NP-MRD: Showing NP-Card for eupalinilide A (NP0027465)

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Record Information

Version

2.0

Created at

2021-06-19 19:36:57 UTC

Updated at

2021-06-29 23:53:36 UTC

NP-MRD ID

NP0027465

Secondary Accession Numbers

None

Natural Product Identification

Common Name

eupalinilide A

Provided By

JEOL Database JEOL Logo

Description

eupalinilide A is found in Eupatorium lindleyanum. eupalinilide A was first documented in 2004 (Huo, L., et al.). Based on a literature review very few articles have been published on (3aR,4R,6R,6aR,9R,9aS,9bS)-6-(chloromethyl)-6,9-dihydroxy-9-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,9H,9aH,9bH-azuleno[4,5-b]furan-4-yl (2E)-4-hydroxy-2-methylbut-2-enoate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192121363D          

 53 55  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306192121363D          

 53 55  0  0  0  0            999 V2000
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    1.7935   -1.5295   -0.4671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4545   -0.5334   -2.4833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3489   -1.9586   -1.5094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0540   -0.0576   -0.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2230   -3.9955    3.8337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9251   -4.2862    2.2427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8173   -3.3555    3.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2294   -0.7589    2.4496 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7198   -3.2446    4.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9089   -1.5678    4.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8187   -2.4962    3.9257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8535    1.7505   -1.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
 28  2  1  0  0  0  0
 10 11  1  0  0  0  0
 19 20  1  0  0  0  0
 14 18  1  0  0  0  0
  8 33  1  6  0  0  0
 11  7  1  0  0  0  0
 14 15  1  6  0  0  0
 18 19  1  0  0  0  0
  7 32  1  6  0  0  0
 28 19  1  0  0  0  0
 11 13  1  6  0  0  0
  3  4  2  0  0  0  0
 11 12  1  0  0  0  0
  2  1  2  3  0  0  0
 28  6  1  0  0  0  0
 20 21  1  0  0  0  0
  8  9  1  0  0  0  0
 21 23  1  0  0  0  0
  7  8  1  0  0  0  0
 21 22  2  0  0  0  0
  9 10  2  0  0  0  0
 14 16  1  0  0  0  0
  8 14  1  0  0  0  0
 16 17  1  0  0  0  0
  7  6  1  0  0  0  0
 23 24  1  0  0  0  0
  6  5  1  0  0  0  0
 23 25  2  0  0  0  0
  5  3  1  0  0  0  0
 25 26  1  0  0  0  0
  3  2  1  0  0  0  0
 26 27  1  0  0  0  0
  9 34  1  0  0  0  0
 10 35  1  0  0  0  0
 18 43  1  0  0  0  0
 18 44  1  0  0  0  0
 19 45  1  1  0  0  0
 12 36  1  0  0  0  0
 12 37  1  0  0  0  0
 12 38  1  0  0  0  0
 28 53  1  6  0  0  0
  6 31  1  1  0  0  0
 15 40  1  0  0  0  0
 13 39  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
 16 41  1  0  0  0  0
 16 42  1  0  0  0  0
 24 46  1  0  0  0  0
 24 47  1  0  0  0  0
 24 48  1  0  0  0  0
 25 49  1  0  0  0  0
 26 50  1  0  0  0  0
 26 51  1  0  0  0  0
 27 52  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0027465

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])C(\[H])=C(\C(=O)O[C@]1([H])C([H])([H])[C@](O[H])(C([H])([H])Cl)[C@]2([H])C([H])=C([H])[C@](O[H])(C([H])([H])[H])[C@]2([H])[C@@]2([H])OC(=O)C(=C([H])[H])[C@]12[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H25ClO7/c1-10(5-7-22)17(23)27-13-8-20(26,9-21)12-4-6-19(3,25)15(12)16-14(13)11(2)18(24)28-16/h4-6,12-16,22,25-26H,2,7-9H2,1,3H3/b10-5+/t12-,13-,14-,15+,16+,19-,20+/m1/s1

> <INCHI_KEY>
IXLMITLRFJSJRS-FSSPUKOTSA-N

> <FORMULA>
C20H25ClO7

> <MOLECULAR_WEIGHT>
412.86

> <EXACT_MASS>
412.1288808

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
40.444454244227344

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.00

> <JCHEM_LOGP>
0.7196133510000002

> <ALOGPS_LOGS>
-2.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.376487405935602

