NP-MRD: Showing NP-Card for methyl 2-[(1s,2r,3r,8r,9s,10r,13r,15r)-13-(furan-3-yl)-2-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadeca-4,11-dien-9-yl]acetate (NP0164329)

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Record Information

Version

2.0

Created at

2022-09-02 23:11:31 UTC

Updated at

2022-09-02 23:11:31 UTC

NP-MRD ID

NP0164329

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2-[(1s,2r,3r,8r,9s,10r,13r,15r)-13-(furan-3-yl)-2-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadeca-4,11-dien-9-yl]acetate

Description

Methyl 2-[(1S,2R,3R,8R,9S,10R,13R,15R)-13-(furan-3-yl)-2-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]Hexadeca-4,11-dien-9-yl]acetate belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. methyl 2-[(1s,2r,3r,8r,9s,10r,13r,15r)-13-(furan-3-yl)-2-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadeca-4,11-dien-9-yl]acetate is found in Azadirachta indica. Based on a literature review very few articles have been published on methyl 2-[(1S,2R,3R,8R,9S,10R,13R,15R)-13-(furan-3-yl)-2-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]Hexadeca-4,11-dien-9-yl]acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032201112D          

 32 36  0  0  1  0            999 V2000
    2.7166    3.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3447    2.8648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1955    2.0534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8236    1.5185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4182    1.7769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2690    0.9655    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8971    0.4306    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1303    1.2219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7149    0.5394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3126    1.1082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2037    1.9259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0381    0.7155    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7823    1.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9315    1.8831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7493    1.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1055    1.2479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5079    0.6791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8889   -0.0959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0712   -0.2047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4735   -0.7735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7479   -0.3808    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9707   -0.6573    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8215   -1.4687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3426   -0.1224    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5653   -0.3989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4161   -1.2103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0628    0.1360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0864    0.9474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8637    1.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0129    2.0353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4918    0.6890    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6410    1.5004    0.0000 C   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
  3  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 17  2  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
  9 19  1  0  0  0  0
 19 20  1  1  0  0  0
 21 20  1  6  0  0  0
  7 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
  6 31  1  0  0  0  0
 24 31  1  0  0  0  0
 31 32  1  1  0  0  0
M  END

     RDKit          3D

 64 68  0  0  0  0  0  0  0  0999 V2000
    0.1601    4.6664    0.3248 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4029    3.3588   -0.1411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6509    2.5994   -0.6158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7666    3.1796   -0.5805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4537    1.2586   -1.1061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7701    0.0692   -0.2858 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0577   -0.1140    0.9912 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5041    0.7045    2.1517 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4293    0.0511    0.8322 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5243    0.7608    0.9901 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6720    2.0933    1.6127 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6987    0.0079    0.4585 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2391    0.4920   -0.8008 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5224    1.0172   -1.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6259    1.3586   -2.3410 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4807    1.0592   -2.8994 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6422    0.5483   -2.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2472   -1.4383    0.4659 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7791   -1.2633    0.1747 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0694   -2.1934    0.9227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0891   -1.5812    1.3827 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2342   -2.3556    0.8336 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8739   -3.1385   -0.2898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4473   -1.5314    0.5678 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5406   -2.4334    0.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8684   -3.5946    1.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2202   -2.2825   -0.9481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9731   -1.1939   -1.9188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5285   -0.8099   -1.7004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7293   -0.8821   -2.5915 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2137   -0.3533   -0.3164 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2356    0.6732    0.0449 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0627    5.4029   -0.5025 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0194    1.1834   -2.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2896    0.2324    2.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3793    0.7491    2.8625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7229    1.7570    1.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7703    2.5009    2.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9876    2.8346    0.8200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4955    2.1234    2.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4899    0.0490    1.2795 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2603    1.1140   -0.2294 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4862    1.7907   -2.8346 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6500    0.2450   -2.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3591   -1.8860    1.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7393   -2.0442   -0.3204 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5526   -1.2899   -0.8880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0496   -1.6458    2.4977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5283   -3.1253    1.6064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1906   -3.7916    0.0049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7750   -1.1440    1.5894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9474   -3.8464    1.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3081   -4.4530    0.6893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6294   -3.3394    2.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0322   -2.9952   -1.1975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1131   -1.6116   -2.9362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6361   -0.3214   -1.7437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1812    0.1213    0.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6072    1.2526   -0.8181 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
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  1
  7 21  1  0
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 20 19  1  0
 19 18  1  0
 18 12  1  0
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 10  9  2  0
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 29 30  2  0
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 31  6  1  0
  9  7  1  0
 14 13  1  0
 31 24  1  0
  9 19  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  6
  8 39  1  0
  8 40  1  0
  8 41  1  0
 21 52  1  1
 19 51  1  6
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 17 48  1  0
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 14 46  1  0
 22 53  1  1
 23 54  1  0
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 26 57  1  0
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 28 60  1  0
 28 61  1  0
 32 62  1  0
 32 63  1  0
 32 64  1  0
M  END


