NP-MRD: Showing NP-Card for Chrysophanol 8-glucoside (NP0051598)

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Record Information

Version

2.0

Created at

2022-04-27 22:54:15 UTC

Updated at

2022-04-27 22:54:15 UTC

NP-MRD ID

NP0051598

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Chrysophanol 8-glucoside

Description

Chrysophanol 8-O-beta-D-glucoside, also known as CP-8-O-GLC, 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. Thus, chrysophanol 8-O-beta-D-glucoside is considered to be an aromatic polyketide. Chrysophanol 8-glucoside is found in Aloe castellorum, Cassia fistula, Kniphofia ensifolia, Picramnia latifolia, Rheum australe, Rheum, Rheum moorcroftianum , Rheum palmatum, Rheum rhaponticum, Rumex nepalensis, Rumex patientia, Rumex spp., Selaginella delicatula and Woodifordia fruticosa. Chrysophanol 8-glucoside was first documented in 2013 (PMID: 23730837). Based on a literature review very few articles have been published on chrysophanol 8-O-beta-D-glucoside (PMID: 27335308).

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652304282200542D          

 30 33  0  0  1  0            999 V2000
    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
    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
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 O   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
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   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
    1.4289    0.0000    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
    2.1434   -1.2375    0.0000 O   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 O   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
  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  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 12 14  1  1  0  0  0
 14 15  1  0  0  0  0
 11 16  1  6  0  0  0
 10 17  1  1  0  0  0
  9 18  1  6  0  0  0
  5 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
  4 23  1  0  0  0  0
 23 24  2  0  0  0  0
 22 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
 21 28  1  0  0  0  0
 28 29  1  0  0  0  0
 26 30  1  0  0  0  0
M  END

     RDKit          3D

 50 53  0  0  0  0  0  0  0  0999 V2000
    7.4184    0.8910    1.2051 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9594    0.6984    0.9712 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0305    1.2640    1.8215 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6808    1.0917    1.6136 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7887    1.6758    2.4896 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2242    0.3423    0.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1291   -0.2342   -0.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4674   -0.0401   -0.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6296   -1.0201   -1.4503 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4463   -1.5529   -2.2495 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2025   -1.2141   -1.6873 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7366   -1.9644   -2.7619 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3804   -2.1261   -2.9541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5392   -1.5552   -2.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0901   -0.8173   -1.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8760   -0.1917   -0.1065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2626   -0.2265   -0.1135 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8242    1.0557   -0.2226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1216    0.9201   -0.7002 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8909    2.2063   -0.6620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9922    2.7026    0.6349 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8851   -0.0954    0.1268 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9717   -1.2699   -0.6042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1994   -0.3768    1.4230 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2075    0.7076    2.2919 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8109   -0.9048    1.1579 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9119   -2.2812    0.9762 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2956   -0.6399   -0.8252 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7867    0.1468    0.3014 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9589    0.6659    1.0808 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6352    1.8582    1.6972 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8932    0.8401    0.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8250    0.0190    1.7627 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138    1.8528    2.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1435    2.2162    3.2629 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1801   -0.4962   -0.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4905   -2.3885   -3.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0260   -2.7008   -3.7773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5984   -1.6787   -2.2425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7057   -0.8046   -0.9386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0701    0.5978   -1.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5208    2.9628   -1.3683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9359    1.9688   -0.9819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8978    2.6079    1.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9341    0.2463    0.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5169   -1.1210   -1.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7819   -1.1934    1.9313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4989    0.6795    2.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1254   -0.7124    2.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5730   -2.6113    1.6445 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  8  2  0
  8  7  1  0
  7  6  2  0
  6  4  1  0
  4  5  1  0
  4  3  2  0
  6 29  1  0
 29 30  2  0
 29 28  1  0
 28 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 12 11  2  0
 11  9  1  0
  9 10  2  0
  3  2  1  0
 11 28  1  0
  9  7  1  0
 26 17  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  8 36  1  0
  5 35  1  0
  3 34  1  0
 17 40  1  6
 19 41  1  6
 20 42  1  0
 20 43  1  0
 21 44  1  0
 22 45  1  1
 23 46  1  0
 24 47  1  1
 25 48  1  0
 26 49  1  1
 27 50  1  0
 14 39  1  0
 13 38  1  0
 12 37  1  0
M  END

  Mrv1652304282200542D          

 30 33  0  0  1  0            999 V2000
    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
    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
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 O   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
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   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
    1.4289    0.0000    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
    2.1434   -1.2375    0.0000 O   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 O   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
  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  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 12 14  1  1  0  0  0
 14 15  1  0  0  0  0
 11 16  1  6  0  0  0
 10 17  1  1  0  0  0
  9 18  1  6  0  0  0
  5 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
  4 23  1  0  0  0  0
 23 24  2  0  0  0  0
 22 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
 21 28  1  0  0  0  0
 28 29  1  0  0  0  0
 26 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051598

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC2=C(C(O)=C1)C(=O)C1=C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C=CC=C1C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O9/c1-8-5-10-14(11(23)6-8)18(26)15-9(16(10)24)3-2-4-12(15)29-21-20(28)19(27)17(25)13(7-22)30-21/h2-6,13,17,19-23,25,27-28H,7H2,1H3/t13-,17-,19+,20-,21-/m1/s1

> <INCHI_KEY>
WMMOMSNMMDMSRB-JNHRPPPUSA-N

> <FORMULA>
C21H20O9

> <MOLECULAR_WEIGHT>
416.382

> <EXACT_MASS>
416.110732224

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
40.83957014184501

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-hydroxy-3-methyl-8-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dihydroanthracene-9,10-dione

