NP-MRD: Showing NP-Card for Kushenol C (NP0053258)

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Record Information

Version

2.0

Created at

2022-04-27 23:58:46 UTC

Updated at

2022-04-27 23:58:46 UTC

NP-MRD ID

NP0053258

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Kushenol C

Description

Kushenol c belongs to the class of organic compounds known as 8-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 8-position. Thus, kushenol c is considered to be a flavonoid. Kushenol C is found in Gentiana macrophylla and Sophora flavescens . Kushenol C was first documented in 2018 (PMID: 29873272). Based on a literature review a small amount of articles have been published on Kushenol c (PMID: 30872054) (PMID: 31001351) (PMID: 33804228) (PMID: 32290603).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282201582D          

 32 34  0  0  1  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  2  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
    0.0000    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
   -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
   -2.8579    0.8250    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
   -3.5724    1.2375    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 O   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
    2.8579    0.8250    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    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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    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    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
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  8 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
 14 16  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
  4 20  1  0  0  0  0
 20 21  2  0  0  0  0
 19 22  1  0  0  0  0
 18 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
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  0  0  0  0
 26 30  1  0  0  0  0
  3 31  1  0  0  0  0
  1 32  1  0  0  0  0
M  END

     RDKit          3D

 58 60  0  0  0  0  0  0  0  0999 V2000
   -1.7945   -1.1834   -1.4876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5425   -0.2962   -0.5006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7396    0.8846   -0.8962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1155   -0.5708    0.8127 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9605    0.6731    1.2149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8828    0.9475    0.1121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0005    2.0753   -0.5455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9982    2.1899   -1.6548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1863    3.2708   -0.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2144   -0.7948    1.9631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2942   -1.9111    1.9206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6879   -3.1499    2.4349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9351   -3.2945    3.0505 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1516   -4.2333    2.3386 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3915   -4.1511    1.7450 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2545   -5.2584    1.6428 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7752   -2.9291    1.2417 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0084   -2.8562    0.6631 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7829   -3.8327    0.5671 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4622   -1.6273    0.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7137   -1.5949   -0.4313 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6047   -0.5696    0.2458 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9459    0.7502   -0.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2660    1.8617    0.2975 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4731    3.1400   -0.1396 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3744    3.3984   -1.1495 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5988    4.6802   -1.6044 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0392    2.3443   -1.6864 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8194    1.0403   -1.2328 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5608    0.0797   -1.8816 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4106   -0.7257    0.8288 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9368   -1.8209    1.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4190   -1.0754   -2.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4026   -2.0778   -1.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2035    1.3946   -1.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5661    1.5851   -0.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2391    0.5248   -1.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9352   -1.3567    0.7479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5330    0.3268    2.1145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3133    1.4842    1.5300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5382    0.0980   -0.1767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5711    1.8128   -2.6124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8887    1.6126   -1.3934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2967    3.2468   -1.7873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8054    4.1833   -0.4295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3280    3.2978   -0.9182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8917    3.2833    0.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8334   -0.7490    2.8877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5763    0.1431    2.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1793   -4.2133    3.3846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1659   -5.1941    2.7435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9034   -6.1295    2.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2803   -2.4019   -0.4759 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5660    1.6483    1.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9501    3.9950    0.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3260    5.2653   -1.1775 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7507    2.5473   -2.4833 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2142    0.2127   -2.6072 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  9  1  0
  7  6  2  3
  6  5  1  0
  5  4  1  0
  4 10  1  0
 10 11  1  0
 11 32  2  0
 32 31  1  0
 31 22  1  0
 22 20  2  0
 20 21  1  0
 20 18  1  0
 18 19  2  0
 18 17  1  0
 17 15  2  0
 15 16  1  0
 15 14  1  0
 14 12  2  0
 12 13  1  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
 29 30  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  3
 12 11  1  0
 29 23  1  0
 17 32  1  0
  8 42  1  0
  8 43  1  0
  8 44  1  0
  9 45  1  0
  9 46  1  0
  9 47  1  0
  6 41  1  0
  5 39  1  0
  5 40  1  0
  4 38  1  6
 10 48  1  0
 10 49  1  0
 21 53  1  0
 16 52  1  0
 14 51  1  0
 13 50  1  0
 24 54  1  0
 25 55  1  0
 27 56  1  0
 28 57  1  0
 30 58  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  1 33  1  0
  1 34  1  0
M  END


  Mrv1652304282201582D          

 32 34  0  0  1  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  2  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
    0.0000    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
   -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
   -2.8579    0.8250    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
   -3.5724    1.2375    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 O   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
    2.8579    0.8250    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    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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    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    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
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  8 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
 14 16  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
  4 20  1  0  0  0  0
 20 21  2  0  0  0  0
 19 22  1  0  0  0  0
 18 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
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  0  0  0  0
 26 30  1  0  0  0  0
  3 31  1  0  0  0  0
  1 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0053258

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CC[C@H](CC1=C2OC(=C(O)C(=O)C2=C(O)C=C1O)C1=CC=C(O)C=C1O)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C25H26O7/c1-12(2)5-6-14(13(3)4)9-17-19(28)11-20(29)21-22(30)23(31)25(32-24(17)21)16-8-7-15(26)10-18(16)27/h5,7-8,10-11,14,26-29,31H,3,6,9H2,1-2,4H3/t14-/m1/s1

