NP-MRD: Showing NP-Card for (2s,5s,10r,13ar)-3a,11,13-tris(acetyloxy)-2,5,8,8-tetramethyl-12-methylidene-4,9-dioxo-10-(pentan-2-yloxy)-1h,2h,3h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl acetate (NP0239504)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 23:07:06 UTC

Updated at

2022-09-06 23:07:06 UTC

NP-MRD ID

NP0239504

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,5s,10r,13ar)-3a,11,13-tris(acetyloxy)-2,5,8,8-tetramethyl-12-methylidene-4,9-dioxo-10-(pentan-2-yloxy)-1h,2h,3h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl acetate

Description

(2S,5S,10R,13aR)-1,11,13-tris(acetyloxy)-2,5,8,8-tetramethyl-12-methylidene-4,9-dioxo-10-(pentan-2-yloxy)-1H,2H,3H,3aH,4H,5H,8H,9H,10H,11H,12H,13H,13aH-cyclopenta[12]annulen-3a-yl acetate belongs to the class of organic compounds known as jatrophane and cyclojatrophane diterpenoids. These are diterpenoids with a structure based on the jatrophane or the 9,13-jatrophane skeleton. Jatrophane can be derived from casbane by 6,10-cyclization and opening of the cyclopropane. Cyclojatrophane diterpenoids are based on the 9,13-cyclization of the jatrophane skeleton yields the 9,13-cyclojatrophane skeleton. (2s,5s,10r,13ar)-3a,11,13-tris(acetyloxy)-2,5,8,8-tetramethyl-12-methylidene-4,9-dioxo-10-(pentan-2-yloxy)-1h,2h,3h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl acetate is found in Euphorbia paralias. Based on a literature review very few articles have been published on (2S,5S,10R,13aR)-1,11,13-tris(acetyloxy)-2,5,8,8-tetramethyl-12-methylidene-4,9-dioxo-10-(pentan-2-yloxy)-1H,2H,3H,3aH,4H,5H,8H,9H,10H,11H,12H,13H,13aH-cyclopenta[12]annulen-3a-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072201072D          

 44 45  0  0  1  0            999 V2000
   -3.8196    3.4573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8196    2.6323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0227    2.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6102    3.1332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0227    3.8477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8477    3.8477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6102    4.5622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4394    1.8354    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7249    2.2479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0104    1.8354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0104    1.0104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2959    2.2479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4185    1.8354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1330    2.2479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2258    1.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4008    1.0385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4394    0.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3675   -0.5802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6175    0.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2362    0.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8196   -0.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6165   -0.3417    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0290   -1.0562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1999    0.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9143   -0.1709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4134    1.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8983    0.3711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7188    0.4573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2037   -0.2101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0543    1.2110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2373    0.9953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5329    1.7656    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.3298    1.9791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8918    2.2847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9349    3.1086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6700    3.4832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3619    3.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7132    4.3070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1999    1.8354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6165    2.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0290    3.1332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6165    3.8477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0290    4.5622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9491    4.3326    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 26 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 39 34  1  6  0  0  0
 26 39  1  0  0  0  0
 39 40  1  0  0  0  0
  2 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  2  0  0  0  0
M  END

