NP-MRD: Showing NP-Card for Questinol (NP0021758)

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Record Information

Version

2.0

Created at

2021-01-06 07:01:45 UTC

Updated at

2021-08-20 00:00:01 UTC

NP-MRD ID

NP0021758

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Questinol

Provided By

NPAtlas

Description

Questinol 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. Questinol is found in Fallopia multiflora and Penicillium. Questinol was first documented in 1964 (PMID: 5838081). Based on a literature review very few articles have been published on Questinol (PMID: 28509846) (PMID: 28586721) (PMID: 32190053) (PMID: 30445748).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105183D          

 34 36  0  0  0  0            999 V2000
   -4.4453   -2.0534   -0.3199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0992   -1.6148   -0.2739 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7559   -0.3016    0.0027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7038    0.6748    0.2537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3318    1.9731    0.5260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3055    2.9567    0.7796 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9883    2.2510    0.5366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0162    1.2997    0.2902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4049    0.0153    0.0217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3941   -1.0276   -0.2464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8038   -2.1832   -0.4858 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0069   -0.6763   -0.2217 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9615   -1.6424   -0.4707 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6600   -2.9267   -0.7426 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3069   -1.2467   -0.4342 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6705    0.0472   -0.1626 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0994    0.4790   -0.1212 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9541   -0.5967   -0.3883 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7132    1.0048    0.0846 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3865    0.6252    0.0509 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4073    1.6548    0.3149 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7244    2.8483    0.5661 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4815   -3.1641   -0.2464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9226   -1.7216   -1.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0044   -1.5850    0.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7653    0.4186    0.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9816    3.8911    0.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6385    3.2552    0.7449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8843   -3.4911   -0.8378 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0449   -2.0015   -0.6285 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2099    1.2468   -0.9108 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2688    0.9094    0.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7811   -1.3486    0.2199 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9631    2.0306    0.3014 H   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  2  0  0  0  0
  9 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
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
  9  3  1  0  0  0  0
 20 12  1  0  0  0  0
 21  8  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  4 26  1  0  0  0  0
  6 27  1  0  0  0  0
  7 28  1  0  0  0  0
 14 29  1  0  0  0  0
 15 30  1  0  0  0  0
 17 31  1  0  0  0  0
 17 32  1  0  0  0  0
 18 33  1  0  0  0  0
 19 34  1  0  0  0  0
M  END

     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
   -4.4453   -2.0534   -0.3199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0992   -1.6148   -0.2739 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7559   -0.3016    0.0027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7038    0.6748    0.2537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3318    1.9731    0.5260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3055    2.9567    0.7796 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9883    2.2510    0.5366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0162    1.2997    0.2902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4049    0.0153    0.0217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3941   -1.0276   -0.2464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8038   -2.1832   -0.4858 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0069   -0.6763   -0.2217 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9615   -1.6424   -0.4707 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6600   -2.9267   -0.7426 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3069   -1.2467   -0.4342 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6705    0.0472   -0.1626 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0994    0.4790   -0.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9541   -0.5967   -0.3883 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7132    1.0048    0.0846 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3865    0.6252    0.0509 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4073    1.6548    0.3149 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7244    2.8483    0.5661 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4815   -3.1641   -0.2464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9226   -1.7216   -1.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0044   -1.5850    0.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7653    0.4186    0.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9816    3.8911    0.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6385    3.2552    0.7449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8843   -3.4911   -0.8378 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0449   -2.0015   -0.6285 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2099    1.2468   -0.9108 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2688    0.9094    0.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7811   -1.3486    0.2199 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9631    2.0306    0.3014 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  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
  9  3  1  0
 20 12  1  0
 21  8  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
M  END


