NP-MRD: Showing NP-Card for (1s,2r,4r,5r,7r,8e,10s,11s,12r)-10-(acetyloxy)-11-[(2r,3r)-2,3-dimethyloxirane-2-carbonyloxy]-4-methyl-13-methylidene-14-oxo-3,6,15-trioxatetracyclo[10.3.0.0²,⁴.0⁵,⁷]pentadec-8-ene-9-carboxylic acid (NP0205976)

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Record Information

Version

2.0

Created at

2022-09-05 02:02:50 UTC

Updated at

2022-09-05 02:02:50 UTC

NP-MRD ID

NP0205976

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,4r,5r,7r,8e,10s,11s,12r)-10-(acetyloxy)-11-[(2r,3r)-2,3-dimethyloxirane-2-carbonyloxy]-4-methyl-13-methylidene-14-oxo-3,6,15-trioxatetracyclo[10.3.0.0²,⁴.0⁵,⁷]pentadec-8-ene-9-carboxylic acid

Description

Leucanthin B belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. (1s,2r,4r,5r,7r,8e,10s,11s,12r)-10-(acetyloxy)-11-[(2r,3r)-2,3-dimethyloxirane-2-carbonyloxy]-4-methyl-13-methylidene-14-oxo-3,6,15-trioxatetracyclo[10.3.0.0²,⁴.0⁵,⁷]pentadec-8-ene-9-carboxylic acid is found in Melampodium leucanthum. Based on a literature review very few articles have been published on leucanthin B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052204022D          

 33 37  0  0  1  0            999 V2000
   -1.0743    0.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6110   -0.0868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8909   -0.8628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6833   -1.0925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2393   -1.3689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4433   -0.9055    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2136   -0.1132    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4935    0.6629    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1581    1.1689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9221    0.8577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6494    0.4682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5737    1.3637    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1885    2.0932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1852    0.8099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3590    1.6163    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9128    2.2278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1761    1.1262    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9464    1.9186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1454    2.1158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4260    1.5207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0843    2.9082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0007    1.0998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2806    1.8759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0927    2.0215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7485    2.5063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6523    0.5938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8820   -0.1986    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4141   -0.8290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6021   -0.9747    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9195   -1.4380    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5146   -2.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4843   -2.1389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0949   -1.4116    0.0000 C   0  0  2  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  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  2  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12 10  1  6  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  6  0  0  0
  8 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 22 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 29 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 33 32  1  6  0  0  0
  6 33  1  0  0  0  0
 30 33  1  0  0  0  0
M  END

     RDKit          3D

 57 61  0  0  0  0  0  0  0  0999 V2000
    0.7406    0.6301    3.1147 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0409   -0.3953    2.6668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8061   -1.2183    3.5409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9671   -1.1396    4.7915 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4543   -2.1706    2.7250 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5370   -1.5077    1.4472 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1283   -0.9994    1.3492 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2040   -0.1803    0.1625 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5321    0.2701    0.3433 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5642   -0.2062   -0.4438 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2713   -1.0560   -1.3223 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9689    0.2105   -0.3237 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2457    1.2263    0.7448 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5399    0.5677   -1.5735 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0448   -0.5552   -0.8986 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8262   -1.8473   -1.6079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7655    0.8901   -0.1886 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1997    2.1899   -0.1651 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5976    3.2005    0.6660 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0061    4.5567    0.6775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5250    2.9684    1.4635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4864    0.6509   -1.4838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7600    0.7027   -2.7483 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4771    0.9399   -2.8267 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4047    0.4901   -3.9562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7744    0.3962   -1.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5717    0.3366   -0.3191 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8894   -0.3005   -0.5451 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8653   -0.8983    0.2467 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1400   -2.0897   -0.2835 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5658   -2.6062   -1.6178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0656   -3.2381    0.6768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9501   -2.4135    0.3429 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3674    1.2372    2.4592 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7426    0.9373    4.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2669   -0.6702    1.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5299   -1.9171    1.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2209   -0.9086   -0.6983 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9793    2.2462    0.3406 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6223    1.0784    1.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3323    1.2750    0.9699 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0845   -0.3695   -0.5039 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7703   -2.4449   -1.6537 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4915   -1.7192   -2.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1048   -2.5073   -1.0477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5622    0.9134    0.5945 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0646    4.5189    0.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0458    4.9122    1.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5368    5.2787    0.0503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5953    1.2056   -4.6298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2395    0.2338   -2.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6774    1.3285    0.1735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2303   -0.9827    1.2995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9531   -2.1459   -2.4226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5742   -3.6929   -1.7183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6185   -2.2569   -1.7969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1094   -2.9542   -0.1468 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 14  1  0
 14 12  1  0
 12 13  1  0
 12 10  1  6
 10 11  2  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  6 33  1  0
 33 32  1  0
 32 30  1  0
 30 31  1  6
 30 29  1  0
 29 28  1  0
 28 27  1  0
 27 26  1  0
 26 22  2  0
 22 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 22 23  1  0
 23 25  1  0
 23 24  2  0
 12 15  1  0
 17  8  1  0
  2  7  1  0
 30 33  1  0
 27 29  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
 15 42  1  1
 13 39  1  0
 13 40  1  0
 13 41  1  0
  8 38  1  6
  7 37  1  1
  6 36  1  1
  1 34  1  0
  1 35  1  0
 33 57  1  6
 31 54  1  0
 31 55  1  0
 31 56  1  0
 29 53  1  1
 27 52  1  1
 26 51  1  0
 17 46  1  1
 20 47  1  0
 20 48  1  0
 20 49  1  0
 25 50  1  0
M  END


