NP-MRD: Showing NP-Card for 5,7,4'-Trihydroxy-6,8-diprenylisoflavone (NP0056602)

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Record Information

Version

2.0

Created at

2022-04-28 02:19:15 UTC

Updated at

2022-04-28 02:19:15 UTC

NP-MRD ID

NP0056602

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,7,4'-Trihydroxy-6,8-diprenylisoflavone

Description

5,7,4'-Trihydroxy-6,8-diprenylisoflavone, also known as 6,8-diisoprenyl-5,7,4'-trihydroxyisoflavone or 6,8-diprenylgenistein, belongs to the class of organic compounds known as 6-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 6-position. Thus, 5,7,4'-trihydroxy-6,8-diprenylisoflavone is considered to be a flavonoid lipid molecule. 5,7,4'-Trihydroxy-6,8-diprenylisoflavone is found in Erythrina senegalensis , Erythrina sigmoidea, Erythrina variegata , Erythrina vogelii, Euchresta horsfieldii , Euchresta japonica , Flemingia macrophylla, Flemingia philippinensis, Glycyrrhiza glabra , Glycyrrhiza inflata , Glycyrrhiza uralensis , Lupinus pilosus, Cudrania tricuspidata , Millettia pachycarpa and Derris scandens . 5,7,4'-Trihydroxy-6,8-diprenylisoflavone was first documented in 2006 (PMID: 16441081). 5,7,4'-Trihydroxy-6,8-diprenylisoflavone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304291919372D          

 30 32  0  0  0  0            999 V2000
   -1.4289   -2.4750    0.0000 C   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
    0.0000   -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 O   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
    1.4289    0.8250    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
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   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
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   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
    4.2868   -2.4750    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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  8 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  2  0  0  0  0
  5 21  1  0  0  0  0
 21 22  1  0  0  0  0
 17 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
  2 30  1  0  0  0  0
M  END

     RDKit          3D

 56 58  0  0  0  0  0  0  0  0999 V2000
   -5.1840   -2.4084   -0.2343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2245   -2.4029    0.8891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7576   -2.4352    2.3003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9238   -2.3672    0.7200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2588   -2.3233   -0.6001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2357   -1.2363   -0.6270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5047    0.0910   -0.7432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8306    0.5283   -0.8470 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5362    1.0617   -0.7677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8565    2.4828   -0.8889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3164    3.1404    0.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4415    3.7878    0.4181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3532    3.9151   -0.7324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8657    4.4570    1.7093 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7739    0.6499   -0.6677 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7419    1.5560   -0.6864 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0092    1.2551   -0.5958 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4201   -0.0362   -0.4743 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7931   -0.4326   -0.3685 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7356    0.1253   -1.2032 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0618   -0.2497   -1.1084 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4664   -1.1769   -0.1901 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8035   -1.5167   -0.1376 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5146   -1.7375    0.6503 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1841   -1.3716    0.5663 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4256   -1.0310   -0.4506 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7808   -2.2186   -0.3400 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0893   -0.7074   -0.5466 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1086   -1.6758   -0.5231 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3574   -3.0092   -0.4070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4971   -1.4122   -0.5675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0920   -2.9555    0.1510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7738   -3.0146   -1.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9598   -2.8072    2.9726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1073   -1.4196    2.5446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6086   -3.1646    2.2875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2952   -2.3699    1.6268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0419   -2.0515   -1.3598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8159   -3.2951   -0.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5546   -0.1503   -0.8393 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0447    3.0705   -1.2359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6224    2.6794   -1.6804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6761    3.0782    1.2335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1001    4.7519   -0.5500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8068    4.2734   -1.6396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9320    3.0057   -0.9393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9598    4.5755    1.7348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3720    5.4672    1.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5087    3.8838    2.5787 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7307    2.0596   -0.6192 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4834    0.8709   -1.9597 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7699    0.2197   -1.7904 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1687   -2.1965    0.5191 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8740   -2.4690    1.3664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5038   -1.8531    1.2561 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1725   -3.4907   -0.3284 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  3
 12 13  1  0
 12 14  1  0
  9 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  2  0
 29 30  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 29  6  1  0
 25 19  1  0
 28 15  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  8 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 13 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 14 49  1  0
 17 50  1  0
 30 56  1  0
 20 51  1  0
 21 52  1  0
 23 53  1  0
 24 54  1  0
 25 55  1  0
M  END


  Mrv1652304291919372D          

 30 32  0  0  0  0            999 V2000
   -1.4289   -2.4750    0.0000 C   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
    0.0000   -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 O   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
    1.4289    0.8250    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
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   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
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   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
    4.2868   -2.4750    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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  8 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  2  0  0  0  0
  5 21  1  0  0  0  0
 21 22  1  0  0  0  0
 17 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
  2 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0056602

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C(O)C(CC=C(C)C)=C2OC=C(C(=O)C2=C1O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H26O5/c1-14(2)5-11-18-22(27)19(12-6-15(3)4)25-21(23(18)28)24(29)20(13-30-25)16-7-9-17(26)10-8-16/h5-10,13,26-28H,11-12H2,1-4H3