  Mrv1652306242105183D          

 34 36  0  0  0  0            999 V2000
   -4.4453   -2.0534   -0.3199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0992   -1.6148   -0.2739 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7559   -0.3016    0.0027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7038    0.6748    0.2537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3318    1.9731    0.5260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3055    2.9567    0.7796 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9883    2.2510    0.5366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0162    1.2997    0.2902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4049    0.0153    0.0217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3941   -1.0276   -0.2464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8038   -2.1832   -0.4858 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0069   -0.6763   -0.2217 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9615   -1.6424   -0.4707 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6600   -2.9267   -0.7426 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3069   -1.2467   -0.4342 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6705    0.0472   -0.1626 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0994    0.4790   -0.1212 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9541   -0.5967   -0.3883 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7132    1.0048    0.0846 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3865    0.6252    0.0509 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4073    1.6548    0.3149 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7244    2.8483    0.5661 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4815   -3.1641   -0.2464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9226   -1.7216   -1.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0044   -1.5850    0.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7653    0.4186    0.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9816    3.8911    0.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6385    3.2552    0.7449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8843   -3.4911   -0.8378 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0449   -2.0015   -0.6285 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2099    1.2468   -0.9108 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2688    0.9094    0.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7811   -1.3486    0.2199 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9631    2.0306    0.3014 H   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  2  0  0  0  0
  9 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
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
  9  3  1  0  0  0  0
 20 12  1  0  0  0  0
 21  8  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  4 26  1  0  0  0  0
  6 27  1  0  0  0  0
  7 28  1  0  0  0  0
 14 29  1  0  0  0  0
 15 30  1  0  0  0  0
 17 31  1  0  0  0  0
 17 32  1  0  0  0  0
 18 33  1  0  0  0  0
 19 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021758

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C2=C(C(=O)C3=C(O[H])C([H])=C(C([H])=C3C2=O)C([H])([H])O[H])C(OC([H])([H])[H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O6/c1-22-12-5-8(18)4-10-14(12)16(21)13-9(15(10)20)2-7(6-17)3-11(13)19/h2-5,17-19H,6H2,1H3

> <INCHI_KEY>
SNBGJGNOQURXCI-UHFFFAOYSA-N

> <FORMULA>
C16H12O6

> <MOLECULAR_WEIGHT>
300.2629

> <EXACT_MASS>
300.063388116

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
29.60127538262617

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,6-dihydroxy-3-(hydroxymethyl)-8-methoxy-9,10-dihydroanthracene-9,10-dione

> <ALOGPS_LOGP>
2.34

> <JCHEM_LOGP>
2.036554398333333

> <ALOGPS_LOGS>
-3.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.15717882758524

