NP-MRD: Showing NP-Card for Eupatolide (NP0044115)

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Record Information

Version

1.0

Created at

2021-11-12 23:50:56 UTC

Updated at

2021-11-26 17:45:36 UTC

NP-MRD ID

NP0044115

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Eupatolide

Description

Eupatolide 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. Eupatolide is found in Cassinia aculeata, Cassinia subtropica, Eupatorium cannabinum , Eupatorium formosanum, Eupatorium glehni, Eupatorium glehnii, Helianthus agrophyllus, Helianthus argophyllus, Hilianthus annuus, Inula japonica, Inula salsoloides, Pentanema britannicum, Rhodanthe floribunda, Stevia alpina var. glutinosa and Viguiera hypargyrea. It was first documented in 2016 (PMID: 27452450). Based on a literature review a significant number of articles have been published on eupatolide (PMID: 33091599) (PMID: 32516579) (PMID: 31417401) (PMID: 29809196).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 39  0  0  0  0  0  0  0  0999 V2000
    3.0761   -1.3366    1.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6464   -0.4750    0.4607 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4638    0.4846   -0.3069 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6720    0.3573   -0.6104 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6027    1.5306   -0.6043 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2629    1.0406   -0.6504 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4209    1.9870    0.1401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8671    2.1288   -0.1235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6665    3.1024    0.7118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6218    1.4179   -1.1751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6065    0.4159   -0.6415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1386   -0.3766    0.5007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2458   -1.3545    0.4297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8221   -2.1195    1.6592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6017   -1.7661   -0.8494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8480   -1.4434   -0.8183 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3686   -1.2707   -2.1156 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2382   -0.2763    0.0427 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3769   -1.9876    1.8375 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1253   -1.4186    1.5900 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9790    1.0282   -1.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9007    2.5703    0.9560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0538    3.4587    1.5814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5664    2.5684    1.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9716    3.9432    0.0824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2271    2.2261   -1.6944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9995    1.0062   -1.9953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5502    0.9633   -0.4076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8874   -0.2329   -1.5249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5530   -0.1466    1.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7136   -1.4713    2.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6370   -2.8535    1.9310 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1134   -2.6758    1.4850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1387   -1.3681   -1.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7064   -2.8816   -0.9435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3879   -2.3287   -0.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4587   -2.1894   -2.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6337   -0.2566    0.9725 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2 18  1  0
 18  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
  3  2  1  0
 16 18  1  0
  1 19  1  0
  1 20  1  0
 18 38  1  1
  6 21  1  6
  7 22  1  0
  9 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  1
 17 37  1  0
M  END


  Mrv1652311132100502D          

 20 21  0  0  1  0            999 V2000
    1.8304   -1.8899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3460   -1.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1701   -1.2843    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4614   -0.5125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8173    0.0031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1279   -0.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3561   -0.1588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2755   -0.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5668    0.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0440    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3809    0.5267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9037   -0.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6124   -0.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7983   -1.0170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0002   -0.8080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5070   -1.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6929   -1.9226    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4015   -2.6944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6704    0.2856    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7997   -2.0215    0.0000 H   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
  2  6  1  0  0  0  0
  6  7  2  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
  3 17  1  0  0  0  0
 17 18  1  1  0  0  0
  4 19  1  1  0  0  0
  3 20  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0044115

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-9-5-4-6-10(2)8-13-14(12(16)7-9)11(3)15(17)18-13/h5,8,12-14,16H,3-4,6-7H2,1-2H3/b9-5+,10-8+/t12-,13-,14-/m1/s1

> <INCHI_KEY>
PDEJECFRCJOMEN-OURLZOILSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.322

> <EXACT_MASS>
248.141244504

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
26.566018193742302

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,4R,11aR)-4-hydroxy-6,10-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one

> <ALOGPS_LOGP>
2.42

> <JCHEM_LOGP>
2.4710048466666663

> <ALOGPS_LOGS>
-2.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.703903554250143

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9283125853709846

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
71.51709999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.41e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
eupatolide

> <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       3.417  -3.528   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.379  -2.326   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.917  -2.397   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.461  -0.957   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.259   0.006   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.972  -0.840   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.531  -0.296   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       7.981  -0.707   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.525   0.734   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.549   1.925   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.044   0.983   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.020  -0.208   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.476  -1.649   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.957  -1.898   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.467  -1.508   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.413  -3.339   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.893  -3.589   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.350  -5.030   0.000  0.00  0.00           O+0
HETATM   19  H   UNK     0       6.851   0.533   0.000  0.00  0.00           H+0
HETATM   20  H   UNK     0       5.226  -3.774   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4   17   20                                             
CONECT    4    3    5    8   19                                             
CONECT    5    4    6                                                       
CONECT    6    5    2    7                                                  
CONECT    7    6                                                            
CONECT    8    4    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16    3   18                                                  
CONECT   18   17                                                            
CONECT   19    4                                                            
CONECT   20    3                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
Eupatolid	ChEBI
8beta-Hydroxy-costunolide	MeSH

