NP-MRD: Showing NP-Card for methyl (4r)-4-(acetyloxy)-4-[(1r,2r,5s)-5-(acetyloxy)-6-[(2z)-oct-2-en-1-yl]-8-oxobicyclo[3.2.1]octa-3,6-dien-2-yl]butanoate (NP0147720)

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Record Information

Version

2.0

Created at

2022-09-02 03:22:29 UTC

Updated at

2022-09-02 03:22:29 UTC

NP-MRD ID

NP0147720

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (4r)-4-(acetyloxy)-4-[(1r,2r,5s)-5-(acetyloxy)-6-[(2z)-oct-2-en-1-yl]-8-oxobicyclo[3.2.1]octa-3,6-dien-2-yl]butanoate

Description

Clavubicyclone belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. methyl (4r)-4-(acetyloxy)-4-[(1r,2r,5s)-5-(acetyloxy)-6-[(2z)-oct-2-en-1-yl]-8-oxobicyclo[3.2.1]octa-3,6-dien-2-yl]butanoate is found in Clavularia viridis. methyl (4r)-4-(acetyloxy)-4-[(1r,2r,5s)-5-(acetyloxy)-6-[(2z)-oct-2-en-1-yl]-8-oxobicyclo[3.2.1]octa-3,6-dien-2-yl]butanoate was first documented in 2006 (PMID: 17020327). Based on a literature review very few articles have been published on Clavubicyclone.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022205222D          

 32 33  0  0  1  0            999 V2000
   12.5406   -5.6300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6022   -4.8073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9206   -4.3425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9822   -3.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3006   -3.0551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3622   -2.2324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6806   -1.7677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9373   -2.1256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2557   -1.6609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3786   -0.8451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8175   -0.2403    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.4502   -1.1223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7123   -0.7533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5412   -2.0734    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6028   -2.8961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9212   -3.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9828   -4.1835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1779   -3.0028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7732   -1.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5300   -0.9836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9948   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5823    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7573    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3448    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5198    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1073    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1073    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2823    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9948    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5823    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7573    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9948    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 14 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 11 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 22 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
M  END

     RDKit          3D

 66 67  0  0  0  0  0  0  0  0999 V2000
   -8.3166    0.8637    1.6453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7915    0.8198    0.2326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4841    0.0604    0.2215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4490    0.7339    1.1133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1850   -0.1382    1.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1171    0.4243    1.8314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9615    0.8262    1.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5983    0.7617   -0.0417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3856   -0.1007   -0.2774 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3548   -0.7746    0.5955 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4232   -1.5516   -0.1384 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7620   -1.6639   -1.4707 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7669   -2.6577   -2.1530 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1709   -0.3109   -1.6506 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8469   -0.2358   -2.5660 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7283   -0.3779   -3.9358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9307   -0.2665   -4.7655 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4296   -0.5965   -4.3707 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2717    0.6336   -1.8088 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2869    0.5920   -0.9661 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6576   -0.7044   -0.3469 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4769   -0.5688    0.8979 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7051    0.2814    0.6758 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6143   -0.3013   -0.3865 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8102    0.5802   -0.5611 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9885    1.6315    0.0955 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7523    0.2030   -1.4939 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9299    0.9394   -1.7636 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7691   -0.0377    1.9836 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6241   -0.7485    3.1790 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9006   -0.2610    4.3546 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1603   -1.8846    3.2276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9256    1.7488    2.1854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0843   -0.0824    2.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4347    0.9747    1.5683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5121    0.2822   -0.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5994    1.8366   -0.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6363   -0.9856    0.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1138    0.0338   -0.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2422    1.7377    0.7182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8355    0.7206    2.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4901   -1.1470    1.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9481   -0.3472   -0.0276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3244    0.5053    2.9221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1962    1.2439    2.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3704    0.4359   -0.7481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2776    1.7778   -0.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1694   -0.7321    1.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6248   -2.5084    0.3277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3886    0.7434   -4.5553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7429   -0.2983   -5.8432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6972   -1.0111   -4.4360 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2777    1.3663   -2.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8729    1.4904   -0.7059 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2416   -1.2463   -1.1518 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8782   -1.5987    1.1312 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2957    0.2263    1.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4996    1.3416    0.5136 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0944   -0.4367   -1.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9999   -1.2968   -0.0882 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7888    1.6360   -2.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7749    0.2435   -2.0128 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1955    1.4983   -0.8518 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4600   -0.4544    5.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9526   -0.8665    4.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6332    0.7933    4.3381 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  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 21  1  0
 21 20  1  0
 20 19  2  0
 19 14  1  0
 14 15  1  6
 15 16  1  0
 16 17  1  0
 16 18  2  0
 14 12  1  0
 12 13  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 22 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
 14  9  1  0
 12 11  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  0
  5 43  1  0
  6 44  1  0
  7 45  1  0
  8 46  1  0
  8 47  1  0
 10 48  1  0
 11 49  1  1
 21 55  1  6
 20 54  1  0
 19 53  1  0
 17 50  1  0
 17 51  1  0
 17 52  1  0
 22 56  1  1
 23 57  1  0
 23 58  1  0
 24 59  1  0
 24 60  1  0
 28 61  1  0
 28 62  1  0
 28 63  1  0
 31 64  1  0
 31 65  1  0
 31 66  1  0
M  END


