NP-MRD: Showing NP-Card for Eupalinilide E (NP0044046)

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Record Information

Version

1.0

Created at

2021-11-12 23:47:07 UTC

Updated at

2021-11-26 17:44:48 UTC

NP-MRD ID

NP0044046

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Eupalinilide E

Description

EUPALINILIDE E belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Eupalinilide E is found in Eupatorium lindleyanum. It was first documented in 2004 (PMID: 15387644). Based on a literature review very few articles have been published on EUPALINILIDE E.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652311132100472D          

 31 33  0  0  1  0            999 V2000
    3.8554    3.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2679    3.9964    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0304    3.2819    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2140    4.0862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2140    2.4776    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6996    1.8326    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8746    1.8326    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3602    2.4776    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5438    3.2819    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8988    3.7963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0217    4.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3767    5.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4997    5.9423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1453    6.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3912    4.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7897    4.9135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2871    3.6399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5878    2.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1007    2.6422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6248    1.3636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0202    0.8492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201    1.1441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1645    2.6612    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2655    1.1061    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1541    1.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8642    0.3717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9493    1.3636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9864    2.1877    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6749    2.6422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3416    2.5759    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8352    3.0204    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  1  1  6  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 11 16  2  0  0  0  0
  9 17  1  0  0  0  0
  3 17  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
  7 22  1  0  0  0  0
  8 23  1  1  0  0  0
  7 24  1  6  0  0  0
  6 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 27 28  1  0  0  0  0
  5 28  1  0  0  0  0
 28 29  1  6  0  0  0
  6 30  1  1  0  0  0
  5 31  1  1  0  0  0
M  END

     RDKit          3D

 52 54  0  0  0  0  0  0  0  0999 V2000
   -0.7454   -2.9350   -2.5698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0127   -1.8691   -2.3663 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2448   -0.8311   -3.3458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1359   -0.7482   -4.5522 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0399    0.1608   -2.7379 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9460   -0.0153   -1.3154 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2270    0.3215   -0.6564 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3910    1.7197   -0.2591 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7013    2.9001   -0.8645 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2649    1.7616    0.7398 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7504    0.3968    1.0857 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9889    0.2103    2.4160 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5871   -0.4511    0.5525 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5654   -0.6155    1.6066 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2704   -1.0605    2.7632 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8854    0.6467    2.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1995    0.1829    3.4137 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.5718   -1.7084    1.3620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1703   -1.6519    0.0872 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1560   -0.6361    0.0397 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5070   -0.8872   -0.1309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8517   -2.0812   -0.2469 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5173    0.1519   -0.1797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9363   -0.2317   -0.3666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2409    1.4395   -0.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3253    2.4816   -0.1227 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6946   -1.4964   -1.1305 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2219   -3.1162   -3.5131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8885   -3.6638   -1.7849 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0660    0.5346   -1.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0407    0.1164   -1.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7188    2.8736   -1.9591 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6417    2.8539   -0.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1902    3.8518   -0.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6035    2.6574    1.2594 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6072    0.1740    0.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7063   -0.4859    2.5404 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0311   -1.4461    0.3464 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4794   -2.0226    2.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6177    1.3595    2.5211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2540    1.1269    1.3117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1454   -1.7078    2.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1074   -2.6863    1.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7128   -2.6144   -0.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1042   -1.3137   -0.2655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3357    0.1226   -1.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5671    0.2855    0.4023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2205    1.7536    0.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9423    3.4265   -0.5497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7244    2.7074    0.8807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1626    2.1420   -0.7673 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6308   -2.0838   -1.0836 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0
 16 14  1  0
 14 15  1  1
 14 13  1  0
 13  7  1  0
  7  6  1  0
  6 27  1  0
 27 19  1  0
 19 20  1  0
 20 21  1  0
 21 23  1  0
 23 25  2  0
 25 26  1  0
 23 24  1  0
 21 22  2  0
 19 18  1  0
 27  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 18 14  1  0
 11 13  1  0
  5  6  1  0
 16 40  1  0
 16 41  1  0
 15 39  1  0
 13 38  1  6
  7 31  1  6
  6 30  1  1
 27 52  1  1
 19 44  1  6
 25 48  1  0
 26 49  1  0
 26 50  1  0
 26 51  1  0
 24 45  1  0
 24 46  1  0
 24 47  1  0
 18 42  1  0
 18 43  1  0
  1 28  1  0
  1 29  1  0
  9 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  6
 12 37  1  0
M  END


  Mrv1652311132100472D          

 31 33  0  0  1  0            999 V2000
    3.8554    3.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2679    3.9964    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0304    3.2819    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2140    4.0862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2140    2.4776    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6996    1.8326    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8746    1.8326    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3602    2.4776    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5438    3.2819    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8988    3.7963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0217    4.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3767    5.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4997    5.9423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1453    6.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3912    4.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7897    4.9135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2871    3.6399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5878    2.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1007    2.6422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6248    1.3636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0202    0.8492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201    1.1441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1645    2.6612    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2655    1.1061    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1541    1.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8642    0.3717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9493    1.3636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9864    2.1877    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6749    2.6422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3416    2.5759    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8352    3.0204    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  1  1  6  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 11 16  2  0  0  0  0
  9 17  1  0  0  0  0
  3 17  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
  7 22  1  0  0  0  0
  8 23  1  1  0  0  0
  7 24  1  6  0  0  0
  6 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 27 28  1  0  0  0  0
  5 28  1  0  0  0  0
 28 29  1  6  0  0  0
  6 30  1  1  0  0  0
  5 31  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0044046

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12OC(=O)C(=C)[C@]1([H])[C@@H](C[C@](O)(CCl)[C@]1([H])[C@H](O)C=C(C)[C@]21[H])OC(=O)C(\C)=C\C