  Mrv1652309052204022D          

 33 37  0  0  1  0            999 V2000
   -1.0743    0.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6110   -0.0868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8909   -0.8628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6833   -1.0925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2393   -1.3689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4433   -0.9055    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2136   -0.1132    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4935    0.6629    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1581    1.1689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9221    0.8577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6494    0.4682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5737    1.3637    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1885    2.0932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1852    0.8099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3590    1.6163    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9128    2.2278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1761    1.1262    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9464    1.9186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1454    2.1158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4260    1.5207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0843    2.9082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0007    1.0998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2806    1.8759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0927    2.0215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7485    2.5063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6523    0.5938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8820   -0.1986    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4141   -0.8290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6021   -0.9747    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9195   -1.4380    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5146   -2.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4843   -2.1389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0949   -1.4116    0.0000 C   0  0  2  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  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  2  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12 10  1  6  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  6  0  0  0
  8 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 17 22  1  0  0  0  0
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 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 22 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 29 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 33 32  1  6  0  0  0
  6 33  1  0  0  0  0
 30 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0205976

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H24O11/c1-7-12-14(31-20(27)21(4)8(2)32-21)13(28-9(3)23)10(18(24)25)6-11-16(29-11)22(5)17(33-22)15(12)30-19(7)26/h6,8,11-17H,1H2,2-5H3,(H,24,25)/b10-6+/t8-,11-,12-,13+,14+,15+,16-,17-,21-,22+/m1/s1

> <INCHI_KEY>
YOARICMECKZMHY-XIMYPQPTSA-N

> <FORMULA>
C22H24O11

> <MOLECULAR_WEIGHT>
464.423

> <EXACT_MASS>
464.131861593

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
43.05436456826601

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,4R,5R,7R,8E,10S,11S,12R)-10-(acetyloxy)-11-[(2R,3R)-2,3-dimethyloxirane-2-carbonyloxy]-4-methyl-13-methylidene-14-oxo-3,6,15-trioxatetracyclo[10.3.0.0^{2,4}.0^{5,7}]pentadec-8-ene-9-carboxylic acid

> <JCHEM_LOGP>
0.7645326020000005

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8698688908931986

> <JCHEM_PKA_STRONGEST_BASIC>
-3.793560562171739

> <JCHEM_POLAR_SURFACE_AREA>
153.79

> <JCHEM_REFRACTIVITY>
103.77199999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,4R,5R,7R,8E,10S,11S,12R)-10-(acetyloxy)-11-[(2R,3R)-2,3-dimethyloxirane-2-carbonyloxy]-4-methyl-13-methylidene-14-oxo-3,6,15-trioxatetracyclo[10.3.0.0^{2,4}.0^{5,7}]pentadec-8-ene-9-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.005   1.112   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.141  -0.162   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.663  -1.611   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -3.142  -2.039   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -0.447  -2.555   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.827  -1.690   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.399  -0.211   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.921   1.237   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.295   2.182   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.721   1.601   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.079   0.874   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.938   2.546   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.218   3.907   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.079   1.512   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.404   3.017   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.437   4.159   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.195   2.102   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.767   3.581   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.271   3.950   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.795   2.839   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.157   5.429   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.735   2.053   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.257   3.502   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.773   3.773   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       3.264   4.678   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.951   1.108   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.380  -0.371   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.373  -1.548   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.857  -1.819   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.583  -2.684   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.694  -3.751   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.771  -3.993   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.044  -2.635   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   33                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9   17                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   12   16                                                  
CONECT   16   15                                                            
CONECT   17    8   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   17   23   26                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   22   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27   29                                                       
CONECT   29   28   27   30                                                  
CONECT   30   29   31   32   33                                             
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32    6   30                                                  
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₄O₁₁

Average Mass

464.4230 Da

Monoisotopic Mass

464.13186 Da

IUPAC Name

(1S,2R,4R,5R,7R,8E,10S,11S,12R)-10-(acetyloxy)-11-[(2R,3R)-2,3-dimethyloxirane-2-carbonyloxy]-4-methyl-13-methylidene-14-oxo-3,6,15-trioxatetracyclo[10.3.0.0^{2,4}.0^{5,7}]pentadec-8-ene-9-carboxylic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C22H24O11/c1-7-12-14(31-20(27)21(4)8(2)32-21)13(28-9(3)23)10(18(24)25)6-11-16(29-11)22(5)17(33-22)15(12)30-19(7)26/h6,8,11-17H,1H2,2-5H3,(H,24,25)/b10-6+/t8-,11-,12-,13+,14+,15+,16-,17-,21-,22+/m1/s1

