NP-MRD: Showing NP-Card for Questin (NP0021757)

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Record Information

Version

2.0

Created at

2021-01-06 07:01:42 UTC

Updated at

2021-07-15 17:37:12 UTC

NP-MRD ID

NP0021757

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Questin

Provided By

NPAtlas

Description

Questin is found in Aspergillus aureoterreus, Penicillium, Rhamnus davurica, Senna artemisioides, Senna lindheimeriana, Senna siamea, Senna tora and Mallotus nudiflorus. Questin was first documented in 1964 (PMID: 5838081). Based on a literature review very few articles have been published on Questin.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105183D          

 33 35  0  0  0  0            999 V2000
   -4.3288    1.9478   -0.3769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0018    1.5365   -0.3172 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5769    0.2879    0.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4852   -0.6681    0.4810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0929   -1.9358    0.8977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0413   -2.8949    1.2914 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7367   -2.2043    0.9059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7928   -1.2693    0.5208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2302   -0.0169    0.1122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2217    0.9659   -0.2935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6780    2.0783   -0.6522 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2118    0.7200   -0.2982 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1537    1.6489   -0.6809 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7767    2.8898   -1.0893 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5243    1.3137   -0.6504 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9128    0.0859   -0.2473 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3603   -0.3362   -0.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9765   -0.8422    0.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6273   -0.5486    0.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6365   -1.5435    0.5263 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9965   -2.6895    0.9027 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7900    2.1231    0.6185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3651    2.9373   -0.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9463    1.2641   -1.0105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5458   -0.4514    0.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4612   -3.5453    0.6516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4287   -3.1905    1.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9344    3.3407   -1.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2444    2.0489   -0.9518 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7244   -0.0214    0.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4100   -1.4108   -0.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9396    0.2094   -0.9927 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2944   -1.8295    0.4586 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
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 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
  9  3  1  0  0  0  0
 19 12  1  0  0  0  0
 20  8  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  4 25  1  0  0  0  0
  6 26  1  0  0  0  0
  7 27  1  0  0  0  0
 14 28  1  0  0  0  0
 15 29  1  0  0  0  0
 17 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
M  END

     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
   -4.3288    1.9478   -0.3769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0018    1.5365   -0.3172 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5769    0.2879    0.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4852   -0.6681    0.4810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0929   -1.9358    0.8977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0413   -2.8949    1.2914 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7367   -2.2043    0.9059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7928   -1.2693    0.5208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2302   -0.0169    0.1122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2217    0.9659   -0.2935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6780    2.0783   -0.6522 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2118    0.7200   -0.2982 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1537    1.6489   -0.6809 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7767    2.8898   -1.0893 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5243    1.3137   -0.6504 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9128    0.0859   -0.2473 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3603   -0.3362   -0.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9765   -0.8422    0.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6273   -0.5486    0.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6365   -1.5435    0.5263 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9965   -2.6895    0.9027 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7900    2.1231    0.6185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3651    2.9373   -0.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9463    1.2641   -1.0105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5458   -0.4514    0.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4612   -3.5453    0.6516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4287   -3.1905    1.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9344    3.3407   -1.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2444    2.0489   -0.9518 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7244   -0.0214    0.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4100   -1.4108   -0.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9396    0.2094   -0.9927 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2944   -1.8295    0.4586 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
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
  9  3  1  0
 19 12  1  0
 20  8  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
 14 28  1  0
 15 29  1  0
 17 30  1  0
 17 31  1  0
 17 32  1  0
 18 33  1  0
M  END


  Mrv1652306242105183D          

 33 35  0  0  0  0            999 V2000
   -4.3288    1.9478   -0.3769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0018    1.5365   -0.3172 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5769    0.2879    0.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4852   -0.6681    0.4810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0929   -1.9358    0.8977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0413   -2.8949    1.2914 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7367   -2.2043    0.9059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7928   -1.2693    0.5208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2302   -0.0169    0.1122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2217    0.9659   -0.2935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6780    2.0783   -0.6522 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2118    0.7200   -0.2982 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1537    1.6489   -0.6809 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7767    2.8898   -1.0893 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5243    1.3137   -0.6504 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9128    0.0859   -0.2473 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3603   -0.3362   -0.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9765   -0.8422    0.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6273   -0.5486    0.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6365   -1.5435    0.5263 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9965   -2.6895    0.9027 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7900    2.1231    0.6185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3651    2.9373   -0.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9463    1.2641   -1.0105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5458   -0.4514    0.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4612   -3.5453    0.6516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4287   -3.1905    1.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9344    3.3407   -1.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2444    2.0489   -0.9518 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7244   -0.0214    0.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4100   -1.4108   -0.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9396    0.2094   -0.9927 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2944   -1.8295    0.4586 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
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 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
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  9  3  1  0  0  0  0
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  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
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 17 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
M  END
> <DATABASE_ID>
NP0021757

