NP-MRD: Showing NP-Card for methyl (3r,3as,5ar,5br,7r,7ar,8r,9s,11ar,11br,12s,13ar,13bs)-7-(acetyloxy)-9,12-dihydroxy-5a,5b,8,11a,13b-pentamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-8-carboxylate (NP0216668)

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Record Information

Version

2.0

Created at

2022-09-05 16:43:37 UTC

Updated at

2022-09-05 16:43:37 UTC

NP-MRD ID

NP0216668

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (3r,3as,5ar,5br,7r,7ar,8r,9s,11ar,11br,12s,13ar,13bs)-7-(acetyloxy)-9,12-dihydroxy-5a,5b,8,11a,13b-pentamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-8-carboxylate

Description

Cavalerol J belongs to the class of organic compounds known as hopanoids. These are terpenoids containing hopane skeleton(A'-Neogammacerane), a pentacyclic structure with four cyclohexane rings and one cyclopentane ring (and often, a side chain emerging from C30). methyl (3r,3as,5ar,5br,7r,7ar,8r,9s,11ar,11br,12s,13ar,13bs)-7-(acetyloxy)-9,12-dihydroxy-5a,5b,8,11a,13b-pentamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-8-carboxylate is found in Eurycorymbus cavaleriei. Based on a literature review very few articles have been published on Cavalerol J.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052218432D          

 39 43  0  0  1  0            999 V2000
    7.4687    1.1499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6880    1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5288    2.2262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0666    0.8741    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1403    0.0524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3816   -0.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8390    0.3498    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4920   -0.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2623    1.0579    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8607    1.7785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0358    1.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6125    1.0830    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2109    1.8036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0141    0.3623    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5908   -0.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7659   -0.3333    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3425   -1.0414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3643    0.3874    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5394    0.4000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9410   -0.3207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1161   -0.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2912   -0.2956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1104    0.4250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9353    0.4376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3129    1.1332    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4685    1.9434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4580    1.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0980    0.9065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5889    2.2416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3597    2.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1378    1.1206    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5611    1.8287    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1595    2.5494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5828    3.2575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1813    3.9782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4077    3.2450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3860    1.8162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7876    1.0955    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7139    1.9172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  6  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  1  0  0  0
  7  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 18 16  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  6  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 31 25  1  6  0  0  0
 19 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  6  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 32 37  1  0  0  0  0
 37 38  1  0  0  0  0
 18 38  1  0  0  0  0
 12 38  1  0  0  0  0
 38 39  1  6  0  0  0
M  END

     RDKit          3D

 91 95  0  0  0  0  0  0  0  0999 V2000
    7.3007   -1.7247   -0.2383 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4654   -0.9526    0.4201 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4621   -0.9622    1.9017 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5299   -0.0757   -0.2917 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6900    1.3724    0.1965 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2860    1.9174    0.3949 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4857    0.9784   -0.5221 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7889    1.3109   -1.9083 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1005   -0.3294   -0.0197 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4607   -1.5015   -0.6241 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0030   -1.5324   -0.2108 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2862   -0.2667   -0.5264 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0414   -0.2580   -2.0150 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0473    0.9521   -0.0760 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3292    2.2302   -0.2369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1308    2.2039   -0.4982 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7846    3.1650    0.3132 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8107    0.9103   -0.4378 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2901    0.9137   -0.1081 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6355    1.3992    1.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9241    1.8721   -1.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3238    1.1607   -2.3850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4577    0.2418   -2.0681 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6277    0.9941   -1.8107 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1878   -0.6295   -0.8436 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2975   -2.0823   -1.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2032   -0.4865    0.1838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8609   -1.4961    0.6244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5598    0.7134    0.7795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5500    0.7757    1.7658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7689   -0.4661   -0.4676 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1731   -1.5491    0.3874 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5077   -1.5409    1.7288 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1611   -2.5144    2.4307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4854   -2.4269    3.8818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5114   -3.5512    1.8125 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6771   -1.5317    0.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0352   -0.1940    0.2669 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2306    0.0867    1.7003 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2909   -1.7064   -1.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0090   -2.3881    0.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7914   -1.9343    2.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2173   -0.2148    2.2784 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5049   -0.6760    2.3472 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7799   -0.0884   -1.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2007    1.3992    1.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2638    1.9732   -0.5333 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1848    2.9597    0.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9143    1.7300    1.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0306    1.8489   -2.4711 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7136    1.9649   -1.9763 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1226    0.3834   -2.4647 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9434   -0.3358    1.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6226   -1.6067   -1.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9834   -0.6851   -2.4757 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1874    0.7727    1.0404 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9005    2.8133   -1.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5066    2.8737    0.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2714    2.6655   -1.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3943    4.0347    0.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8466    0.5145   -1.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8105    1.8157    1.8572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3651    2.2668    1.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1233    0.6714    1.9240 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3002    2.7213   -1.3787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7456    1.9693   -3.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.6851   -0.3413   -2.9751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3952    0.4125   -2.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1603   -2.0606   -2.0912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5963   -2.7735   -0.5803 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.6839    1.8587    2.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2866    0.2603    2.7019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5268    0.4243    1.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2266   -0.6662   -1.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5470   -2.5168   -0.0433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6946   -2.9868    4.4233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4423   -2.9479    4.0815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5682   -1.3738    4.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4731   -2.0727   -0.7715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2435   -2.1725    0.9788 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4475    1.1050    1.9940 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0510   -0.5652    2.0685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6625   -0.2366    2.3131 H   0  0  0  0  0  0  0  0  0  0  0  0
 30 29  1  0
 29 27  1  0
 27 28  2  0
 25 27  1  1
 25 26  1  0
 25 23  1  0
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 23 22  1  0
 22 21  1  0
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 18 16  1  0
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 14  7  1  0
  7  8  1  6
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  6  5  1  0
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  9 10  1  0
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 12 13  1  6
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  4  2  1  0
  2  3  1  0
  2  1  2  3
 31 25  1  0
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 12 14  1  0
  9  7  1  0
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 35 86  1  0
 31 82  1  6
  3 42  1  0
  3 43  1  0
  3 44  1  0
  1 40  1  0
  1 41  1  0
M  END


  Mrv1652309052218432D          

 39 43  0  0  1  0            999 V2000
    7.4687    1.1499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6880    1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5288    2.2262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0666    0.8741    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1403    0.0524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3816   -0.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8390    0.3498    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4920   -0.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2623    1.0579    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8607    1.7785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0358    1.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6125    1.0830    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2109    1.8036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0141    0.3623    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5908   -0.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7659   -0.3333    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3425   -1.0414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3643    0.3874    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5394    0.4000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9410   -0.3207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1161   -0.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2912   -0.2956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1104    0.4250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9353    0.4376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3129    1.1332    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4685    1.9434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4580    1.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0980    0.9065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5889    2.2416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3597    2.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1378    1.1206    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5611    1.8287    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1595    2.5494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5828    3.2575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1813    3.9782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4077    3.2450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3860    1.8162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7876    1.0955    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7139    1.9172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  6  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  1  0  0  0
  7  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 18 16  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  6  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 31 25  1  6  0  0  0
 19 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  6  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 32 37  1  0  0  0  0
 37 38  1  0  0  0  0
 18 38  1  0  0  0  0
 12 38  1  0  0  0  0
 38 39  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0216668

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@]1(C)[C@@H](O)CC[C@]2(C)[C@H]3[C@@H](O)C[C@@H]4[C@@]5(C)CC[C@H]([C@@H]5CC[C@@]4(C)[C@]3(C)C[C@@H](OC(C)=O)[C@@H]12)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C33H52O6/c1-18(2)20-10-13-29(4)21(20)11-15-31(6)24(29)16-22(35)26-30(5)14-12-25(36)33(8,28(37)38-9)27(30)23(39-19(3)34)17-32(26,31)7/h20-27,35-36H,1,10-17H2,2-9H3/t20-,21-,22-,23+,24+,25-,26+,27+,29-,30+,31+,32+,33-/m0/s1

