NP-MRD: Showing NP-Card for methyl (4r,5e)-4-(acetyloxy)-6-[(1s,2r,3r,4r,7s)-7-(acetyloxy)-3-butyl-10-oxotricyclo[5.3.0.0¹,⁴]dec-8-en-2-yl]hex-5-enoate (NP0283574)

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Record Information

Version

2.0

Created at

2022-09-09 10:53:36 UTC

Updated at

2022-09-09 10:53:36 UTC

NP-MRD ID

NP0283574

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (4r,5e)-4-(acetyloxy)-6-[(1s,2r,3r,4r,7s)-7-(acetyloxy)-3-butyl-10-oxotricyclo[5.3.0.0¹,⁴]dec-8-en-2-yl]hex-5-enoate

Description

Tricycloclavulone belongs to the class of organic compounds known as clavulones and derivatives. These are ester derivatives of prostanoids. methyl (4r,5e)-4-(acetyloxy)-6-[(1s,2r,3r,4r,7s)-7-(acetyloxy)-3-butyl-10-oxotricyclo[5.3.0.0¹,⁴]dec-8-en-2-yl]hex-5-enoate is found in Clavularia viridis. methyl (4r,5e)-4-(acetyloxy)-6-[(1s,2r,3r,4r,7s)-7-(acetyloxy)-3-butyl-10-oxotricyclo[5.3.0.0¹,⁴]dec-8-en-2-yl]hex-5-enoate was first documented in 2004 (PMID: 15070361). Based on a literature review a small amount of articles have been published on Tricycloclavulone (PMID: 21573291) (PMID: 15957891).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092212532D          

 32 34  0  0  1  0            999 V2000
    6.7614  -11.0160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7614  -10.1910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4759   -9.7785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4759   -8.9535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1904   -8.5410    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.4039   -7.7441    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9914   -7.0296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1664   -7.0296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7539   -6.3151    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9289   -6.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5164   -5.6007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6914   -5.6007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2789   -6.3151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2789   -4.8862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4539   -4.8862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1664   -5.6007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7539   -4.8862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9289   -4.8862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1664   -4.1717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2008   -7.9576    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.9051   -7.1874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2132   -6.7381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5463   -6.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2382   -7.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0247   -7.9144    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.8485   -7.8712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2979   -8.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1217   -8.5200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9233   -9.2982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3203   -8.6846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6792   -9.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9873   -8.7545    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
  6 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  0  0  0  0
 32 31  1  6  0  0  0
  5 32  1  0  0  0  0
 20 32  1  0  0  0  0
M  END