     RDKit          3D

 92 93  0  0  0  0  0  0  0  0999 V2000
    0.6325   -0.3053   -2.5106 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0068    0.2387   -1.4743 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8507    0.9080   -0.4607 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4920    1.9842   -1.1726 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4371    3.2834   -0.7611 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1194    4.3566   -1.5426 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8070    3.5629    0.2811 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9692   -0.0851   -0.0806 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1174    0.3920   -0.1868 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2896    0.7489   -0.3868 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5915    2.0816   -1.0586 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2417    0.6935    0.8382 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6872    0.7608    0.4440 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0748   -0.3706   -0.4937 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5849   -0.4525    1.3629 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3499    0.4623    2.0840 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5183   -1.8495    1.8024 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9449   -2.3180    2.2083 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7317   -1.9426    3.0850 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0571   -2.7618    0.7234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1218   -3.1924    0.4245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4480   -2.9529    1.0247 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0026   -4.3614    1.3353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3967   -2.3469    0.0060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6141   -2.9920   -0.9882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9686   -1.0259    0.3197 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1384   -0.8373    1.7403 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9240   -1.6137    2.5322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0336   -1.3592    3.9774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5470   -2.5441    2.0040 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2514   -0.6859   -0.3226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3740    0.8042   -0.1126 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8662    1.5078   -1.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9681    1.2910    0.2628 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6575    2.4722   -0.4227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4151    3.6612    0.2460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0836    4.9354   -0.4617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4861    3.6284    1.5009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0497    0.1272   -0.0550 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4870    0.1483   -1.3959 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8926   -0.8396   -2.3120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5286   -0.5278   -3.5218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9380   -1.5827   -4.4532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7324    0.6917   -3.7733 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1248   -0.8199   -3.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7038   -0.2405   -2.5752 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3205    1.2947    0.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9219    4.8267   -0.9478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3498    5.1209   -1.8521 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5405    3.9650   -2.4808 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7176   -1.0223   -0.6912 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8325    0.0058   -1.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6516    2.0450   -1.3720 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4498    2.9496   -0.4257 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0420    2.1479   -2.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0361   -0.2366    1.4241 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0336    1.5343    1.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2550    0.6287    1.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9539    1.7309    0.0386 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9218   -0.0436   -1.5400 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4010   -1.2206   -0.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1101   -0.6624   -0.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5160   -2.5069    1.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3739   -1.6282    2.9326 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7544   -3.2824    2.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0138   -1.0988    3.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4612   -1.6768    3.9257 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3355   -2.9270    3.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9323   -3.0926    0.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1879   -3.8840   -0.4571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4838   -2.4134    1.9573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5175   -4.3563    2.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7110   -4.6573    0.5431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1645   -5.0731    1.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7356   -0.5173    4.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0338   -1.0922    4.3833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3792   -2.2291    4.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3635   -0.9819   -1.3813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1478   -1.1412    0.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0906    1.0158    0.7055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8469    1.9687   -1.1452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0354    0.7753   -2.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1886    2.2737   -1.7243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9841    1.4036    1.3645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0610    4.7345   -1.5531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1816    5.4238   -0.0769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9325    5.6314   -0.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2233    0.0745    0.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8216    1.1311   -1.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9481   -1.2493   -5.5117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2856   -2.4828   -4.3256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9805   -1.9388   -4.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 12  1  0
 12 10  1  0
 10 11  1  0
 10  9  1  0
  9  8  1  0
  8  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  3  2  1  0
  2  1  2  3
  2 40  1  0
 40 41  1  0
 41 42  1  0
 42 43  1  0
 42 44  2  0
 40 39  1  0
 39 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 36 38  2  0
 34 32  1  0
 32 33  1  0
 32 31  1  0
 31 26  1  0
 26 27  1  1
 27 28  1  0
 28 29  1  0
 28 30  2  0
 26 24  1  0
 24 25  2  0
 24 22  1  0
 22 23  1  0
 22 21  1  0
 21 20  2  0
 20 17  1  0
 17 18  1  0
 17 19  1  0
 17 15  1  0
 15 16  2  0
 15  8  1  0
 26 39  1  0
 14 60  1  0
 14 61  1  0
 14 62  1  0
 13 58  1  0
 13 59  1  0
 12 56  1  0
 12 57  1  0
 10 52  1  6
 11 53  1  0
 11 54  1  0
 11 55  1  0
  8 51  1  6
  3 47  1  1
  6 48  1  0
  6 49  1  0
  6 50  1  0
  1 45  1  0
  1 46  1  0
 40 89  1  6
 43 90  1  0
 43 91  1  0
 43 92  1  0
 39 88  1  1
 34 84  1  1
 37 85  1  0
 37 86  1  0
 37 87  1  0
 32 80  1  1
 33 81  1  0
 33 82  1  0
 33 83  1  0
 31 78  1  0
 31 79  1  0
 29 75  1  0
 29 76  1  0
 29 77  1  0
 22 71  1  1
 23 72  1  0
 23 73  1  0
 23 74  1  0
 21 70  1  0
 20 69  1  0
 18 63  1  0
 18 64  1  0
 18 65  1  0
 19 66  1  0
 19 67  1  0
 19 68  1  0
M  END


  Mrv1652309072201072D          

 44 45  0  0  1  0            999 V2000
   -3.8196    3.4573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8196    2.6323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0227    2.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6102    3.1332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0227    3.8477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8477    3.8477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6102    4.5622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4394    1.8354    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7249    2.2479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0104    1.8354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0104    1.0104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2959    2.2479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4185    1.8354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1330    2.2479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2258    1.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4008    1.0385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4394    0.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3675   -0.5802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6175    0.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2362    0.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8196   -0.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6165   -0.3417    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0290   -1.0562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1999    0.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9143   -0.1709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4134    1.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8983    0.3711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7188    0.4573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2037   -0.2101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0543    1.2110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2373    0.9953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5329    1.7656    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.3298    1.9791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8918    2.2847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9349    3.1086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6700    3.4832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3619    3.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7132    4.3070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1999    1.8354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6165    2.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0290    3.1332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6165    3.8477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0290    4.5622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9491    4.3326    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 26 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 39 34  1  6  0  0  0
 26 39  1  0  0  0  0
 39 40  1  0  0  0  0
  2 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0239504