> <INCHI_KEY>
UCHYSPNEUSDFQR-UHFFFAOYSA-N

> <FORMULA>
C25H26O5

> <MOLECULAR_WEIGHT>
406.478

> <EXACT_MASS>
406.178023937

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
45.37386173135975

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,7-dihydroxy-3-(4-hydroxyphenyl)-6,8-bis(3-methylbut-2-en-1-yl)-4H-chromen-4-one

> <ALOGPS_LOGP>
4.97

> <JCHEM_LOGP>
6.534006388333335

> <ALOGPS_LOGS>
-5.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.885391090301058

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.194589708070328

> <JCHEM_PKA_STRONGEST_BASIC>
-5.354958137399455

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
120.16849999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.15e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,8-diprenylgenistein

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-19         0                                  
HETATM    1  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   30                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   21                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    8   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   14   21                                                  
CONECT   21   20    5   22                                                  
CONECT   22   21                                                            
CONECT   23   17   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                                                       
CONECT   30    2                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Value	Source
6,8-Diisoprenyl-5,7,4'-trihydroxyisoflavone	ChEBI
6,8-Diprenylgenistein	ChEBI
8-(gamma,gamma-Dimethylallyl)-wighteone	ChEBI
8-Prenylwighteone	ChEBI
8-(g,g-Dimethylallyl)-wighteone	Generator
8-(Γ,γ-dimethylallyl)-wighteone	Generator

Chemical Formula

C₂₅H₂₆O₅

Average Mass

406.4780 Da

Monoisotopic Mass

406.17802 Da

IUPAC Name

5,7-dihydroxy-3-(4-hydroxyphenyl)-6,8-bis(3-methylbut-2-en-1-yl)-4H-chromen-4-one

Traditional Name

6,8-diprenylgenistein

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C(O)C(CC=C(C)C)=C2OC=C(C(=O)C2=C1O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C25H26O5/c1-14(2)5-11-18-22(27)19(12-6-15(3)4)25-21(23(18)28)24(29)20(13-30-25)16-7-9-17(26)10-8-16/h5-10,13,26-28H,11-12H2,1-4H3

InChI Key

UCHYSPNEUSDFQR-UHFFFAOYSA-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
Erythrina senegalensis	Plant	KNApSAcK
Erythrina sigmoidea	Plant	KNApSAcK
Erythrina variegata	Plant	KNApSAcK
Erythrina vogelii	Plant	KNApSAcK
Euchresta horsfieldii	Plant	KNApSAcK
Euchresta japonica	Plant	KNApSAcK
Flemingia macrophylla	LOTUS Database	35616633
Flemingia philippinensis	LOTUS Database	35616633
Glycyrrhiza glabra	Plant	KNApSAcK
Glycyrrhiza inflata	Plant	KNApSAcK
Glycyrrhiza uralensis	Plant	KNApSAcK
Lupinus pilosus	Plant	KNApSAcK
Maclura tricuspidata	Plant	KNApSAcK
Millettia pachycarpa	Plant	KNApSAcK
Solori scandens	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 6-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavans

Direct Parent

6-prenylated isoflavanones

Alternative Parents

Substituents

6-prenylated isoflavanone
Hydroxyisoflavonoid
Isoflavone
Chromone
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

7-hydroxyisoflavones (CHEBI:66263 )
Isoflavonoids (LMPK12050191 )

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	4.97	ALOGPS
logP	6.53	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	6.19	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	120.17 m³·mol⁻¹	ChemAxon
Polarizability	45.37 Å³	ChemAxon
Number of Rings	3	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

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

480783

PDB ID

Not Available

ChEBI ID

66263

Good Scents ID

Not Available

References

General References

He J, Chen L, Heber D, Shi W, Lu QY: Antibacterial compounds from Glycyrrhiza uralensis. J Nat Prod. 2006 Jan;69(1):121-4. doi: 10.1021/np058069d. [PubMed:16441081 ]

Showing NP-Card for 5,7,4'-Trihydroxy-6,8-diprenylisoflavone (NP0056602)

MOL for NP0056602 (5,7,4'-Trihydroxy-6,8-diprenylisoflavone)

3D MOL for NP0056602 (5,7,4'-Trihydroxy-6,8-diprenylisoflavone)

3D SDF for NP0056602 (5,7,4'-Trihydroxy-6,8-diprenylisoflavone)

3D-SDF for NP0056602 (5,7,4'-Trihydroxy-6,8-diprenylisoflavone)

PDB for NP0056602 (5,7,4'-Trihydroxy-6,8-diprenylisoflavone)

3D PDB for NP0056602 (5,7,4'-Trihydroxy-6,8-diprenylisoflavone)

SMILES for NP0056602 (5,7,4'-Trihydroxy-6,8-diprenylisoflavone)

INCHI for NP0056602 (5,7,4'-Trihydroxy-6,8-diprenylisoflavone)

Structure for NP0056602 (5,7,4'-Trihydroxy-6,8-diprenylisoflavone)

3D Structure for NP0056602 (5,7,4'-Trihydroxy-6,8-diprenylisoflavone)