NP-MRD: Showing NP-Card for methyl (1r,2s,7r,8s,9s)-8-[(2s)-2-[(2s,3r,4s,5s)-4-(acetyloxy)-3-hydroxy-2,5-dimethoxyoxolan-3-yl]-2-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}ethyl]-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0²,⁷]dodec-3-ene-3-carboxylate (NP0145116)

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Record Information

Version

2.0

Created at

2022-09-02 00:14:50 UTC

Updated at

2022-09-02 00:14:50 UTC

NP-MRD ID

NP0145116

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1r,2s,7r,8s,9s)-8-[(2s)-2-[(2s,3r,4s,5s)-4-(acetyloxy)-3-hydroxy-2,5-dimethoxyoxolan-3-yl]-2-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}ethyl]-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0²,⁷]dodec-3-ene-3-carboxylate

Description

Methyl (1R,2S,7R,8S,9S)-8-[(2S)-2-[(2S,3R,4S,5S)-4-(acetyloxy)-3-hydroxy-2,5-dimethoxyoxolan-3-yl]-2-{[(2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}ethyl]-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0²,⁷]Dodec-3-ene-3-carboxylate belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. methyl (1r,2s,7r,8s,9s)-8-[(2s)-2-[(2s,3r,4s,5s)-4-(acetyloxy)-3-hydroxy-2,5-dimethoxyoxolan-3-yl]-2-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}ethyl]-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0²,⁷]dodec-3-ene-3-carboxylate is found in Tinospora crispa. Based on a literature review very few articles have been published on methyl (1R,2S,7R,8S,9S)-8-[(2S)-2-[(2S,3R,4S,5S)-4-(acetyloxy)-3-hydroxy-2,5-dimethoxyoxolan-3-yl]-2-{[(2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}ethyl]-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0²,⁷]Dodec-3-ene-3-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022202142D          

 59 63  0  0  1  0            999 V2000
   -1.1091    3.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1992    2.5407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5341    2.0526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2211    2.3846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6243    1.2326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3796    0.9006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4697    0.0806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8046   -0.4076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0494   -0.0756    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5356   -0.6574    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1618   -1.0982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8101   -1.4354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2737   -2.0621    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5373   -1.9110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0738   -2.5377    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7992   -3.3157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3357   -3.9425    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0611   -4.7204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5976   -5.3472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3230   -6.1252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8594   -6.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5120   -6.2764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1467   -3.7913    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6832   -4.4180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7131   -3.9938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0306   -4.8936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4957   -3.2699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4213   -3.0133    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2323   -2.8621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7688   -3.4889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4942   -4.2668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5798   -3.3377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8848   -2.3865    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1594   -1.6086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9704   -1.4574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5069   -2.0841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2450   -0.6794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5483   -2.8401    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2541   -3.0319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2933   -2.4857    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4445   -1.6747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2224   -1.4001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8605   -3.0848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4661   -3.8094    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8205   -4.5544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6429   -4.6200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6551   -3.6582    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0561   -4.2254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2478   -5.0278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3512   -5.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0386   -5.2630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3551   -0.5628    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2652    0.3883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7382    1.1852    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5176    0.9149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7922    0.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6122    0.0467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0408    0.7444    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0694    1.5689    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
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 28 33  1  0  0  0  0
 15 33  1  0  0  0  0
 33 34  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 38 13  1  6  0  0  0
 38 39  1  1  0  0  0
 38 40  1  0  0  0  0
 40 41  1  1  0  0  0
 41 42  1  0  0  0  0
 40 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  6  0  0  0
 45 46  1  0  0  0  0
 44 47  1  0  0  0  0
 38 47  1  0  0  0  0
 47 48  1  1  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 49 51  2  0  0  0  0
 10 52  1  0  0  0  0
 52 53  1  1  0  0  0
 54 53  1  1  0  0  0
 54 55  1  0  0  0  0
 55 56  1  0  0  0  0
 52 56  1  0  0  0  0
 56 57  2  0  0  0  0
 54 58  1  0  0  0  0
  5 58  1  0  0  0  0
  9 58  1  0  0  0  0
 58 59  1  6  0  0  0
M  END

     RDKit          3D

113117  0  0  0  0  0  0  0  0999 V2000
    3.9043    1.1854    2.0852 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1074    1.8778    1.1432 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2200    1.6576   -0.2525 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0907    0.7963   -0.5342 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4013    2.3719   -1.1793 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5252    3.2494   -0.7439 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6521    4.0128   -1.6780 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2465    3.2323   -2.8869 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1290    2.1188   -3.2949 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5153    0.7454   -3.3827 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5556    0.8455   -4.4571 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1983    0.0364   -2.1800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8753    0.3235   -1.1964 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7085   -0.4567   -0.0401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1193    0.0179    1.0487 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0874   -0.6512    1.2862 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0744   -1.8980    1.7539 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8159   -2.8935    0.6494 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8474   -2.8216   -0.3306 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8200   -3.6703   -1.4409 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8622   -3.6347   -2.4717 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8491   -4.4714   -1.5092 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0344   -2.0938    2.8258 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3720   -3.0642    3.7704 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2769   -4.2370    4.0341 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2292   -5.1572    5.0847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3079   -4.4881    3.3494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2584   -0.7509    3.3823 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0157   -0.7365    4.5447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4921   -0.0401    5.6510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2002    0.0478    6.9414 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6290    0.5421    5.5609 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0281   -0.0304    2.2357 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2215    1.2746    2.7786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4174    1.8098    3.1446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4554    3.1957    3.6941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4566    1.1526    3.0222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2884    0.3111   -1.5459 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7125    1.0045   -2.6671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0637    1.0050   -0.4046 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8748    2.0472   -0.9225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5151    3.2469   -0.3788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8351    0.0687    0.1983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8942   -1.0901   -0.5199 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6136   -2.1384    0.3525 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7080   -2.9845    0.4252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9566   -1.0247   -1.6726 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5911   -1.2364   -2.9209 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3190   -2.3058   -3.7532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0081   -2.4979   -5.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4485   -3.1090   -3.3297 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6284   -0.0845   -4.0760 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8098   -0.2840   -3.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3618    1.0965   -3.1333 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4377    1.3524   -4.5569 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3186    0.6994   -5.1221 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9668    0.7709   -6.3259 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4836    2.1760   -2.6239 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1254    3.4828   -3.1492 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1834    1.8520    2.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8903    0.9188    1.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4661    0.2333    2.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3962    3.4586    0.3047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2663    4.3817   -1.1809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2096    4.9305   -1.9573 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1596    4.0122   -3.7095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8064    2.8983   -2.7768 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3951    2.3264   -4.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1938   -0.0342   -4.5408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0447    1.8377   -4.5001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0288    0.8274   -5.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1285   -1.0763   -2.3869 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1540    0.0833   -1.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6098    1.3503   -0.8388 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2156    1.0947    1.0023 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0996   -2.1085    2.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1356   -2.6959    0.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7118   -3.9308    1.0409 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7285   -3.0543   -2.0974 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4720   -3.1800   -3.4077 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1464   -4.6930   -2.7333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8940   -2.4584    2.3049 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3327   -5.2139    4.9696 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309022202142D          

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M  END
> <DATABASE_ID>
NP0145116

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1O[C@H](OC)[C@@](O)([C@H](C[C@]2(C)[C@@H]3C[C@@H](OC3=O)[C@@]3(C)[C@@H]2CCC=C3C(=O)OC)O[C@@H]2O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]2OC(C)=O)[C@@H]1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C39H54O20/c1-17(40)51-16-24-28(52-18(2)41)29(53-19(3)42)30(54-20(4)43)34(56-24)58-27(39(47)31(55-21(5)44)35(49-9)59-36(39)50-10)15-37(6)23-14-26(57-33(23)46)38(7)22(32(45)48-8)12-11-13-25(37)38/h12,23-31,34-36,47H,11,13-16H2,1-10H3/t23-,24-,25-,26-,27+,28-,29+,30-,31-,34+,35+,36+,37-,38-,39-/m1/s1

> <INCHI_KEY>
ONVAYUYWVYCTAN-GBHOPJRWSA-N

> <FORMULA>
C39H54O20

> <MOLECULAR_WEIGHT>
842.841

> <EXACT_MASS>
842.320844139

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
113

> <JCHEM_AVERAGE_POLARIZABILITY>
82.7599665815138

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1R,2S,7R,8S,9S)-8-[(2S)-2-[(2S,3R,4S,5S)-4-(acetyloxy)-3-hydroxy-2,5-dimethoxyoxolan-3-yl]-2-{[(2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}ethyl]-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0^{2,7}]dodec-3-ene-3-carboxylate

> <ALOGPS_LOGP>
2.26

> <JCHEM_LOGP>
1.1675911470000009

> <ALOGPS_LOGS>
-3.77

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.101149111129967

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6840367576929203

> <JCHEM_POLAR_SURFACE_AREA>
250.47999999999993

> <JCHEM_REFRACTIVITY>
190.57190000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
20

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.43e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,2S,7R,8S,9S)-8-[(2S)-2-[(2S,3R,4S,5S)-4-(acetyloxy)-3-hydroxy-2,5-dimethoxyoxolan-3-yl]-2-{[(2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}ethyl]-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0^{2,7}]dodec-3-ene-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.070   6.273   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.239   4.743   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.997   3.832   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.413   4.451   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.165   2.301   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.575   1.681   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.744   0.150   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.502  -0.761   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.092  -0.141   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.000  -1.227   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.302  -2.050   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.512  -2.679   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.511  -3.849   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.003  -3.567   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.004  -4.737   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.492  -6.189   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.493  -7.359   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.981  -8.811   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.982  -9.981   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.470 -11.434   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.471 -12.604   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.956 -11.716   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -4.007  -7.077   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -5.009  -8.247   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -6.931  -7.455   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -7.524  -9.135   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -6.525  -6.104   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -4.520  -5.625   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -6.034  -5.343   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -7.035  -6.513   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -6.522  -7.965   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -8.549  -6.230   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -3.518  -4.455   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -4.031  -3.003   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -5.545  -2.720   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -6.546  -3.890   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -6.057  -1.268   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       1.023  -5.302   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -0.474  -5.659   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       2.414  -4.640   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       2.696  -3.126   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       4.149  -2.614   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       3.473  -5.758   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       2.737  -7.111   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       3.398  -8.501   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       4.933  -8.624   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       1.223  -6.829   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       0.105  -7.887   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       0.463  -9.385   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      -0.656 -10.444   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       1.939  -9.824   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0       2.530  -1.051   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       2.362   0.725   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       1.378   2.212   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0       2.833   1.708   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0       3.345   0.256   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0       4.876   0.087   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0       0.076   1.390   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       0.130   2.929   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   58                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   58                                                  
CONECT   10    9   11   12   52                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   38                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   33                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   17   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   23   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   28   15   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   13   39   40   47                                             
CONECT   39   38                                                            
CONECT   40   38   41   43                                                  
CONECT   41   40   42                                                       
CONECT   42   41                                                            
CONECT   43   40   44                                                       
CONECT   44   43   45   47                                                  
CONECT   45   44   46                                                       
CONECT   46   45                                                            
CONECT   47   44   38   48                                                  
CONECT   48   47   49                                                       
CONECT   49   48   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49                                                            
CONECT   52   10   53   56                                                  
CONECT   53   52   54                                                       
CONECT   54   53   55   58                                                  
CONECT   55   54   56                                                       
CONECT   56   55   52   57                                                  
CONECT   57   56                                                            
CONECT   58   54    5    9   59                                             
CONECT   59   58                                                            
MASTER        0    0    0    0    0    0    0    0   59    0  126    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1R,2S,7R,8S,9S)-8-[(2S)-2-[(2S,3R,4S,5S)-4-(acetyloxy)-3-hydroxy-2,5-dimethoxyoxolan-3-yl]-2-{[(2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}ethyl]-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0,]dodec-3-ene-3-carboxylic acid	Generator

Chemical Formula

C₃₉H₅₄O₂₀

Average Mass

842.8410 Da

Monoisotopic Mass

842.32084 Da

IUPAC Name

methyl (1R,2S,7R,8S,9S)-8-[(2S)-2-[(2S,3R,4S,5S)-4-(acetyloxy)-3-hydroxy-2,5-dimethoxyoxolan-3-yl]-2-{[(2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}ethyl]-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0^{2,7}]dodec-3-ene-3-carboxylate

Traditional Name

CAS Registry Number

Not Available

SMILES

CO[C@H]1O[C@H](OC)[C@@](O)([C@H](C[C@]2(C)[C@@H]3C[C@@H](OC3=O)[C@@]3(C)[C@@H]2CCC=C3C(=O)OC)O[C@@H]2O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]2OC(C)=O)[C@@H]1OC(C)=O

InChI Identifier

InChI=1S/C39H54O20/c1-17(40)51-16-24-28(52-18(2)41)29(53-19(3)42)30(54-20(4)43)34(56-24)58-27(39(47)31(55-21(5)44)35(49-9)59-36(39)50-10)15-37(6)23-14-26(57-33(23)46)38(7)22(32(45)48-8)12-11-13-25(37)38/h12,23-31,34-36,47H,11,13-16H2,1-10H3/t23-,24-,25-,26-,27+,28-,29+,30-,31-,34+,35+,36+,37-,38-,39-/m1/s1

InChI Key

ONVAYUYWVYCTAN-GBHOPJRWSA-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
Tinospora crispa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty acyl glycosides of mono- and disaccharides

Alternative Parents

Substituents

Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Glycosyl compound
O-glycosyl compound
Caprolactone
Oxepane
Gamma butyrolactone
Monosaccharide
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Tetrahydrofuran
Tertiary alcohol
Lactone
Carboxylic acid ester
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Carbonyl group
Alcohol
Organooxygen compound
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	2.26	ALOGPS
logP	1.17	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	11.1	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	250.48 Å²	ChemAxon
Rotatable Bond Count	20	ChemAxon
Refractivity	190.57 m³·mol⁻¹	ChemAxon
Polarizability	82.76 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

163032634

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (1r,2s,7r,8s,9s)-8-[(2s)-2-[(2s,3r,4s,5s)-4-(acetyloxy)-3-hydroxy-2,5-dimethoxyoxolan-3-yl]-2-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}ethyl]-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0²,⁷]dodec-3-ene-3-carboxylate (NP0145116)

MOL for NP0145116 (methyl (1r,2s,7r,8s,9s)-8-[(2s)-2-[(2s,3r,4s,5s)-4-(acetyloxy)-3-hydroxy-2,5-dimethoxyoxolan-3-yl]-2-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}ethyl]-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0²,⁷]dodec-3-ene-3-carboxylate)

3D MOL for NP0145116 (methyl (1r,2s,7r,8s,9s)-8-[(2s)-2-[(2s,3r,4s,5s)-4-(acetyloxy)-3-hydroxy-2,5-dimethoxyoxolan-3-yl]-2-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}ethyl]-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0²,⁷]dodec-3-ene-3-carboxylate)

3D SDF for NP0145116 (methyl (1r,2s,7r,8s,9s)-8-[(2s)-2-[(2s,3r,4s,5s)-4-(acetyloxy)-3-hydroxy-2,5-dimethoxyoxolan-3-yl]-2-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}ethyl]-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0²,⁷]dodec-3-ene-3-carboxylate)

3D-SDF for NP0145116 (methyl (1r,2s,7r,8s,9s)-8-[(2s)-2-[(2s,3r,4s,5s)-4-(acetyloxy)-3-hydroxy-2,5-dimethoxyoxolan-3-yl]-2-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}ethyl]-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0²,⁷]dodec-3-ene-3-carboxylate)

PDB for NP0145116 (methyl (1r,2s,7r,8s,9s)-8-[(2s)-2-[(2s,3r,4s,5s)-4-(acetyloxy)-3-hydroxy-2,5-dimethoxyoxolan-3-yl]-2-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}ethyl]-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0²,⁷]dodec-3-ene-3-carboxylate)

3D PDB for NP0145116 (methyl (1r,2s,7r,8s,9s)-8-[(2s)-2-[(2s,3r,4s,5s)-4-(acetyloxy)-3-hydroxy-2,5-dimethoxyoxolan-3-yl]-2-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}ethyl]-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0²,⁷]dodec-3-ene-3-carboxylate)

SMILES for NP0145116 (methyl (1r,2s,7r,8s,9s)-8-[(2s)-2-[(2s,3r,4s,5s)-4-(acetyloxy)-3-hydroxy-2,5-dimethoxyoxolan-3-yl]-2-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}ethyl]-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0²,⁷]dodec-3-ene-3-carboxylate)

INCHI for NP0145116 (methyl (1r,2s,7r,8s,9s)-8-[(2s)-2-[(2s,3r,4s,5s)-4-(acetyloxy)-3-hydroxy-2,5-dimethoxyoxolan-3-yl]-2-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}ethyl]-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0²,⁷]dodec-3-ene-3-carboxylate)

Structure for NP0145116 (methyl (1r,2s,7r,8s,9s)-8-[(2s)-2-[(2s,3r,4s,5s)-4-(acetyloxy)-3-hydroxy-2,5-dimethoxyoxolan-3-yl]-2-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}ethyl]-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0²,⁷]dodec-3-ene-3-carboxylate)

3D Structure for NP0145116 (methyl (1r,2s,7r,8s,9s)-8-[(2s)-2-[(2s,3r,4s,5s)-4-(acetyloxy)-3-hydroxy-2,5-dimethoxyoxolan-3-yl]-2-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}ethyl]-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0²,⁷]dodec-3-ene-3-carboxylate)