NP-MRD: Showing NP-Card for 4,9,10'-trihydroxy-7-methoxy-7'-methyl-3',4'-dihydrospiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-3,5,8,9'-tetrone (NP0254854)

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Record Information

Version

2.0

Created at

2022-09-07 19:08:31 UTC

Updated at

2022-09-07 19:08:32 UTC

NP-MRD ID

NP0254854

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,9,10'-trihydroxy-7-methoxy-7'-methyl-3',4'-dihydrospiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-3,5,8,9'-tetrone

Description

4,9,10'-Trihydroxy-7-methoxy-7'-methyl-4',5,8,9'-tetrahydro-3H,3'H-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-3,5,8,9'-tetrone belongs to the class of organic compounds known as pyranochromenes. These are organic heterocyclic compounds containing a pyran ring fused to a chromene (1-benzopyran) moiety. 4,9,10'-trihydroxy-7-methoxy-7'-methyl-3',4'-dihydrospiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-3,5,8,9'-tetrone is found in Actinoplanes ianthinogenes. 4,9,10'-Trihydroxy-7-methoxy-7'-methyl-4',5,8,9'-tetrahydro-3H,3'H-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-3,5,8,9'-tetrone is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241505332D          

 36 41  0  0  0  0            999 V2000
    3.8030   -5.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5877   -5.2859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2007   -4.7337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0289   -3.9268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6418   -3.3746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4701   -2.5676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4265   -3.6293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0395   -3.0771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8677   -2.2701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8242   -3.3318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5385   -2.9191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6245   -2.0985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1518   -3.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4065   -2.6862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2134   -2.5144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7656   -3.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5725   -2.9556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1247   -3.5685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9317   -3.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4839   -4.0097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2908   -3.8380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2292   -4.7944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4222   -4.9662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1675   -5.7509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8700   -4.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0631   -4.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8084   -5.3097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5109   -3.9121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7040   -4.0838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8164   -4.2247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9959   -4.1387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3830   -4.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5547   -5.4978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5983   -4.4362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9854   -4.9884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1571   -5.7953    0.0000 O   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  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
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 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 18 25  2  0  0  0  0
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 26 27  1  0  0  0  0
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 16 28  1  0  0  0  0
 28 29  1  0  0  0  0
 13 29  1  0  0  0  0
 13 30  1  0  0  0  0
 30 31  1  0  0  0  0
 10 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
  7 34  1  0  0  0  0
 34 35  1  0  0  0  0
  3 35  1  0  0  0  0
 35 36  2  0  0  0  0
M  END

     RDKit          3D

 52 57  0  0  0  0  0  0  0  0999 V2000
    7.2391    2.5037    2.1646 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2637    1.1872    1.5925 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2268    0.7739    0.7490 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3725    0.9932   -0.5485 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3586    0.6057   -1.5195 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4866    0.8102   -2.7632 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1479   -0.0405   -1.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1440   -0.4359   -1.9251 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3037   -0.2030   -3.2829 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0007   -1.0508   -1.4567 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8275   -1.2894   -0.1093 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8476   -0.8875    0.7611 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7401   -1.0967    2.1344 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0038   -0.2676    0.3057 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0284    0.1265    1.2645 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9190   -0.0681    2.5020 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6125   -1.9142    0.1312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2071   -1.6353   -0.9862 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1957   -2.7413   -1.1573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5140   -2.2981   -1.6932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0043   -1.1421   -0.8863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3464   -1.0746   -0.5895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7835   -0.0040    0.1520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1269    0.0692    0.4526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5394    1.1534    1.1979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9813    1.2955    1.5598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6739    2.0557    1.5880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3829    1.9985    1.3072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6015    2.8937    1.7089 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8870    0.9603    0.5743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5225    0.8851    0.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6071    1.7916    0.6513 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0858   -0.2100   -0.4878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7384   -0.3569   -0.8341 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7880   -1.5721   -2.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6941   -1.8748   -3.3021 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2851    2.5218    2.7666 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0702    2.6471    2.8611 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1827    3.2847    1.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2858    1.4816   -0.8970 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6501   -0.4434   -3.9906 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9018   -1.5468    2.4698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7308   -3.5255   -1.7853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3711   -3.2024   -0.1625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2347   -3.1402   -1.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4988   -2.0537   -2.7843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0602   -1.8186   -0.9112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8416   -0.6898    0.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5742    0.7751    0.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1415    0.7866    2.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1998    2.3730    1.6515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5299    2.6101    1.1394 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  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 17  1  0
 18 17  1  1
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 30  2  0
 30 28  1  0
 28 29  2  0
 28 27  1  0
 27 25  1  0
 25 26  1  0
 25 24  2  0
 30 31  1  0
 31 32  1  0
 31 33  2  0
 33 34  1  0
 18 35  1  0
 35 36  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  2  0
 15  3  1  0
 14  7  1  0
 35 10  1  0
 34 18  1  0
 33 21  1  0
 24 23  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  4 40  1  0
  9 41  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  0
 20 46  1  0
 22 47  1  0
 26 49  1  0
 26 50  1  0
 26 51  1  0
 24 48  1  0
 32 52  1  0
 13 42  1  0
M  END