> <INCHI_KEY>
DICJXAYCQPWCBL-DGGVPMNRSA-N

> <FORMULA>
C33H52O6

> <MOLECULAR_WEIGHT>
544.773

> <EXACT_MASS>
544.376389394

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
91

> <JCHEM_AVERAGE_POLARIZABILITY>
62.65041414285621

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1R,2R,5S,6R,9S,10R,12S,13R,14R,17S,18R,19R,20R)-20-(acetyloxy)-12,17-dihydroxy-1,2,9,14,18-pentamethyl-6-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosane-18-carboxylate

> <JCHEM_LOGP>
4.609228952333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.44925026216237

> <JCHEM_PKA_STRONGEST_BASIC>
-0.25695518845607246

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
149.73110000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,2R,5S,6R,9S,10R,12S,13R,14R,17S,18R,19R,20R)-20-(acetyloxy)-12,17-dihydroxy-1,2,9,14,18-pentamethyl-6-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosane-18-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      13.941   2.146   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.484   2.645   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.187   4.156   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.324   1.632   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.462   0.098   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.046  -0.507   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.033   0.653   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.385  -0.744   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.823   1.975   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.073   3.320   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.534   3.343   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.743   2.022   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.994   3.367   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.493   0.676   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.703  -0.645   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.163  -0.622   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.373  -1.944   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.413   0.723   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.874   0.747   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.623  -0.599   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.083  -0.575   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.543  -0.552   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.206   0.793   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.746   0.817   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.584   2.115   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.875   3.628   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.855   2.664   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -2.050   1.692   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -1.099   4.184   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -2.538   4.733   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.124   2.092   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.914   3.414   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.164   4.759   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.955   6.081   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.205   7.426   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       4.494   6.057   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       4.454   3.390   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.204   2.045   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       5.066   3.579   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   14                                             
CONECT    8    7                                                            
CONECT    9    7    4   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   38                                             
CONECT   13   12                                                            
CONECT   14   12    7   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   38                                                  
CONECT   19   18   20   21   31                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27   31                                             
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29                                                            
CONECT   31   25   19   32                                                  
CONECT   32   31   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   32   38                                                       
CONECT   38   37   18   12   39                                             
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₅₂O₆

Average Mass

544.7730 Da

Monoisotopic Mass

544.37639 Da

IUPAC Name

methyl (1R,2R,5S,6R,9S,10R,12S,13R,14R,17S,18R,19R,20R)-20-(acetyloxy)-12,17-dihydroxy-1,2,9,14,18-pentamethyl-6-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosane-18-carboxylate

Traditional Name

methyl (1R,2R,5S,6R,9S,10R,12S,13R,14R,17S,18R,19R,20R)-20-(acetyloxy)-12,17-dihydroxy-1,2,9,14,18-pentamethyl-6-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosane-18-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@]1(C)[C@@H](O)CC[C@]2(C)[C@H]3[C@@H](O)C[C@@H]4[C@@]5(C)CC[C@H]([C@@H]5CC[C@@]4(C)[C@]3(C)C[C@@H](OC(C)=O)[C@@H]12)C(C)=C

InChI Identifier

InChI=1S/C33H52O6/c1-18(2)20-10-13-29(4)21(20)11-15-31(6)24(29)16-22(35)26-30(5)14-12-25(36)33(8,28(37)38-9)27(30)23(39-19(3)34)17-32(26,31)7/h20-27,35-36H,1,10-17H2,2-9H3/t20-,21-,22-,23+,24+,25-,26+,27+,29-,30+,31+,32+,33-/m0/s1

InChI Key

DICJXAYCQPWCBL-DGGVPMNRSA-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
Eurycorymbus cavaleriei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hopanoids. These are terpenoids containing hopane skeleton(A'-Neogammacerane), a pentacyclic structure with four cyclohexane rings and one cyclopentane ring (and often, a side chain emerging from C30).

