NP-MRD: Showing NP-Card for 5,7,30 ,40 -tetrahydroxy-6,8-diprenylisoflavone (NP0331741)

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Record Information

Version

1.0

Created at

2023-08-01 08:00:31 UTC

Updated at

2024-04-19 09:50:05 UTC

NP-MRD ID

NP0331741

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,7,30 ,40 -tetrahydroxy-6,8-diprenylisoflavone

Description

6,8-Diprenylorobol 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, 6,8-diprenylorobol is considered to be a flavonoid. It was first documented in 2002 (PMID: 12127165). Based on a literature review a significant number of articles have been published on 6,8-diprenylorobol (PMID: 35052675) (PMID: 33382531) (PMID: 33312341) (PMID: 27649772) (PMID: 27584953).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282204192D          

 31 33  0  0  0  0            999 V2000
   -0.7145   -0.4125    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 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 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
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   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
    2.1434   -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
    2.8579   -1.6500    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
    4.2868   -1.6500    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
    3.5724   -2.8875    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
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    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
   -1.4289   -2.4750    0.0000 C   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
   -2.8579   -2.4750    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    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
  4 15  1  0  0  0  0
 15 16  2  0  0  0  0
 14 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 20 23  1  0  0  0  0
 19 24  1  0  0  0  0
  3 25  1  0  0  0  0
  2 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
  1 31  1  0  0  0  0
M  END

     RDKit          3D

 57 59  0  0  0  0  0  0  0  0999 V2000
   -4.4040    4.5543   -2.2801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9441    3.8895   -1.0059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9566    3.6148    0.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6690    3.5828   -0.8463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1793    2.9363    0.3710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4632    1.6578    0.1319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0376    0.4659   -0.1704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4089    0.4094   -0.2708 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3347   -0.6996   -0.3861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0276   -1.9689   -0.7027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6352   -2.6207    0.4782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2979   -3.8421    0.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2802   -4.6537    0.1460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9579   -4.4260    2.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0441   -0.6135   -0.2803 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7528   -1.7147   -0.4812 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0592   -1.7456   -0.4056 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7773   -0.6125   -0.1075 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2291   -0.6034   -0.0135 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0118   -1.2303   -0.9564 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3952   -1.2321   -0.8877 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0456   -0.5803    0.1684 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4249   -0.6203    0.1772 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2707    0.0446    1.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8731    0.6978    2.1654 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8869    0.0314    1.0168 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0327    0.5532    0.1053 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7077    1.5700    0.3743 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6738    0.5733    0.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0535    1.7218    0.2347 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5196    2.9266    0.5397 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8769    4.1172   -3.1481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1526    5.6251   -2.1688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4818    4.3651   -2.3880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9477    3.9831   -0.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0063    2.5357    0.2822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7038    4.1901    0.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9785    3.8205   -1.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5470    3.5704    1.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0519    2.6567    1.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9868   -0.3637   -0.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -2.6920   -1.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7705   -1.7658   -1.5024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3784   -2.0849    1.0449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2731   -4.2058    0.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2421   -5.6621    0.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5674   -4.7003   -0.9368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8471   -3.7134    2.9183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0184   -4.5716    1.8479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4733   -5.3780    2.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6081   -2.6555   -0.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4878   -1.7352   -1.7762 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9608   -1.7288   -1.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9753   -0.1876    0.8842 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8527    0.7358    2.2759 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2613    0.5234    1.7584 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4015    3.2557    0.6689 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 27  1  0
 27 28  2  0
 27 29  1  0
 29 30  2  0
 30 31  1  0
 18 19  1  0
 19 26  2  0
 26 24  1  0
 24 25  1  0
 24 22  2  0
 22 23  1  0
 22 21  1  0
 21 20  2  0
 30  6  1  0
 20 19  1  0
 29 15  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  8 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  0
 13 45  1  0
 13 46  1  0
 13 47  1  0
 14 48  1  0
 14 49  1  0
 14 50  1  0
 17 51  1  0
 31 57  1  0
 26 56  1  0
 25 55  1  0
 23 54  1  0
 21 53  1  0
 20 52  1  0
M  END


  Mrv1652304282204192D          

 31 33  0  0  0  0            999 V2000
   -0.7145   -0.4125    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 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 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
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   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
    2.1434   -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
    2.8579   -1.6500    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
    4.2868   -1.6500    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
    3.5724   -2.8875    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
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    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
   -1.4289   -2.4750    0.0000 C   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
   -2.8579   -2.4750    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    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
  4 15  1  0  0  0  0
 15 16  2  0  0  0  0
 14 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 20 23  1  0  0  0  0
 19 24  1  0  0  0  0
  3 25  1  0  0  0  0
  2 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
  1 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331741

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C25H26O6/c1-13(2)5-8-16-22(28)17(9-6-14(3)4)25-21(23(16)29)24(30)18(12-31-25)15-7-10-19(26)20(27)11-15/h5-7,10-12,26-29H,8-9H2,1-4H3

> <INCHI_KEY>
OAUIRSVJXOFAOO-UHFFFAOYSA-N

> <FORMULA>
C25H26O6

> <MOLECULAR_WEIGHT>
422.477

> <EXACT_MASS>
422.172938557

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
46.33736954476042

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
4.58

> <JCHEM_LOGP>
6.230441066666666

> <ALOGPS_LOGS>
-4.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.852686761537822

