NP-MRD: Showing NP-Card for methyl 3-(acetyloxy)-2,13,20,21,25-pentahydroxy-5,8,22-trimethyl-11-methylidene-24-oxahexacyclo[15.5.3.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]pentacosane-14-carboxylate (NP0187187)

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Record Information

Version

2.0

Created at

2022-09-04 03:16:15 UTC

Updated at

2022-09-04 03:16:15 UTC

NP-MRD ID

NP0187187

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 3-(acetyloxy)-2,13,20,21,25-pentahydroxy-5,8,22-trimethyl-11-methylidene-24-oxahexacyclo[15.5.3.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]pentacosane-14-carboxylate

Description

Methyl 3-(acetyloxy)-2,13,20,21,25-pentahydroxy-5,8,22-trimethyl-11-methylidene-24-oxahexacyclo[15.5.3.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]Pentacosane-14-carboxylate belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms. methyl 3-(acetyloxy)-2,13,20,21,25-pentahydroxy-5,8,22-trimethyl-11-methylidene-24-oxahexacyclo[15.5.3.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]pentacosane-14-carboxylate is found in Agrobacterium rhizogenes. Methyl 3-(acetyloxy)-2,13,20,21,25-pentahydroxy-5,8,22-trimethyl-11-methylidene-24-oxahexacyclo[15.5.3.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]Pentacosane-14-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231520092D          

 42 47  0  0  0  0            999 V2000
    1.7535   -2.2478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5785   -2.2408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9849   -1.5228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6564   -2.0021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5664   -0.8119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1615   -1.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3318   -1.5415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8443   -0.8472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3554   -1.6109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5948   -2.2891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7558   -1.3115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9033   -0.6797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3893    0.0120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1425   -0.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8105    0.1597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2278   -1.1450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9811   -1.4814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5598   -1.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6451   -2.4497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1935   -1.2927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2787   -0.4721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0879    0.7265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2806    1.4646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9386    0.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3975    1.3645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0333    2.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2102    2.1594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4923    2.7903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3115   -0.0994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1524   -0.0982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7387    0.6155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5635    0.6171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3885    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8024   -0.0949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    0.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6274   -0.0933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0414   -0.8069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6303   -1.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0442   -2.2359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8053   -1.5239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3914   -0.8102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4793   -1.6305    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  2  0  0  0  0
  3  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
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
  8 21  1  0  0  0  0
 13 21  1  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 24 29  1  0  0  0  0
  8 29  1  0  0  0  0
 29 30  1  0  0  0  0
  5 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 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
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
  5 41  1  0  0  0  0
 34 41  1  0  0  0  0
 41 42  1  0  0  0  0
M  END

     RDKit          3D

 90 95  0  0  0  0  0  0  0  0999 V2000
    6.2327    1.3169    1.2110 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2172    1.0699    0.3952 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2468    1.6856   -0.9471 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3276    1.1179   -1.9579 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4763   -0.0373   -1.3741 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4973   -1.1578   -1.3169 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4321   -0.4175   -2.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0269    0.0485   -1.9519 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6670   -0.5376   -0.5820 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8114   -2.0382   -0.8409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7528   -0.2585   -0.2050 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8242   -1.0427   -0.8189 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8940   -2.4296   -0.5326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9531   -3.4281   -1.4739 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0186    1.0737    1.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6683   -0.0726    0.4452 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9670   -1.0798    1.5015 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6987   -0.8588    2.7435 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5303   -2.3141    1.3638 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8045   -3.2443    2.3530 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9601    0.4459   -0.0709 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9321    1.8677   -0.0199 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2252    0.9805    2.1694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5395    1.2270    2.8763 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -4.6124    1.7574    1.9730 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5301    3.1022    1.7067 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7554    0.9025    0.7172 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3486   -0.4016    1.1499 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0470    1.9360    0.9202 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2819    0.8953    2.2247 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1135    2.7930   -0.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3279    1.6235   -1.2836 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4317   -1.4940   -2.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9105   -2.3198   -0.8423 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5398   -2.2661   -1.8911 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7547   -0.5920    0.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7126   -1.0367   -1.9484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7263   -4.9875   -0.2857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0308   -5.2237   -0.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4144   -5.4822   -1.9572 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5280   -0.8402   -2.4892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5668    2.2968   -1.2278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6130    1.1746   -2.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6781    2.7206   -1.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5491    2.6324   -0.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3620    2.6163    1.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8497    1.7466    1.6084 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5654    0.7003    2.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7723   -2.8533    3.3831 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7832    2.3038   -0.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3921   -0.8629    0.9702 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8095    0.6408    1.8792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4920    2.4816    0.7583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5217    1.7179    2.6635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9252   -0.0426    2.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9577    0.2761    3.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4019    3.0233    3.5437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5889    1.6074    2.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4174    3.5399    1.6775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5657    1.4199    0.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6858   -1.0424    0.2871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7965   -0.9406    1.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3315   -0.1211    1.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
 31 30  1  0
 30 28  1  0
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  3 45  1  0
  3 46  1  0
  1 43  1  0
  1 44  1  0
 34 78  1  0
 34 79  1  0
 33 77  1  0
M  END