     RDKit          3D

 66 68  0  0  0  0  0  0  0  0999 V2000
   -4.0714   -5.1942   -0.3458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0700   -4.2352    0.2877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4205   -3.4922   -0.8242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3794   -2.4896   -0.3854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9417   -1.4623    0.4934 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2385   -0.1365    0.6805 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1784   -0.1309    0.9201 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1626    0.4547    0.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6170    0.3323    0.6843 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0596   -1.0867    0.6378 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4626   -1.3152    1.0219 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4093   -0.6902    0.1001 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1152   -0.1460   -0.9878 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7842   -0.6687    0.4100 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7075   -0.0695   -0.4698 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4043    1.2899    0.0846 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9924    2.3556    0.7481 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8229    3.3345    0.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8214    2.4947    1.9798 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9543    0.3853   -0.4483 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5775    0.5240   -1.8119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5756    0.3285   -2.5010 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8204    1.0492   -2.4433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5195    1.7000   -1.5345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7906    1.6526   -0.2486 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9467    2.7785   -0.0844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5012    4.0127    0.1057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7045    5.2703    0.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7721    4.0883    0.1256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6795    1.4054    0.9100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9554   -0.0722    0.8474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0480   -0.6715   -0.1830 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4822   -4.6760   -1.2360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5666   -6.1086   -0.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9103   -5.4178    0.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7013   -3.5468    0.9264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3942   -4.8534    0.8956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9138   -4.2650   -1.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2111   -3.0621   -1.4708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9745   -2.0784   -1.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6103   -3.0980    0.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2785   -1.9398    1.4642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7375    0.3159    1.6146 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5863   -0.7049    1.8014 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9718    1.0530   -0.5742 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5648    0.6019    1.7914 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8302   -1.5084   -0.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3362   -1.6531    1.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6123   -2.4331    1.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6387   -0.8843    2.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7419   -0.3828   -0.2228 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6568    1.0362   -0.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4885   -0.3888   -1.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1668    4.1681   -0.3082 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6221    3.6870    0.6983 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2667    2.8123   -0.8678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1250    0.9271   -3.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4896    2.2061   -1.6792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3163    5.9541    0.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5277    5.7801   -0.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7381    5.0511    0.7707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1779    1.7302    1.8429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6462    1.9301    0.7524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7424   -0.4754    1.8809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0288   -0.2830    0.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4814   -1.0887   -1.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5 32  1  0
 32 31  1  0
 31 30  1  0
 30 25  1  0
 25 26  1  1
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 27 28  1  0
 27 29  2  0
 25 24  1  0
 24 23  2  0
 23 21  1  0
 21 22  2  0
 20 21  1  6
 20  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
  9 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
  6  5  1  0
 20 32  1  0
 20 25  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  2 37  1  0
  3 38  1  0
  3 39  1  0
  4 40  1  0
  4 41  1  0
  5 42  1  1
 32 66  1  6
 31 64  1  0
 31 65  1  0
 30 62  1  0
 30 63  1  0
 28 59  1  0
 28 60  1  0
 28 61  1  0
 24 58  1  0
 23 57  1  0
  6 43  1  1
  7 44  1  0
  8 45  1  0
  9 46  1  1
 10 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 15 51  1  0
 15 52  1  0
 15 53  1  0
 18 54  1  0
 18 55  1  0
 18 56  1  0
M  END


  Mrv1652309092212532D          

 32 34  0  0  1  0            999 V2000
    6.7614  -11.0160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7614  -10.1910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4759   -9.7785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4759   -8.9535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1904   -8.5410    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.4039   -7.7441    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9914   -7.0296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1664   -7.0296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7539   -6.3151    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9289   -6.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5164   -5.6007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6914   -5.6007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2789   -6.3151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2789   -4.8862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4539   -4.8862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1664   -5.6007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7539   -4.8862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9289   -4.8862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1664   -4.1717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2008   -7.9576    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.9051   -7.1874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2132   -6.7381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5463   -6.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2382   -7.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0247   -7.9144    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.8485   -7.8712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2979   -8.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1217   -8.5200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9233   -9.2982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3203   -8.6846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6792   -9.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9873   -8.7545    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
  6 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  0  0  0  0
 32 31  1  6  0  0  0
  5 32  1  0  0  0  0
 20 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0283574

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC[C@@H]1[C@H]2CC[C@]3(OC(C)=O)C=CC(=O)[C@]23[C@@H]1\C=C\[C@@H](CCC(=O)OC)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H34O7/c1-5-6-7-19-20(10-8-18(31-16(2)26)9-11-23(29)30-4)25-21(19)12-14-24(25,32-17(3)27)15-13-22(25)28/h8,10,13,15,18-21H,5-7,9,11-12,14H2,1-4H3/b10-8+/t18-,19-,20+,21+,24-,25-/m0/s1

> <INCHI_KEY>
GNUQDKRCUAQQRE-RCVMNBAESA-N

> <FORMULA>
C25H34O7

> <MOLECULAR_WEIGHT>
446.54

> <EXACT_MASS>
446.230453435

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
48.732919046407986

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (4R,5E)-4-(acetyloxy)-6-[(1S,2R,3R,4R,7S)-7-(acetyloxy)-3-butyl-10-oxotricyclo[5.3.0.0^{1,4}]dec-8-en-2-yl]hex-5-enoate