InChI Key

YOARICMECKZMHY-XIMYPQPTSA-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
Melampodium leucanthum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Sesquiterpenoid
Tetracarboxylic acid or derivatives
Gamma butyrolactone
Oxirane carboxylic acid
Oxirane carboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Tetrahydrofuran
Enoate ester
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.76	ChemAxon
pKa (Strongest Acidic)	3.87	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	153.79 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	103.77 m³·mol⁻¹	ChemAxon
Polarizability	43.05 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00011886

Chemspider ID

24691686

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44584274

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2r,4r,5r,7r,8e,10s,11s,12r)-10-(acetyloxy)-11-[(2r,3r)-2,3-dimethyloxirane-2-carbonyloxy]-4-methyl-13-methylidene-14-oxo-3,6,15-trioxatetracyclo[10.3.0.0²,⁴.0⁵,⁷]pentadec-8-ene-9-carboxylic acid (NP0205976)

MOL for NP0205976 ((1s,2r,4r,5r,7r,8e,10s,11s,12r)-10-(acetyloxy)-11-[(2r,3r)-2,3-dimethyloxirane-2-carbonyloxy]-4-methyl-13-methylidene-14-oxo-3,6,15-trioxatetracyclo[10.3.0.0²,⁴.0⁵,⁷]pentadec-8-ene-9-carboxylic acid)

3D MOL for NP0205976 ((1s,2r,4r,5r,7r,8e,10s,11s,12r)-10-(acetyloxy)-11-[(2r,3r)-2,3-dimethyloxirane-2-carbonyloxy]-4-methyl-13-methylidene-14-oxo-3,6,15-trioxatetracyclo[10.3.0.0²,⁴.0⁵,⁷]pentadec-8-ene-9-carboxylic acid)

3D SDF for NP0205976 ((1s,2r,4r,5r,7r,8e,10s,11s,12r)-10-(acetyloxy)-11-[(2r,3r)-2,3-dimethyloxirane-2-carbonyloxy]-4-methyl-13-methylidene-14-oxo-3,6,15-trioxatetracyclo[10.3.0.0²,⁴.0⁵,⁷]pentadec-8-ene-9-carboxylic acid)

3D-SDF for NP0205976 ((1s,2r,4r,5r,7r,8e,10s,11s,12r)-10-(acetyloxy)-11-[(2r,3r)-2,3-dimethyloxirane-2-carbonyloxy]-4-methyl-13-methylidene-14-oxo-3,6,15-trioxatetracyclo[10.3.0.0²,⁴.0⁵,⁷]pentadec-8-ene-9-carboxylic acid)

PDB for NP0205976 ((1s,2r,4r,5r,7r,8e,10s,11s,12r)-10-(acetyloxy)-11-[(2r,3r)-2,3-dimethyloxirane-2-carbonyloxy]-4-methyl-13-methylidene-14-oxo-3,6,15-trioxatetracyclo[10.3.0.0²,⁴.0⁵,⁷]pentadec-8-ene-9-carboxylic acid)

3D PDB for NP0205976 ((1s,2r,4r,5r,7r,8e,10s,11s,12r)-10-(acetyloxy)-11-[(2r,3r)-2,3-dimethyloxirane-2-carbonyloxy]-4-methyl-13-methylidene-14-oxo-3,6,15-trioxatetracyclo[10.3.0.0²,⁴.0⁵,⁷]pentadec-8-ene-9-carboxylic acid)

SMILES for NP0205976 ((1s,2r,4r,5r,7r,8e,10s,11s,12r)-10-(acetyloxy)-11-[(2r,3r)-2,3-dimethyloxirane-2-carbonyloxy]-4-methyl-13-methylidene-14-oxo-3,6,15-trioxatetracyclo[10.3.0.0²,⁴.0⁵,⁷]pentadec-8-ene-9-carboxylic acid)

INCHI for NP0205976 ((1s,2r,4r,5r,7r,8e,10s,11s,12r)-10-(acetyloxy)-11-[(2r,3r)-2,3-dimethyloxirane-2-carbonyloxy]-4-methyl-13-methylidene-14-oxo-3,6,15-trioxatetracyclo[10.3.0.0²,⁴.0⁵,⁷]pentadec-8-ene-9-carboxylic acid)

Structure for NP0205976 ((1s,2r,4r,5r,7r,8e,10s,11s,12r)-10-(acetyloxy)-11-[(2r,3r)-2,3-dimethyloxirane-2-carbonyloxy]-4-methyl-13-methylidene-14-oxo-3,6,15-trioxatetracyclo[10.3.0.0²,⁴.0⁵,⁷]pentadec-8-ene-9-carboxylic acid)

3D Structure for NP0205976 ((1s,2r,4r,5r,7r,8e,10s,11s,12r)-10-(acetyloxy)-11-[(2r,3r)-2,3-dimethyloxirane-2-carbonyloxy]-4-methyl-13-methylidene-14-oxo-3,6,15-trioxatetracyclo[10.3.0.0²,⁴.0⁵,⁷]pentadec-8-ene-9-carboxylic acid)