> <INCHI_IDENTIFIER>
InChI=1S/C20H25ClO6/c1-5-9(2)18(23)26-13-7-20(25,8-21)16-12(22)6-10(3)14(16)17-15(13)11(4)19(24)27-17/h5-6,12-17,22,25H,4,7-8H2,1-3H3/b9-5+/t12-,13-,14+,15-,16-,17-,20+/m1/s1

> <INCHI_KEY>
RQLHOJWFBMNYHW-PBDZIAQESA-N

> <FORMULA>
C20H25ClO6

> <MOLECULAR_WEIGHT>
396.86

> <EXACT_MASS>
396.1339662

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
40.135596139047436

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,4R,6R,6aS,7R,9aR,9bR)-6-(chloromethyl)-6,7-dihydroxy-9-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl (2E)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
1.91

> <JCHEM_LOGP>
1.9631691110000005

> <ALOGPS_LOGS>
-2.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.611193922343503

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.548268588107305

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0368092649935834

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
100.31679999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.35e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,4R,6R,6aS,7R,9aR,9bR)-6-(chloromethyl)-6,7-dihydroxy-9-methyl-3-methylidene-2-oxo-3aH,4H,5H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-NOV-21         0                                  
HETATM    1  C   UNK     0       7.197   6.126   0.000  0.00  0.00           C+0
HETATM    2 Cl   UNK     0       7.967   7.460   0.000  0.00  0.00          Cl+0
HETATM    3  C   UNK     0       5.657   6.126   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.999   7.628   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.999   4.625   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.039   3.421   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.499   3.421   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.539   4.625   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.882   6.126   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.678   7.086   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.907   8.609   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.703   9.569   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.933  11.092   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.271  12.052   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.730   9.007   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.341   9.172   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.269   6.794   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.097   4.084   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.188   4.932   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.166   2.545   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.038   1.585   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.651   2.136   0.000  0.00  0.00           O+0
HETATM   23  H   UNK     0       4.040   4.968   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       4.229   2.065   0.000  0.00  0.00           H+0
HETATM   25  C   UNK     0       5.888   2.136   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.346   0.694   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.372   2.545   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.441   4.084   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.726   4.932   0.000  0.00  0.00           O+0
HETATM   30  H   UNK     0       4.371   4.808   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       7.159   5.638   0.000  0.00  0.00           H+0
CONECT    1    2    3                                                       
CONECT    2    1                                                            
CONECT    3    1    4    5   17                                             
CONECT    4    3                                                            
CONECT    5    3    6   28   31                                             
CONECT    6    5    7   25   30                                             
CONECT    7    6    8   22   24                                             
CONECT    8    7    9   18   23                                             
CONECT    9    8   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12                                                            
CONECT   16   11                                                            
CONECT   17    9    3                                                       
CONECT   18    8   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20    7                                                       
CONECT   23    8                                                            
CONECT   24    7                                                            
CONECT   25    6   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27    5   29                                                  
CONECT   29   28                                                            
CONECT   30    6                                                            
CONECT   31    5                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₅ClO₆

Average Mass

396.8600 Da

Monoisotopic Mass

396.13397 Da

IUPAC Name

(3aR,4R,6R,6aS,7R,9aR,9bR)-6-(chloromethyl)-6,7-dihydroxy-9-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl (2E)-2-methylbut-2-enoate

Traditional Name

(3aR,4R,6R,6aS,7R,9aR,9bR)-6-(chloromethyl)-6,7-dihydroxy-9-methyl-3-methylidene-2-oxo-3aH,4H,5H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl (2E)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

[H][C@]12OC(=O)C(=C)[C@]1([H])[C@@H](C[C@](O)(CCl)[C@]1([H])[C@H](O)C=C(C)[C@]21[H])OC(=O)C(\C)=C\C

InChI Identifier

InChI=1S/C20H25ClO6/c1-5-9(2)18(23)26-13-7-20(25,8-21)16-12(22)6-10(3)14(16)17-15(13)11(4)19(24)27-17/h5-6,12-17,22,25H,4,7-8H2,1-3H3/b9-5+/t12-,13-,14+,15-,16-,17-,20+/m1/s1

InChI Key

RQLHOJWFBMNYHW-PBDZIAQESA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Eupatorium lindleyanum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

Guaianolide-skeleton
Guaiane sesquiterpenoid
Sesquiterpenoid
Fatty acid ester
Dicarboxylic acid or derivatives
Gamma butyrolactone
Fatty acyl
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Chlorohydrin
Secondary alcohol
Halohydrin
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Alkyl chloride
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Alkyl halide
Carbonyl group
Organohalogen compound
Organochloride
Organooxygen compound
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	1.91	ALOGPS
logP	1.96	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	13.55	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	100.32 m³·mol⁻¹	ChemAxon
Polarizability	40.14 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00023181

Chemspider ID

9363755

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11188671

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Huo J, Yang SP, Ding J, Yue JM: Cytotoxic sesquiterpene lactones from Eupatorium lindleyanum. J Nat Prod. 2004 Sep;67(9):1470-5. doi: 10.1021/np040023h. [PubMed:15387644 ]

Showing NP-Card for Eupalinilide E (NP0044046)

MOL for NP0044046 (Eupalinilide E)

3D MOL for NP0044046 (Eupalinilide E)

3D SDF for NP0044046 (Eupalinilide E)

3D-SDF for NP0044046 (Eupalinilide E)

PDB for NP0044046 (Eupalinilide E)

3D PDB for NP0044046 (Eupalinilide E)

SMILES for NP0044046 (Eupalinilide E)

INCHI for NP0044046 (Eupalinilide E)

Structure for NP0044046 (Eupalinilide E)

3D Structure for NP0044046 (Eupalinilide E)