NP-MRD: Showing NP-Card for 1,4,5-trihydroxy-2-methyl-7-{[(2r,3r,4s,5r,6r)-3,4,5,6-tetrahydroxy-2-methyloxan-2-yl]oxy}anthracene-9,10-dione (NP0174968)

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Record Information

Version

2.0

Created at

2022-09-03 12:19:28 UTC

Updated at

2022-09-03 12:19:29 UTC

NP-MRD ID

NP0174968

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,4,5-trihydroxy-2-methyl-7-{[(2r,3r,4s,5r,6r)-3,4,5,6-tetrahydroxy-2-methyloxan-2-yl]oxy}anthracene-9,10-dione

Description

1,4,5-Trihydroxy-2-methyl-7-{[(2R,3R,4S,5R,6R)-3,4,5,6-tetrahydroxy-2-methyloxan-2-yl]oxy}-9,10-dihydroanthracene-9,10-dione 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. 1,4,5-trihydroxy-2-methyl-7-{[(2r,3r,4s,5r,6r)-3,4,5,6-tetrahydroxy-2-methyloxan-2-yl]oxy}anthracene-9,10-dione is found in Frangula alnus. Based on a literature review very few articles have been published on 1,4,5-trihydroxy-2-methyl-7-{[(2R,3R,4S,5R,6R)-3,4,5,6-tetrahydroxy-2-methyloxan-2-yl]oxy}-9,10-dihydroanthracene-9,10-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032214192D          

 32 35  0  0  1  0            999 V2000
    5.0013   -0.4125    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
    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
    3.5724    2.0625    0.0000 O   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
    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
   -0.7145   -0.4125    0.0000 O   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
   -1.5269   -1.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0980   -1.0942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6283   -1.7262    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4408   -1.5830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3461   -2.5015    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8764   -3.1335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4663   -2.6447    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7485   -3.4200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9966   -2.0127    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8091   -2.1560    0.0000 O   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
    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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 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
 16 15  1  6  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  1  0  0  0
 14 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 12 30  1  0  0  0  0
 30 31  1  0  0  0  0
  6 31  1  0  0  0  0
 31 32  2  0  0  0  0
M  END

     RDKit          3D

 52 55  0  0  0  0  0  0  0  0999 V2000
    7.1221    1.9610    0.7512 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0034    1.0438    0.3903 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3017   -0.1252   -0.2273 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2941   -1.0151   -0.5846 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6296   -2.1662   -1.1966 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9925   -0.6558   -0.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7109    0.5390    0.3450 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7264    1.4030    0.6884 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4455    2.6147    1.3261 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3330    0.9251    0.6659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0941    2.0189    1.2402 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2604    0.0152    0.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0431    0.3561    0.5958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1095   -0.4655    0.2784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3594   -0.0508    0.6021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5693   -0.7022    0.3849 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5454   -2.0472    1.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7741   -0.9635   -0.9473 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4596   -0.0035   -1.6365 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8407   -0.2544   -1.7141 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2420    1.3955   -1.1591 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9411    1.8327   -1.3734 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6721    1.4934    0.2690 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8487    2.4560    0.8871 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6449    0.1805    0.9933 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8595   -0.4317    1.1032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8535   -1.6637   -0.3501 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4501   -2.0447   -0.6618 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7388   -3.2277   -1.2856 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4960   -1.1820   -0.3217 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8805   -1.5395   -0.6288 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0460   -2.6347   -1.1970 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1624    2.1005    1.8558 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9983    2.9363    0.2280 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1003    1.5558    0.4545 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3090   -0.3973   -0.4568 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1283   -2.9138   -1.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1959    3.2327    1.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2061    1.3042    1.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5800   -2.2369    1.5984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7503   -2.8901    0.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3471   -2.0879    1.8854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1068   -0.0378   -2.7090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3690    0.5120   -1.4330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9011    2.0617   -1.7620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9352    2.8219   -1.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7005    1.8943    0.3396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8817    2.2307    0.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2875    0.4023    2.0415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9154   -1.3535    0.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6608   -2.3342   -0.6153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0150   -3.8627   -1.5373 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6 31  1  0
 31 32  2  0
 31 30  1  0
 30 28  2  0
 28 29  1  0
 28 27  1  0
 27 14  2  0
 14 15  1  0
 16 15  1  6
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 14 13  1  0
 13 12  2  0
 12 10  1  0
 10 11  2  0
 10  7  1  0
  7  8  2  0
  8  9  1  0
  8  2  1  0
  7  6  1  0
 12 30  1  0
 25 16  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  3 36  1  0
  5 37  1  0
 29 52  1  0
 27 51  1  0
 17 40  1  0
 17 41  1  0
 17 42  1  0
 19 43  1  6
 20 44  1  0
 21 45  1  6
 22 46  1  0
 23 47  1  6
 24 48  1  0
 25 49  1  1
 26 50  1  0
 13 39  1  0
  9 38  1  0
M  END