  Mrv1533004231520092D          

 42 47  0  0  0  0            999 V2000
    1.7535   -2.2478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5785   -2.2408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9849   -1.5228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6564   -2.0021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5664   -0.8119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1615   -1.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3318   -1.5415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8443   -0.8472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3554   -1.6109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5948   -2.2891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7558   -1.3115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9033   -0.6797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3893    0.0120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1425   -0.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8105    0.1597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2278   -1.1450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9811   -1.4814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5598   -1.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6451   -2.4497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1935   -1.2927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2787   -0.4721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0879    0.7265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2806    1.4646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9386    0.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3975    1.3645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0333    2.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2102    2.1594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4923    2.7903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3115   -0.0994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1524   -0.0982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7387    0.6155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5635    0.6171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3885    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8024   -0.0949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    0.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6274   -0.0933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0414   -0.8069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6303   -1.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0442   -2.2359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8053   -1.5239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3914   -0.8102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4793   -1.6305    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  2  0  0  0  0
  3  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
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
  8 21  1  0  0  0  0
 13 21  1  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 24 29  1  0  0  0  0
  8 29  1  0  0  0  0
 29 30  1  0  0  0  0
  5 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 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
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
  5 41  1  0  0  0  0
 34 41  1  0  0  0  0
 41 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0187187

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C12CCC34C(O)OCC5(C(C)C(O)C(O)CC35)C(O)C(OC(C)=O)C4C1(C)CCC1(C)CCC(=C)CC21O

> <INCHI_IDENTIFIER>
InChI=1S/C32H48O10/c1-16-7-8-27(4)9-10-28(5)23-22(42-18(3)33)24(36)30-15-41-25(37)29(23,20(30)13-19(34)21(35)17(30)2)11-12-31(28,26(38)40-6)32(27,39)14-16/h17,19-25,34-37,39H,1,7-15H2,2-6H3

> <INCHI_KEY>
SHSLNYHFLPFNSE-UHFFFAOYSA-N

> <FORMULA>
C32H48O10

> <MOLECULAR_WEIGHT>
592.726

> <EXACT_MASS>
592.324747746

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
90

> <JCHEM_AVERAGE_POLARIZABILITY>
62.83848559119107

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 3-(acetyloxy)-2,13,20,21,25-pentahydroxy-5,8,22-trimethyl-11-methylidene-24-oxahexacyclo[15.5.3.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]pentacosane-14-carboxylate

> <ALOGPS_LOGP>
0.79

> <JCHEM_LOGP>
0.7916661813333323

> <ALOGPS_LOGS>
-2.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.222281909198813

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.916499865156368

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1533391519664082

> <JCHEM_POLAR_SURFACE_AREA>
162.98000000000002

> <JCHEM_REFRACTIVITY>
148.6793

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.86e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 3-(acetyloxy)-2,13,20,21,25-pentahydroxy-5,8,22-trimethyl-11-methylidene-24-oxahexacyclo[15.5.3.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]pentacosane-14-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       3.273  -4.196   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.813  -4.183   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.572  -2.843   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.825  -3.737   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.791  -1.516   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.035  -2.871   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.486  -2.877   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.576  -1.581   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.663  -3.007   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.110  -4.273   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -1.411  -2.448   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.686  -1.269   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.727   0.022   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.133  -0.606   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.380   0.298   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.292  -2.137   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.698  -2.765   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.045  -3.041   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.204  -4.573   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.361  -2.413   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.520  -0.881   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.164   1.356   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.524   2.734   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.752   1.267   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.609   2.547   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.929   3.929   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.392   4.031   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.786   5.209   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.448  -0.186   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.018  -0.183   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.246   1.149   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.785   1.152   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.325   1.155   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.098  -0.177   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.865   1.158   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.638  -0.174   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.411  -1.506   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.643  -2.841   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       9.416  -4.174   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       7.103  -2.845   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       6.331  -1.512   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       6.495  -3.044   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   30   41                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   21   29                                             
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   21   22                                             
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20    8   13                                                  
CONECT   22   13   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   24    8   30                                                  
CONECT   30   29    5   31   32                                             
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36   41                                             
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40    5   34   42                                             
CONECT   42   41                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   94    0
END

