NP-MRD: Showing NP-Card for 9-methyl-3-(4-methyl-3-pentenyl)-2,3-dihydronaphtho[1,8-bc]pyran-7,8-dion+ (NP0024815)

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Record Information

Version

2.0

Created at

2021-06-19 17:06:02 UTC

Updated at

2021-06-29 23:49:22 UTC

NP-MRD ID

NP0024815

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-methyl-3-(4-methyl-3-pentenyl)-2,3-dihydronaphtho[1,8-bc]pyran-7,8-dion+

Provided By

JEOL Database JEOL Logo

Description

(4S)-12-methyl-4-(4-methylpent-3-en-1-yl)-2-oxatricyclo[7.3.1.0⁵,¹³]Trideca-1(12),5(13),6,8-tetraene-10,11-dione belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone). 9-methyl-3-(4-methyl-3-pentenyl)-2,3-dihydronaphtho[1,8-bc]pyran-7,8-dion+ is found in Eremophila serrulata. 9-methyl-3-(4-methyl-3-pentenyl)-2,3-dihydronaphtho[1,8-bc]pyran-7,8-dion+ was first documented in 2007 (Ndi, C. P., et al.). Based on a literature review very few articles have been published on (4S)-12-methyl-4-(4-methylpent-3-en-1-yl)-2-oxatricyclo[7.3.1.0⁵,¹³]Trideca-1(12),5(13),6,8-tetraene-10,11-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119063D          

 42 44  0  0  0  0            999 V2000
   -1.6563    3.4816    0.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4854    3.5463   -0.7744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8567    3.9247   -2.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8004    3.3089   -0.4485 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3685    2.9192    0.8885 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1409    1.5948    0.8355 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3060    0.3692    0.4042 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1439    0.0505    1.3488 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6281   -0.2770    2.6556 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4238   -1.4155    2.6813 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4589   -2.1759    3.7873 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6718   -1.9010    5.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3200   -3.3883    3.8319 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3784   -4.0959    4.8293 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1358   -3.7407    2.5986 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8282   -4.7492    2.5765 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0693   -2.8386    1.4375 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8418   -3.1168    0.3015 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7925   -2.2650   -0.7993 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9735   -1.1388   -0.7681 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1946   -0.8613    0.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2389   -1.7158    1.4861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3761    3.2799    1.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1959    4.4347    0.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3474    2.6929   -0.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0129    3.9600   -2.8509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5610    3.1956   -2.6002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3278    4.9130   -2.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5536    3.4148   -1.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0647    3.7100    1.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6105    2.8732    1.6732 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9892    1.7133    0.1469 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5874    1.4197    1.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8918    0.5326   -0.5984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4671   -0.7817    0.9716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5307    0.9047    1.4510 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0059   -2.7413    5.2575 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3449   -1.7546    5.8853 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0490   -1.0049    4.9525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4851   -3.9950    0.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3944   -2.4788   -1.6797 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9440   -0.4768   -1.6317 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  2  0  0  0  0
 10  9  1  0  0  0  0
 22 21  2  0  0  0  0
 21  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 17 15  1  0  0  0  0
 15 16  2  0  0  0  0
 10 11  2  0  0  0  0
 13 14  2  0  0  0  0
 11 13  1  0  0  0  0
  7  6  1  0  0  0  0
 13 15  1  0  0  0  0
  6  5  1  0  0  0  0
 10 22  1  0  0  0  0
  5  4  1  0  0  0  0
 18 19  1  0  0  0  0
  4  2  2  3  0  0  0
 17 22  1  0  0  0  0
  2  1  1  0  0  0  0
 19 20  2  0  0  0  0
  2  3  1  0  0  0  0
 20 21  1  0  0  0  0
 11 12  1  0  0  0  0
  7 34  1  6  0  0  0
 19 41  1  0  0  0  0
 20 42  1  0  0  0  0
 18 40  1  0  0  0  0
  8 35  1  0  0  0  0
  8 36  1  0  0  0  0
  6 32  1  0  0  0  0
  6 33  1  0  0  0  0
  5 30  1  0  0  0  0
  5 31  1  0  0  0  0
  4 29  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  3 26  1  0  0  0  0
  3 27  1  0  0  0  0
  3 28  1  0  0  0  0
 12 37  1  0  0  0  0
 12 38  1  0  0  0  0
 12 39  1  0  0  0  0
M  END