  Mrv1652309032214192D          

 32 35  0  0  1  0            999 V2000
    5.0013   -0.4125    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
    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
    3.5724    2.0625    0.0000 O   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
    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
   -0.7145   -0.4125    0.0000 O   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
   -1.5269   -1.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0980   -1.0942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6283   -1.7262    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4408   -1.5830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3461   -2.5015    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8764   -3.1335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4663   -2.6447    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7485   -3.4200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9966   -2.0127    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8091   -2.1560    0.0000 O   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
    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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 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
 16 15  1  6  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  1  0  0  0
 14 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 12 30  1  0  0  0  0
 30 31  1  0  0  0  0
  6 31  1  0  0  0  0
 31 32  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0174968

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(O)=C2C(=O)C3=C(O)C=C(O[C@]4(C)O[C@@H](O)[C@H](O)[C@H](O)[C@H]4O)C=C3C(=O)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O11/c1-6-3-9(22)12-13(14(6)24)15(25)8-4-7(5-10(23)11(8)16(12)26)31-21(2)19(29)17(27)18(28)20(30)32-21/h3-5,17-20,22-24,27-30H,1-2H3/t17-,18+,19+,20+,21+/m0/s1

> <INCHI_KEY>
ASBSHYKVFMWGHT-SRHPJPHMSA-N

> <FORMULA>
C21H20O11

> <MOLECULAR_WEIGHT>
448.38

> <EXACT_MASS>
448.100561464

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
42.54779128634474

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,4,5-trihydroxy-2-methyl-7-{[(2R,3R,4S,5R,6R)-3,4,5,6-tetrahydroxy-2-methyloxan-2-yl]oxy}-9,10-dihydroanthracene-9,10-dione

> <ALOGPS_LOGP>
0.88

> <JCHEM_LOGP>
2.4139718099999996

> <ALOGPS_LOGS>
-2.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.800844623541623

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.9511533199067195

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7158634376280313

> <JCHEM_POLAR_SURFACE_AREA>
194.20999999999998

> <JCHEM_REFRACTIVITY>
106.34939999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.19e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,4,5-trihydroxy-2-methyl-7-{[(2R,3R,4S,5R,6R)-3,4,5,6-tetrahydroxy-2-methyloxan-2-yl]oxy}anthracene-9,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       9.336  -0.770   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       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.850  -2.043   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.183  -2.043   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.173  -3.222   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.689  -2.955   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.646  -4.669   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.636  -5.849   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.870  -4.937   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.397  -6.384   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.860  -3.757   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -3.377  -4.025   0.000  0.00  0.00           O+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       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   31                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    2    9                                                  
CONECT    9    8                                                            
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   30                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   27                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18   25                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   16   26                                                  
CONECT   26   25                                                            
CONECT   27   14   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   12   31                                                  
CONECT   31   30    6   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₀O₁₁

Average Mass

448.3800 Da

Monoisotopic Mass

448.10056 Da

IUPAC Name

1,4,5-trihydroxy-2-methyl-7-{[(2R,3R,4S,5R,6R)-3,4,5,6-tetrahydroxy-2-methyloxan-2-yl]oxy}-9,10-dihydroanthracene-9,10-dione

