NP-MRD: Showing NP-Card for Knipholone (NP0051618)

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Record Information

Version

2.0

Created at

2022-04-27 22:55:18 UTC

Updated at

2022-04-27 22:55:18 UTC

NP-MRD ID

NP0051618

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Knipholone

Description

Knipholone belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone. Knipholone is an extremely weak basic (essentially neutral) compound (based on its pKa). Knipholone is found in Bulbine abyssinica, Bulbine capitata, Bulbine frutescens, Bulbine latifolia, Bulbine narcissifolia, Kniphofia foliosa , Kniphofia insignis and Senna didymobotrya. Knipholone was first documented in 1999 (PMID: 10630123). An anthraquinone that is anthracene-9,10-dione substituted by hydroxy groups at positions 4 and 6, a methyl group at position 2 and a 3-acetyl-2,6-dihydroxy-4-methoxyphenyl group at position 1 (PMID: 16716917) (PMID: 17388630) (PMID: 18663391) (PMID: 19345716).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251512362D          

 32 35  0  0  0  0            999 V2000
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    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
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   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
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    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
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 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
    2.1434   -1.2375    0.0000 C   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
    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
    3.5724   -0.4125    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
    5.0013   -0.4125    0.0000 O   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
    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
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0573   -3.5549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 14 32  1  0  0  0  0
 20 32  2  0  0  0  0
M  END

     RDKit          3D

 50 53  0  0  0  0  0  0  0  0999 V2000
   -4.2764    2.4364   -3.0218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0369    1.3180   -2.2372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8135    0.8273   -1.8688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6425    1.4059   -2.2460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4087    0.9176   -1.8789 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7614    1.6098   -2.3352 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3523   -0.1764   -1.1159 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9219   -0.7312   -0.7023 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5188   -1.6750   -1.5144 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9015   -2.1330   -2.7838 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7278   -2.1674   -1.0723 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3151   -1.7492    0.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5303   -2.2597    0.5303 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6707   -0.8015    0.8809 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4561   -0.2714    0.4890 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7826    0.7323    1.3150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3356    1.1635    0.8706 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3777    1.1763    2.5418 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6841    2.1193    3.2594 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2350    2.5625    4.4422 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4371    2.0616    4.8649 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1645    1.0980    4.1499 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3518    0.6535    4.6412 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6098    0.6573    2.9670 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2808   -0.3405    2.1470 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3800   -0.8032    2.5269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5201   -0.8313   -0.6854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3570   -1.9523    0.0987 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7464   -0.3334   -1.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9903   -0.9233   -0.6748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2497   -2.1033    0.1428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0683   -0.3272   -1.1143 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4864    2.6111   -3.7977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2280    3.3396   -2.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2479    2.4511   -3.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7015    2.2949   -2.8662 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6073    2.4045   -2.8919 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1109   -2.8818   -2.6505 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6800   -2.6496   -3.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5818   -1.2767   -3.4312 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2099   -2.9180   -1.7107 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9912   -2.9553   -0.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2536    2.4979    2.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6808    3.3137    5.0122 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8793    2.3992    5.7878 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0435    0.0445    4.4128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9273   -2.5485    0.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9375   -1.9948    1.1968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4007   -2.2438    0.2563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9109   -3.0477   -0.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7 27  1  0
 27 28  1  0
 27 29  2  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  2  0
 29  3  1  0
 15  8  1  0
 24 18  1  0
 25 14  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  6 37  1  0
 28 47  1  0
 31 48  1  0
 31 49  1  0
 31 50  1  0
 10 38  1  0
 10 39  1  0
 10 40  1  0
 11 41  1  0
 13 42  1  0
 19 43  1  0
 20 44  1  0
 21 45  1  0
 23 46  1  0
M  END


  Mrv1533004251512362D          

 32 35  0  0  0  0            999 V2000
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    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
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   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
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    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
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 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
    2.1434   -1.2375    0.0000 C   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
    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
    3.5724   -0.4125    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
    5.0013   -0.4125    0.0000 O   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
    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
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0573   -3.5549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 14 32  1  0  0  0  0
 20 32  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0051618

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C(C(O)=C1C(C)=O)C1=C(C)C=C(O)C2=C1C(=O)C1=CC=CC(O)=C1C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H18O8/c1-9-7-13(27)20-21(22(29)11-5-4-6-12(26)18(11)24(20)31)16(9)19-14(28)8-15(32-3)17(10(2)25)23(19)30/h4-8,26-28,30H,1-3H3

> <INCHI_KEY>
DUENHQWYLVQDQK-UHFFFAOYSA-N

> <FORMULA>
C24H18O8

> <MOLECULAR_WEIGHT>
434.4

> <EXACT_MASS>
434.10016754

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
43.05393847492053

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(3-acetyl-2,6-dihydroxy-4-methoxyphenyl)-4,5-dihydroxy-2-methyl-9,10-dihydroanthracene-9,10-dione

> <ALOGPS_LOGP>
3.47

> <JCHEM_LOGP>
5.2150677923333335

> <ALOGPS_LOGS>
-4.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.92348182360957