Chemical Formula

C₁₅H₂₀O₃

Average Mass

248.3220 Da

Monoisotopic Mass

248.14124 Da

IUPAC Name

(3aR,4R,11aR)-4-hydroxy-6,10-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one

Traditional Name

eupatolide

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H20O3/c1-9-5-4-6-10(2)8-13-14(12(16)7-9)11(3)15(17)18-13/h5,8,12-14,16H,3-4,6-7H2,1-2H3/b9-5+,10-8+/t12-,13-,14-/m1/s1

InChI Key

PDEJECFRCJOMEN-OURLZOILSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Pyridine-d5, 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
Cassinia aculeata	LOTUS Database	35616633
Cassinia subtropica	LOTUS Database	35616633
Eupatorium cannabinum	Plant	KNApSAcK
Eupatorium formosanum	Plant	KNApSAcK
Eupatorium glehni	LOTUS Database	35616633
Eupatorium glehnii	Plant	KNApSAcK
Helianthus agrophyllus	Plant	KNApSAcK
Helianthus argophyllus	LOTUS Database	35616633
Hilianthus annuus	-	KNApSAcK
Inula japonica	LOTUS Database	35616633
Inula salsoloides	LOTUS Database	35616633
Pentanema britannicum	LOTUS Database	35616633
Rhodanthe floribunda	LOTUS Database	35616633
Stevia alpina var. glutinosa	Plant	KNApSAcK
Viguiera hypargyrea	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
Germacrane sesquiterpenoid
Sesquiterpenoid
Gamma butyrolactone
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

germacranolide (CHEBI:4935 )
Germacrenes (C09440 )

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	2.42	ALOGPS
logP	2.47	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	14.7	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	71.52 m³·mol⁻¹	ChemAxon
Polarizability	26.57 Å³	ChemAxon
Number of Rings	2	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

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281460

PDB ID

Not Available

ChEBI ID

4935

Good Scents ID

rw1531091

References

General References

Wu XD, Ding LF, Tu WC, Yang H, Su J, Peng LY, Li Y, Zhao QS: Bioactive sesquiterpenoids from the flowers of Inula japonica. Phytochemistry. 2016 Sep;129:68-76. doi: 10.1016/j.phytochem.2016.07.008. Epub 2016 Jul 21. [PubMed:27452450 ]
Ma X, Wu K, Xu A, Jiao P, Li H, Xing L: The sesquiterpene lactone eupatolide induces apoptosis in non-small cell lung cancer cells by suppressing STAT3 signaling. Environ Toxicol Pharmacol. 2021 Jan;81:103513. doi: 10.1016/j.etap.2020.103513. Epub 2020 Oct 20. [PubMed:33091599 ]
Frey M, Klaiber I, Conrad J, Spring O: CYP71BL9, the missing link in costunolide synthesis of sunflower. Phytochemistry. 2020 Sep;177:112430. doi: 10.1016/j.phytochem.2020.112430. Epub 2020 Jun 6. [PubMed:32516579 ]
Avila-Carrasco L, Majano P, Sanchez-Tomero JA, Selgas R, Lopez-Cabrera M, Aguilera A, Gonzalez Mateo G: Natural Plants Compounds as Modulators of Epithelial-to-Mesenchymal Transition. Front Pharmacol. 2019 Jul 30;10:715. doi: 10.3389/fphar.2019.00715. eCollection 2019. [PubMed:31417401 ]
Boldbaatar A, Lee S, Han S, Jeong AL, Ka HI, Buyanravjikh S, Lee JH, Lim JS, Lee MS, Yang Y: Erratum: Eupatolide inhibits the TGF-beta1-induced migration of breast cancer cells via downregulation of SMAD3 phosphorylation and transcriptional repression of ALK5. Oncol Lett. 2018 Jun;15(6):8885. doi: 10.3892/ol.2018.8427. Epub 2018 Apr 4. [PubMed:29809196 ]

Showing NP-Card for Eupatolide (NP0044115)

MOL for NP0044115 (Eupatolide)

3D MOL for NP0044115 (Eupatolide)

3D SDF for NP0044115 (Eupatolide)

3D-SDF for NP0044115 (Eupatolide)

PDB for NP0044115 (Eupatolide)

3D PDB for NP0044115 (Eupatolide)

SMILES for NP0044115 (Eupatolide)

INCHI for NP0044115 (Eupatolide)

Structure for NP0044115 (Eupatolide)

3D Structure for NP0044115 (Eupatolide)