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
   -1.6563    3.4816    0.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4854    3.5463   -0.7744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8567    3.9247   -2.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8004    3.3089   -0.4485 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3685    2.9192    0.8885 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1409    1.5948    0.8355 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3060    0.3692    0.4042 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1439    0.0505    1.3488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6281   -0.2770    2.6556 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4238   -1.4155    2.6813 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4589   -2.1759    3.7873 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6718   -1.9010    5.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3200   -3.3883    3.8319 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3784   -4.0959    4.8293 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1358   -3.7407    2.5986 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8282   -4.7492    2.5765 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0693   -2.8386    1.4375 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8418   -3.1168    0.3015 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7925   -2.2650   -0.7993 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9735   -1.1388   -0.7681 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1946   -0.8613    0.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2389   -1.7158    1.4861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3761    3.2799    1.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1959    4.4347    0.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3474    2.6929   -0.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0129    3.9600   -2.8509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5610    3.1956   -2.6002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3278    4.9130   -2.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5536    3.4148   -1.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0647    3.7100    1.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6105    2.8732    1.6732 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9892    1.7133    0.1469 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5874    1.4197    1.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8918    0.5326   -0.5984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4671   -0.7817    0.9716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5307    0.9047    1.4510 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0059   -2.7413    5.2575 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3449   -1.7546    5.8853 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0490   -1.0049    4.9525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4851   -3.9950    0.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3944   -2.4788   -1.6797 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9440   -0.4768   -1.6317 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  2  0
 10  9  1  0
 22 21  2  0
 21  7  1  0
  7  8  1  0
  8  9  1  0
 17 15  1  0
 15 16  2  0
 10 11  2  0
 13 14  2  0
 11 13  1  0
  7  6  1  0
 13 15  1  0
  6  5  1  0
 10 22  1  0
  5  4  1  0
 18 19  1  0
  4  2  2  3
 17 22  1  0
  2  1  1  0
 19 20  2  0
  2  3  1  0
 20 21  1  0
 11 12  1  0
  7 34  1  6
 19 41  1  0
 20 42  1  0
 18 40  1  0
  8 35  1  0
  8 36  1  0
  6 32  1  0
  6 33  1  0
  5 30  1  0
  5 31  1  0
  4 29  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
 12 37  1  0
 12 38  1  0
 12 39  1  0
M  END


  Mrv1652306192119063D          

 42 44  0  0  0  0            999 V2000
   -1.6563    3.4816    0.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4854    3.5463   -0.7744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8567    3.9247   -2.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8004    3.3089   -0.4485 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3685    2.9192    0.8885 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1409    1.5948    0.8355 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3060    0.3692    0.4042 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1439    0.0505    1.3488 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6281   -0.2770    2.6556 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4238   -1.4155    2.6813 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4589   -2.1759    3.7873 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6718   -1.9010    5.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3200   -3.3883    3.8319 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3784   -4.0959    4.8293 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1358   -3.7407    2.5986 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8282   -4.7492    2.5765 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0693   -2.8386    1.4375 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8418   -3.1168    0.3015 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7925   -2.2650   -0.7993 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9735   -1.1388   -0.7681 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1946   -0.8613    0.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2389   -1.7158    1.4861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3761    3.2799    1.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1959    4.4347    0.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3474    2.6929   -0.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0129    3.9600   -2.8509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5610    3.1956   -2.6002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3278    4.9130   -2.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5536    3.4148   -1.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0647    3.7100    1.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6105    2.8732    1.6732 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9892    1.7133    0.1469 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5874    1.4197    1.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8918    0.5326   -0.5984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4671   -0.7817    0.9716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5307    0.9047    1.4510 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0059   -2.7413    5.2575 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3449   -1.7546    5.8853 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0490   -1.0049    4.9525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4851   -3.9950    0.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3944   -2.4788   -1.6797 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9440   -0.4768   -1.6317 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  2  0  0  0  0
 10  9  1  0  0  0  0
 22 21  2  0  0  0  0
 21  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 17 15  1  0  0  0  0
 15 16  2  0  0  0  0
 10 11  2  0  0  0  0
 13 14  2  0  0  0  0
 11 13  1  0  0  0  0
  7  6  1  0  0  0  0
 13 15  1  0  0  0  0
  6  5  1  0  0  0  0
 10 22  1  0  0  0  0
  5  4  1  0  0  0  0
 18 19  1  0  0  0  0
  4  2  2  3  0  0  0
 17 22  1  0  0  0  0
  2  1  1  0  0  0  0
 19 20  2  0  0  0  0
  2  3  1  0  0  0  0
 20 21  1  0  0  0  0
 11 12  1  0  0  0  0
  7 34  1  6  0  0  0
 19 41  1  0  0  0  0
 20 42  1  0  0  0  0
 18 40  1  0  0  0  0
  8 35  1  0  0  0  0
  8 36  1  0  0  0  0
  6 32  1  0  0  0  0
  6 33  1  0  0  0  0
  5 30  1  0  0  0  0
  5 31  1  0  0  0  0
  4 29  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  3 26  1  0  0  0  0
  3 27  1  0  0  0  0
  3 28  1  0  0  0  0
 12 37  1  0  0  0  0
 12 38  1  0  0  0  0
 12 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0024815