> <INCHI_KEY>
WAAPHYJTKSTXSX-CQSZACIVSA-N

> <FORMULA>
C25H26O7

> <MOLECULAR_WEIGHT>
438.476

> <EXACT_MASS>
438.167853177

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
45.315103794899535

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2,4-dihydroxyphenyl)-3,5,7-trihydroxy-8-[(2R)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-4H-chromen-4-one

> <ALOGPS_LOGP>
3.88

> <JCHEM_LOGP>
5.444964840000001

> <ALOGPS_LOGS>
-4.05

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.823360131591895

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.659628112870989

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8712279208824247

> <JCHEM_POLAR_SURFACE_AREA>
127.45000000000002

> <JCHEM_REFRACTIVITY>
123.78269999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.94e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
kushenol C

> <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       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335   1.540   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       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    6   32                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   31                                                  
CONECT    4    3    5   20                                                  
CONECT    5    4    6   17                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    8   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17    5   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20   22                                                  
CONECT   20   19    4   21                                                  
CONECT   21   20                                                            
CONECT   22   19                                                            
CONECT   23   18   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   30                                                  
CONECT   27   26   28                                                       
CONECT   28   27   23   29                                                  
CONECT   29   28                                                            
CONECT   30   26                                                            
CONECT   31    3                                                            
CONECT   32    1                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₆O₇

Average Mass

438.4760 Da

Monoisotopic Mass

438.16785 Da

IUPAC Name

2-(2,4-dihydroxyphenyl)-3,5,7-trihydroxy-8-[(2R)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-4H-chromen-4-one

Traditional Name

kushenol C

CAS Registry Number

Not Available

SMILES

CC(C)=CC[C@H](CC1=C2OC(=C(O)C(=O)C2=C(O)C=C1O)C1=CC=C(O)C=C1O)C(C)=C

InChI Identifier

InChI=1S/C25H26O7/c1-12(2)5-6-14(13(3)4)9-17-19(28)11-20(29)21-22(30)23(31)25(32-24(17)21)16-8-7-15(26)10-18(16)27/h5,7-8,10-11,14,26-29,31H,3,6,9H2,1-2,4H3/t14-/m1/s1

InChI Key

WAAPHYJTKSTXSX-CQSZACIVSA-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
Gentiana macrophylla	LOTUS Database	35616633
Sophora flavescens	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 8-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

8-prenylated flavones

Alternative Parents

Substituents

8-prenylated flavone
3-hydroxyflavone
Hydroxyflavonoid
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
3-hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
Bicyclic monoterpenoid
Aromatic monoterpenoid
Monoterpenoid
Resorcinol
1-hydroxy-2-unsubstituted benzenoid
Pyranone
1-hydroxy-4-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Organoheterocyclic compound
Oxacycle
Polyol
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12112514 )

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	3.88	ALOGPS
logP	5.44	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	6.66	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	127.45 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	123.78 m³·mol⁻¹	ChemAxon
Polarizability	45.32 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00005021

Chemspider ID

4587187

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5481237

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Song SS, Sun CP, Zhou JJ, Chu L: Flavonoids as human carboxylesterase 2 inhibitors: Inhibition potentials and molecular docking simulations. Int J Biol Macromol. 2019 Jun 15;131:201-208. doi: 10.1016/j.ijbiomac.2019.03.060. Epub 2019 Mar 11. [PubMed:30872054 ]
Yim D, Kim MJ, Shin Y, Lee SJ, Shin JG, Kim DH: Inhibition of Cytochrome P450 Activities by Sophora flavescens Extract and Its Prenylated Flavonoids in Human Liver Microsomes. Evid Based Complement Alternat Med. 2019 Mar 13;2019:2673769. doi: 10.1155/2019/2673769. eCollection 2019. [PubMed:31001351 ]
Cho BO, Kim JH, Che DN, Kang HJ, Shin JY, Hao S, Park JH, Wang F, Lee YJ, Jang SI: Kushenol C Prevents Tert-Butyl Hydroperoxide and Acetaminophen-Induced Liver Injury. Molecules. 2021 Mar 15;26(6). pii: molecules26061635. doi: 10.3390/molecules26061635. [PubMed:33804228 ]
Cho BO, Che DN, Kim JS, Kim JH, Shin JY, Kang HJ, Jang SI: In vitro Anti-Inflammatory and Anti-Oxidative Stress Activities of Kushenol C Isolated from the Roots of Sophora flavescens. Molecules. 2020 Apr 12;25(8). pii: molecules25081768. doi: 10.3390/molecules25081768. [PubMed:32290603 ]
Kim JH, Cho IS, So YK, Kim HH, Kim YH: Kushenol A and 8-prenylkaempferol, tyrosinase inhibitors, derived from Sophora flavescens. J Enzyme Inhib Med Chem. 2018 Dec;33(1):1048-1054. doi: 10.1080/14756366.2018.1477776. [PubMed:29873272 ]

Showing NP-Card for Kushenol C (NP0053258)

MOL for NP0053258 (Kushenol C)

3D MOL for NP0053258 (Kushenol C)

3D SDF for NP0053258 (Kushenol C)

3D-SDF for NP0053258 (Kushenol C)

PDB for NP0053258 (Kushenol C)

3D PDB for NP0053258 (Kushenol C)

SMILES for NP0053258 (Kushenol C)

INCHI for NP0053258 (Kushenol C)

Structure for NP0053258 (Kushenol C)

3D Structure for NP0053258 (Kushenol C)