NP-MRD: Showing NP-Card for [(2r,3s,4s,5r,6s)-6-[(4,7-dihydroxy-3-methyl-9,10-dioxoanthracen-2-yl)oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate (NP0268754)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-08 13:58:58 UTC

Updated at

2022-09-08 13:58:58 UTC

NP-MRD ID

NP0268754

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2r,3s,4s,5r,6s)-6-[(4,7-dihydroxy-3-methyl-9,10-dioxoanthracen-2-yl)oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate

Description

1,3,6-Trihydroxy-2-methyl-9,10-anthraquinone-3-O-(6'-O-acetyl)-beta-D-glucopyranoside, also known as 1,3,6-tmaqag, belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group. 1,3,6-Trihydroxy-2-methyl-9,10-anthraquinone-3-O-(6'-O-acetyl)-beta-D-glucopyranoside is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. [(2r,3s,4s,5r,6s)-6-[(4,7-dihydroxy-3-methyl-9,10-dioxoanthracen-2-yl)oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate is found in Rubia yunnanensis. Based on a literature review very few articles have been published on 1,3,6-trihydroxy-2-methyl-9,10-anthraquinone-3-O-(6'-O-acetyl)-beta-D-glucopyranoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082215582D          

 34 37  0  0  1  0            999 V2000
    7.8592   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  1  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
    4.2868    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
    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   -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
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    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
    1.4289   -0.0000    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 O   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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 20 26  1  0  0  0  0
 26 27  1  0  0  0  0
 12 27  1  0  0  0  0
 27 28  2  0  0  0  0
  8 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
  6 33  1  0  0  0  0
 33 34  1  6  0  0  0
M  END

     RDKit          3D

 56 59  0  0  0  0  0  0  0  0999 V2000
   -7.7395    0.7178    1.3465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2466    0.8925    1.4021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6854    1.0660    2.5018 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5057    0.8618    0.2567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0990    1.0167    0.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5770    0.9336   -1.2076 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2415    1.0782   -1.2769 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4392    0.0099   -0.9996 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8709    0.0226    0.2697 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4686    0.0507    0.5445 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4953    0.0710   -0.3579 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8207    0.0989    0.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1325    0.1068    1.3956 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1311    0.0870    2.3436 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3859    0.0937    3.6768 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8208    0.0594    1.8994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2611    0.0381    2.9399 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5477    0.1365    1.7661 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8881    0.1448    2.9601 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6020    0.1572    0.7313 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9379    0.1853    1.0918 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9247    0.2047    0.1254 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6198    0.1969   -1.2177 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6119    0.2163   -2.1910 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2894    0.1690   -1.5780 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2985    0.1495   -0.6084 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8881    0.1199   -0.9582 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5373    0.1114   -2.1491 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1153   -1.3334   -1.1947 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1994   -2.3209   -1.4766 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0247   -1.1507   -2.3992 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5094   -2.3548   -2.8819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1647   -0.2778   -1.8596 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0787    0.0160   -2.8521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0205   -0.2379    1.8050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2523    1.5186    1.9268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0952    0.7679    0.3028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5714    0.2998    0.8545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8670    2.0426    0.6074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0377    1.8206   -1.7408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6306    0.0267   -1.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2779    0.0653   -1.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1437    0.1102    4.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2793    1.0534    3.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0468   -0.7286    3.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2390   -0.1102    2.4482 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1700    0.1912    2.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9712    0.2266    0.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9517    1.1109   -2.5434 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0053    0.1620   -2.6250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7532   -1.6175   -0.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1746   -3.0121   -0.7577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4866   -0.5498   -3.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9083   -3.1173   -2.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6866   -0.9145   -1.1155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1128   -0.6824   -3.5511 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 13 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
  8 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 31 33  1  0
 33 34  1  0
 33  6  1  0
 16 10  1  0
 26 20  1  0
 27 12  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  6
  8 41  1  6
 11 42  1  0
 15 43  1  0
 17 44  1  0
 17 45  1  0
 17 46  1  0
 21 47  1  0
 22 48  1  0
 24 49  1  0
 25 50  1  0
 29 51  1  1
 30 52  1  0
 31 53  1  6
 32 54  1  0
 33 55  1  1
 34 56  1  0
M  END


  Mrv1652309082215582D          

 34 37  0  0  1  0            999 V2000
    7.8592   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  1  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
    4.2868    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
    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   -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
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    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
    1.4289   -0.0000    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 O   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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 20 26  1  0  0  0  0
 26 27  1  0  0  0  0
 12 27  1  0  0  0  0
 27 28  2  0  0  0  0
  8 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
  6 33  1  0  0  0  0
 33 34  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0268754

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@H]1O[C@@H](OC2=CC3=C(C(O)=C2C)C(=O)C2=CC=C(O)C=C2C3=O)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C23H22O11/c1-8-14(33-23-22(31)21(30)20(29)15(34-23)7-32-9(2)24)6-13-16(17(8)26)19(28)11-4-3-10(25)5-12(11)18(13)27/h3-6,15,20-23,25-26,29-31H,7H2,1-2H3/t15-,20-,21+,22-,23-/m1/s1

> <INCHI_KEY>
NZFWKPNBKZRWCW-NOGCDZMRSA-N

> <FORMULA>
C23H22O11

> <MOLECULAR_WEIGHT>
474.418

> <EXACT_MASS>
474.116211528

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
46.014332873060766

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6S)-6-[(4,7-dihydroxy-3-methyl-9,10-dioxo-9,10-dihydroanthracen-2-yl)oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate

> <JCHEM_LOGP>
1.344488816

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.630210208055653

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.241936933332207

> <JCHEM_PKA_STRONGEST_BASIC>
-3.649102817017959

> <JCHEM_POLAR_SURFACE_AREA>
180.04999999999998

> <JCHEM_REFRACTIVITY>
113.43079999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6S)-6-[(4,7-dihydroxy-3-methyl-9,10-dioxoanthracen-2-yl)oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      10.669  -0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      12.003   3.850   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      14.670   2.310   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      13.337  -0.000   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      14.670  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   33                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   29                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   27                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   10   17                                                  
CONECT   17   16                                                            
CONECT   18   13   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   20   27                                                  
CONECT   27   26   12   28                                                  
CONECT   28   27                                                            
CONECT   29    8   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    6   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
1,3,6-Tmaqag	ChEBI
1,3,6-Trihydroxy-2-methyl-9,10-anthraquinone-3-O-(6'-O-acetyl)-b-D-glucopyranoside	Generator
1,3,6-Trihydroxy-2-methyl-9,10-anthraquinone-3-O-(6'-O-acetyl)-β-D-glucopyranoside	Generator
1,3,6-Trihydroxy-2-methyl-9,10-anthraquinone-3-O-(6'-acetylglucoside)	MeSH

Chemical Formula

C₂₃H₂₂O₁₁

Average Mass

474.4180 Da

Monoisotopic Mass

474.11621 Da

IUPAC Name

[(2R,3S,4S,5R,6S)-6-[(4,7-dihydroxy-3-methyl-9,10-dioxo-9,10-dihydroanthracen-2-yl)oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate

Traditional Name

[(2R,3S,4S,5R,6S)-6-[(4,7-dihydroxy-3-methyl-9,10-dioxoanthracen-2-yl)oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@H]1O[C@@H](OC2=CC3=C(C(O)=C2C)C(=O)C2=CC=C(O)C=C2C3=O)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C23H22O11/c1-8-14(33-23-22(31)21(30)20(29)15(34-23)7-32-9(2)24)6-13-16(17(8)26)19(28)11-4-3-10(25)5-12(11)18(13)27/h3-6,15,20-23,25-26,29-31H,7H2,1-2H3/t15-,20-,21+,22-,23-/m1/s1

InChI Key

NZFWKPNBKZRWCW-NOGCDZMRSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Rubia yunnanensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Hydroxyanthraquinones

Alternative Parents

Substituents

Hydroxyanthraquinone
Phenolic glycoside
Glycosyl compound
O-glycosyl compound
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monosaccharide
Oxane
Vinylogous acid
Secondary alcohol
Carboxylic acid ester
Ketone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Polyol
Monocarboxylic acid or derivatives
Acetal
Organic oxygen compound
Organic oxide
Alcohol
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:69536 )
acetate ester (CHEBI:69536 )
monosaccharide derivative (CHEBI:69536 )
dihydroxyanthraquinone (CHEBI:69536 )

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	1.34	ChemAxon
pKa (Strongest Acidic)	7.24	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	180.05 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	113.43 m³·mol⁻¹	ChemAxon
Polarizability	46.01 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

Not Available

Chemspider ID

30786448

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

195713

PDB ID

Not Available

ChEBI ID

69536

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(2r,3s,4s,5r,6s)-6-[(4,7-dihydroxy-3-methyl-9,10-dioxoanthracen-2-yl)oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate (NP0268754)

MOL for NP0268754 ([(2r,3s,4s,5r,6s)-6-[(4,7-dihydroxy-3-methyl-9,10-dioxoanthracen-2-yl)oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate)

3D MOL for NP0268754 ([(2r,3s,4s,5r,6s)-6-[(4,7-dihydroxy-3-methyl-9,10-dioxoanthracen-2-yl)oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate)

3D SDF for NP0268754 ([(2r,3s,4s,5r,6s)-6-[(4,7-dihydroxy-3-methyl-9,10-dioxoanthracen-2-yl)oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate)

3D-SDF for NP0268754 ([(2r,3s,4s,5r,6s)-6-[(4,7-dihydroxy-3-methyl-9,10-dioxoanthracen-2-yl)oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate)

PDB for NP0268754 ([(2r,3s,4s,5r,6s)-6-[(4,7-dihydroxy-3-methyl-9,10-dioxoanthracen-2-yl)oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate)

3D PDB for NP0268754 ([(2r,3s,4s,5r,6s)-6-[(4,7-dihydroxy-3-methyl-9,10-dioxoanthracen-2-yl)oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate)

SMILES for NP0268754 ([(2r,3s,4s,5r,6s)-6-[(4,7-dihydroxy-3-methyl-9,10-dioxoanthracen-2-yl)oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate)

INCHI for NP0268754 ([(2r,3s,4s,5r,6s)-6-[(4,7-dihydroxy-3-methyl-9,10-dioxoanthracen-2-yl)oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate)

Structure for NP0268754 ([(2r,3s,4s,5r,6s)-6-[(4,7-dihydroxy-3-methyl-9,10-dioxoanthracen-2-yl)oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate)

3D Structure for NP0268754 ([(2r,3s,4s,5r,6s)-6-[(4,7-dihydroxy-3-methyl-9,10-dioxoanthracen-2-yl)oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate)