NP-MRD: Showing NP-Card for (6-{[14,15-dihydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl]methoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl)oxidanesulfonic acid (NP0197783)

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Record Information

Version

2.0

Created at

2022-09-04 16:06:33 UTC

Updated at

2022-09-04 16:06:33 UTC

NP-MRD ID

NP0197783

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6-{[14,15-dihydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl]methoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl)oxidanesulfonic acid

Description

(6-{[14,15-Dihydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadecan-5-yl]methoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl)oxidanesulfonic acid belongs to the class of organic compounds known as diterpene glycosides. (6-{[14,15-dihydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl]methoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl)oxidanesulfonic acid is found in Diplospora dubia. These are diterpenoids in which an isoprene unit is glycosylated (6-{[14,15-dihydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadecan-5-yl]methoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl)oxidanesulfonic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201503412D          

 39 43  0  0  0  0            999 V2000
    3.8136   -1.4224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1184   -0.9782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8017   -1.7400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3031   -2.3952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9864   -3.1570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4878   -3.8122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1711   -4.5740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6725   -5.2291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3559   -5.9909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3531   -4.6806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0364   -5.4424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2183   -5.5491    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.4002   -5.6557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3250   -6.3671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1117   -4.7310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8517   -4.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0336   -4.1321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1683   -3.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6669   -2.6085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6765   -0.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4294    0.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6242    0.5960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0661   -0.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8257    0.7777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3132   -0.7987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7596   -1.4229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1726    0.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4028    0.5335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1586    1.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0038    1.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2474    0.1857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7854   -0.2403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4825    0.2009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2972   -0.8873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9928   -1.6541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1637   -0.8483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3012   -1.6618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  2  0  0  0  0
 12 15  1  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
  2 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 23 33  1  0  0  0  0
 28 33  1  0  0  0  0
 30 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 34 38  1  0  0  0  0
 28 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END

     RDKit          3D

 83 87  0  0  0  0  0  0  0  0999 V2000
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    0.4857   -1.8073   -0.5197 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3767   -2.3722    0.5475 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0430   -1.6541    1.4145 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0130   -0.7795    1.1647 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2058   -1.3627    1.7314 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3121   -0.7254    1.1943 C   0  0  1  0  0  0  0  0  0  0  0  0
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    6.8336   -0.5934   -0.6454 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0999    0.7555    1.1878 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7018    1.2707   -0.0389 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7953    2.3625   -0.6735 S   0  0  0  0  0  6  0  0  0  0  0  0
    6.1280    2.0554   -2.0972 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0406    2.3868    0.1814 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0831    3.8961   -0.5691 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1036    1.1391    2.2383 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9306    2.5221    2.2783 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7661    0.5185    1.9211 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -4.1016    0.7637    1.5204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8727    0.4984    0.6107 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.8550   -0.8106    1.3976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7121   -1.0877   -0.0570 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8909    1.7551   -0.1670 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4232    1.7759   -1.4356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3062    2.2879   -0.2185 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7818    2.3294   -1.5392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4300    3.6622    0.3402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9810    3.7447    1.6514 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2708   -1.3677   -1.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8057   -3.1690    1.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2900   -0.5612    0.1413 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1651   -0.9867    1.8897 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9111   -1.1692   -0.9027 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0917    1.2288    1.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4691    0.8002    3.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5172    2.8841    2.9883 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2419    0.2954    2.8994 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4559    1.7234    0.3732 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1125   -3.2316   -1.9952 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4287   -3.7422   -2.6162 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9327   -2.0851   -2.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.6969    3.9055    2.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
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 12 15  1  0
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 12 14  2  0
 10 16  1  0
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  2 20  1  0
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 31 32  1  0
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 30 34  1  0
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 36 37  1  6
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 33  2  1  0
 18  5  1  0
 33 23  1  0
 30 25  1  0
 36 28  1  0
  1 40  1  0
  1 41  1  0
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 33 77  1  6
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 35 79  1  0
 37 80  1  0
 38 81  1  0
 38 82  1  0
 39 83  1  0
M  END


  Mrv1533004201503412D          

 39 43  0  0  0  0            999 V2000
    3.8136   -1.4224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1184   -0.9782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8017   -1.7400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3031   -2.3952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9864   -3.1570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4878   -3.8122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1711   -4.5740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6725   -5.2291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3559   -5.9909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3531   -4.6806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0364   -5.4424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2183   -5.5491    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.4002   -5.6557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3250   -6.3671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1117   -4.7310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8517   -4.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0336   -4.1321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1683   -3.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6669   -2.6085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6765   -0.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4294    0.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6242    0.5960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0661   -0.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8257    0.7777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3132   -0.7987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7596   -1.4229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9506   -1.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6469   -0.4671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1726    0.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4028    0.5335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1586    1.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0038    1.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2474    0.1857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7854   -0.2403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4825    0.2009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2972   -0.8873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9928   -1.6541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1637   -0.8483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3012   -1.6618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  2  0  0  0  0
 12 15  1  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
  2 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 23 33  1  0  0  0  0
 28 33  1  0  0  0  0
 30 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 34 38  1  0  0  0  0
 28 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0197783

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(COC2OC(CO)C(OS(O)(=O)=O)C(O)C2O)CCCC2(C)C3CCC4CC3(CCC12)C(O)C4(O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C26H44O12S/c1-23(13-36-21-19(30)18(29)20(15(11-27)37-21)38-39(33,34)35)7-3-8-24(2)16(23)6-9-25-10-14(4-5-17(24)25)26(32,12-28)22(25)31/h14-22,27-32H,3-13H2,1-2H3,(H,33,34,35)

> <INCHI_KEY>
HJEHDEXPBQDTOL-UHFFFAOYSA-N

> <FORMULA>
C26H44O12S

> <MOLECULAR_WEIGHT>
580.69

> <EXACT_MASS>
580.255348031

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
59.072278125735274

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6-{[14,15-dihydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl]methoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl)oxidanesulfonic acid

> <ALOGPS_LOGP>
-0.74

> <JCHEM_LOGP>
-2.1507942098620076

> <ALOGPS_LOGS>
-2.42

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.15183500753718

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.9764060677645778

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9828347284982035

> <JCHEM_POLAR_SURFACE_AREA>
203.43999999999997

> <JCHEM_REFRACTIVITY>
134.482

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.23e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6-{[14,15-dihydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl]methoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl)oxidanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0       7.119  -2.655   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.821  -1.826   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.230  -3.248   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.166  -4.471   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.575  -5.893   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.511  -7.116   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.919  -8.538   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.855  -9.761   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.264 -11.183   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.392  -8.737   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.801 -10.159   0.000  0.00  0.00           O+0
HETATM   12  S   UNK     0       2.274 -10.358   0.000  0.00  0.00           S+0
HETATM   13  O   UNK     0       0.747 -10.557   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.473 -11.885   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.075  -8.831   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.456  -7.514   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.929  -7.713   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.048  -6.092   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.112  -4.869   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.863  -0.692   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.402   0.777   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.899   1.113   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.857  -0.022   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.408   1.452   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.318  -1.491   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.285  -2.656   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.774  -2.341   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.208  -0.872   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.322   0.124   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.752   0.996   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.296   2.224   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.874   1.924   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.328   0.347   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.466  -0.449   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -2.767   0.375   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -2.422  -1.656   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -1.853  -3.088   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -0.306  -1.583   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -0.562  -3.102   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   20   25                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12                                                            
CONECT   16   10   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    5   19                                                  
CONECT   19   18                                                            
CONECT   20    2   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25   33                                             
CONECT   24   23                                                            
CONECT   25   23    2   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   33   38                                             
CONECT   29   28   30                                                       
CONECT   30   29   31   34                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   23   28                                                  
CONECT   34   30   35   36   38                                             
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36                                                            
CONECT   38   34   28   39                                                  
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Value	Source
(6-{[14,15-dihydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0,.0,]hexadecan-5-yl]methoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl)oxidanesulfonate	Generator
(6-{[14,15-dihydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0,.0,]hexadecan-5-yl]methoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl)oxidanesulphonate	Generator
(6-{[14,15-dihydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0,.0,]hexadecan-5-yl]methoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl)oxidanesulphonic acid	Generator
(6-{[14,15-dihydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl]methoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl)oxidanesulfonate	Generator
(6-{[14,15-dihydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl]methoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl)oxidanesulphonate	Generator
(6-{[14,15-dihydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl]methoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl)oxidanesulphonic acid	Generator

Chemical Formula

C₂₆H₄₄O₁₂S

Average Mass

580.6900 Da

Monoisotopic Mass

580.25535 Da

IUPAC Name

(6-{[14,15-dihydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl]methoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl)oxidanesulfonic acid

Traditional Name

(6-{[14,15-dihydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl]methoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl)oxidanesulfonic acid

CAS Registry Number

Not Available

SMILES

CC1(COC2OC(CO)C(OS(O)(=O)=O)C(O)C2O)CCCC2(C)C3CCC4CC3(CCC12)C(O)C4(O)CO

InChI Identifier

InChI=1S/C26H44O12S/c1-23(13-36-21-19(30)18(29)20(15(11-27)37-21)38-39(33,34)35)7-3-8-24(2)16(23)6-9-25-10-14(4-5-17(24)25)26(32,12-28)22(25)31/h14-22,27-32H,3-13H2,1-2H3,(H,33,34,35)

InChI Key

HJEHDEXPBQDTOL-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Diplospora dubia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Diterpene glycosides

Alternative Parents

Substituents

Diterpene glycoside
Diterpenoid
Kaurane diterpenoid
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Monosaccharide sulfate
Monosaccharide
Oxane
Sulfuric acid monoester
Sulfate-ester
Sulfuric acid ester
Alkyl sulfate
Organic sulfuric acid or derivatives
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
Organoheterocyclic compound
Acetal
Oxacycle
Primary alcohol
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	-0.74	ALOGPS
logP	-2.2	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	-2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	203.44 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	134.48 m³·mol⁻¹	ChemAxon
Polarizability	59.07 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

75597415

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (6-{[14,15-dihydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl]methoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl)oxidanesulfonic acid (NP0197783)

MOL for NP0197783 ((6-{[14,15-dihydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl]methoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl)oxidanesulfonic acid)

3D MOL for NP0197783 ((6-{[14,15-dihydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl]methoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl)oxidanesulfonic acid)

3D SDF for NP0197783 ((6-{[14,15-dihydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl]methoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl)oxidanesulfonic acid)

3D-SDF for NP0197783 ((6-{[14,15-dihydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl]methoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl)oxidanesulfonic acid)

PDB for NP0197783 ((6-{[14,15-dihydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl]methoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl)oxidanesulfonic acid)

3D PDB for NP0197783 ((6-{[14,15-dihydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl]methoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl)oxidanesulfonic acid)

SMILES for NP0197783 ((6-{[14,15-dihydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl]methoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl)oxidanesulfonic acid)

INCHI for NP0197783 ((6-{[14,15-dihydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl]methoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl)oxidanesulfonic acid)

Structure for NP0197783 ((6-{[14,15-dihydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl]methoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl)oxidanesulfonic acid)

3D Structure for NP0197783 ((6-{[14,15-dihydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl]methoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl)oxidanesulfonic acid)