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.550019512118357

> <JCHEM_PKA_STRONGEST_BASIC>
-2.552198596871203

> <JCHEM_POLAR_SURFACE_AREA>
113.29

> <JCHEM_REFRACTIVITY>
102.44769999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.59e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 53 55  0  0  0  0  0  0  0  0999 V2000
   -1.6828    2.2634    1.4322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6533    2.1883    0.5793 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5205    3.0808    0.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6206    4.0608    1.4173 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4758    2.6166   -0.1438 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1014    1.3157   -0.6368 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6676    1.1670   -2.0441 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1906   -0.0215   -2.9183 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4200   -0.2944   -3.7496 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4960    0.3778   -3.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2236    1.2050   -2.1206 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0104    0.6789   -0.9233 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6574    2.5316   -2.3906 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5577   -1.2978   -2.2875 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2687   -2.1623   -3.4260 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246   -2.0771   -1.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8395   -3.6500   -0.8474 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.8451   -1.0002   -1.6957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9801   -0.1487   -0.4296 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3202   -0.8023    0.6688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0697   -1.6364    1.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2531   -1.8819    1.2632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2367   -2.2749    2.5003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8246   -3.5441    3.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9208   -1.7042    2.8928 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9016   -2.2139    3.8924 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1801   -2.1546    3.2767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4179    1.2704   -0.5798 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5473    1.6123    1.3578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6898    2.9967    2.2363 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5574    0.5906    0.0437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3294    2.0718   -2.5809 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4458    0.3768   -3.6250 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4075   -0.9498   -4.6126 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4674    0.3337   -3.8065 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8599    1.3071   -0.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0881    0.7099   -1.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7511   -0.3518   -0.6690 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3674    3.0874   -1.6440 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0378   -3.0436   -3.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4446   -2.3363   -1.9003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7935   -1.5295   -0.4671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4545   -0.5334   -2.4833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3489   -1.9586   -1.5094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0540   -0.0576   -0.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2230   -3.9955    3.8337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9251   -4.2862    2.2427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8173   -3.3555    3.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2294   -0.7589    2.4496 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7198   -3.2446    4.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9089   -1.5678    4.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8187   -2.4962    3.9257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8535    1.7505   -1.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
 28  2  1  0
 10 11  1  0
 19 20  1  0
 14 18  1  0
  8 33  1  6
 11  7  1  0
 14 15  1  6
 18 19  1  0
  7 32  1  6
 28 19  1  0
 11 13  1  6
  3  4  2  0
 11 12  1  0
  2  1  2  3
 28  6  1  0
 20 21  1  0
  8  9  1  0
 21 23  1  0
  7  8  1  0
 21 22  2  0
  9 10  2  0
 14 16  1  0
  8 14  1  0
 16 17  1  0
  7  6  1  0
 23 24  1  0
  6  5  1  0
 23 25  2  0
  5  3  1  0
 25 26  1  0
  3  2  1  0
 26 27  1  0
  9 34  1  0
 10 35  1  0
 18 43  1  0
 18 44  1  0
 19 45  1  1
 12 36  1  0
 12 37  1  0
 12 38  1  0
 28 53  1  6
  6 31  1  1
 15 40  1  0
 13 39  1  0
  1 29  1  0
  1 30  1  0
 16 41  1  0
 16 42  1  0
 24 46  1  0
 24 47  1  0
 24 48  1  0
 25 49  1  0
 26 50  1  0
 26 51  1  0
 27 52  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.683   2.263   1.432  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.653   2.188   0.579  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.521   3.081   0.706  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.621   4.061   1.417  0.00  0.00           O+0
HETATM    5  O   UNK     0       1.476   2.617  -0.144  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.101   1.316  -0.637  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.668   1.167  -2.044  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.191  -0.022  -2.918  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.420  -0.294  -3.750  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.496   0.378  -3.332  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.224   1.205  -2.121  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.010   0.679  -0.923  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.657   2.532  -2.391  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.558  -1.298  -2.288  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.269  -2.162  -3.426  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.525  -2.077  -1.369  0.00  0.00           C+0
HETATM   17 Cl   UNK     0       0.840  -3.650  -0.847  0.00  0.00          Cl+0
