NP-MRD: Showing NP-Card for (2s)-3-[(1r,2s,3s,4s,5s)-2-(acetyloxy)-5-chloro-4-hydroxy-4-methyl-3-{[(2z)-2-methylbut-2-enoyl]oxy}cyclohexyl]-1-[(2s)-3,3-dimethyloxiran-2-yl]but-3-en-2-yl (2z)-2-methylbut-2-enoate (NP0320340)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-11 21:56:12 UTC

Updated at

2022-09-11 21:56:12 UTC

NP-MRD ID

NP0320340

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-3-[(1r,2s,3s,4s,5s)-2-(acetyloxy)-5-chloro-4-hydroxy-4-methyl-3-{[(2z)-2-methylbut-2-enoyl]oxy}cyclohexyl]-1-[(2s)-3,3-dimethyloxiran-2-yl]but-3-en-2-yl (2z)-2-methylbut-2-enoate

Description

(2S)-3-[(1R,2S,3S,4S,5S)-2-(acetyloxy)-5-chloro-4-hydroxy-4-methyl-3-{[(2Z)-2-methylbut-2-enoyl]oxy}cyclohexyl]-1-[(2S)-3,3-dimethyloxiran-2-yl]but-3-en-2-yl (2Z)-2-methylbut-2-enoate belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review very few articles have been published on (2S)-3-[(1R,2S,3S,4S,5S)-2-(acetyloxy)-5-chloro-4-hydroxy-4-methyl-3-{[(2Z)-2-methylbut-2-enoyl]oxy}cyclohexyl]-1-[(2S)-3,3-dimethyloxiran-2-yl]but-3-en-2-yl (2Z)-2-methylbut-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112223562D          

 36 37  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5395   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6002   -4.2778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -4.2778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1401   -3.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6704   -2.3317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 O   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
  3  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  3 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 17  2  1  1  0  0  0
 17 18  1  0  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  6  0  0  0
 21 23  1  1  0  0  0
 21 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 30 31  1  0  0  0  0
 24 32  1  0  0  0  0
 17 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
M  END

     RDKit          3D

 75 76  0  0  0  0  0  0  0  0999 V2000
    0.1365   -1.2989    0.8982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4888   -0.7649   -0.1227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9612   -0.6246   -0.0090 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6437   -1.3958   -1.1313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1417   -1.3880   -0.9523 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4940   -2.0176    0.3354 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9084   -2.5740   -0.8830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4016   -2.5220   -1.0889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2731   -3.8869   -1.3102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3763    0.7150    0.0301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1124    1.2167    1.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4004    0.4191    2.0120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5272    2.6110    1.0909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1510    3.4808   -0.0348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2339    3.1358    2.0769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6221    2.2973    3.2074 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2113   -0.3285   -1.3005 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1335    1.0279   -1.8524 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6278    2.1307   -1.2093 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2222    3.3245   -2.4021 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7174    1.7575   -0.2993 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6963    2.9519   -0.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2860    1.6981    1.0500 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5187    0.5229   -0.6519 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2294    0.2615    0.4924 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5648    0.4210    0.7412 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1427    0.8676   -0.2544 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2553    0.1296    1.9621 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5648   -0.4089    3.1654 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5577    0.3450    2.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3544    0.8794    0.8963 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7147   -0.4776   -1.3318 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1055   -1.8246   -1.1246 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5920   -2.6797   -2.0877 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9827   -4.0928   -1.7823 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6872   -2.1956   -3.2443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3998   -1.6344    1.8115 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2114   -1.4757    0.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3458   -1.1085    0.9289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4196   -0.9545   -2.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2392   -2.4267   -1.1489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6098   -0.3923   -1.0447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5784   -2.2854   -2.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8700   -1.7621   -0.4209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8015   -3.5302   -0.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0174   -4.6800   -1.4909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7519   -3.7209   -2.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5046   -4.1915   -0.5591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0980    2.8493   -0.9472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9213    4.2545   -0.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1405    3.9093    0.2180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5389    4.1872    2.0712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3082    1.4826    2.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2170    2.8979    3.9234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7722    1.8845    3.7886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1358   -1.0470   -2.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2261    1.2068   -1.9354 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2147    1.0121   -2.9321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1288    2.7114   -0.5967 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3904    2.8706   -1.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2650    2.9665    0.6686 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1299    3.8974   -0.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6895    2.4525    1.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3107    0.9153   -1.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0963   -0.0150    4.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7169   -1.5078    3.1575 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4916   -0.1193    3.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0559    0.1134    2.9737 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4087    0.9786    1.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0408    1.9003    0.5894 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3536    0.2148    0.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9195   -0.3532   -2.4563 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9475   -4.6724   -2.7133 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4092   -4.5013   -0.9501 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0753   -4.0396   -1.5007 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 13  2  0
 13 14  1  0
 13 11  1  0
 11 12  2  0
 11 10  1  0
 10  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  3  2  1  0
  2  1  2  3
  2 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  1
 21 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
 28 30  2  0
 30 31  1  0
 24 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 34 36  2  0
  7  5  1  0
 32 17  1  0
 16 53  1  0
 16 54  1  0
 16 55  1  0
 15 52  1  0
 14 49  1  0
 14 50  1  0
 14 51  1  0
  3 39  1  1
  4 40  1  0
  4 41  1  0
  5 42  1  1
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
  9 47  1  0
  9 48  1  0
  1 37  1  0
  1 38  1  0
 17 56  1  6
 18 57  1  0
 18 58  1  0
 19 59  1  1
 22 60  1  0
 22 61  1  0
 22 62  1  0
 23 63  1  0
 24 64  1  6
 29 65  1  0
 29 66  1  0
 29 67  1  0
 30 68  1  0
 31 69  1  0
 31 70  1  0
 31 71  1  0
 32 72  1  6
 35 73  1  0
 35 74  1  0
 35 75  1  0
M  END