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC(C)O[C@@H]1C(OC(C)=O)C(=C)C(OC(C)=O)[C@H]2C(OC(C)=O)[C@@H](C)CC2(OC(C)=O)C(=O)[C@@H](C)\C=C\C(C)(C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C33H48O11/c1-12-13-19(4)40-29-28(43-23(8)36)20(5)27(42-22(7)35)25-26(41-21(6)34)18(3)16-33(25,44-24(9)37)30(38)17(2)14-15-32(10,11)31(29)39/h14-15,17-19,25-29H,5,12-13,16H2,1-4,6-11H3/b15-14+/t17-,18-,19?,25+,26?,27?,28?,29+,33?/m0/s1

> <INCHI_KEY>
LSTWTKOOHNOJLH-CXUOALPKSA-N

> <FORMULA>
C33H48O11

> <MOLECULAR_WEIGHT>
620.736

> <EXACT_MASS>
620.319662366

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
92

> <JCHEM_AVERAGE_POLARIZABILITY>
65.59143395643692

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,5S,10R,13aR)-3a,11,13-tris(acetyloxy)-2,5,8,8-tetramethyl-12-methylidene-4,9-dioxo-10-(pentan-2-yloxy)-1H,2H,3H,3aH,4H,5H,8H,9H,10H,11H,12H,13H,13aH-cyclopenta[12]annulen-1-yl acetate

> <JCHEM_LOGP>
4.589415527666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.36854073120319

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.10040929042982

> <JCHEM_PKA_STRONGEST_BASIC>
-4.235058500385025

> <JCHEM_POLAR_SURFACE_AREA>
148.57

> <JCHEM_REFRACTIVITY>
158.5327

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,5S,10R,13aR)-3a,11,13-tris(acetyloxy)-2,5,8,8-tetramethyl-12-methylidene-4,9-dioxo-10-(pentan-2-yloxy)-1H,2H,3H,5H,10H,11H,13H,13aH-cyclopenta[12]annulen-1-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -7.130   6.454   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.130   4.914   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.642   4.515   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -4.872   5.849   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -5.642   7.182   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.182   7.182   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.872   8.516   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -4.553   3.426   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.220   4.196   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.886   3.426   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.886   1.886   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.552   4.196   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.781   3.426   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.115   4.196   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.155   1.939   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.615   1.939   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -4.553   0.451   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.419  -1.083   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.019   0.317   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.041   0.052   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -7.130  -1.036   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -8.617  -0.638   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -9.387  -1.972   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -9.706   0.451   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0     -11.040  -0.319   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0     -10.105   1.939   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0     -11.010   0.693   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0     -12.542   0.854   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -13.447  -0.392   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0     -13.168   2.261   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0     -11.643   1.858   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -12.195   3.296   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -13.682   3.694   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -10.998   4.265   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0     -11.079   5.803   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0     -12.451   6.502   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0     -13.742   5.663   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0     -12.531   8.040   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -9.706   3.426   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -8.617   4.515   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -9.387   5.849   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -8.617   7.182   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -9.387   8.516   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -7.372   8.088   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   40                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    3    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15    8   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   31   39                                             
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   26   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   39                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   34   26   40                                                  
CONECT   40   39    2   41                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   90    0
END

View in JSmol

Synonyms

Value	Source
(2S,5S,10R,13AR)-1,11,13-tris(acetyloxy)-2,5,8,8-tetramethyl-12-methylidene-4,9-dioxo-10-(pentan-2-yloxy)-1H,2H,3H,3ah,4H,5H,8H,9H,10H,11H,12H,13H,13ah-cyclopenta[12]annulen-3a-yl acetic acid	Generator

Chemical Formula

C₃₃H₄₈O₁₁

Average Mass

620.7360 Da

Monoisotopic Mass

620.31966 Da

IUPAC Name

(2S,5S,10R,13aR)-3a,11,13-tris(acetyloxy)-2,5,8,8-tetramethyl-12-methylidene-4,9-dioxo-10-(pentan-2-yloxy)-1H,2H,3H,3aH,4H,5H,8H,9H,10H,11H,12H,13H,13aH-cyclopenta[12]annulen-1-yl acetate

Traditional Name

(2S,5S,10R,13aR)-3a,11,13-tris(acetyloxy)-2,5,8,8-tetramethyl-12-methylidene-4,9-dioxo-10-(pentan-2-yloxy)-1H,2H,3H,5H,10H,11H,13H,13aH-cyclopenta[12]annulen-1-yl acetate