HETATM   18  C   UNK     0      -0.845  -1.000  -1.696  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.980  -0.149  -0.430  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.320  -0.802   0.669  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.070  -1.636   1.436  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.253  -1.882   1.263  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.237  -2.275   2.500  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.825  -3.544   3.042  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.921  -1.704   2.893  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.902  -2.214   3.892  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.180  -2.155   3.277  0.00  0.00           O+0
HETATM   28  C   UNK     0      -0.418   1.270  -0.580  0.00  0.00           C+0
HETATM   29  H   UNK     0      -2.547   1.612   1.358  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.690   2.997   2.236  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.557   0.591   0.044  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.329   2.072  -2.581  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.446   0.377  -3.625  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.408  -0.950  -4.613  0.00  0.00           H+0
HETATM   35  H   UNK     0       4.467   0.334  -3.807  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.860   1.307  -0.039  0.00  0.00           H+0
HETATM   37  H   UNK     0       5.088   0.710  -1.127  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.751  -0.352  -0.669  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.367   3.087  -1.644  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.038  -3.044  -3.073  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.445  -2.336  -1.900  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.794  -1.530  -0.467  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.454  -0.533  -2.483  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.349  -1.959  -1.509  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.054  -0.058  -0.220  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.223  -3.995   3.834  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.925  -4.286   2.243  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.817  -3.356   3.465  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.229  -0.759   2.450  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.720  -3.245   4.201  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.909  -1.568   4.775  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.819  -2.496   3.926  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.854   1.751  -1.467  0.00  0.00           H+0
CONECT    1    2   29   30                                                  
CONECT    2   28    1    3                                                  
CONECT    3    4    5    2                                                  
CONECT    4    3                                                            
CONECT    5    6    3                                                       
CONECT    6   28    7    5   31                                             
CONECT    7   11   32    8    6                                             
CONECT    8   33    9    7   14                                             
CONECT    9    8   10   34                                                  
CONECT   10   11    9   35                                                  
CONECT   11   10    7   13   12                                             
CONECT   12   11   36   37   38                                             
CONECT   13   11   39                                                       
CONECT   14   18   15   16    8                                             
CONECT   15   14   40                                                       
CONECT   16   14   17   41   42                                             
CONECT   17   16                                                            
CONECT   18   14   19   43   44                                             
CONECT   19   20   18   28   45                                             
CONECT   20   19   21                                                       
CONECT   21   20   23   22                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23   46   47   48                                             
CONECT   25   23   26   49                                                  
CONECT   26   25   27   50   51                                             
CONECT   27   26   52                                                       
CONECT   28    2   19    6   53                                             
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    6                                                            
CONECT   32    7                                                            
CONECT   33    8                                                            
CONECT   34    9                                                            
CONECT   35   10                                                            
CONECT   36   12                                                            
CONECT   37   12                                                            
CONECT   38   12                                                            
CONECT   39   13                                                            
CONECT   40   15                                                            
CONECT   41   16                                                            
CONECT   42   16                                                            
CONECT   43   18                                                            
CONECT   44   18                                                            
CONECT   45   19                                                            
CONECT   46   24                                                            
CONECT   47   24                                                            
CONECT   48   24                                                            
CONECT   49   25                                                            
CONECT   50   26                                                            
CONECT   51   26                                                            
CONECT   52   27                                                            
CONECT   53   28                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  110    0
END