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.193493193250995

> <JCHEM_PKA_STRONGEST_BASIC>
-5.355057161215451

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
122.14939999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.93e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,8-diprenylorobol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334   3.850   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       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    6   31                                                  
CONECT    2    1    3   26                                                  
CONECT    3    2    4   25                                                  
CONECT    4    3    5   15                                                  
CONECT    5    4    6   12                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    5   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14    4   16                                                  
CONECT   16   15                                                            
CONECT   17   14   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
CONECT   23   20                                                            
CONECT   24   19                                                            
CONECT   25    3                                                            
CONECT   26    2   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31    1                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₆O₆

Average Mass

422.4770 Da

Monoisotopic Mass

422.17294 Da

IUPAC Name

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

Traditional Name

6,8-diprenylorobol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C25H26O6/c1-13(2)5-8-16-22(28)17(9-6-14(3)4)25-21(23(16)29)24(30)18(12-31-25)15-7-10-19(26)20(27)11-15/h5-7,10-12,26-29H,8-9H2,1-4H3

InChI Key

OAUIRSVJXOFAOO-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	[¹H, ] NMR Spectrum (2D, 500 MHz, C3D6O, experimental)	dongholee@korea.ac.kr	Not Available	Not Available	2023-08-01	View Spectrum

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

Not Available

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
Isoflavone
Hydroxyisoflavonoid
Chromone
Benzopyran
1-benzopyran
Catechol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Phenol
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Isoflavonoids (LMPK12050240 )

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	4.58	ALOGPS
logP	6.23	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	6.19	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	122.15 m³·mol⁻¹	ChemAxon
Polarizability	46.34 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

C00009524

Chemspider ID

20024572

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21148065

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Fukai T, Marumo A, Kaitou K, Kanda T, Terada S, Nomura T: Anti-Helicobacter pylori flavonoids from licorice extract. Life Sci. 2002 Aug 9;71(12):1449-63. doi: 10.1016/s0024-3205(02)01864-7. [PubMed:12127165 ]
Song J, Song G, Park S, Lim W: Inhibitory Effects of 6,8-Diprenylorobol on Endometriosis Progression in Humans by Disrupting Calcium Homeostasis and Mitochondrial Function. Antioxidants (Basel). 2022 Jan 17;11(1). pii: antiox11010171. doi: 10.3390/antiox11010171. [PubMed:35052675 ]
Choi YJ, Lee J, Ha SH, Lee HK, Lim HM, Yu SH, Lee CM, Nam MJ, Yang YH, Park K, Choi YS, Jang KY, Park SH: 6,8-Diprenylorobol induces apoptosis in human colon cancer cells via activation of intracellular reactive oxygen species and p53. Environ Toxicol. 2021 May;36(5):914-925. doi: 10.1002/tox.23093. Epub 2020 Dec 31. [PubMed:33382531 ]
Lee CM, Lee J, Jang SN, Shon JC, Wu Z, Park K, Liu KH, Park SH: 6,8-Diprenylorobol Induces Apoptosis in Human Hepatocellular Carcinoma Cells via Activation of FOXO3 and Inhibition of CYP2J2. Oxid Med Cell Longev. 2020 Nov 19;2020:8887251. doi: 10.1155/2020/8887251. eCollection 2020. [PubMed:33312341 ]
Tuan Anh HL, Tuan DT, Trang DT, Tai BH, Nhiem NX, Yen PH, Kiem PV, Minh CV, Duc TM, Kang HK, Kim YC, Kim YH: Prenylated isoflavones from Cudrania tricuspidata inhibit NO production in RAW 264.7 macrophages and suppress HL-60 cells proliferation. J Asian Nat Prod Res. 2017 May;19(5):510-518. doi: 10.1080/10286020.2016.1232253. Epub 2016 Sep 21. [PubMed:27649772 ]
Sun F, Li Q, Xu J: Chemical Composition of Roots Flemingia philippinensis and Their Inhibitory Kinetics on Aromatase. Chem Biodivers. 2017 Jan;14(1). doi: 10.1002/cbdv.201600193. Epub 2017 Jan 3. [PubMed:27584953 ]

Showing NP-Card for 5,7,30 ,40 -tetrahydroxy-6,8-diprenylisoflavone (NP0331741)

MOL for NP0331741 (5,7,30 ,40 -tetrahydroxy-6,8-diprenylisoflavone)

3D MOL for NP0331741 (5,7,30 ,40 -tetrahydroxy-6,8-diprenylisoflavone)

3D SDF for NP0331741 (5,7,30 ,40 -tetrahydroxy-6,8-diprenylisoflavone)

3D-SDF for NP0331741 (5,7,30 ,40 -tetrahydroxy-6,8-diprenylisoflavone)

PDB for NP0331741 (5,7,30 ,40 -tetrahydroxy-6,8-diprenylisoflavone)

3D PDB for NP0331741 (5,7,30 ,40 -tetrahydroxy-6,8-diprenylisoflavone)

SMILES for NP0331741 (5,7,30 ,40 -tetrahydroxy-6,8-diprenylisoflavone)

INCHI for NP0331741 (5,7,30 ,40 -tetrahydroxy-6,8-diprenylisoflavone)

Structure for NP0331741 (5,7,30 ,40 -tetrahydroxy-6,8-diprenylisoflavone)

3D Structure for NP0331741 (5,7,30 ,40 -tetrahydroxy-6,8-diprenylisoflavone)