> <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])[H])C(OC([H])([H])[H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O5/c1-7-3-9-13(11(18)4-7)16(20)14-10(15(9)19)5-8(17)6-12(14)21-2/h3-6,17-18H,1-2H3

> <INCHI_KEY>
UUNPIWCQMVNINR-UHFFFAOYSA-N

> <FORMULA>
C16H12O5

> <MOLECULAR_WEIGHT>
284.267

> <EXACT_MASS>
284.068473486

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
29.041217733927656

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,6-dihydroxy-8-methoxy-3-methyl-9,10-dihydroanthracene-9,10-dione

> <ALOGPS_LOGP>
2.94

> <JCHEM_LOGP>
3.317325554999999

> <ALOGPS_LOGS>
-3.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.390119943669944

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.283268017596118

> <JCHEM_PKA_STRONGEST_BASIC>
-4.893921085387394

> <JCHEM_POLAR_SURFACE_AREA>
83.83000000000001

> <JCHEM_REFRACTIVITY>
76.61719999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.98e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
questin

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
   -4.3288    1.9478   -0.3769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0018    1.5365   -0.3172 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5769    0.2879    0.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4852   -0.6681    0.4810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0929   -1.9358    0.8977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0413   -2.8949    1.2914 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7367   -2.2043    0.9059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7928   -1.2693    0.5208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2302   -0.0169    0.1122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2217    0.9659   -0.2935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6780    2.0783   -0.6522 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2118    0.7200   -0.2982 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1537    1.6489   -0.6809 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7767    2.8898   -1.0893 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5243    1.3137   -0.6504 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9128    0.0859   -0.2473 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3603   -0.3362   -0.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9765   -0.8422    0.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6273   -0.5486    0.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6365   -1.5435    0.5263 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9965   -2.6895    0.9027 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7900    2.1231    0.6185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3651    2.9373   -0.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9463    1.2641   -1.0105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5458   -0.4514    0.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4612   -3.5453    0.6516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4287   -3.1905    1.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9344    3.3407   -1.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2444    2.0489   -0.9518 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7244   -0.0214    0.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4100   -1.4108   -0.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9396    0.2094   -0.9927 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2944   -1.8295    0.4586 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
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
  9  3  1  0
 19 12  1  0
 20  8  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
 14 28  1  0
 15 29  1  0
 17 30  1  0
 17 31  1  0
 17 32  1  0
 18 33  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      -4.329   1.948  -0.377  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.002   1.537  -0.317  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.577   0.288   0.091  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.485  -0.668   0.481  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.093  -1.936   0.898  0.00  0.00           C+0
HETATM    6  O   UNK     0      -4.041  -2.895   1.291  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.737  -2.204   0.906  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.793  -1.269   0.521  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.230  -0.017   0.112  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.222   0.966  -0.294  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.678   2.078  -0.652  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.212   0.720  -0.298  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.154   1.649  -0.681  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.777   2.890  -1.089  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.524   1.314  -0.650  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.913   0.086  -0.247  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.360  -0.336  -0.191  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.977  -0.842   0.135  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.627  -0.549   0.118  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.637  -1.544   0.526  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.997  -2.689   0.903  0.00  0.00           O+0
HETATM   22  H   UNK     0      -4.790   2.123   0.619  0.00  0.00           H+0
HETATM   23  H   UNK     0      -4.365   2.937  -0.901  0.00  0.00           H+0
HETATM   24  H   UNK     0      -4.946   1.264  -1.010  0.00  0.00           H+0
HETATM   25  H   UNK     0      -4.546  -0.451   0.472  0.00  0.00           H+0
HETATM   26  H   UNK     0      -4.461  -3.545   0.652  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.429  -3.191   1.230  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.934   3.341  -1.193  0.00  0.00           H+0
HETATM   29  H   UNK     0       4.244   2.049  -0.952  0.00  0.00           H+0
HETATM   30  H   UNK     0       5.724  -0.021   0.809  0.00  0.00           H+0
HETATM   31  H   UNK     0       5.410  -1.411  -0.374  0.00  0.00           H+0
HETATM   32  H   UNK     0       5.940   0.209  -0.993  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.294  -1.829   0.459  0.00  0.00           H+0
CONECT    1    2   22   23   24                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5   25                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5   26                                                       
CONECT    7    5    8   27                                                  
CONECT    8    7    9   20                                                  
CONECT    9    8   10    3                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   19                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13   28                                                       
CONECT   15   13   16   29                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   30   31   32                                             
CONECT   18   16   19   33                                                  
CONECT   19   18   20   12                                                  
CONECT   20   19   21    8                                                  
CONECT   21   20                                                            
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    4                                                            
CONECT   26    6                                                            
CONECT   27    7                                                            
CONECT   28   14                                                            
CONECT   29   15                                                            
CONECT   30   17                                                            
CONECT   31   17                                                            
CONECT   32   17                                                            
CONECT   33   18                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