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.246334569364872

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9453240586977527

> <JCHEM_POLAR_SURFACE_AREA>
104.05999999999999

> <JCHEM_REFRACTIVITY>
78.39189999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.86e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,6-dihydroxy-3-(hydroxymethyl)-8-methoxyanthracene-9,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
   -4.4453   -2.0534   -0.3199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0992   -1.6148   -0.2739 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7559   -0.3016    0.0027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7038    0.6748    0.2537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3318    1.9731    0.5260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3055    2.9567    0.7796 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9883    2.2510    0.5366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0162    1.2997    0.2902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4049    0.0153    0.0217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3941   -1.0276   -0.2464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8038   -2.1832   -0.4858 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0069   -0.6763   -0.2217 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9615   -1.6424   -0.4707 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6600   -2.9267   -0.7426 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3069   -1.2467   -0.4342 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6705    0.0472   -0.1626 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0994    0.4790   -0.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9541   -0.5967   -0.3883 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7132    1.0048    0.0846 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3865    0.6252    0.0509 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4073    1.6548    0.3149 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7244    2.8483    0.5661 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4815   -3.1641   -0.2464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9226   -1.7216   -1.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0044   -1.5850    0.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7653    0.4186    0.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9816    3.8911    0.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6385    3.2552    0.7449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8843   -3.4911   -0.8378 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0449   -2.0015   -0.6285 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2099    1.2468   -0.9108 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2688    0.9094    0.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7811   -1.3486    0.2199 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9631    2.0306    0.3014 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  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
  9  3  1  0
 20 12  1  0
 21  8  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -4.445  -2.053  -0.320  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.099  -1.615  -0.274  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.756  -0.302   0.003  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.704   0.675   0.254  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.332   1.973   0.526  0.00  0.00           C+0
HETATM    6  O   UNK     0      -4.306   2.957   0.780  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.988   2.251   0.537  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.016   1.300   0.290  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.405   0.015   0.022  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.394  -1.028  -0.246  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.804  -2.183  -0.486  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.007  -0.676  -0.222  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.962  -1.642  -0.471  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.660  -2.927  -0.743  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.307  -1.247  -0.434  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.671   0.047  -0.163  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.099   0.479  -0.121  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.954  -0.597  -0.388  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.713   1.005   0.085  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.387   0.625   0.051  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.407   1.655   0.315  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.724   2.848   0.566  0.00  0.00           O+0
HETATM   23  H   UNK     0      -4.481  -3.164  -0.246  0.00  0.00           H+0
HETATM   24  H   UNK     0      -4.923  -1.722  -1.256  0.00  0.00           H+0
HETATM   25  H   UNK     0      -5.004  -1.585   0.534  0.00  0.00           H+0
HETATM   26  H   UNK     0      -4.765   0.419   0.237  0.00  0.00           H+0
HETATM   27  H   UNK     0      -3.982   3.891   0.973  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.639   3.255   0.745  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.884  -3.491  -0.838  0.00  0.00           H+0
HETATM   30  H   UNK     0       4.045  -2.002  -0.629  0.00  0.00           H+0
HETATM   31  H   UNK     0       5.210   1.247  -0.911  0.00  0.00           H+0
HETATM   32  H   UNK     0       5.269   0.909   0.887  0.00  0.00           H+0
HETATM   33  H   UNK     0       5.781  -1.349   0.220  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.963   2.031   0.301  0.00  0.00           H+0
CONECT    1    2   23   24   25                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5   26                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5   27                                                       
CONECT    7    5    8   28                                                  
CONECT    8    7    9   21                                                  
CONECT    9    8   10    3                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   20                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13   29                                                       
CONECT   15   13   16   30                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   18   31   32                                             
CONECT   18   17   33                                                       
CONECT   19   16   20   34                                                  
CONECT   20   19   21   12                                                  
CONECT   21   20   22    8                                                  
CONECT   22   21                                                            
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    4                                                            
CONECT   27    6                                                            
CONECT   28    7                                                            
CONECT   29   14                                                            
CONECT   30   15                                                            
CONECT   31   17                                                            
CONECT   32   17                                                            
CONECT   33   18                                                            
CONECT   34   19                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

RDKit          3D

34 36  0  0  0  0  0  0  0  0999 V2000
   -4.4453   -2.0534   -0.3199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0992   -1.6148   -0.2739 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7559   -0.3016    0.0027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7038    0.6748    0.2537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3318    1.9731    0.5260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3055    2.9567    0.7796 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9883    2.2510    0.5366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0162    1.2997    0.2902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4049    0.0153    0.0217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3941   -1.0276   -0.2464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8038   -2.1832   -0.4858 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0069   -0.6763   -0.2217 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9615   -1.6424   -0.4707 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6600   -2.9267   -0.7426 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3069   -1.2467   -0.4342 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6705    0.0472   -0.1626 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0994    0.4790   -0.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9541   -0.5967   -0.3883 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7132    1.0048    0.0846 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3865    0.6252    0.0509 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4073    1.6548    0.3149 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7244    2.8483    0.5661 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4815   -3.1641   -0.2464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9226   -1.7216   -1.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0044   -1.5850    0.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7653    0.4186    0.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9816    3.8911    0.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6385    3.2552    0.7449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8843   -3.4911   -0.8378 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0449   -2.0015   -0.6285 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2099    1.2468   -0.9108 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2688    0.9094    0.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7811   -1.3486    0.2199 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9631    2.0306    0.3014 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  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
  9  3  1  0
 20 12  1  0
 21  8  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
1,6-Dihydroxy-3-(hydroxymethyl)-8-methoxy-9,10-anthracenedione	Kegg
1,6-Dihydroxy-3-hydroxymethyl-8-methoxyanthraquinone	HMDB

