NP-MRD: Showing NP-Card for Coronopilin (NP0051860)

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Record Information

Version

2.0

Created at

2022-04-27 23:04:03 UTC

Updated at

2022-04-27 23:04:03 UTC

NP-MRD ID

NP0051860

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Coronopilin

Description

Coronopilin 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). Coronopilin is found in Ambrosia arborescens, Ambrosia artemisiifolia, Ambrosia psilostachya, Ambrosia psilostachya var. coronopifolia, Ambrosia trifida, Hymenoclea salsola, Iva spp., Parthenium confertum, Parthenium hysterophorus , Parthenium incanum and Parthenium schottii. Coronopilin was first documented in 2005 (PMID: 15997155). Based on a literature review a significant number of articles have been published on Coronopilin (PMID: 29112407) (PMID: 24910974) (PMID: 34789056) (PMID: 30466970) (PMID: 28863191) (PMID: 24023312).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
    3.9239    0.0514    0.4641 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9114   -0.6131   -0.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7009   -2.0526    0.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5262   -2.9580    0.3266 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3886   -2.2859   -0.2632 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7410   -1.1119   -0.7374 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7772   -0.0764   -0.8109 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3604    1.3056   -0.4017 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2083    1.7279   -1.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1510    1.4581   -0.6565 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3418    2.4097    0.4829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4640    0.0550   -0.4177 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8008   -0.5285   -1.6710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6243   -0.2112    0.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5381   -1.7243    0.7361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2349   -2.1212    0.1383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9654   -3.2285   -0.2488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4240   -0.8513    0.1559 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0663   -0.6065    1.5824 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7222   -0.4226    1.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9684    1.1158    0.3339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3400   -1.3776   -1.7446 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1241    0.0126   -1.8811 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2297    1.9769   -0.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2409    1.4419    0.6798 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2667    2.8481   -1.3626 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3354    1.3182   -2.2570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8739    1.8175   -1.4598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2360    2.2403    1.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4109    2.5526    1.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4793    3.4369    0.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2181    0.1733   -2.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5538   -0.0382   -0.0781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5856    0.2679    1.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3923   -2.2582    0.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5746   -1.9552    1.8189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0545   -0.7250    1.6833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4563   -1.4012    2.2883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4283    0.3377    2.0041 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  6 18  1  0
 18 19  1  1
 18 16  1  0
 16 17  2  0
 16 15  1  0
 15 14  1  0
 14 12  1  0
 12 13  1  6
 12 10  1  0
  2  7  1  0
 12 18  1  0
 11 29  1  0
 11 30  1  0
 11 31  1  0
 10 28  1  6
  9 26  1  0
  9 27  1  0
  8 24  1  0
  8 25  1  0
  7 23  1  6
  6 22  1  6
  1 20  1  0
  1 21  1  0
 19 37  1  0
 19 38  1  0
 19 39  1  0
 15 35  1  0
 15 36  1  0
 14 33  1  0
 14 34  1  0
 13 32  1  0
M  END


  Mrv1652304282201042D          

 19 21  0  0  1  0            999 V2000
    2.0090    2.2026    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4946    1.5576    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6696    1.5576    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1552    2.2026    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3388    3.0069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0821    3.3648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8254    3.0069    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4704    3.5213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6172    1.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3057    2.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5802    1.0885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2252    0.5741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2151    0.8690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9491    0.8690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6592    0.0966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7444    1.0885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7814    1.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1037    0.8311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6303    2.7454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  6  0  0  0
  4  9  1  6  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  3 13  1  6  0  0  0
  2 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
  1 17  1  0  0  0  0
  2 18  1  6  0  0  0
  1 19  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0051860

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CC[C@@H]2[C@@H](OC(=O)C2=C)[C@]2(C)C(=O)CC[C@@]12O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-8-4-5-10-9(2)13(17)19-12(10)14(3)11(16)6-7-15(8,14)18/h8,10,12,18H,2,4-7H2,1,3H3/t8-,10-,12+,14-,15+/m0/s1

> <INCHI_KEY>
GEUJJEYGSRWXPC-JISBIHODSA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.321

