NP-MRD: Showing NP-Card for 9-O-demethyltrigonostemone (NP0034879)

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Record Information

Version

2.0

Created at

2021-06-20 18:28:55 UTC

Updated at

2021-06-30 00:05:32 UTC

NP-MRD ID

NP0034879

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-O-demethyltrigonostemone

Provided By

JEOL Database JEOL Logo

Description

9-Hydroxy-3,6-dimethoxy-1,1,7-trimethyl-1,2-dihydrophenanthren-2-one belongs to the class of organic compounds known as phenanthrols. Phenanthrols are compounds containing a phenanthrene (or its hydrogenated derivative) to which a hydroxyl group is attached. 9-O-demethyltrigonostemone is found in Strophioblachia fimbricalyx. 9-O-demethyltrigonostemone was first documented in 2009 (Seephonkai, P., et al.). Based on a literature review very few articles have been published on 9-hydroxy-3,6-dimethoxy-1,1,7-trimethyl-1,2-dihydrophenanthren-2-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202120283D          

 43 45  0  0  0  0            999 V2000
   -2.5692    5.0890    0.6401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3111    4.4381    0.7919 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3466    3.2300    1.4763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5207    2.2581    1.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4007    0.9253    1.6881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3269    0.5772    2.6941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2855   -0.7225    3.2257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3346   -1.6409    2.7950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3288   -2.8997    3.3414 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6178   -1.3085    1.8205 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5824   -2.2501    1.4040 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5495   -1.9501    0.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5550   -2.9918    0.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5647   -0.6743   -0.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5465   -0.4498   -1.0563 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6146    0.8392   -1.6508 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6084    0.2671    0.2790 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6038   -0.0121    1.2515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3807    1.5677    3.2022 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3158    1.6752    4.7436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7826    1.0908    2.7736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2280    2.9949    2.6597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8557    3.9339    3.1571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7860    5.7127    1.5117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3803    4.3777    0.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4966    5.7526   -0.2271 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0939    2.4835    0.2132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0078   -1.0234    3.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0320   -2.9665    4.0071 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5776   -3.2450    1.8488 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3841   -3.9401    0.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5677   -2.6559    0.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4873   -3.1891   -1.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8161    1.6103   -0.9000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7034    1.0622   -2.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4504    0.8374   -2.3571 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6486    1.2546   -0.1619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5343    0.7247    5.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3214    2.0024    5.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0407    2.4011    5.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0325    0.1126    3.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5600    1.7943    3.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8544    1.0054    1.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 17  2  0  0  0  0
 17 18  1  0  0  0  0
  6 19  1  0  0  0  0
  5  4  1  0  0  0  0
  4  3  2  0  0  0  0
  3 22  1  0  0  0  0
 22 19  1  0  0  0  0
 12 14  1  0  0  0  0
 22 23  2  0  0  0  0
 10  8  2  0  0  0  0
 12 13  1  0  0  0  0
 18  5  2  0  0  0  0
 14 15  1  0  0  0  0
  6  7  2  0  0  0  0
 15 16  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  6  5  1  0  0  0  0
  3  2  1  0  0  0  0
 10 11  1  0  0  0  0
  2  1  1  0  0  0  0
 11 12  2  0  0  0  0
 19 20  1  0  0  0  0
 10 18  1  0  0  0  0
 19 21  1  0  0  0  0
 17 37  1  0  0  0  0
 11 30  1  0  0  0  0
  7 28  1  0  0  0  0
  4 27  1  0  0  0  0
 13 31  1  0  0  0  0
 13 32  1  0  0  0  0
 13 33  1  0  0  0  0
 16 34  1  0  0  0  0
 16 35  1  0  0  0  0
 16 36  1  0  0  0  0
  9 29  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
 20 38  1  0  0  0  0
 20 39  1  0  0  0  0
 20 40  1  0  0  0  0
 21 41  1  0  0  0  0
 21 42  1  0  0  0  0
 21 43  1  0  0  0  0
M  END