Chemical Formula

C₁₆H₁₂O₆

Average Mass

300.2629 Da

Monoisotopic Mass

300.06339 Da

IUPAC Name

1,6-dihydroxy-3-(hydroxymethyl)-8-methoxy-9,10-dihydroanthracene-9,10-dione

Traditional Name

1,6-dihydroxy-3-(hydroxymethyl)-8-methoxyanthracene-9,10-dione

CAS Registry Number

Not Available

SMILES

COC1=C2C(=O)C3=C(O)C=C(CO)C=C3C(=O)C2=CC(O)=C1

InChI Identifier

InChI=1S/C16H12O6/c1-22-12-5-8(18)4-10-14(12)16(21)13-9(15(10)20)2-7(6-17)3-11(13)19/h2-5,17-19H,6H2,1H3

InChI Key

SNBGJGNOQURXCI-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
Fallopia multiflora	LOTUS Database	35616633
Penicillium	NPAtlas	5838081
Polygonum cuspidatum	KNApSAcK Database	22123792

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

Organic compounds

Super Class

Benzenoids

Class

Anthracenes

Sub Class

Anthraquinones

Direct Parent

Hydroxyanthraquinones

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aromatic homopolycyclic 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	120.9 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.34	ALOGPS
logP	2.04	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	7.25	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	78.39 m³·mol⁻¹	ChemAxon
Polarizability	29.6 Å³	ChemAxon
Number of Rings	3	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

NPAtlas ID

NPA020485

HMDB ID

HMDB0034443

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

147621

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

rw1842911

References

General References

Noinart J, Buttachon S, Dethoup T, Gales L, Pereira JA, Urbatzka R, Freitas S, Lee M, Silva AMS, Pinto MMM, Vasconcelos V, Kijjoa A: A New Ergosterol Analog, a New Bis-Anthraquinone and Anti-Obesity Activity of Anthraquinones from the Marine Sponge-Associated Fungus Talaromyces stipitatus KUFA 0207. Mar Drugs. 2017 May 16;15(5). pii: md15050139. doi: 10.3390/md15050139. [PubMed:28509846 ]
May Zin WW, Buttachon S, Dethoup T, Pereira JA, Gales L, Inacio A, Costa PM, Lee M, Sekeroglu N, Silva AMS, Pinto MMM, Kijjoa A: Antibacterial and antibiofilm activities of the metabolites isolated from the culture of the mangrove-derived endophytic fungus Eurotium chevalieri KUFA 0006. Phytochemistry. 2017 Sep;141:86-97. doi: 10.1016/j.phytochem.2017.05.015. Epub 2017 Jun 3. [PubMed:28586721 ]
Mahmoodian A, Stickings CE: Studies in the biochemistry of micro-organisms. 115. Metabolites of Penicillium frequentans Westling: isolation of sulochrin, asterric acid, (+)-bisdechlorogeodin and two new substituted anthraquinones, questin and questinol. Biochem J. 1964 Aug;92(2):369-78. doi: 10.1042/bj0920369. [PubMed:5838081 ]
Cheng W, Li Y, Yang W, Wu S, Wei M, Gao Y, Kang C, Zhang S, Li Y: Simultaneous Determination of 13 Constituents of Radix Polygoni Multiflori in Rat Plasma and Its Application in a Pharmacokinetic Study. Int J Anal Chem. 2020 Mar 3;2020:4508374. doi: 10.1155/2020/4508374. eCollection 2020. [PubMed:32190053 ]
Kang HH, Zhang HB, Zhong MJ, Ma LY, Liu DS, Liu WZ, Ren H: Potential Antiviral Xanthones from a Coastal Saline Soil Fungus Aspergillus iizukae. Mar Drugs. 2018 Nov 15;16(11). pii: md16110449. doi: 10.3390/md16110449. [PubMed:30445748 ]

Showing NP-Card for Questinol (NP0021758)

MOL for NP0021758 (Questinol)

3D MOL for NP0021758 (Questinol)

3D SDF for NP0021758 (Questinol)

3D-SDF for NP0021758 (Questinol)

PDB for NP0021758 (Questinol)

3D PDB for NP0021758 (Questinol)

SMILES for NP0021758 (Questinol)

INCHI for NP0021758 (Questinol)

Structure for NP0021758 (Questinol)

3D Structure for NP0021758 (Questinol)