  Mrv1533004241505332D          

 36 41  0  0  0  0            999 V2000
    3.8030   -5.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5877   -5.2859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2007   -4.7337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0289   -3.9268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6418   -3.3746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4701   -2.5676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4265   -3.6293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0395   -3.0771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8677   -2.2701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8242   -3.3318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5385   -2.9191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6245   -2.0985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1518   -3.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4065   -2.6862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2134   -2.5144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7656   -3.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5725   -2.9556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1247   -3.5685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9317   -3.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4839   -4.0097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2908   -3.8380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2292   -4.7944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4222   -4.9662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1675   -5.7509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8700   -4.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0631   -4.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8084   -5.3097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5109   -3.9121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7040   -4.0838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8164   -4.2247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9959   -4.1387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3830   -4.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5547   -5.4978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5983   -4.4362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9854   -4.9884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1571   -5.7953    0.0000 O   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  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
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 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
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 20 22  1  0  0  0  0
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 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 18 25  2  0  0  0  0
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 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 16 28  1  0  0  0  0
 28 29  1  0  0  0  0
 13 29  1  0  0  0  0
 13 30  1  0  0  0  0
 30 31  1  0  0  0  0
 10 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
  7 34  1  0  0  0  0
 34 35  1  0  0  0  0
  3 35  1  0  0  0  0
 35 36  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0254854

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=O)C2=C(O)C3=C(OC4(CCC5=CC6=C(C(=O)OC(C)=C6)C(O)=C5O4)C3=O)C(O)=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H16O11/c1-8-5-10-6-9-3-4-25(35-21(9)19(29)13(10)24(32)34-8)23(31)16-18(28)14-11(26)7-12(33-2)17(27)15(14)20(30)22(16)36-25/h5-7,28-30H,3-4H2,1-2H3

> <INCHI_KEY>
NIHLMIADSHAEBH-UHFFFAOYSA-N

> <FORMULA>
C25H16O11

> <MOLECULAR_WEIGHT>
492.392

> <EXACT_MASS>
492.069261335

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
48.09513914507181

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,9,10'-trihydroxy-7-methoxy-7'-methyl-4',5,8,9'-tetrahydro-3H,3'H-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-3,5,8,9'-tetrone

> <ALOGPS_LOGP>
3.19

> <JCHEM_LOGP>
4.925682982666666

> <ALOGPS_LOGS>
-4.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.505078408743042

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.682689397355137

> <JCHEM_PKA_STRONGEST_BASIC>
-3.475016254454517

> <JCHEM_POLAR_SURFACE_AREA>
165.89

> <JCHEM_REFRACTIVITY>
123.96709999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.95e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,9,10'-trihydroxy-7-methoxy-7'-methyl-3',4'-dihydrospiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-3,5,8,9'-tetrone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       7.099  -9.392   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.564  -9.867   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.708  -8.836   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.387  -7.330   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.531  -6.299   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      10.211  -4.793   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      11.996  -6.775   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.140  -5.744   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.820  -4.238   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      14.605  -6.219   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.939  -5.449   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      16.099  -3.917   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      17.083  -6.479   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.559  -5.014   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      19.065  -4.694   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.096  -5.838   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      21.602  -5.517   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      22.633  -6.661   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      24.139  -6.341   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      25.170  -7.485   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      26.676  -7.164   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      24.694  -8.950   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      23.188  -9.270   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      22.713 -10.735   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      22.157  -8.126   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      20.651  -8.447   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      20.176  -9.911   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      19.620  -7.303   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      18.114  -7.623   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      16.457  -7.886   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      14.926  -7.726   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      13.782  -8.756   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      14.102 -10.263   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      12.317  -8.281   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.173  -9.312   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      11.493 -10.818   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   35                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   34                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   31                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   29   30                                             
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   28                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   18   26                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   16   29                                                  
CONECT   29   28   13                                                       
CONECT   30   13   31                                                       
CONECT   31   30   10   32                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32    7   35                                                  
CONECT   35   34    3   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   82    0
END