  Mrv1652309032201112D          

 32 36  0  0  1  0            999 V2000
    2.7166    3.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3447    2.8648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1955    2.0534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8236    1.5185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4182    1.7769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2690    0.9655    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8971    0.4306    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1303    1.2219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7149    0.5394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3126    1.1082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2037    1.9259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0381    0.7155    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7823    1.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9315    1.8831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7493    1.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1055    1.2479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5079    0.6791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8889   -0.0959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0712   -0.2047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4735   -0.7735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7479   -0.3808    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9707   -0.6573    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8215   -1.4687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3426   -0.1224    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5653   -0.3989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4161   -1.2103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0628    0.1360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0864    0.9474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8637    1.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0129    2.0353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4918    0.6890    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6410    1.5004    0.0000 C   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
  3  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 17  2  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
  9 19  1  0  0  0  0
 19 20  1  1  0  0  0
 21 20  1  6  0  0  0
  7 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
  6 31  1  0  0  0  0
 24 31  1  0  0  0  0
 31 32  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0164329

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C[C@H]1[C@@]2(C)[C@H](O[C@@H]3C[C@H](C(C)=C23)C2=COC=C2)[C@H](O)[C@@H]2C(C)=CCC(=O)[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O6/c1-13-6-7-19(27)25(3)18(11-20(28)30-5)26(4)22-14(2)16(15-8-9-31-12-15)10-17(22)32-24(26)23(29)21(13)25/h6,8-9,12,16-18,21,23-24,29H,7,10-11H2,1-5H3/t16-,17-,18-,21+,23-,24-,25+,26-/m1/s1

> <INCHI_KEY>
KUCNSNKUGFEHJF-YFPDVXTCSA-N

> <FORMULA>
C26H32O6

> <MOLECULAR_WEIGHT>
440.536

> <EXACT_MASS>
440.21988875

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
46.56451582266059

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-[(1S,2R,3R,8R,9S,10R,13R,15R)-13-(furan-3-yl)-2-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.0^{3,8}.0^{11,15}]hexadeca-4,11-dien-9-yl]acetate

> <ALOGPS_LOGP>
3.54

> <JCHEM_LOGP>
2.5843523820000005

> <ALOGPS_LOGS>
-3.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.30343115060833

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.807104249037966

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8595597211300907

> <JCHEM_POLAR_SURFACE_AREA>
85.97

> <JCHEM_REFRACTIVITY>
118.92149999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.08e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl [(1S,2R,3R,8R,9S,10R,13R,15R)-13-(furan-3-yl)-2-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.0^{3,8}.0^{11,15}]hexadeca-4,11-dien-9-yl]acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       5.071   6.346   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.243   5.348   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.965   3.833   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       7.137   2.834   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.514   3.317   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.236   1.802   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.408   0.804   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.843   2.281   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.935   1.007   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.050   2.069   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.847   3.595   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.405   1.336   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.794   2.001   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.072   3.515   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.599   3.718   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      13.264   2.329   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      12.148   1.268   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.126  -0.179   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.599  -0.382   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.484  -1.444   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.129  -0.711   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.679  -1.227   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.400  -2.742   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.506  -0.228   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.055  -0.745   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.777  -2.259   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.117   0.254   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.161   1.768   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.612   2.285   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.891   3.799   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.785   1.286   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.063   2.801   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   31                                                  
CONECT    7    6    8    9   21                                             
CONECT    8    7                                                            
CONECT    9    7   10   19                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   18                                                  
CONECT   13   12   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   13                                                       
CONECT   18   12   19                                                       
CONECT   19   18    9   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20    7   22                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   31                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29    6   24   32                                             
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Value	Source
Methyl 2-[(1S,2R,3R,8R,9S,10R,13R,15R)-13-(furan-3-yl)-2-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.0,.0,]hexadeca-4,11-dien-9-yl]acetic acid	Generator