RDKit          3D

53 55  0  0  0  0  0  0  0  0999 V2000
   -1.6828    2.2634    1.4322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6533    2.1883    0.5793 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5205    3.0808    0.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6206    4.0608    1.4173 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4758    2.6166   -0.1438 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1014    1.3157   -0.6368 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6676    1.1670   -2.0441 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1906   -0.0215   -2.9183 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4200   -0.2944   -3.7496 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4960    0.3778   -3.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2236    1.2050   -2.1206 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0104    0.6789   -0.9233 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6574    2.5316   -2.3906 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5577   -1.2978   -2.2875 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2687   -2.1623   -3.4260 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246   -2.0771   -1.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8395   -3.6500   -0.8474 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.8451   -1.0002   -1.6957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9801   -0.1487   -0.4296 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3202   -0.8023    0.6688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0697   -1.6364    1.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2531   -1.8819    1.2632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2367   -2.2749    2.5003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8246   -3.5441    3.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9208   -1.7042    2.8928 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9016   -2.2139    3.8924 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1801   -2.1546    3.2767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4179    1.2704   -0.5798 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5473    1.6123    1.3578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6898    2.9967    2.2363 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5574    0.5906    0.0437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3294    2.0718   -2.5809 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4458    0.3768   -3.6250 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4075   -0.9498   -4.6126 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4674    0.3337   -3.8065 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8599    1.3071   -0.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0881    0.7099   -1.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7511   -0.3518   -0.6690 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3674    3.0874   -1.6440 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0378   -3.0436   -3.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4446   -2.3363   -1.9003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7935   -1.5295   -0.4671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4545   -0.5334   -2.4833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3489   -1.9586   -1.5094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0540   -0.0576   -0.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2230   -3.9955    3.8337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9251   -4.2862    2.2427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8173   -3.3555    3.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2294   -0.7589    2.4496 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7198   -3.2446    4.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9089   -1.5678    4.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8187   -2.4962    3.9257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8535    1.7505   -1.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
 28  2  1  0
 10 11  1  0
 19 20  1  0
 14 18  1  0
  8 33  1  6
 11  7  1  0
 14 15  1  6
 18 19  1  0
  7 32  1  6
 28 19  1  0
 11 13  1  6
  3  4  2  0
 11 12  1  0
  2  1  2  3
 28  6  1  0
 20 21  1  0
  8  9  1  0
 21 23  1  0
  7  8  1  0
 21 22  2  0
  9 10  2  0
 14 16  1  0
  8 14  1  0
 16 17  1  0
  7  6  1  0
 23 24  1  0
  6  5  1  0
 23 25  2  0
  5  3  1  0
 25 26  1  0
  3  2  1  0
 26 27  1  0
  9 34  1  0
 10 35  1  0
 18 43  1  0
 18 44  1  0
 19 45  1  1
 12 36  1  0
 12 37  1  0
 12 38  1  0
 28 53  1  6
  6 31  1  1
 15 40  1  0
 13 39  1  0
  1 29  1  0
  1 30  1  0
 16 41  1  0
 16 42  1  0
 24 46  1  0
 24 47  1  0
 24 48  1  0
 25 49  1  0
 26 50  1  0
 26 51  1  0
 27 52  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
(3AR,4R,6R,6ar,9R,9as,9BS)-6-(chloromethyl)-6,9-dihydroxy-9-methyl-3-methylidene-2-oxo-2H,3H,3ah,4H,5H,6H,6ah,9H,9ah,9BH-azuleno[4,5-b]furan-4-yl (2E)-4-hydroxy-2-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₀H₂₅ClO₇

Average Mass

412.8600 Da

Monoisotopic Mass

412.12888 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])C(\[H])=C(\C(=O)O[C@]1([H])C([H])([H])[C@](O[H])(C([H])([H])Cl)[C@]2([H])C([H])=C([H])[C@](O[H])(C([H])([H])[H])[C@]2([H])[C@@]2([H])OC(=O)C(=C([H])[H])[C@]12[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C20H25ClO7/c1-10(5-7-22)17(23)27-13-8-20(26,9-21)12-4-6-19(3,25)15(12)16-14(13)11(2)18(24)28-16/h4-6,12-16,22,25-26H,2,7-9H2,1,3H3/b10-5+/t12-,13-,14-,15+,16+,19-,20+/m1/s1

InChI Key

IXLMITLRFJSJRS-FSSPUKOTSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
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

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Eupatorium lindleyanum	JEOL database	Huo, L., et al, J. Nat. Prod. 67, 1470 (2004)

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
Halohydrin
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Alkyl chloride
Primary alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Alkyl halide
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	ALOGPS
logP	0.72	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	13.55	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	102.45 m³·mol⁻¹	ChemAxon
Polarizability	40.44 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

Not Available

Chemspider ID

9582190

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11407295

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Huo, L., et al. (2004). Huo, L., et al, J. Nat. Prod. 67, 1470 (2004). J. Nat. Prod..

Showing NP-Card for eupalinilide A (NP0027465)

MOL for NP0027465 (eupalinilide A)

3D MOL for NP0027465 (eupalinilide A)

3D SDF for NP0027465 (eupalinilide A)

3D-SDF for NP0027465 (eupalinilide A)

PDB for NP0027465 (eupalinilide A)

3D PDB for NP0027465 (eupalinilide A)

SMILES for NP0027465 (eupalinilide A)

INCHI for NP0027465 (eupalinilide A)

Structure for NP0027465 (eupalinilide A)

3D Structure for NP0027465 (eupalinilide A)