     RDKit          3D

 43 45  0  0  0  0  0  0  0  0999 V2000
   -2.5692    5.0890    0.6401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3111    4.4381    0.7919 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3466    3.2300    1.4763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5207    2.2581    1.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4007    0.9253    1.6881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3269    0.5772    2.6941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2855   -0.7225    3.2257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3346   -1.6409    2.7950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3288   -2.8997    3.3414 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6178   -1.3085    1.8205 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5824   -2.2501    1.4040 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5495   -1.9501    0.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5550   -2.9918    0.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5647   -0.6743   -0.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5465   -0.4498   -1.0563 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6146    0.8392   -1.6508 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6084    0.2671    0.2790 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6038   -0.0121    1.2515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3807    1.5677    3.2022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3158    1.6752    4.7436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7826    1.0908    2.7736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2280    2.9949    2.6597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8557    3.9339    3.1571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7860    5.7127    1.5117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3803    4.3777    0.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4966    5.7526   -0.2271 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0939    2.4835    0.2132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0078   -1.0234    3.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0320   -2.9665    4.0071 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5776   -3.2450    1.8488 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3841   -3.9401    0.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5677   -2.6559    0.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4873   -3.1891   -1.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8161    1.6103   -0.9000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7034    1.0622   -2.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4504    0.8374   -2.3571 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6486    1.2546   -0.1619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5343    0.7247    5.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3214    2.0024    5.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0407    2.4011    5.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0325    0.1126    3.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5600    1.7943    3.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8544    1.0054    1.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 17  2  0
 17 18  1  0
  6 19  1  0
  5  4  1  0
  4  3  2  0
  3 22  1  0
 22 19  1  0
 12 14  1  0
 22 23  2  0
 10  8  2  0
 12 13  1  0
 18  5  2  0
 14 15  1  0
  6  7  2  0
 15 16  1  0
  7  8  1  0
  8  9  1  0
  6  5  1  0
  3  2  1  0
 10 11  1  0
  2  1  1  0
 11 12  2  0
 19 20  1  0
 10 18  1  0
 19 21  1  0
 17 37  1  0
 11 30  1  0
  7 28  1  0
  4 27  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
  9 29  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
 20 38  1  0
 20 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
 21 43  1  0
M  END


  Mrv1652306202120283D          

 43 45  0  0  0  0            999 V2000
   -2.5692    5.0890    0.6401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3111    4.4381    0.7919 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3466    3.2300    1.4763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5207    2.2581    1.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4007    0.9253    1.6881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3269    0.5772    2.6941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2855   -0.7225    3.2257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3346   -1.6409    2.7950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3288   -2.8997    3.3414 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6178   -1.3085    1.8205 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5824   -2.2501    1.4040 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5495   -1.9501    0.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5550   -2.9918    0.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5647   -0.6743   -0.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5465   -0.4498   -1.0563 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6146    0.8392   -1.6508 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6084    0.2671    0.2790 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6038   -0.0121    1.2515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3807    1.5677    3.2022 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3158    1.6752    4.7436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7826    1.0908    2.7736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2280    2.9949    2.6597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8557    3.9339    3.1571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7860    5.7127    1.5117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3803    4.3777    0.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4966    5.7526   -0.2271 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0939    2.4835    0.2132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0078   -1.0234    3.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0320   -2.9665    4.0071 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5776   -3.2450    1.8488 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3841   -3.9401    0.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5677   -2.6559    0.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4873   -3.1891   -1.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8161    1.6103   -0.9000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7034    1.0622   -2.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4504    0.8374   -2.3571 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6486    1.2546   -0.1619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5343    0.7247    5.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3214    2.0024    5.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0407    2.4011    5.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0325    0.1126    3.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5600    1.7943    3.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8544    1.0054    1.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 17  2  0  0  0  0
 17 18  1  0  0  0  0
  6 19  1  0  0  0  0
  5  4  1  0  0  0  0
  4  3  2  0  0  0  0
  3 22  1  0  0  0  0
 22 19  1  0  0  0  0
 12 14  1  0  0  0  0
 22 23  2  0  0  0  0
 10  8  2  0  0  0  0
 12 13  1  0  0  0  0
 18  5  2  0  0  0  0
 14 15  1  0  0  0  0
  6  7  2  0  0  0  0
 15 16  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  6  5  1  0  0  0  0
  3  2  1  0  0  0  0
 10 11  1  0  0  0  0
  2  1  1  0  0  0  0
 11 12  2  0  0  0  0
 19 20  1  0  0  0  0
 10 18  1  0  0  0  0
 19 21  1  0  0  0  0
 17 37  1  0  0  0  0
 11 30  1  0  0  0  0
  7 28  1  0  0  0  0
  4 27  1  0  0  0  0
 13 31  1  0  0  0  0
 13 32  1  0  0  0  0
 13 33  1  0  0  0  0
 16 34  1  0  0  0  0
 16 35  1  0  0  0  0
 16 36  1  0  0  0  0
  9 29  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
 20 38  1  0  0  0  0
 20 39  1  0  0  0  0
 20 40  1  0  0  0  0
 21 41  1  0  0  0  0
 21 42  1  0  0  0  0
 21 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0034879