View in JSmol

Synonyms

Value	Source
Methyl 3-(acetyloxy)-2,13,20,21,25-pentahydroxy-5,8,22-trimethyl-11-methylidene-24-oxahexacyclo[15.5.3.0,.0,.0,.0,]pentacosane-14-carboxylic acid	Generator
Methyl 3-(acetyloxy)-2,13,20,21,25-pentahydroxy-5,8,22-trimethyl-11-methylidene-24-oxahexacyclo[15.5.3.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]pentacosane-14-carboxylic acid	Generator

Chemical Formula

C₃₂H₄₈O₁₀

Average Mass

592.7260 Da

Monoisotopic Mass

592.32475 Da

IUPAC Name

methyl 3-(acetyloxy)-2,13,20,21,25-pentahydroxy-5,8,22-trimethyl-11-methylidene-24-oxahexacyclo[15.5.3.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]pentacosane-14-carboxylate

Traditional Name

methyl 3-(acetyloxy)-2,13,20,21,25-pentahydroxy-5,8,22-trimethyl-11-methylidene-24-oxahexacyclo[15.5.3.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]pentacosane-14-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C12CCC34C(O)OCC5(C(C)C(O)C(O)CC35)C(O)C(OC(C)=O)C4C1(C)CCC1(C)CCC(=C)CC21O

InChI Identifier

InChI=1S/C32H48O10/c1-16-7-8-27(4)9-10-28(5)23-22(42-18(3)33)24(36)30-15-41-25(37)29(23,20(30)13-19(34)21(35)17(30)2)11-12-31(28,26(38)40-6)32(27,39)14-16/h17,19-25,34-37,39H,1,7-15H2,2-6H3

InChI Key

SHSLNYHFLPFNSE-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
Agrobacterium rhizogenes	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxanes

Sub Class

Not Available

Direct Parent

Oxanes

Alternative Parents

Substituents

Dicarboxylic acid or derivatives
Oxane
Cyclic alcohol
Tertiary alcohol
Methyl ester
Secondary alcohol
Hemiacetal
Carboxylic acid ester
Polyol
Carboxylic acid derivative
Oxacycle
Organic oxide
Organooxygen compound
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
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	0.79	ALOGPS
logP	0.79	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	11.92	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	162.98 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	148.68 m³·mol⁻¹	ChemAxon
Polarizability	62.84 Å³	ChemAxon
Number of Rings	6	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 3-(acetyloxy)-2,13,20,21,25-pentahydroxy-5,8,22-trimethyl-11-methylidene-24-oxahexacyclo[15.5.3.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]pentacosane-14-carboxylate (NP0187187)

MOL for NP0187187 (methyl 3-(acetyloxy)-2,13,20,21,25-pentahydroxy-5,8,22-trimethyl-11-methylidene-24-oxahexacyclo[15.5.3.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]pentacosane-14-carboxylate)

3D MOL for NP0187187 (methyl 3-(acetyloxy)-2,13,20,21,25-pentahydroxy-5,8,22-trimethyl-11-methylidene-24-oxahexacyclo[15.5.3.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]pentacosane-14-carboxylate)

3D SDF for NP0187187 (methyl 3-(acetyloxy)-2,13,20,21,25-pentahydroxy-5,8,22-trimethyl-11-methylidene-24-oxahexacyclo[15.5.3.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]pentacosane-14-carboxylate)

3D-SDF for NP0187187 (methyl 3-(acetyloxy)-2,13,20,21,25-pentahydroxy-5,8,22-trimethyl-11-methylidene-24-oxahexacyclo[15.5.3.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]pentacosane-14-carboxylate)

PDB for NP0187187 (methyl 3-(acetyloxy)-2,13,20,21,25-pentahydroxy-5,8,22-trimethyl-11-methylidene-24-oxahexacyclo[15.5.3.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]pentacosane-14-carboxylate)

3D PDB for NP0187187 (methyl 3-(acetyloxy)-2,13,20,21,25-pentahydroxy-5,8,22-trimethyl-11-methylidene-24-oxahexacyclo[15.5.3.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]pentacosane-14-carboxylate)

SMILES for NP0187187 (methyl 3-(acetyloxy)-2,13,20,21,25-pentahydroxy-5,8,22-trimethyl-11-methylidene-24-oxahexacyclo[15.5.3.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]pentacosane-14-carboxylate)

INCHI for NP0187187 (methyl 3-(acetyloxy)-2,13,20,21,25-pentahydroxy-5,8,22-trimethyl-11-methylidene-24-oxahexacyclo[15.5.3.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]pentacosane-14-carboxylate)

Structure for NP0187187 (methyl 3-(acetyloxy)-2,13,20,21,25-pentahydroxy-5,8,22-trimethyl-11-methylidene-24-oxahexacyclo[15.5.3.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]pentacosane-14-carboxylate)

3D Structure for NP0187187 (methyl 3-(acetyloxy)-2,13,20,21,25-pentahydroxy-5,8,22-trimethyl-11-methylidene-24-oxahexacyclo[15.5.3.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]pentacosane-14-carboxylate)