CAS Registry Number

Not Available

SMILES

CCCC(C)O[C@@H]1C(OC(C)=O)C(=C)C(OC(C)=O)[C@H]2C(OC(C)=O)[C@@H](C)CC2(OC(C)=O)C(=O)[C@@H](C)\C=C\C(C)(C)C1=O

InChI Identifier

InChI=1S/C33H48O11/c1-12-13-19(4)40-29-28(43-23(8)36)20(5)27(42-22(7)35)25-26(41-21(6)34)18(3)16-33(25,44-24(9)37)30(38)17(2)14-15-32(10,11)31(29)39/h14-15,17-19,25-29H,5,12-13,16H2,1-4,6-11H3/b15-14+/t17-,18-,19?,25+,26?,27?,28?,29+,33?/m0/s1

InChI Key

LSTWTKOOHNOJLH-CXUOALPKSA-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
Euphorbia paralias	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as jatrophane and cyclojatrophane diterpenoids. These are diterpenoids with a structure based on the jatrophane or the 9,13-jatrophane skeleton. Jatrophane can be derived from casbane by 6,10-cyclization and opening of the cyclopropane. Cyclojatrophane diterpenoids are based on the 9,13-cyclization of the jatrophane skeleton yields the 9,13-cyclojatrophane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Jatrophane and cyclojatrophane diterpenoids

Alternative Parents

Substituents

Jatrophane diterpenoid
Tetracarboxylic acid or derivatives
Alpha-acyloxy ketone
Cyclic ketone
Ketone
Carboxylic acid ester
Ether
Dialkyl ether
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	4.59	ChemAxon
pKa (Strongest Acidic)	15.1	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	148.57 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	158.53 m³·mol⁻¹	ChemAxon
Polarizability	65.59 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	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

162844511

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,5s,10r,13ar)-3a,11,13-tris(acetyloxy)-2,5,8,8-tetramethyl-12-methylidene-4,9-dioxo-10-(pentan-2-yloxy)-1h,2h,3h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl acetate (NP0239504)

MOL for NP0239504 ((2s,5s,10r,13ar)-3a,11,13-tris(acetyloxy)-2,5,8,8-tetramethyl-12-methylidene-4,9-dioxo-10-(pentan-2-yloxy)-1h,2h,3h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl acetate)

3D MOL for NP0239504 ((2s,5s,10r,13ar)-3a,11,13-tris(acetyloxy)-2,5,8,8-tetramethyl-12-methylidene-4,9-dioxo-10-(pentan-2-yloxy)-1h,2h,3h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl acetate)

3D SDF for NP0239504 ((2s,5s,10r,13ar)-3a,11,13-tris(acetyloxy)-2,5,8,8-tetramethyl-12-methylidene-4,9-dioxo-10-(pentan-2-yloxy)-1h,2h,3h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl acetate)

3D-SDF for NP0239504 ((2s,5s,10r,13ar)-3a,11,13-tris(acetyloxy)-2,5,8,8-tetramethyl-12-methylidene-4,9-dioxo-10-(pentan-2-yloxy)-1h,2h,3h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl acetate)

PDB for NP0239504 ((2s,5s,10r,13ar)-3a,11,13-tris(acetyloxy)-2,5,8,8-tetramethyl-12-methylidene-4,9-dioxo-10-(pentan-2-yloxy)-1h,2h,3h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl acetate)

3D PDB for NP0239504 ((2s,5s,10r,13ar)-3a,11,13-tris(acetyloxy)-2,5,8,8-tetramethyl-12-methylidene-4,9-dioxo-10-(pentan-2-yloxy)-1h,2h,3h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl acetate)

SMILES for NP0239504 ((2s,5s,10r,13ar)-3a,11,13-tris(acetyloxy)-2,5,8,8-tetramethyl-12-methylidene-4,9-dioxo-10-(pentan-2-yloxy)-1h,2h,3h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl acetate)

INCHI for NP0239504 ((2s,5s,10r,13ar)-3a,11,13-tris(acetyloxy)-2,5,8,8-tetramethyl-12-methylidene-4,9-dioxo-10-(pentan-2-yloxy)-1h,2h,3h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl acetate)

Structure for NP0239504 ((2s,5s,10r,13ar)-3a,11,13-tris(acetyloxy)-2,5,8,8-tetramethyl-12-methylidene-4,9-dioxo-10-(pentan-2-yloxy)-1h,2h,3h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl acetate)

3D Structure for NP0239504 ((2s,5s,10r,13ar)-3a,11,13-tris(acetyloxy)-2,5,8,8-tetramethyl-12-methylidene-4,9-dioxo-10-(pentan-2-yloxy)-1h,2h,3h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl acetate)