Chemical Formula

C₂₆H₃₂O₆

Average Mass

440.5360 Da

Monoisotopic Mass

440.21989 Da

IUPAC Name

methyl 2-[(1S,2R,3R,8R,9S,10R,13R,15R)-13-(furan-3-yl)-2-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.0^{3,8}.0^{11,15}]hexadeca-4,11-dien-9-yl]acetate

Traditional Name

methyl [(1S,2R,3R,8R,9S,10R,13R,15R)-13-(furan-3-yl)-2-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.0^{3,8}.0^{11,15}]hexadeca-4,11-dien-9-yl]acetate

CAS Registry Number

Not Available

SMILES

COC(=O)C[C@H]1[C@@]2(C)[C@H](O[C@@H]3C[C@H](C(C)=C23)C2=COC=C2)[C@H](O)[C@@H]2C(C)=CCC(=O)[C@]12C

InChI Identifier

InChI=1S/C26H32O6/c1-13-6-7-19(27)25(3)18(11-20(28)30-5)26(4)22-14(2)16(15-8-9-31-12-15)10-17(22)32-24(26)23(29)21(13)25/h6,8-9,12,16-18,21,23-24,29H,7,10-11H2,1-5H3/t16-,17-,18-,21+,23-,24-,25+,26-/m1/s1

InChI Key

KUCNSNKUGFEHJF-YFPDVXTCSA-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
Azadirachta indica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
Cyclohexenone
Cyclic alcohol
Furan
Tetrahydrofuran
Methyl ester
Heteroaromatic compound
Secondary alcohol
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Carbonyl group
Organooxygen compound
Organic oxygen compound
Alcohol
Hydrocarbon derivative
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	3.54	ALOGPS
logP	2.58	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	13.81	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	85.97 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	118.92 m³·mol⁻¹	ChemAxon
Polarizability	46.56 Å³	ChemAxon
Number of Rings	5	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

162893251

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 2-[(1s,2r,3r,8r,9s,10r,13r,15r)-13-(furan-3-yl)-2-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadeca-4,11-dien-9-yl]acetate (NP0164329)

MOL for NP0164329 (methyl 2-[(1s,2r,3r,8r,9s,10r,13r,15r)-13-(furan-3-yl)-2-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadeca-4,11-dien-9-yl]acetate)

3D MOL for NP0164329 (methyl 2-[(1s,2r,3r,8r,9s,10r,13r,15r)-13-(furan-3-yl)-2-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadeca-4,11-dien-9-yl]acetate)

3D SDF for NP0164329 (methyl 2-[(1s,2r,3r,8r,9s,10r,13r,15r)-13-(furan-3-yl)-2-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadeca-4,11-dien-9-yl]acetate)

3D-SDF for NP0164329 (methyl 2-[(1s,2r,3r,8r,9s,10r,13r,15r)-13-(furan-3-yl)-2-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadeca-4,11-dien-9-yl]acetate)

PDB for NP0164329 (methyl 2-[(1s,2r,3r,8r,9s,10r,13r,15r)-13-(furan-3-yl)-2-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadeca-4,11-dien-9-yl]acetate)

3D PDB for NP0164329 (methyl 2-[(1s,2r,3r,8r,9s,10r,13r,15r)-13-(furan-3-yl)-2-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadeca-4,11-dien-9-yl]acetate)

SMILES for NP0164329 (methyl 2-[(1s,2r,3r,8r,9s,10r,13r,15r)-13-(furan-3-yl)-2-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadeca-4,11-dien-9-yl]acetate)

INCHI for NP0164329 (methyl 2-[(1s,2r,3r,8r,9s,10r,13r,15r)-13-(furan-3-yl)-2-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadeca-4,11-dien-9-yl]acetate)

Structure for NP0164329 (methyl 2-[(1s,2r,3r,8r,9s,10r,13r,15r)-13-(furan-3-yl)-2-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadeca-4,11-dien-9-yl]acetate)

3D Structure for NP0164329 (methyl 2-[(1s,2r,3r,8r,9s,10r,13r,15r)-13-(furan-3-yl)-2-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadeca-4,11-dien-9-yl]acetate)