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C([H])=C(C(OC([H])([H])[H])=C([H])C2=C2C([H])=C(OC([H])([H])[H])C(=O)C(C2=C1[H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C19H20O4/c1-10-6-13-11(7-16(10)22-4)12-8-17(23-5)18(21)19(2,3)14(12)9-15(13)20/h6-9,20H,1-5H3

> <INCHI_KEY>
LPMUQQPZLWUZEQ-UHFFFAOYSA-N

> <FORMULA>
C19H20O4

> <MOLECULAR_WEIGHT>
312.365

> <EXACT_MASS>
312.136159124

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
34.73739963452457

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-hydroxy-3,6-dimethoxy-1,1,7-trimethyl-1,2-dihydrophenanthren-2-one

> <ALOGPS_LOGP>
3.79

> <JCHEM_LOGP>
4.0616376333333335

> <ALOGPS_LOGS>
-4.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.525336907875342

> <JCHEM_PKA_STRONGEST_BASIC>
-4.56608975199134

> <JCHEM_POLAR_SURFACE_AREA>
55.76

> <JCHEM_REFRACTIVITY>
91.0045

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.98e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-hydroxy-3,6-dimethoxy-1,1,7-trimethylphenanthren-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 43 45  0  0  0  0  0  0  0  0999 V2000
   -2.5692    5.0890    0.6401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3111    4.4381    0.7919 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3466    3.2300    1.4763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5207    2.2581    1.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4007    0.9253    1.6881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3269    0.5772    2.6941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2855   -0.7225    3.2257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3346   -1.6409    2.7950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3288   -2.8997    3.3414 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6178   -1.3085    1.8205 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5824   -2.2501    1.4040 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5495   -1.9501    0.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5550   -2.9918    0.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5647   -0.6743   -0.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5465   -0.4498   -1.0563 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6146    0.8392   -1.6508 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6084    0.2671    0.2790 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6038   -0.0121    1.2515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3807    1.5677    3.2022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3158    1.6752    4.7436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7826    1.0908    2.7736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2280    2.9949    2.6597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8557    3.9339    3.1571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7860    5.7127    1.5117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3803    4.3777    0.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4966    5.7526   -0.2271 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0939    2.4835    0.2132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0078   -1.0234    3.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0320   -2.9665    4.0071 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5776   -3.2450    1.8488 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3841   -3.9401    0.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5677   -2.6559    0.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4873   -3.1891   -1.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8161    1.6103   -0.9000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7034    1.0622   -2.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4504    0.8374   -2.3571 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6486    1.2546   -0.1619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5343    0.7247    5.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3214    2.0024    5.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0407    2.4011    5.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0325    0.1126    3.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5600    1.7943    3.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8544    1.0054    1.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 17  2  0
 17 18  1  0
  6 19  1  0
  5  4  1  0
  4  3  2  0
  3 22  1  0
 22 19  1  0
 12 14  1  0
 22 23  2  0
 10  8  2  0
 12 13  1  0
 18  5  2  0
 14 15  1  0
  6  7  2  0
 15 16  1  0
  7  8  1  0
  8  9  1  0
  6  5  1  0
  3  2  1  0
 10 11  1  0
  2  1  1  0
 11 12  2  0
 19 20  1  0
 10 18  1  0
 19 21  1  0
 17 37  1  0
 11 30  1  0
  7 28  1  0
  4 27  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
  9 29  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
 20 38  1  0
 20 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