Traditional Name

1,4,5-trihydroxy-2-methyl-7-{[(2R,3R,4S,5R,6R)-3,4,5,6-tetrahydroxy-2-methyloxan-2-yl]oxy}anthracene-9,10-dione

CAS Registry Number

Not Available

SMILES

CC1=CC(O)=C2C(=O)C3=C(O)C=C(O[C@]4(C)O[C@@H](O)[C@H](O)[C@H](O)[C@H]4O)C=C3C(=O)C2=C1O

InChI Identifier

InChI=1S/C21H20O11/c1-6-3-9(22)12-13(14(6)24)15(25)8-4-7(5-10(23)11(8)16(12)26)31-21(2)19(29)17(27)18(28)20(30)32-21/h3-5,17-20,22-24,27-30H,1-2H3/t17-,18+,19+,20+,21+/m0/s1

InChI Key

ASBSHYKVFMWGHT-SRHPJPHMSA-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
Frangula alnus	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

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	0.88	ALOGPS
logP	2.41	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	7.95	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	194.21 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	106.35 m³·mol⁻¹	ChemAxon
Polarizability	42.55 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162984622

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1,4,5-trihydroxy-2-methyl-7-{[(2r,3r,4s,5r,6r)-3,4,5,6-tetrahydroxy-2-methyloxan-2-yl]oxy}anthracene-9,10-dione (NP0174968)

MOL for NP0174968 (1,4,5-trihydroxy-2-methyl-7-{[(2r,3r,4s,5r,6r)-3,4,5,6-tetrahydroxy-2-methyloxan-2-yl]oxy}anthracene-9,10-dione)

3D MOL for NP0174968 (1,4,5-trihydroxy-2-methyl-7-{[(2r,3r,4s,5r,6r)-3,4,5,6-tetrahydroxy-2-methyloxan-2-yl]oxy}anthracene-9,10-dione)

3D SDF for NP0174968 (1,4,5-trihydroxy-2-methyl-7-{[(2r,3r,4s,5r,6r)-3,4,5,6-tetrahydroxy-2-methyloxan-2-yl]oxy}anthracene-9,10-dione)

3D-SDF for NP0174968 (1,4,5-trihydroxy-2-methyl-7-{[(2r,3r,4s,5r,6r)-3,4,5,6-tetrahydroxy-2-methyloxan-2-yl]oxy}anthracene-9,10-dione)

PDB for NP0174968 (1,4,5-trihydroxy-2-methyl-7-{[(2r,3r,4s,5r,6r)-3,4,5,6-tetrahydroxy-2-methyloxan-2-yl]oxy}anthracene-9,10-dione)

3D PDB for NP0174968 (1,4,5-trihydroxy-2-methyl-7-{[(2r,3r,4s,5r,6r)-3,4,5,6-tetrahydroxy-2-methyloxan-2-yl]oxy}anthracene-9,10-dione)

SMILES for NP0174968 (1,4,5-trihydroxy-2-methyl-7-{[(2r,3r,4s,5r,6r)-3,4,5,6-tetrahydroxy-2-methyloxan-2-yl]oxy}anthracene-9,10-dione)

INCHI for NP0174968 (1,4,5-trihydroxy-2-methyl-7-{[(2r,3r,4s,5r,6r)-3,4,5,6-tetrahydroxy-2-methyloxan-2-yl]oxy}anthracene-9,10-dione)

Structure for NP0174968 (1,4,5-trihydroxy-2-methyl-7-{[(2r,3r,4s,5r,6r)-3,4,5,6-tetrahydroxy-2-methyloxan-2-yl]oxy}anthracene-9,10-dione)

3D Structure for NP0174968 (1,4,5-trihydroxy-2-methyl-7-{[(2r,3r,4s,5r,6r)-3,4,5,6-tetrahydroxy-2-methyloxan-2-yl]oxy}anthracene-9,10-dione)