NP-MRD: Showing NP-Card for Eupalinilide J (NP0044049)

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Record Information

Version

1.0

Created at

2021-11-12 23:47:16 UTC

Updated at

2021-11-26 17:44:50 UTC

NP-MRD ID

NP0044049

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Eupalinilide J

Description

Eupalinilide J belongs to the class of organic compounds known as ambrosanolides and secoambrosanolides. These are sesquiterpene lactones from the Ambrosia family, with a backbone derivative of azuleno[6,5-b]furan-2-one (ambrosanolides) or azuleno[4,5-b]furan-2-one (secoambrosanolides). Eupalinilide J 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 J.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652311132100472D          

 37 40  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652311132100472D          

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M  END
> <DATABASE_ID>
NP0044049

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12O[C@@]1(C)[C@]1([H])[C@@]3([H])OC(=O)C(=C)[C@]3([H])[C@@H](C[C@](O)(CO)[C@]1([H])[C@@H]2OC(C)=O)OC(=O)C(\C)=C\CO

> <INCHI_IDENTIFIER>
InChI=1S/C22H28O10/c1-9(5-6-23)19(26)30-12-7-22(28,8-24)15-14(16-13(12)10(2)20(27)31-16)21(4)18(32-21)17(15)29-11(3)25/h5,12-18,23-24,28H,2,6-8H2,1,3-4H3/b9-5+/t12-,13-,14+,15+,16+,17+,18-,21+,22+/m1/s1

> <INCHI_KEY>
XXDDPYGIIXZQBL-ROZFHUFVSA-N

> <FORMULA>
C22H28O10

> <MOLECULAR_WEIGHT>
452.456

> <EXACT_MASS>
452.168247102

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
44.37056643661181

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,6R,7R,9R,10S,11S,12R,14S)-11-(acetyloxy)-9-hydroxy-9-(hydroxymethyl)-14-methyl-5-methylidene-4-oxo-3,13-dioxatetracyclo[8.4.0.0^{2,6}.0^{12,14}]tetradecan-7-yl (2E)-4-hydroxy-2-methylbut-2-enoate

> <ALOGPS_LOGP>
0.06

> <JCHEM_LOGP>
-0.9343858126666651

> <ALOGPS_LOGS>
-2.11

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.096155399929831

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.537243509200767

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5521985981046047

> <JCHEM_POLAR_SURFACE_AREA>
152.12

> <JCHEM_REFRACTIVITY>
106.6997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.50e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,6R,7R,9R,10S,11S,12R,14S)-11-(acetyloxy)-9-hydroxy-9-(hydroxymethyl)-14-methyl-5-methylidene-4-oxo-3,13-dioxatetracyclo[8.4.0.0^{2,6}.0^{12,14}]tetradecan-7-yl (2E)-4-hydroxy-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       7.052   0.957   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.889  -0.336   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.691  -1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.241  -2.742   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.779  -2.663   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       9.747  -3.861   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       9.193  -5.298   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.671  -5.537   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      10.160  -6.497   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.180  -1.176   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.262   0.361   0.000  0.00  0.00           O+0
HETATM   12  H   UNK     0      10.700  -1.419   0.000  0.00  0.00           H+0
HETATM   13  C   UNK     0       6.459  -4.069   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.331  -5.603   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.937  -6.259   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       7.927  -4.536   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.934  -4.285   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.815  -3.227   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.376  -3.777   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.133  -5.298   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.695  -5.848   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.452  -7.368   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.987  -7.918   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.230  -9.439   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.501  -4.877   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.329  -6.269   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.944  -1.693   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.224  -0.836   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.805   0.646   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.266   0.705   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.410   1.985   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.734  -0.740   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.252  -1.159   0.000  0.00  0.00           C+0
HETATM   34  H   UNK     0       5.440  -2.361   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.531  -2.306   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0       8.039  -4.059   0.000  0.00  0.00           H+0
HETATM   37  H   UNK     0       6.407   0.210   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   10   11                                             
CONECT    3    2    4   28   37                                             
CONECT    4    3    5   13   36                                             
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    5    2   11   12                                             
CONECT   11   10    2                                                       
CONECT   12   10                                                            
CONECT   13    4   14   16   17                                             
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13                                                            
CONECT   17   13   18                                                       
CONECT   18   17   19   27                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   26                                                  
CONECT   21   20   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   21                                                            
CONECT   26   20                                                            
CONECT   27   18   28   32   35                                             
CONECT   28   27    3   29   34                                             
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   27   33                                                  
CONECT   33   32                                                            
CONECT   34   28                                                            
CONECT   35   27                                                            
CONECT   36    4                                                            
CONECT   37    3                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₈O₁₀

Average Mass

452.4560 Da

Monoisotopic Mass

452.16825 Da

IUPAC Name

(1S,2S,6R,7R,9R,10S,11S,12R,14S)-11-(acetyloxy)-9-hydroxy-9-(hydroxymethyl)-14-methyl-5-methylidene-4-oxo-3,13-dioxatetracyclo[8.4.0.0^{2,6}.0^{12,14}]tetradecan-7-yl (2E)-4-hydroxy-2-methylbut-2-enoate

Traditional Name

CAS Registry Number

Not Available

SMILES

[H][C@]12O[C@@]1(C)[C@]1([H])[C@@]3([H])OC(=O)C(=C)[C@]3([H])[C@@H](C[C@](O)(CO)[C@]1([H])[C@@H]2OC(C)=O)OC(=O)C(\C)=C\CO

InChI Identifier

InChI=1S/C22H28O10/c1-9(5-6-23)19(26)30-12-7-22(28,8-24)15-14(16-13(12)10(2)20(27)31-16)21(4)18(32-21)17(15)29-11(3)25/h5,12-18,23-24,28H,2,6-8H2,1,3-4H3/b9-5+/t12-,13-,14+,15+,16+,17+,18-,21+,22+/m1/s1

InChI Key

XXDDPYGIIXZQBL-ROZFHUFVSA-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 ambrosanolides and secoambrosanolides. These are sesquiterpene lactones from the Ambrosia family, with a backbone derivative of azuleno[6,5-b]furan-2-one (ambrosanolides) or azuleno[4,5-b]furan-2-one (secoambrosanolides).

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Ambrosanolides and secoambrosanolides

Alternative Parents

Substituents

Secoambrosanolide
Guaianolide-skeleton
Sesquiterpenoid
Guaiane sesquiterpenoid
Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Gamma butyrolactone
Oxane
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Alcohol
Organic oxide
Primary alcohol
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	0.06	ALOGPS
logP	-0.93	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	13.54	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	152.12 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	106.7 m³·mol⁻¹	ChemAxon
Polarizability	44.37 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

C00023187

Chemspider ID

9503411

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11328460

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 J (NP0044049)

MOL for NP0044049 (Eupalinilide J)

3D MOL for NP0044049 (Eupalinilide J)

3D SDF for NP0044049 (Eupalinilide J)

3D-SDF for NP0044049 (Eupalinilide J)

PDB for NP0044049 (Eupalinilide J)

3D PDB for NP0044049 (Eupalinilide J)

SMILES for NP0044049 (Eupalinilide J)

INCHI for NP0044049 (Eupalinilide J)

Structure for NP0044049 (Eupalinilide J)

3D Structure for NP0044049 (Eupalinilide J)