View in JSmol

Synonyms

Value	Source
7,8-Dideoxy-6-oxo-griseorhodin C	MeSH
DDO-griseorhodin C	MeSH

Chemical Formula

C₂₅H₁₆O₁₁

Average Mass

492.3920 Da

Monoisotopic Mass

492.06926 Da

IUPAC Name

4,9,10'-trihydroxy-7-methoxy-7'-methyl-4',5,8,9'-tetrahydro-3H,3'H-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-3,5,8,9'-tetrone

Traditional Name

4,9,10'-trihydroxy-7-methoxy-7'-methyl-3',4'-dihydrospiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-3,5,8,9'-tetrone

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)C2=C(O)C3=C(OC4(CCC5=CC6=C(C(=O)OC(C)=C6)C(O)=C5O4)C3=O)C(O)=C2C1=O

InChI Identifier

InChI=1S/C25H16O11/c1-8-5-10-6-9-3-4-25(35-21(9)19(29)13(10)24(32)34-8)23(31)16-18(28)14-11(26)7-12(33-2)17(27)15(14)20(30)22(16)36-25/h5-7,28-30H,3-4H2,1-2H3

InChI Key

NIHLMIADSHAEBH-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, 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
Actinoplanes ianthinogenes	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranochromenes. These are organic heterocyclic compounds containing a pyran ring fused to a chromene (1-benzopyran) moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Pyranochromenes

Alternative Parents

Substituents

Pyranochromene
Naphthofuran
Naphthoquinone
Isocoumarin
Naphthalene
2-benzopyran
Coumaran
Benzofuran
Quinone
Aryl ketone
Aryl alkyl ketone
1-hydroxy-4-unsubstituted benzenoid
Ketal
Pyranone
Pyran
Benzenoid
Vinylogous ester
Heteroaromatic compound
Vinylogous acid
Lactone
Ketone
Polyol
Acetal
Oxacycle
Aldehyde
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
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	3.19	ALOGPS
logP	4.93	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	7.68	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	165.89 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	123.97 m³·mol⁻¹	ChemAxon
Polarizability	48.1 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

9870278

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4,9,10'-trihydroxy-7-methoxy-7'-methyl-3',4'-dihydrospiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-3,5,8,9'-tetrone (NP0254854)

MOL for NP0254854 (4,9,10'-trihydroxy-7-methoxy-7'-methyl-3',4'-dihydrospiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-3,5,8,9'-tetrone)

3D MOL for NP0254854 (4,9,10'-trihydroxy-7-methoxy-7'-methyl-3',4'-dihydrospiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-3,5,8,9'-tetrone)

3D SDF for NP0254854 (4,9,10'-trihydroxy-7-methoxy-7'-methyl-3',4'-dihydrospiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-3,5,8,9'-tetrone)

3D-SDF for NP0254854 (4,9,10'-trihydroxy-7-methoxy-7'-methyl-3',4'-dihydrospiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-3,5,8,9'-tetrone)

PDB for NP0254854 (4,9,10'-trihydroxy-7-methoxy-7'-methyl-3',4'-dihydrospiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-3,5,8,9'-tetrone)

3D PDB for NP0254854 (4,9,10'-trihydroxy-7-methoxy-7'-methyl-3',4'-dihydrospiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-3,5,8,9'-tetrone)

SMILES for NP0254854 (4,9,10'-trihydroxy-7-methoxy-7'-methyl-3',4'-dihydrospiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-3,5,8,9'-tetrone)

INCHI for NP0254854 (4,9,10'-trihydroxy-7-methoxy-7'-methyl-3',4'-dihydrospiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-3,5,8,9'-tetrone)

Structure for NP0254854 (4,9,10'-trihydroxy-7-methoxy-7'-methyl-3',4'-dihydrospiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-3,5,8,9'-tetrone)

3D Structure for NP0254854 (4,9,10'-trihydroxy-7-methoxy-7'-methyl-3',4'-dihydrospiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-3,5,8,9'-tetrone)