 21 43  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.569   5.089   0.640  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.311   4.438   0.792  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.347   3.230   1.476  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.521   2.258   1.076  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.401   0.925   1.688  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.327   0.577   2.694  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.286  -0.723   3.226  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.335  -1.641   2.795  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.329  -2.900   3.341  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.618  -1.309   1.821  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.582  -2.250   1.404  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.550  -1.950   0.438  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.555  -2.992   0.035  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.565  -0.674  -0.127  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.547  -0.450  -1.056  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.615   0.839  -1.651  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.608   0.267   0.279  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.604  -0.012   1.252  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.381   1.568   3.202  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.316   1.675   4.744  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.783   1.091   2.774  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.228   2.995   2.660  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.856   3.934   3.157  0.00  0.00           O+0
HETATM   24  H   UNK     0      -2.786   5.713   1.512  0.00  0.00           H+0
HETATM   25  H   UNK     0      -3.380   4.378   0.450  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.497   5.753  -0.227  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.094   2.483   0.213  0.00  0.00           H+0
HETATM   28  H   UNK     0      -2.008  -1.023   3.979  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.032  -2.966   4.007  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.578  -3.245   1.849  0.00  0.00           H+0
HETATM   31  H   UNK     0       3.384  -3.940   0.555  0.00  0.00           H+0
HETATM   32  H   UNK     0       4.568  -2.656   0.280  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.487  -3.189  -1.040  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.816   1.610  -0.900  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.703   1.062  -2.216  0.00  0.00           H+0
HETATM   36  H   UNK     0       4.450   0.837  -2.357  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.649   1.255  -0.162  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.534   0.725   5.241  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.321   2.002   5.071  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.041   2.401   5.131  0.00  0.00           H+0
HETATM   41  H   UNK     0      -4.032   0.113   3.199  0.00  0.00           H+0
HETATM   42  H   UNK     0      -4.560   1.794   3.095  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.854   1.005   1.682  0.00  0.00           H+0
CONECT    1    2   24   25   26                                             
CONECT    2    3    1                                                       
CONECT    3    4   22    2                                                  
CONECT    4    5    3   27                                                  
CONECT    5    4   18    6                                                  
CONECT    6   19    7    5                                                  
CONECT    7    6    8   28                                                  
CONECT    8   10    7    9                                                  
CONECT    9    8   29                                                       
CONECT   10    8   11   18                                                  
CONECT   11   10   12   30                                                  
CONECT   12   14   13   11                                                  
CONECT   13   12   31   32   33                                             
CONECT   14   17   12   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   34   35   36                                             
CONECT   17   14   18   37                                                  
CONECT   18   17    5   10                                                  
CONECT   19    6   22   20   21                                             
CONECT   20   19   38   39   40                                             
CONECT   21   19   41   42   43                                             
CONECT   22    3   19   23                                                  
CONECT   23   22                                                            
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    4                                                            
CONECT   28    7                                                            
CONECT   29    9                                                            
CONECT   30   11                                                            
CONECT   31   13                                                            
CONECT   32   13                                                            
CONECT   33   13                                                            
CONECT   34   16                                                            
CONECT   35   16                                                            
CONECT   36   16                                                            
CONECT   37   17                                                            
CONECT   38   20                                                            
CONECT   39   20                                                            
CONECT   40   20                                                            
CONECT   41   21                                                            
CONECT   42   21                                                            
CONECT   43   21                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   90    0
END