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Hopanoids

Direct Parent

Hopanoids

Alternative Parents

Substituents

Hopane-skeleton
Triterpenoid
Steroid ester
6-hydroxysteroid
Hydroxysteroid
1-hydroxysteroid
Steroid
Beta-hydroxy acid
Hydroxy acid
Dicarboxylic acid or derivatives
Cyclic alcohol
Methyl ester
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Organic oxide
Organooxygen compound
Alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	4.61	ChemAxon
pKa (Strongest Acidic)	14.45	ChemAxon
pKa (Strongest Basic)	-0.26	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	149.73 m³·mol⁻¹	ChemAxon
Polarizability	62.65 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

102258957

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (3r,3as,5ar,5br,7r,7ar,8r,9s,11ar,11br,12s,13ar,13bs)-7-(acetyloxy)-9,12-dihydroxy-5a,5b,8,11a,13b-pentamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-8-carboxylate (NP0216668)

MOL for NP0216668 (methyl (3r,3as,5ar,5br,7r,7ar,8r,9s,11ar,11br,12s,13ar,13bs)-7-(acetyloxy)-9,12-dihydroxy-5a,5b,8,11a,13b-pentamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-8-carboxylate)

3D MOL for NP0216668 (methyl (3r,3as,5ar,5br,7r,7ar,8r,9s,11ar,11br,12s,13ar,13bs)-7-(acetyloxy)-9,12-dihydroxy-5a,5b,8,11a,13b-pentamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-8-carboxylate)

3D SDF for NP0216668 (methyl (3r,3as,5ar,5br,7r,7ar,8r,9s,11ar,11br,12s,13ar,13bs)-7-(acetyloxy)-9,12-dihydroxy-5a,5b,8,11a,13b-pentamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-8-carboxylate)

3D-SDF for NP0216668 (methyl (3r,3as,5ar,5br,7r,7ar,8r,9s,11ar,11br,12s,13ar,13bs)-7-(acetyloxy)-9,12-dihydroxy-5a,5b,8,11a,13b-pentamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-8-carboxylate)

PDB for NP0216668 (methyl (3r,3as,5ar,5br,7r,7ar,8r,9s,11ar,11br,12s,13ar,13bs)-7-(acetyloxy)-9,12-dihydroxy-5a,5b,8,11a,13b-pentamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-8-carboxylate)

3D PDB for NP0216668 (methyl (3r,3as,5ar,5br,7r,7ar,8r,9s,11ar,11br,12s,13ar,13bs)-7-(acetyloxy)-9,12-dihydroxy-5a,5b,8,11a,13b-pentamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-8-carboxylate)

SMILES for NP0216668 (methyl (3r,3as,5ar,5br,7r,7ar,8r,9s,11ar,11br,12s,13ar,13bs)-7-(acetyloxy)-9,12-dihydroxy-5a,5b,8,11a,13b-pentamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-8-carboxylate)

INCHI for NP0216668 (methyl (3r,3as,5ar,5br,7r,7ar,8r,9s,11ar,11br,12s,13ar,13bs)-7-(acetyloxy)-9,12-dihydroxy-5a,5b,8,11a,13b-pentamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-8-carboxylate)

Structure for NP0216668 (methyl (3r,3as,5ar,5br,7r,7ar,8r,9s,11ar,11br,12s,13ar,13bs)-7-(acetyloxy)-9,12-dihydroxy-5a,5b,8,11a,13b-pentamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-8-carboxylate)

3D Structure for NP0216668 (methyl (3r,3as,5ar,5br,7r,7ar,8r,9s,11ar,11br,12s,13ar,13bs)-7-(acetyloxy)-9,12-dihydroxy-5a,5b,8,11a,13b-pentamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-8-carboxylate)