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C(=C(C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])[C@@]1([H])C2=C3C(OC1([H])[H])=C(C(=O)C(=O)C3=C([H])C([H])=C2[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C19H20O3/c1-11(2)6-4-7-13-10-22-19-12(3)17(20)18(21)15-9-5-8-14(13)16(15)19/h5-6,8-9,13H,4,7,10H2,1-3H3/t13-/m1/s1

> <INCHI_KEY>
QJZOFSVFRGKNEJ-CYBMUJFWSA-N

> <FORMULA>
C19H20O3

> <MOLECULAR_WEIGHT>
296.366

> <EXACT_MASS>
296.141244504

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
33.055262595040276

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S)-12-methyl-4-(4-methylpent-3-en-1-yl)-2-oxatricyclo[7.3.1.0^{5,13}]trideca-1(12),5(13),6,8-tetraene-10,11-dione

> <ALOGPS_LOGP>
3.55

> <JCHEM_LOGP>
4.025705748

> <ALOGPS_LOGS>
-4.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.858992829807553

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
88.7494

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.64e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S)-12-methyl-4-(4-methylpent-3-en-1-yl)-2-oxatricyclo[7.3.1.0^{5,13}]trideca-1(12),5(13),6,8-tetraene-10,11-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
   -1.6563    3.4816    0.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4854    3.5463   -0.7744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8567    3.9247   -2.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8004    3.3089   -0.4485 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3685    2.9192    0.8885 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1409    1.5948    0.8355 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3060    0.3692    0.4042 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1439    0.0505    1.3488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6281   -0.2770    2.6556 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4238   -1.4155    2.6813 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4589   -2.1759    3.7873 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6718   -1.9010    5.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3200   -3.3883    3.8319 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3784   -4.0959    4.8293 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1358   -3.7407    2.5986 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8282   -4.7492    2.5765 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0693   -2.8386    1.4375 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8418   -3.1168    0.3015 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7925   -2.2650   -0.7993 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9735   -1.1388   -0.7681 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1946   -0.8613    0.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2389   -1.7158    1.4861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3761    3.2799    1.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1959    4.4347    0.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3474    2.6929   -0.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0129    3.9600   -2.8509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5610    3.1956   -2.6002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3278    4.9130   -2.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5536    3.4148   -1.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0647    3.7100    1.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6105    2.8732    1.6732 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9892    1.7133    0.1469 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5874    1.4197    1.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8918    0.5326   -0.5984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4671   -0.7817    0.9716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5307    0.9047    1.4510 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0059   -2.7413    5.2575 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3449   -1.7546    5.8853 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0490   -1.0049    4.9525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4851   -3.9950    0.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3944   -2.4788   -1.6797 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9440   -0.4768   -1.6317 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  2  0
 10  9  1  0
 22 21  2  0
 21  7  1  0
  7  8  1  0
  8  9  1  0
 17 15  1  0
 15 16  2  0
 10 11  2  0
 13 14  2  0
 11 13  1  0
  7  6  1  0
 13 15  1  0
  6  5  1  0
 10 22  1  0
  5  4  1  0
 18 19  1  0
  4  2  2  3
 17 22  1  0
  2  1  1  0
 19 20  2  0
  2  3  1  0
 20 21  1  0
 11 12  1  0
  7 34  1  6
 19 41  1  0
 20 42  1  0
 18 40  1  0
  8 35  1  0
  8 36  1  0
  6 32  1  0
  6 33  1  0
  5 30  1  0
  5 31  1  0
  4 29  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
 12 37  1  0
 12 38  1  0
 12 39  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.656   3.482   0.167  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.485   3.546  -0.774  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.857   3.925  -2.186  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.800   3.309  -0.449  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.369   2.919   0.889  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.141   1.595   0.836  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.306   0.369   0.404  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.144   0.051   1.349  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.628  -0.277   2.656  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.424  -1.416   2.681  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.459  -2.176   3.787  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.672  -1.901   5.034  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.320  -3.388   3.832  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.378  -4.096   4.829  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.136  -3.741   2.599  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.828  -4.749   2.576  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.069  -2.839   1.438  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.842  -3.117   0.302  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.793  -2.265  -0.799  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.974  -1.139  -0.768  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.195  -0.861   0.366  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.239  -1.716   1.486  0.00  0.00           C+0
HETATM   23  H   UNK     0      -1.376   3.280   1.202  0.00  0.00           H+0
HETATM   24  H   UNK     0      -2.196   4.435   0.161  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.347   2.693  -0.148  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.013   3.960  -2.851  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.561   3.196  -2.600  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.328   4.913  -2.203  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.554   3.415  -1.231  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.065   3.710   1.196  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.611   2.873   1.673  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.989   1.713   0.147  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.587   1.420   1.823  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.892   0.533  -0.598  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.467  -0.782   0.972  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.531   0.905   1.451  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.006  -2.741   5.258  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.345  -1.755   5.885  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.049  -1.005   4.952  0.00  0.00           H+0