  Mrv1652309112223562D          

 36 37  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5395   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6002   -4.2778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -4.2778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1401   -3.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6704   -2.3317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 O   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
  3  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  3 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 17  2  1  1  0  0  0
 17 18  1  0  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  6  0  0  0
 21 23  1  1  0  0  0
 21 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 30 31  1  0  0  0  0
 24 32  1  0  0  0  0
 17 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0320340

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(\C)C(=O)O[C@@H](C[C@@H]1OC1(C)C)C(=C)[C@H]1C[C@H](Cl)[C@@](C)(O)[C@@H](OC(=O)C(\C)=C/C)[C@H]1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H39ClO8/c1-10-14(3)24(30)34-19(13-21-26(7,8)36-21)16(5)18-12-20(28)27(9,32)23(22(18)33-17(6)29)35-25(31)15(4)11-2/h10-11,18-23,32H,5,12-13H2,1-4,6-9H3/b14-10-,15-11-/t18-,19+,20+,21+,22+,23+,27-/m1/s1

> <INCHI_KEY>
XOBNWEYRIDTWMJ-DXIGDJAYSA-N

> <FORMULA>
C27H39ClO8

> <MOLECULAR_WEIGHT>
527.05

> <EXACT_MASS>
526.2333459

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
55.35384552229476

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-3-[(1R,2S,3S,4S,5S)-2-(acetyloxy)-5-chloro-4-hydroxy-4-methyl-3-{[(2Z)-2-methylbut-2-enoyl]oxy}cyclohexyl]-1-[(2S)-3,3-dimethyloxiran-2-yl]but-3-en-2-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_LOGP>
4.684439786333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.00403708232043

> <JCHEM_PKA_STRONGEST_BASIC>
-3.671834180193044

> <JCHEM_POLAR_SURFACE_AREA>
111.66000000000003

> <JCHEM_REFRACTIVITY>
135.371

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-3-[(1R,2S,3S,4S,5S)-2-(acetyloxy)-5-chloro-4-hydroxy-4-methyl-3-{[(2Z)-2-methylbut-2-enoyl]oxy}cyclohexyl]-1-[(2S)-3,3-dimethyloxiran-2-yl]but-3-en-2-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.874  -5.390   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.104  -6.724   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.987  -7.985   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.220  -7.985   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   20 Cl   UNK     0      -4.001  -6.930   0.000  0.00  0.00          Cl+0
HETATM   21  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.861  -6.067   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -6.851  -4.353   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    7                                                       
CONECT    7    6    5    8    9                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    3   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15                                                            
CONECT   17    2   18   32                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21   25   32                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30                                                            
CONECT   32   24   17   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   74    0
END

View in JSmol

Synonyms

Value	Source
(2S)-3-[(1R,2S,3S,4S,5S)-2-(Acetyloxy)-5-chloro-4-hydroxy-4-methyl-3-{[(2Z)-2-methylbut-2-enoyl]oxy}cyclohexyl]-1-[(2S)-3,3-dimethyloxiran-2-yl]but-3-en-2-yl (2Z)-2-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₇H₃₉ClO₈

Average Mass

527.0500 Da

Monoisotopic Mass

526.23335 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C\C=C(\C)C(=O)O[C@@H](C[C@@H]1OC1(C)C)C(=C)[C@H]1C[C@H](Cl)[C@@](C)(O)[C@@H](OC(=O)C(\C)=C/C)[C@H]1OC(C)=O

InChI Identifier

InChI=1S/C27H39ClO8/c1-10-14(3)24(30)34-19(13-21-26(7,8)36-21)16(5)18-12-20(28)27(9,32)23(22(18)33-17(6)29)35-25(31)15(4)11-2/h10-11,18-23,32H,5,12-13H2,1-4,6-9H3/b14-10-,15-11-/t18-,19+,20+,21+,22+,23+,27-/m1/s1