> <JCHEM_LOGP>
3.4739703176666676

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.053319224298823

> <JCHEM_POLAR_SURFACE_AREA>
95.97

> <JCHEM_REFRACTIVITY>
118.55789999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (4R,5E)-4-(acetyloxy)-6-[(1S,2R,3R,4R,7S)-7-(acetyloxy)-3-butyl-10-oxotricyclo[5.3.0.0^{1,4}]dec-8-en-2-yl]hex-5-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      12.621 -20.563   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.621 -19.023   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.955 -18.253   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.955 -16.713   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.289 -15.943   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.687 -14.456   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.917 -13.122   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.377 -13.122   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.607 -11.788   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.067 -11.788   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.297 -10.455   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.757 -10.455   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       7.987 -11.788   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       7.987  -9.121   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.447  -9.121   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      13.377 -10.455   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      12.607  -9.121   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.067  -9.121   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      13.377  -7.787   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      17.175 -14.854   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.623 -13.416   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      15.331 -12.578   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      17.820 -12.447   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      19.111 -13.286   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      18.713 -14.774   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      20.251 -14.693   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      21.089 -15.985   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      22.627 -15.904   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      20.390 -17.357   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      19.265 -16.211   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      18.068 -17.180   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      16.776 -16.342   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   32                                                  
CONECT    6    5    7   20                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14                                                            
CONECT   16    9   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    6   21   25   32                                             
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   20   26   30                                             
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   25   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31    5   20                                                  
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₄O₇

Average Mass

446.5400 Da

Monoisotopic Mass

446.23045 Da

IUPAC Name

methyl (4R,5E)-4-(acetyloxy)-6-[(1S,2R,3R,4R,7S)-7-(acetyloxy)-3-butyl-10-oxotricyclo[5.3.0.0^{1,4}]dec-8-en-2-yl]hex-5-enoate

Traditional Name

methyl (4R,5E)-4-(acetyloxy)-6-[(1S,2R,3R,4R,7S)-7-(acetyloxy)-3-butyl-10-oxotricyclo[5.3.0.0^{1,4}]dec-8-en-2-yl]hex-5-enoate

CAS Registry Number

Not Available

SMILES

CCCC[C@@H]1[C@H]2CC[C@]3(OC(C)=O)C=CC(=O)[C@]23[C@@H]1\C=C\[C@@H](CCC(=O)OC)OC(C)=O

InChI Identifier

InChI=1S/C25H34O7/c1-5-6-7-19-20(10-8-18(31-16(2)26)9-11-23(29)30-4)25-21(19)12-14-24(25,32-17(3)27)15-13-22(25)28/h8,10,13,15,18-21H,5-7,9,11-12,14H2,1-4H3/b10-8+/t18-,19-,20+,21+,24-,25-/m0/s1

InChI Key

GNUQDKRCUAQQRE-RCVMNBAESA-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
Clavularia viridis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as clavulones and derivatives. These are ester derivatives of prostanoids.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Clavulones and derivatives

Alternative Parents

Substituents

Clavulone
Prostaglandin skeleton
Tricarboxylic acid or derivatives
Fatty acid methyl ester
Fatty acid ester
Methyl ester
Ketone
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	3.47	ChemAxon
pKa (Strongest Basic)	-6.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	95.97 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	118.56 m³·mol⁻¹	ChemAxon
Polarizability	48.73 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