HETATM   40  H   UNK     0       4.485  -3.995   0.274  0.00  0.00           H+0
HETATM   41  H   UNK     0       4.394  -2.479  -1.680  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.944  -0.477  -1.632  0.00  0.00           H+0
CONECT    1    2   23   24   25                                             
CONECT    2    4    1    3                                                  
CONECT    3    2   26   27   28                                             
CONECT    4    5    2   29                                                  
CONECT    5    6    4   30   31                                             
CONECT    6    7    5   32   33                                             
CONECT    7   21    8    6   34                                             
CONECT    8    7    9   35   36                                             
CONECT    9   10    8                                                       
CONECT   10    9   11   22                                                  
CONECT   11   10   13   12                                                  
CONECT   12   11   37   38   39                                             
CONECT   13   14   11   15                                                  
CONECT   14   13                                                            
CONECT   15   17   16   13                                                  
CONECT   16   15                                                            
CONECT   17   18   15   22                                                  
CONECT   18   17   19   40                                                  
CONECT   19   18   20   41                                                  
CONECT   20   19   21   42                                                  
CONECT   21   22    7   20                                                  
CONECT   22   21   10   17                                                  
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    3                                                            
CONECT   27    3                                                            
CONECT   28    3                                                            
CONECT   29    4                                                            
CONECT   30    5                                                            
CONECT   31    5                                                            
CONECT   32    6                                                            
CONECT   33    6                                                            
CONECT   34    7                                                            
CONECT   35    8                                                            
CONECT   36    8                                                            
CONECT   37   12                                                            
CONECT   38   12                                                            
CONECT   39   12                                                            
CONECT   40   18                                                            
CONECT   41   19                                                            
CONECT   42   20                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   88    0
END

RDKit          3D

42 44  0  0  0  0  0  0  0  0999 V2000
   -1.6563    3.4816    0.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4854    3.5463   -0.7744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8567    3.9247   -2.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8004    3.3089   -0.4485 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3685    2.9192    0.8885 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1409    1.5948    0.8355 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3060    0.3692    0.4042 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1439    0.0505    1.3488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6281   -0.2770    2.6556 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4238   -1.4155    2.6813 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4589   -2.1759    3.7873 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6718   -1.9010    5.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3200   -3.3883    3.8319 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3784   -4.0959    4.8293 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1358   -3.7407    2.5986 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8282   -4.7492    2.5765 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0693   -2.8386    1.4375 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8418   -3.1168    0.3015 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7925   -2.2650   -0.7993 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9735   -1.1388   -0.7681 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1946   -0.8613    0.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2389   -1.7158    1.4861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3761    3.2799    1.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1959    4.4347    0.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3474    2.6929   -0.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0129    3.9600   -2.8509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5610    3.1956   -2.6002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3278    4.9130   -2.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5536    3.4148   -1.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0647    3.7100    1.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6105    2.8732    1.6732 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9892    1.7133    0.1469 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5874    1.4197    1.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8918    0.5326   -0.5984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4671   -0.7817    0.9716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5307    0.9047    1.4510 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0059   -2.7413    5.2575 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3449   -1.7546    5.8853 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0490   -1.0049    4.9525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4851   -3.9950    0.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3944   -2.4788   -1.6797 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9440   -0.4768   -1.6317 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  2  0
 10  9  1  0
 22 21  2  0
 21  7  1  0
  7  8  1  0
  8  9  1  0
 17 15  1  0
 15 16  2  0
 10 11  2  0
 13 14  2  0
 11 13  1  0
  7  6  1  0
 13 15  1  0
  6  5  1  0
 10 22  1  0
  5  4  1  0
 18 19  1  0
  4  2  2  3
 17 22  1  0
  2  1  1  0
 19 20  2  0
  2  3  1  0
 20 21  1  0
 11 12  1  0
  7 34  1  6
 19 41  1  0
 20 42  1  0
 18 40  1  0
  8 35  1  0
  8 36  1  0
  6 32  1  0
  6 33  1  0
  5 30  1  0
  5 31  1  0
  4 29  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
 12 37  1  0
 12 38  1  0
 12 39  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₀O₃