InChI Key

XOBNWEYRIDTWMJ-DXIGDJAYSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Bisabolane sesquiterpenoid
Tricarboxylic acid or derivatives
Cyclohexyl halide
Cyclohexanol
Fatty acid ester
Cyclitol or derivatives
Fatty acyl
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Carboxylic acid ester
Chlorohydrin
Halohydrin
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Ether
Oxirane
Dialkyl ether
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Alkyl chloride
Carbonyl group
Organic oxygen compound
Alkyl halide
Organochloride
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	4.68	ChemAxon
pKa (Strongest Acidic)	13	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Hydrogen Acceptor Count	5	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

163033908

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-3-[(1r,2s,3s,4s,5s)-2-(acetyloxy)-5-chloro-4-hydroxy-4-methyl-3-{[(2z)-2-methylbut-2-enoyl]oxy}cyclohexyl]-1-[(2s)-3,3-dimethyloxiran-2-yl]but-3-en-2-yl (2z)-2-methylbut-2-enoate (NP0320340)

MOL for NP0320340 ((2s)-3-[(1r,2s,3s,4s,5s)-2-(acetyloxy)-5-chloro-4-hydroxy-4-methyl-3-{[(2z)-2-methylbut-2-enoyl]oxy}cyclohexyl]-1-[(2s)-3,3-dimethyloxiran-2-yl]but-3-en-2-yl (2z)-2-methylbut-2-enoate)

3D MOL for NP0320340 ((2s)-3-[(1r,2s,3s,4s,5s)-2-(acetyloxy)-5-chloro-4-hydroxy-4-methyl-3-{[(2z)-2-methylbut-2-enoyl]oxy}cyclohexyl]-1-[(2s)-3,3-dimethyloxiran-2-yl]but-3-en-2-yl (2z)-2-methylbut-2-enoate)

3D SDF for NP0320340 ((2s)-3-[(1r,2s,3s,4s,5s)-2-(acetyloxy)-5-chloro-4-hydroxy-4-methyl-3-{[(2z)-2-methylbut-2-enoyl]oxy}cyclohexyl]-1-[(2s)-3,3-dimethyloxiran-2-yl]but-3-en-2-yl (2z)-2-methylbut-2-enoate)

3D-SDF for NP0320340 ((2s)-3-[(1r,2s,3s,4s,5s)-2-(acetyloxy)-5-chloro-4-hydroxy-4-methyl-3-{[(2z)-2-methylbut-2-enoyl]oxy}cyclohexyl]-1-[(2s)-3,3-dimethyloxiran-2-yl]but-3-en-2-yl (2z)-2-methylbut-2-enoate)

PDB for NP0320340 ((2s)-3-[(1r,2s,3s,4s,5s)-2-(acetyloxy)-5-chloro-4-hydroxy-4-methyl-3-{[(2z)-2-methylbut-2-enoyl]oxy}cyclohexyl]-1-[(2s)-3,3-dimethyloxiran-2-yl]but-3-en-2-yl (2z)-2-methylbut-2-enoate)

3D PDB for NP0320340 ((2s)-3-[(1r,2s,3s,4s,5s)-2-(acetyloxy)-5-chloro-4-hydroxy-4-methyl-3-{[(2z)-2-methylbut-2-enoyl]oxy}cyclohexyl]-1-[(2s)-3,3-dimethyloxiran-2-yl]but-3-en-2-yl (2z)-2-methylbut-2-enoate)

SMILES for NP0320340 ((2s)-3-[(1r,2s,3s,4s,5s)-2-(acetyloxy)-5-chloro-4-hydroxy-4-methyl-3-{[(2z)-2-methylbut-2-enoyl]oxy}cyclohexyl]-1-[(2s)-3,3-dimethyloxiran-2-yl]but-3-en-2-yl (2z)-2-methylbut-2-enoate)

INCHI for NP0320340 ((2s)-3-[(1r,2s,3s,4s,5s)-2-(acetyloxy)-5-chloro-4-hydroxy-4-methyl-3-{[(2z)-2-methylbut-2-enoyl]oxy}cyclohexyl]-1-[(2s)-3,3-dimethyloxiran-2-yl]but-3-en-2-yl (2z)-2-methylbut-2-enoate)

Structure for NP0320340 ((2s)-3-[(1r,2s,3s,4s,5s)-2-(acetyloxy)-5-chloro-4-hydroxy-4-methyl-3-{[(2z)-2-methylbut-2-enoyl]oxy}cyclohexyl]-1-[(2s)-3,3-dimethyloxiran-2-yl]but-3-en-2-yl (2z)-2-methylbut-2-enoate)

3D Structure for NP0320340 ((2s)-3-[(1r,2s,3s,4s,5s)-2-(acetyloxy)-5-chloro-4-hydroxy-4-methyl-3-{[(2z)-2-methylbut-2-enoyl]oxy}cyclohexyl]-1-[(2s)-3,3-dimethyloxiran-2-yl]but-3-en-2-yl (2z)-2-methylbut-2-enoate)