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.134405019520025

> <JCHEM_PKA_STRONGEST_BASIC>
-4.890219378308258

> <JCHEM_POLAR_SURFACE_AREA>
141.36

> <JCHEM_REFRACTIVITY>
116.11799999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.59e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
knipholone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.001 -11.550   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.668 -11.550   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.668  -0.770   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  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+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       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       7.574  -6.636   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   14                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    3   11                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    7   15   32                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   32                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   29                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   23   30                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   14   20                                                  
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
(+)-m-Knipholone	ChEMBL

Chemical Formula

C₂₄H₁₈O₈

Average Mass

434.4000 Da

Monoisotopic Mass

434.10017 Da

IUPAC Name

1-(3-acetyl-2,6-dihydroxy-4-methoxyphenyl)-4,5-dihydroxy-2-methyl-9,10-dihydroanthracene-9,10-dione

Traditional Name

knipholone

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C(C(O)=C1C(C)=O)C1=C(C)C=C(O)C2=C1C(=O)C1=CC=CC(O)=C1C2=O

InChI Identifier

InChI=1S/C24H18O8/c1-9-7-13(27)20-21(22(29)11-5-4-6-12(26)18(11)24(20)31)16(9)19-14(28)8-15(32-3)17(10(2)25)23(19)30/h4-8,26-28,30H,1-3H3

InChI Key

DUENHQWYLVQDQK-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
Bulbine abyssinica	LOTUS Database	35616633
Bulbine capitata	Plant	KNApSAcK
Bulbine frutescens	LOTUS Database	35616633
Bulbine latifolia	LOTUS Database	35616633
Bulbine narcissifolia	Plant	KNApSAcK
Kniphofia foliosa	Plant	KNApSAcK
Kniphofia insignis	LOTUS Database	35616633
Senna didymobotrya	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Anthraquinone
9,10-anthraquinone
Alkyl-phenylketone
Methoxyphenol
Acetophenone
Phenylketone
Phenoxy compound
Benzoyl
Anisole
Methoxybenzene
Aryl alkyl ketone
Aryl ketone
Resorcinol
Phenol ether
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Ether
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

polyphenol (CHEBI:6141 )
methyl ketone (CHEBI:6141 )
aromatic ketone (CHEBI:6141 )
methoxybenzene (CHEBI:6141 )
anthraquinone (CHEBI:6141 )
Anthraquinone type (C10365 )

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	3.47	ALOGPS
logP	5.22	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	7.13	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	141.36 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	116.12 m³·mol⁻¹	ChemAxon
Polarizability	43.05 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002834

Chemspider ID

Not Available

KEGG Compound ID

C10365

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Knipholone

METLIN ID

Not Available

PubChem Compound

442753

PDB ID

Not Available

ChEBI ID

6141

Good Scents ID

Not Available

References

General References

Bringmann G, Menche D, Bezabih M, Abegaz BM, Kaminsky R: Antiplasmodial activity of knipholone and related natural phenylanthraquinones. Planta Med. 1999 Dec;65(8):757-8. doi: 10.1055/s-2006-960859. [PubMed:10630123 ]
Wube AA, Bucar F, Asres K, Gibbons S, Adams M, Streit B, Bodensieck A, Bauer R: Knipholone, a selective inhibitor of leukotriene metabolism. Phytomedicine. 2006 Jun;13(6):452-6. doi: 10.1016/j.phymed.2005.01.012. Epub 2005 Sep 19. [PubMed:16716917 ]
Bringmann G, Noll TF, Gulder T, Dreyer M, Grune M, Moskau D: Polyketide folding in higher plants: biosynthesis of the phenylanthraquinone knipholone. J Org Chem. 2007 Apr 27;72(9):3247-52. doi: 10.1021/jo062566x. Epub 2007 Mar 28. [PubMed:17388630 ]
Bringmann G, Mutanyatta-Comar J, Knauer M, Abegaz BM: Knipholone and related 4-phenylanthraquinones: structurally, pharmacologically, and biosynthetically remarkable natural products. Nat Prod Rep. 2008 Aug;25(4):696-718. doi: 10.1039/b803784c. Epub 2008 Jun 23. [PubMed:18663391 ]
Habtemariam S, Dagne E: Prooxidant action of knipholone anthrone: copper dependent reactive oxygen species generation and DNA damage. Food Chem Toxicol. 2009 Jul;47(7):1490-4. doi: 10.1016/j.fct.2009.03.032. Epub 2009 Apr 5. [PubMed:19345716 ]

Showing NP-Card for Knipholone (NP0051618)

MOL for NP0051618 (Knipholone)

3D MOL for NP0051618 (Knipholone)

3D SDF for NP0051618 (Knipholone)

3D-SDF for NP0051618 (Knipholone)

PDB for NP0051618 (Knipholone)

3D PDB for NP0051618 (Knipholone)

SMILES for NP0051618 (Knipholone)

INCHI for NP0051618 (Knipholone)

Structure for NP0051618 (Knipholone)

3D Structure for NP0051618 (Knipholone)