  Mrv1652309022205222D          

 32 33  0  0  1  0            999 V2000
   12.5406   -5.6300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6022   -4.8073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9206   -4.3425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9822   -3.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3006   -3.0551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3622   -2.2324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6806   -1.7677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9373   -2.1256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2557   -1.6609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3786   -0.8451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8175   -0.2403    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.4502   -1.1223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7123   -0.7533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5412   -2.0734    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6028   -2.8961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9212   -3.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9828   -4.1835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1779   -3.0028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7732   -1.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5300   -0.9836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9948   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5823    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7573    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3448    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5198    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1073    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1073    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2823    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9948    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5823    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7573    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9948    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 14 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 11 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 22 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0147720

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC\C=C/CC1=C[C@@H]2[C@@H](C=C[C@@]1(OC(C)=O)C2=O)[C@@H](CCC(=O)OC)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H34O7/c1-5-6-7-8-9-10-11-19-16-21-20(14-15-25(19,24(21)29)32-18(3)27)22(31-17(2)26)12-13-23(28)30-4/h9-10,14-16,20-22H,5-8,11-13H2,1-4H3/b10-9-/t20-,21-,22-,25+/m1/s1

> <INCHI_KEY>
YIWFJLGLYGKPCC-WGXSZPDRSA-N

> <FORMULA>
C25H34O7

> <MOLECULAR_WEIGHT>
446.54

> <EXACT_MASS>
446.230453435

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
49.154298064280795

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (4R)-4-(acetyloxy)-4-[(1R,2R,5S)-5-(acetyloxy)-6-[(2Z)-oct-2-en-1-yl]-8-oxobicyclo[3.2.1]octa-3,6-dien-2-yl]butanoate

> <ALOGPS_LOGP>
4.07

> <JCHEM_LOGP>
3.808363618333332

> <ALOGPS_LOGS>
-5.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.831574829821587

> <JCHEM_PKA_STRONGEST_BASIC>
-6.542925278270823

> <JCHEM_POLAR_SURFACE_AREA>
95.97

> <JCHEM_REFRACTIVITY>
121.36059999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.04e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (4R)-4-(acetyloxy)-4-[(1R,2R,5S)-5-(acetyloxy)-6-[(2Z)-oct-2-en-1-yl]-8-oxobicyclo[3.2.1]octa-3,6-dien-2-yl]butanoate

> <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      23.409 -10.509   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      23.524  -8.974   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      22.252  -8.106   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      22.367  -6.570   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.094  -5.703   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      21.210  -4.167   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      19.937  -3.300   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.550  -3.968   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.277  -3.100   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.507  -1.577   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.459  -0.449   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.774  -2.095   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      14.396  -1.406   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      15.944  -3.870   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      16.059  -5.406   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      14.786  -6.274   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.901  -7.809   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      13.399  -5.605   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      14.510  -3.308   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.056  -1.836   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.924  -0.564   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.154   0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.614   0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.844   2.104   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.304   2.104   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.534   0.770   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       9.534   3.437   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.994   3.437   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      14.924   2.104   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      14.154   3.437   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.614   3.437   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      14.924   4.771   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   21                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    9   15   19                                             
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   14   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   11   22                                                  
CONECT   22   21   23   29                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27                                                            
CONECT   29   22   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   66    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)-4-(acetyloxy)-4-[(1R,2R,5S)-5-(acetyloxy)-6-[(2Z)-oct-2-en-1-yl]-8-oxobicyclo[3.2.1]octa-3,6-dien-2-yl]butanoate

Traditional Name

methyl (4R)-4-(acetyloxy)-4-[(1R,2R,5S)-5-(acetyloxy)-6-[(2Z)-oct-2-en-1-yl]-8-oxobicyclo[3.2.1]octa-3,6-dien-2-yl]butanoate

