
1-(2-Allyl-4-pentenoyl)-3-cyclohexyl-urea	HMDB
1-(2-Allyl-4-pentenoyl)-3-cyclohexylurea	HMDB
3',5'-Diprenyl-4,2',4'-trihydroxy-6-methoxychalcone	HMDB
Cyclohexylureide OF diallylacetic acid	HMDB

Chemical Formula

C₂₆H₃₀O₅

Average Mass

422.5134 Da

Monoisotopic Mass

422.20932 Da

IUPAC Name

(2E)-1-[2,4-dihydroxy-6-methoxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one

Traditional Name

5'-prenylxanthohumol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C26H30O5/c1-16(2)6-13-20-24(29)21(14-7-17(3)4)26(31-5)23(25(20)30)22(28)15-10-18-8-11-19(27)12-9-18/h6-12,15,27,29-30H,13-14H2,1-5H3/b15-10+

InChI Key

HOTYOZVURUOVTK-XNTDXEJSSA-N

Experimental Spectra

Not Available

Predicted Spectra

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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Humulus lupulus	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-prenylated chalcones. These are chalcones featuring a C5-isoprenoid unit at the 3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

3-prenylated chalcones

Alternative Parents

Substituents

3-prenylated chalcone
2'-hydroxychalcone
Cinnamylphenol
Hydroxycinnamic acid or derivatives
Methoxyphenol
Phenoxy compound
Phenol ether
Resorcinol
Styrene
Anisole
Methoxybenzene
Benzoyl
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
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 (LMPK12120296 )

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	4.9	ALOGPS
logP	6.93	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	7.52	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	8	ChemAxon
Refractivity	127.77 m³·mol⁻¹	ChemAxon
Polarizability	48.57 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

HMDB0035066

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013690

KNApSAcK ID

C00014473

Chemspider ID

10361526

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23250008

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3',5'-Diprenyl-4,2',4'-trihydroxy-6-methoxychalcone (NP0060669)

MOL for NP0060669 (3',5'-Diprenyl-4,2',4'-trihydroxy-6-methoxychalcone)

3D MOL for NP0060669 (3',5'-Diprenyl-4,2',4'-trihydroxy-6-methoxychalcone)

3D SDF for NP0060669 (3',5'-Diprenyl-4,2',4'-trihydroxy-6-methoxychalcone)

3D-SDF for NP0060669 (3',5'-Diprenyl-4,2',4'-trihydroxy-6-methoxychalcone)

PDB for NP0060669 (3',5'-Diprenyl-4,2',4'-trihydroxy-6-methoxychalcone)

3D PDB for NP0060669 (3',5'-Diprenyl-4,2',4'-trihydroxy-6-methoxychalcone)

SMILES for NP0060669 (3',5'-Diprenyl-4,2',4'-trihydroxy-6-methoxychalcone)

INCHI for NP0060669 (3',5'-Diprenyl-4,2',4'-trihydroxy-6-methoxychalcone)

Structure for NP0060669 (3',5'-Diprenyl-4,2',4'-trihydroxy-6-methoxychalcone)

3D Structure for NP0060669 (3',5'-Diprenyl-4,2',4'-trihydroxy-6-methoxychalcone)