Average Mass

296.3660 Da

Monoisotopic Mass

296.14124 Da

IUPAC Name

(4S)-12-methyl-4-(4-methylpent-3-en-1-yl)-2-oxatricyclo[7.3.1.0^{5,13}]trideca-1(12),5(13),6,8-tetraene-10,11-dione

Traditional Name

(4S)-12-methyl-4-(4-methylpent-3-en-1-yl)-2-oxatricyclo[7.3.1.0^{5,13}]trideca-1(12),5(13),6,8-tetraene-10,11-dione

CAS Registry Number

Not Available

SMILES

[H]C(=C(C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])[C@@]1([H])C2=C3C(OC1([H])[H])=C(C(=O)C(=O)C3=C([H])C([H])=C2[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C19H20O3/c1-11(2)6-4-7-13-10-22-19-12(3)17(20)18(21)15-9-5-8-14(13)16(15)19/h5-6,8-9,13H,4,7,10H2,1-3H3/t13-/m1/s1

InChI Key

QJZOFSVFRGKNEJ-CYBMUJFWSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, 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
Eremophila serrulata	JEOL database	Ndi, C. P., et al, Phytochemistry 68, 2684 (2007)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Naphthoquinone
Benzopyran
Isochromane
2-benzopyran
Quinone
Aryl ketone
Vinylogous ester
Ketone
Cyclic ketone
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.55	ALOGPS
logP	4.03	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	88.75 m³·mol⁻¹	ChemAxon
Polarizability	33.06 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

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

24862426

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ndi, C. P., et al. (2007). Ndi, C. P., et al, Phytochemistry 68, 2684 (2007). Phytochem..

Showing NP-Card for 9-methyl-3-(4-methyl-3-pentenyl)-2,3-dihydronaphtho[1,8-bc]pyran-7,8-dion+ (NP0024815)

MOL for NP0024815 (9-methyl-3-(4-methyl-3-pentenyl)-2,3-dihydronaphtho[1,8-bc]pyran-7,8-dion+)

3D MOL for NP0024815 (9-methyl-3-(4-methyl-3-pentenyl)-2,3-dihydronaphtho[1,8-bc]pyran-7,8-dion+)

3D SDF for NP0024815 (9-methyl-3-(4-methyl-3-pentenyl)-2,3-dihydronaphtho[1,8-bc]pyran-7,8-dion+)

3D-SDF for NP0024815 (9-methyl-3-(4-methyl-3-pentenyl)-2,3-dihydronaphtho[1,8-bc]pyran-7,8-dion+)

PDB for NP0024815 (9-methyl-3-(4-methyl-3-pentenyl)-2,3-dihydronaphtho[1,8-bc]pyran-7,8-dion+)

3D PDB for NP0024815 (9-methyl-3-(4-methyl-3-pentenyl)-2,3-dihydronaphtho[1,8-bc]pyran-7,8-dion+)

SMILES for NP0024815 (9-methyl-3-(4-methyl-3-pentenyl)-2,3-dihydronaphtho[1,8-bc]pyran-7,8-dion+)

INCHI for NP0024815 (9-methyl-3-(4-methyl-3-pentenyl)-2,3-dihydronaphtho[1,8-bc]pyran-7,8-dion+)

Structure for NP0024815 (9-methyl-3-(4-methyl-3-pentenyl)-2,3-dihydronaphtho[1,8-bc]pyran-7,8-dion+)

3D Structure for NP0024815 (9-methyl-3-(4-methyl-3-pentenyl)-2,3-dihydronaphtho[1,8-bc]pyran-7,8-dion+)