9617079

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11442216

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Mondal S, Yadav RN, Ghosh S: Unprecedented influence of remote substituents on reactivity and stereoselectivity in Cu(I)-catalysed [2 + 2] photocycloaddition. An approach towards the synthesis of tricycloclavulone. Org Biomol Chem. 2011 Jul 7;9(13):4903-13. doi: 10.1039/c1ob05233k. Epub 2011 May 13. [PubMed:21573291 ]
Harmata M, Wacharasindhu S: The [4 + 3]-cycloaddition/quasi-Favorskii process. Synthesis of the carbocyclic core of tricycloclavulone. Org Lett. 2005 Jun 23;7(13):2563-5. doi: 10.1021/ol050598l. [PubMed:15957891 ]
Ito H, Hasegawa M, Takenaka Y, Kobayashi T, Iguchi K: Enantioselective total synthesis of (+)-tricycloclavulone. J Am Chem Soc. 2004 Apr 14;126(14):4520-1. doi: 10.1021/ja049750p. [PubMed:15070361 ]
LOTUS database [Link]

Showing NP-Card for methyl (4r,5e)-4-(acetyloxy)-6-[(1s,2r,3r,4r,7s)-7-(acetyloxy)-3-butyl-10-oxotricyclo[5.3.0.0¹,⁴]dec-8-en-2-yl]hex-5-enoate (NP0283574)

MOL for NP0283574 (methyl (4r,5e)-4-(acetyloxy)-6-[(1s,2r,3r,4r,7s)-7-(acetyloxy)-3-butyl-10-oxotricyclo[5.3.0.0¹,⁴]dec-8-en-2-yl]hex-5-enoate)

3D MOL for NP0283574 (methyl (4r,5e)-4-(acetyloxy)-6-[(1s,2r,3r,4r,7s)-7-(acetyloxy)-3-butyl-10-oxotricyclo[5.3.0.0¹,⁴]dec-8-en-2-yl]hex-5-enoate)

3D SDF for NP0283574 (methyl (4r,5e)-4-(acetyloxy)-6-[(1s,2r,3r,4r,7s)-7-(acetyloxy)-3-butyl-10-oxotricyclo[5.3.0.0¹,⁴]dec-8-en-2-yl]hex-5-enoate)

3D-SDF for NP0283574 (methyl (4r,5e)-4-(acetyloxy)-6-[(1s,2r,3r,4r,7s)-7-(acetyloxy)-3-butyl-10-oxotricyclo[5.3.0.0¹,⁴]dec-8-en-2-yl]hex-5-enoate)

PDB for NP0283574 (methyl (4r,5e)-4-(acetyloxy)-6-[(1s,2r,3r,4r,7s)-7-(acetyloxy)-3-butyl-10-oxotricyclo[5.3.0.0¹,⁴]dec-8-en-2-yl]hex-5-enoate)

3D PDB for NP0283574 (methyl (4r,5e)-4-(acetyloxy)-6-[(1s,2r,3r,4r,7s)-7-(acetyloxy)-3-butyl-10-oxotricyclo[5.3.0.0¹,⁴]dec-8-en-2-yl]hex-5-enoate)

SMILES for NP0283574 (methyl (4r,5e)-4-(acetyloxy)-6-[(1s,2r,3r,4r,7s)-7-(acetyloxy)-3-butyl-10-oxotricyclo[5.3.0.0¹,⁴]dec-8-en-2-yl]hex-5-enoate)

INCHI for NP0283574 (methyl (4r,5e)-4-(acetyloxy)-6-[(1s,2r,3r,4r,7s)-7-(acetyloxy)-3-butyl-10-oxotricyclo[5.3.0.0¹,⁴]dec-8-en-2-yl]hex-5-enoate)

Structure for NP0283574 (methyl (4r,5e)-4-(acetyloxy)-6-[(1s,2r,3r,4r,7s)-7-(acetyloxy)-3-butyl-10-oxotricyclo[5.3.0.0¹,⁴]dec-8-en-2-yl]hex-5-enoate)

3D Structure for NP0283574 (methyl (4r,5e)-4-(acetyloxy)-6-[(1s,2r,3r,4r,7s)-7-(acetyloxy)-3-butyl-10-oxotricyclo[5.3.0.0¹,⁴]dec-8-en-2-yl]hex-5-enoate)