> <ALOGPS_LOGP>
0.63

> <JCHEM_LOGP>
1.2069287273333331

> <ALOGPS_LOGS>
-2.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.20015864465172

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.292998886973361

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923462446413

> <JCHEM_POLAR_SURFACE_AREA>
153.75

> <JCHEM_REFRACTIVITY>
102.29839999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.85e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
chrysophanol 8-glucoside

> <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       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      13.337   4.620   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      12.003   6.930   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       9.336   8.470   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.668   6.930   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   23                                                  
CONECT    5    4    6   19                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10   18                                                  
CONECT   10    9   11   17                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12    8                                                       
CONECT   14   12   15                                                       
CONECT   15   14                                                            
CONECT   16   11                                                            
CONECT   17   10                                                            
CONECT   18    9                                                            
CONECT   19    5   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   28                                                  
CONECT   22   21   23   25                                                  
CONECT   23   22    4   24                                                  
CONECT   24   23                                                            
CONECT   25   22   26                                                       
CONECT   26   25   27   30                                                  
CONECT   27   26   28                                                       
CONECT   28   27   21   29                                                  
CONECT   29   28                                                            
CONECT   30   26                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
8-Hydroxy-6-methyl-9,10-dioxo-9,10-dihydroanthracen-1-yl beta-D-glucopyranoside	ChEBI
Chrysophanol 8-glucoside	ChEBI
8-Hydroxy-6-methyl-9,10-dioxo-9,10-dihydroanthracen-1-yl b-D-glucopyranoside	Generator
8-Hydroxy-6-methyl-9,10-dioxo-9,10-dihydroanthracen-1-yl β-D-glucopyranoside	Generator
Chrysophanol 8-O-b-D-glucoside	Generator
Chrysophanol 8-O-β-D-glucoside	Generator
CP-8-O-GLC	MeSH
Chrysophanol 8-O-glucoside	MeSH
Chrysophanol-8-O-glucoside	MeSH

Chemical Formula

C₂₁H₂₀O₉

Average Mass

416.3820 Da

Monoisotopic Mass

416.11073 Da

IUPAC Name

1-hydroxy-3-methyl-8-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dihydroanthracene-9,10-dione

Traditional Name

chrysophanol 8-glucoside

CAS Registry Number

Not Available

SMILES

CC1=CC2=C(C(O)=C1)C(=O)C1=C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C=CC=C1C2=O

InChI Identifier

InChI=1S/C21H20O9/c1-8-5-10-14(11(23)6-8)18(26)15-9(16(10)24)3-2-4-12(15)29-21-20(28)19(27)17(25)13(7-22)30-21/h2-6,13,17,19-23,25,27-28H,7H2,1H3/t13-,17-,19+,20-,21-/m1/s1

InChI Key

WMMOMSNMMDMSRB-JNHRPPPUSA-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
Aloe castellorum	LOTUS Database	35616633
Cassia fistula	LOTUS Database	35616633
Kniphofia ensifolia	LOTUS Database	35616633
Picramnia latifolia	LOTUS Database	35616633
Rheum australe	LOTUS Database	35616633
Rheum L.	-	KNApSAcK
Rheum moorcroftianum	Plant	KNApSAcK
Rheum palmatum	LOTUS Database	35616633
Rheum rhaponticum	LOTUS Database	35616633
Rumex nepalensis	LOTUS Database	35616633
Rumex patientia	LOTUS Database	35616633
Rumex spp.	Plant	KNApSAcK
Selaginella delicatula	LOTUS Database	35616633
Woodifordia fruticosa	-	KNApSAcK

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

9,10-anthraquinone
Anthraquinone
Phenolic glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monosaccharide
Oxane
Vinylogous acid
Ketone
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Primary alcohol
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:3688 )
Anthracenes and phenanthrenes (C10316 )
Anthraquinone type (C10316 )
Anthracenes and phenanthrenes (LMPK13040007 )

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	0.63	ALOGPS
logP	1.21	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	8.29	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	153.75 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	102.3 m³·mol⁻¹	ChemAxon
Polarizability	40.84 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

C00002807

Chemspider ID

391079

KEGG Compound ID

C10316

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442731

PDB ID

Not Available

ChEBI ID

3688

Good Scents ID

Not Available

References

General References

Chen T, Li H, Zou D, Liu Y, Chen C, Zhou G, Li Y: Separation of three anthraquinone glycosides including two isomers by preparative high-performance liquid chromatography and high-speed countercurrent chromatography from Rheum tanguticum Maxim. ex Balf. J Sep Sci. 2016 Aug;39(16):3105-12. doi: 10.1002/jssc.201600487. Epub 2016 Jul 18. [PubMed:27335308 ]
Chen Y, Zhu J: Anti-HBV effect of individual traditional Chinese herbal medicine in vitro and in vivo: an analytic review. J Viral Hepat. 2013 Jul;20(7):445-52. doi: 10.1111/jvh.12112. [PubMed:23730837 ]

Showing NP-Card for Chrysophanol 8-glucoside (NP0051598)

MOL for NP0051598 (Chrysophanol 8-glucoside)

3D MOL for NP0051598 (Chrysophanol 8-glucoside)

3D SDF for NP0051598 (Chrysophanol 8-glucoside)

3D-SDF for NP0051598 (Chrysophanol 8-glucoside)

PDB for NP0051598 (Chrysophanol 8-glucoside)

3D PDB for NP0051598 (Chrysophanol 8-glucoside)

SMILES for NP0051598 (Chrysophanol 8-glucoside)

INCHI for NP0051598 (Chrysophanol 8-glucoside)

Structure for NP0051598 (Chrysophanol 8-glucoside)

3D Structure for NP0051598 (Chrysophanol 8-glucoside)