RDKit          3D

33 35  0  0  0  0  0  0  0  0999 V2000
   -4.3288    1.9478   -0.3769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0018    1.5365   -0.3172 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5769    0.2879    0.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4852   -0.6681    0.4810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0929   -1.9358    0.8977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0413   -2.8949    1.2914 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7367   -2.2043    0.9059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7928   -1.2693    0.5208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2302   -0.0169    0.1122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2217    0.9659   -0.2935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6780    2.0783   -0.6522 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2118    0.7200   -0.2982 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1537    1.6489   -0.6809 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7767    2.8898   -1.0893 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5243    1.3137   -0.6504 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9128    0.0859   -0.2473 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3603   -0.3362   -0.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9765   -0.8422    0.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6273   -0.5486    0.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6365   -1.5435    0.5263 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9965   -2.6895    0.9027 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7900    2.1231    0.6185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3651    2.9373   -0.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9463    1.2641   -1.0105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5458   -0.4514    0.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4612   -3.5453    0.6516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4287   -3.1905    1.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9344    3.3407   -1.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2444    2.0489   -0.9518 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7244   -0.0214    0.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4100   -1.4108   -0.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9396    0.2094   -0.9927 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2944   -1.8295    0.4586 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
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
  9  3  1  0
 19 12  1  0
 20  8  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
 14 28  1  0
 15 29  1  0
 17 30  1  0
 17 31  1  0
 17 32  1  0
 18 33  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
1,6-Dihydroxy-3-methyl-8-(methyloxy)anthracene-9,10-dione	ChEBI
1,6-Dihydroxy-8-methoxy-3-methyl-9,10-anthraquinone	ChEBI
3,8-Dihydroxy-1-methoxy-6-methylanthracene-9,10-dione	ChEBI
Emodin-8-methyl ether	ChEBI

Chemical Formula

C₁₆H₁₂O₅

Average Mass

284.2670 Da

Monoisotopic Mass

284.06847 Da

IUPAC Name

1,6-dihydroxy-8-methoxy-3-methyl-9,10-dihydroanthracene-9,10-dione

Traditional Name

questin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C16H12O5/c1-7-3-9-13(11(18)4-7)16(20)14-10(15(9)19)5-8(17)6-12(14)21-2/h3-6,17-18H,1-2H3

InChI Key

UUNPIWCQMVNINR-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
Aspergillus aureoterreus	LOTUS Database	35616633
Penicillium	NPAtlas	5838081
Polygonum cuspidatum	KNApSAcK Database	22123792
Polygonum multiflorum	KNApSAcK Database	22123792
Rhamnus davurica	Plant	KNApSAcK
Rumex patientia	KNApSAcK Database	22123792
Senna artemisioides	LOTUS Database	35616633
Senna didymobotrya	KNApSAcK Database	22123792
Senna lindheimeriana	LOTUS Database	35616633
Senna obtusifolia	KNApSAcK Database	22123792
Senna occidentalis	KNApSAcK Database	22123792
Senna siamea	LOTUS Database	35616633
Senna sophera	KNApSAcK Database	22123792
Senna tora	LOTUS Database	35616633
Trewia nudiflora	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Aspergillus fumigatus	KNApSAcK Database	22123792
Aspergillus terreus IMI16043	KNApSAcK Database	22123792
Microascus tardifaciens	KNApSAcK Database	22123792

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as hydroxyanthraquinones. These 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
Aryl ketone
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Vinylogous acid
Ketone
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

hydroxyanthraquinones (CHEBI:16200 )
Anthraquinone type (C01448 )

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	2.94	ALOGPS
logP	3.32	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	7.28	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	76.62 m³·mol⁻¹	ChemAxon
Polarizability	29.04 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

NPA004626

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00000570

Chemspider ID

141217

KEGG Compound ID

C01448

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

160717

PDB ID

Not Available

ChEBI ID

16200

Good Scents ID

Not Available

References

General References

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 ]

Showing NP-Card for Questin (NP0021757)

MOL for NP0021757 (Questin)

3D MOL for NP0021757 (Questin)

3D SDF for NP0021757 (Questin)

3D-SDF for NP0021757 (Questin)

PDB for NP0021757 (Questin)

3D PDB for NP0021757 (Questin)

SMILES for NP0021757 (Questin)

INCHI for NP0021757 (Questin)

Structure for NP0021757 (Questin)

3D Structure for NP0021757 (Questin)