RDKit          3D

43 45  0  0  0  0  0  0  0  0999 V2000
   -2.5692    5.0890    0.6401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3111    4.4381    0.7919 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3466    3.2300    1.4763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5207    2.2581    1.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4007    0.9253    1.6881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3269    0.5772    2.6941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2855   -0.7225    3.2257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3346   -1.6409    2.7950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3288   -2.8997    3.3414 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6178   -1.3085    1.8205 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5824   -2.2501    1.4040 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5495   -1.9501    0.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5550   -2.9918    0.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5647   -0.6743   -0.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5465   -0.4498   -1.0563 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6146    0.8392   -1.6508 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6084    0.2671    0.2790 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6038   -0.0121    1.2515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3807    1.5677    3.2022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3158    1.6752    4.7436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7826    1.0908    2.7736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2280    2.9949    2.6597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8557    3.9339    3.1571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7860    5.7127    1.5117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3803    4.3777    0.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4966    5.7526   -0.2271 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0939    2.4835    0.2132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0078   -1.0234    3.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0320   -2.9665    4.0071 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5776   -3.2450    1.8488 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3841   -3.9401    0.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5677   -2.6559    0.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4873   -3.1891   -1.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8161    1.6103   -0.9000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7034    1.0622   -2.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4504    0.8374   -2.3571 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6486    1.2546   -0.1619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5343    0.7247    5.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3214    2.0024    5.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0407    2.4011    5.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0325    0.1126    3.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5600    1.7943    3.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8544    1.0054    1.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 17  2  0
 17 18  1  0
  6 19  1  0
  5  4  1  0
  4  3  2  0
  3 22  1  0
 22 19  1  0
 12 14  1  0
 22 23  2  0
 10  8  2  0
 12 13  1  0
 18  5  2  0
 14 15  1  0
  6  7  2  0
 15 16  1  0
  7  8  1  0
  8  9  1  0
  6  5  1  0
  3  2  1  0
 10 11  1  0
  2  1  1  0
 11 12  2  0
 19 20  1  0
 10 18  1  0
 19 21  1  0
 17 37  1  0
 11 30  1  0
  7 28  1  0
  4 27  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
  9 29  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
 20 38  1  0
 20 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
 21 43  1  0
M  END

View in JSmol

Synonyms

Value	Source
9-O-Demethyltrigonostemone	ChEMBL

Chemical Formula

C₁₉H₂₀O₄

Average Mass

312.3650 Da

Monoisotopic Mass

312.13616 Da

IUPAC Name

9-hydroxy-3,6-dimethoxy-1,1,7-trimethyl-1,2-dihydrophenanthren-2-one

Traditional Name

9-hydroxy-3,6-dimethoxy-1,1,7-trimethylphenanthren-2-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C2C([H])=C(C(OC([H])([H])[H])=C([H])C2=C2C([H])=C(OC([H])([H])[H])C(=O)C(C2=C1[H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C19H20O4/c1-10-6-13-11(7-16(10)22-4)12-8-17(23-5)18(21)19(2,3)14(12)9-15(13)20/h6-9,20H,1-5H3

InChI Key

LPMUQQPZLWUZEQ-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Strophioblachia fimbricalyx	JEOL database	Seephonkai, P., et al, J. Nat. Prod. 72, 1892 (2009)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthrols. Phenanthrols are compounds containing a phenanthrene (or its hydrogenated derivative) to which a hydroxyl group is attached.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Phenanthrols

Direct Parent

Phenanthrols

Alternative Parents

Substituents

Phenanthrol
Hydrophenanthrene
1-naphthol
Naphthalene
Anisole
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Cyclic ketone
Ketone
Ether
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
Aromatic homopolycyclic compound

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	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.79	ALOGPS
logP	4.06	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	8.53	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	91 m³·mol⁻¹	ChemAxon
Polarizability	34.74 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00047692

Chemspider ID

24656076

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44557096

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Seephonkai, P., et al. (2009). Seephonkai, P., et al, J. Nat. Prod. 72, 1892 (2009). J. Nat. Prod..

Showing NP-Card for 9-O-demethyltrigonostemone (NP0034879)

MOL for NP0034879 (9-O-demethyltrigonostemone)

3D MOL for NP0034879 (9-O-demethyltrigonostemone)

3D SDF for NP0034879 (9-O-demethyltrigonostemone)

3D-SDF for NP0034879 (9-O-demethyltrigonostemone)

PDB for NP0034879 (9-O-demethyltrigonostemone)

3D PDB for NP0034879 (9-O-demethyltrigonostemone)

SMILES for NP0034879 (9-O-demethyltrigonostemone)

INCHI for NP0034879 (9-O-demethyltrigonostemone)

Structure for NP0034879 (9-O-demethyltrigonostemone)

3D Structure for NP0034879 (9-O-demethyltrigonostemone)