> <EXACT_MASS>
264.136159124

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
27.61886426397497

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aS,6S,6aR,9aS,9bR)-6a-hydroxy-6,9a-dimethyl-3-methylidene-dodecahydroazuleno[4,5-b]furan-2,9-dione

> <ALOGPS_LOGP>
0.81

> <JCHEM_LOGP>
2.1128991966666666

> <ALOGPS_LOGS>
-2.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.682161389625676

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.925013894105028

> <JCHEM_PKA_STRONGEST_BASIC>
-3.268647643221926

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
68.41020000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.39e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
coronopilin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       3.750   4.111   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.790   2.907   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.250   2.907   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.290   4.111   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.632   5.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.020   6.281   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.407   5.613   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.611   6.573   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.152   3.570   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.437   4.419   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.083   2.032   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.287   1.072   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.402   1.622   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.638   1.622   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.097   0.180   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.123   2.032   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.192   3.570   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.060   1.551   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.910   5.125   0.000  0.00  0.00           O+0
CONECT    1    2    7   17   19                                             
CONECT    2    1    3   14   18                                             
CONECT    3    2    4   13                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    1    8                                                  
CONECT    8    7                                                            
CONECT    9    4   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    3                                                       
CONECT   14    2   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16    1                                                       
CONECT   18    2                                                            
CONECT   19    1                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₄

Average Mass

264.3210 Da

Monoisotopic Mass

264.13616 Da

IUPAC Name

(3aS,6S,6aR,9aS,9bR)-6a-hydroxy-6,9a-dimethyl-3-methylidene-dodecahydroazuleno[4,5-b]furan-2,9-dione

Traditional Name

coronopilin

CAS Registry Number

Not Available

SMILES

C[C@H]1CC[C@@H]2[C@@H](OC(=O)C2=C)[C@]2(C)C(=O)CC[C@@]12O

InChI Identifier

InChI=1S/C15H20O4/c1-8-4-5-10-9(2)13(17)19-12(10)14(3)11(16)6-7-15(8,14)18/h8,10,12,18H,2,4-7H2,1,3H3/t8-,10-,12+,14-,15+/m0/s1

InChI Key

GEUJJEYGSRWXPC-JISBIHODSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Ambrosia arborescens	LOTUS Database	35616633
Ambrosia artemisiifolia	Plant	KNApSAcK
Ambrosia psilostachya	LOTUS Database	35616633
Ambrosia psilostachya var. coronopifolia	Plant	KNApSAcK
Ambrosia trifida	LOTUS Database	35616633
Hymenoclea salsola	Plant	KNApSAcK
Iva spp.	Plant	KNApSAcK
Parthenium confertum	Plant	KNApSAcK
Parthenium hysterophorus	Plant	KNApSAcK
Parthenium incanum	Plant	KNApSAcK
Parthenium schottii	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

Ambrosanolide
Pseudoguaiane sesquiterpenoid
Sesquiterpenoid
Gamma butyrolactone
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Ketone
Lactone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

sesquiterpene lactone (CHEBI:3888 )
pseudoguaianolide (C09381 )

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	0.81	ALOGPS
logP	2.11	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	13.93	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.41 m³·mol⁻¹	ChemAxon
Polarizability	27.62 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

C00003239

Chemspider ID

225689

KEGG Compound ID

C09381

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

257278

PDB ID

Not Available

ChEBI ID

3888

Good Scents ID

rw1428551

References

General References

Das R, Geethangili M, Majhi A, Das B, Rao YK, Tzeng YM: A new highly oxygenated pseudoguaianolide from a collection of the flowers of Parthenium hysterophorus. Chem Pharm Bull (Tokyo). 2005 Jul;53(7):861-2. doi: 10.1248/cpb.53.861. [PubMed:15997155 ]
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Showing NP-Card for Coronopilin (NP0051860)

MOL for NP0051860 (Coronopilin)

3D MOL for NP0051860 (Coronopilin)

3D SDF for NP0051860 (Coronopilin)

3D-SDF for NP0051860 (Coronopilin)

PDB for NP0051860 (Coronopilin)

3D PDB for NP0051860 (Coronopilin)

SMILES for NP0051860 (Coronopilin)

INCHI for NP0051860 (Coronopilin)

Structure for NP0051860 (Coronopilin)

3D Structure for NP0051860 (Coronopilin)