CAS Registry Number

Not Available

SMILES

CCCCC\C=C/CC1=C[C@@H]2[C@@H](C=C[C@@]1(OC(C)=O)C2=O)[C@@H](CCC(=O)OC)OC(C)=O

InChI Identifier

InChI=1S/C25H34O7/c1-5-6-7-8-9-10-11-19-16-21-20(14-15-25(19,24(21)29)32-18(3)27)22(31-17(2)26)12-13-23(28)30-4/h9-10,14-16,20-22H,5-8,11-13H2,1-4H3/b10-9-/t20-,21-,22-,25+/m1/s1

InChI Key

YIWFJLGLYGKPCC-WGXSZPDRSA-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 prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Prostaglandins and related compounds

Alternative Parents

Substituents

Prostaglandin skeleton
Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acid methyl ester
Alpha-acyloxy ketone
Cyclohexenone
Methyl ester
Ketone
Carboxylic acid ester
Carboxylic acid derivative
Organic oxide
Organic oxygen compound
Organooxygen 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	4.07	ALOGPS
logP	3.81	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	12.83	ChemAxon
pKa (Strongest Basic)	-6.5	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	15	ChemAxon
Refractivity	121.36 m³·mol⁻¹	ChemAxon
Polarizability	49.15 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

10195717

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21581827

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ito H, Takeguchi S, Kawagishi T, Iguchi K: Total synthesis of (+/-)-clavubicyclone. Org Lett. 2006 Oct 12;8(21):4883-5. doi: 10.1021/ol061947u. [PubMed:17020327 ]
LOTUS database [Link]

Showing NP-Card for methyl (4r)-4-(acetyloxy)-4-[(1r,2r,5s)-5-(acetyloxy)-6-[(2z)-oct-2-en-1-yl]-8-oxobicyclo[3.2.1]octa-3,6-dien-2-yl]butanoate (NP0147720)

MOL for NP0147720 (methyl (4r)-4-(acetyloxy)-4-[(1r,2r,5s)-5-(acetyloxy)-6-[(2z)-oct-2-en-1-yl]-8-oxobicyclo[3.2.1]octa-3,6-dien-2-yl]butanoate)

3D MOL for NP0147720 (methyl (4r)-4-(acetyloxy)-4-[(1r,2r,5s)-5-(acetyloxy)-6-[(2z)-oct-2-en-1-yl]-8-oxobicyclo[3.2.1]octa-3,6-dien-2-yl]butanoate)

3D SDF for NP0147720 (methyl (4r)-4-(acetyloxy)-4-[(1r,2r,5s)-5-(acetyloxy)-6-[(2z)-oct-2-en-1-yl]-8-oxobicyclo[3.2.1]octa-3,6-dien-2-yl]butanoate)

3D-SDF for NP0147720 (methyl (4r)-4-(acetyloxy)-4-[(1r,2r,5s)-5-(acetyloxy)-6-[(2z)-oct-2-en-1-yl]-8-oxobicyclo[3.2.1]octa-3,6-dien-2-yl]butanoate)

PDB for NP0147720 (methyl (4r)-4-(acetyloxy)-4-[(1r,2r,5s)-5-(acetyloxy)-6-[(2z)-oct-2-en-1-yl]-8-oxobicyclo[3.2.1]octa-3,6-dien-2-yl]butanoate)

3D PDB for NP0147720 (methyl (4r)-4-(acetyloxy)-4-[(1r,2r,5s)-5-(acetyloxy)-6-[(2z)-oct-2-en-1-yl]-8-oxobicyclo[3.2.1]octa-3,6-dien-2-yl]butanoate)

SMILES for NP0147720 (methyl (4r)-4-(acetyloxy)-4-[(1r,2r,5s)-5-(acetyloxy)-6-[(2z)-oct-2-en-1-yl]-8-oxobicyclo[3.2.1]octa-3,6-dien-2-yl]butanoate)

INCHI for NP0147720 (methyl (4r)-4-(acetyloxy)-4-[(1r,2r,5s)-5-(acetyloxy)-6-[(2z)-oct-2-en-1-yl]-8-oxobicyclo[3.2.1]octa-3,6-dien-2-yl]butanoate)

Structure for NP0147720 (methyl (4r)-4-(acetyloxy)-4-[(1r,2r,5s)-5-(acetyloxy)-6-[(2z)-oct-2-en-1-yl]-8-oxobicyclo[3.2.1]octa-3,6-dien-2-yl]butanoate)

3D Structure for NP0147720 (methyl (4r)-4-(acetyloxy)-4-[(1r,2r,5s)-5-(acetyloxy)-6-[(2z)-oct-2-en-1-yl]-8-oxobicyclo[3.2.1]octa-3,6-dien-2-yl]butanoate)