NP-MRD: Showing NP-Card for Isoalantolactone (NP0051915)

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Record Information

Version

2.0

Created at

2022-04-27 23:07:03 UTC

Updated at

2022-04-27 23:07:03 UTC

NP-MRD ID

NP0051915

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isoalantolactone

Description

Isoalantolactone belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. Isoalantolactone is found in Abutilon indicum , Ambrosia artemisioides, Artemisia feddei, Bidens subalternans, Carpesium longifolium, Carpesium macrocephalum, Craspedia glauca, Eupatorium cannabinum, Critonia quadrangularis, Flourensia riparia, Flourensia riparia Grisebach, Hypochoeris cretensis, Inula grandis, Inula helenium , Inula henium, Inula japonica, Inula magnifica, Inula racemosa , Inula royleana, Inula salicina , Liatris cylindrica, Ratibida columnifera, Rudbeckia mollis, Saussurea lappa , Telekia speciosa, Tritomaria quinquedentata, Tritomaria quinquedentata (Huds.), Xanthium canadense Mill., Xanthium indicum and Xanthium strumarium. Isoalantolactone was first documented in 2020 (PMID: 33289551). Based on a literature review a significant number of articles have been published on isoalantolactone (PMID: 34368878) (PMID: 35209195) (PMID: 35389600) (PMID: 35145916) (PMID: 34683920) (PMID: 33959604).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
    4.2463    0.6854   -0.0048 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2084   -0.1262   -0.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0648   -1.2013   -1.1202 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6873   -1.3243   -2.2088 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1083   -2.0915   -0.6569 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5105   -1.5637    0.5375 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0732   -1.8420    0.5736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8381   -0.7411    0.1432 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0336   -0.7484   -1.3635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1995   -0.9957    0.7573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1998    0.0711    0.3725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7423    1.4571    0.7316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3440    1.6228    0.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9960    2.6597   -0.5057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3592    0.5972    0.6363 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0168    0.8679    0.1186 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9541   -0.1617    0.6598 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1096    0.6140   -0.6477 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2384    1.4398    0.7588 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0093   -2.1448    1.3697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1397   -2.7185   -0.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2462   -2.2119    1.5897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2610   -1.4281   -1.7983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0207   -1.1983   -1.6478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0150    0.2630   -1.7900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5761   -1.9517    0.3097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1139   -1.0948    1.8565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1158   -0.1308    0.9868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4602   -0.0036   -0.6841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4172    2.1740    0.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7275    1.5670    1.8544 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0276    2.7612   -0.8466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7690    3.3966   -0.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3159    0.5540    1.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3373    1.8564    0.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0559    0.9484   -0.9885 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2429    0.1428    1.7026 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  6
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  3
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17  6  1  0
  6  7  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
 15  8  1  0
  2 17  1  0
  7  8  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
 12 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  1
 16 35  1  0
 16 36  1  0
 17 37  1  1
  6 20  1  1
  7 21  1  0
  7 22  1  0
  1 18  1  0
  1 19  1  0
M  END


  Mrv1652304282201072D          

 17 19  0  0  1  0            999 V2000
    4.7812    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0668    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    0.2854    0.0000 C   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  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 10 12  1  1  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
  9 16  1  1  0  0  0
  6 17  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0051915

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12CCCC(=C)[C@@H]1C[C@H]1[C@@H](C2)OC(=O)C1=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h11-13H,1-2,4-8H2,3H3/t11-,12+,13-,15-/m1/s1

> <INCHI_KEY>
CVUANYCQTOGILD-QVHKTLOISA-N

> <FORMULA>
C15H20O2

> <MOLECULAR_WEIGHT>
232.323

> <EXACT_MASS>
232.146329884

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
26.09053678000899

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,4aS,8aR,9aR)-8a-methyl-3,5-dimethylidene-dodecahydronaphtho[2,3-b]furan-2-one

> <ALOGPS_LOGP>
3.15

> <JCHEM_LOGP>
3.357975322

> <ALOGPS_LOGS>
-3.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.864710029813113

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
66.1974

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.28e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isoalantolactone

> <JCHEM_VEBER_RULE>
1

$$$$

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       8.925   2.073   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.591   5.923   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.591   1.303   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.650   5.553   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.320   2.843   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.258   0.533   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   11                                                  
CONECT    6    5    7    8   17                                             
CONECT    7    6    1                                                       
CONECT    8    6    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10    5                                                       
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    9                                                       
CONECT   17    6                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Value	Source
8beta-Hydroxyeudesma-4(14),11(13)-dien-12-Oic acid gamma-lactone	ChEBI
Iso-alantolacton	ChEBI
8b-Hydroxyeudesma-4(14),11(13)-dien-12-Oate g-lactone	Generator
8b-Hydroxyeudesma-4(14),11(13)-dien-12-Oic acid g-lactone	Generator
8beta-Hydroxyeudesma-4(14),11(13)-dien-12-Oate gamma-lactone	Generator
8Β-hydroxyeudesma-4(14),11(13)-dien-12-Oate γ-lactone	Generator
8Β-hydroxyeudesma-4(14),11(13)-dien-12-Oic acid γ-lactone	Generator

Chemical Formula

C₁₅H₂₀O₂

Average Mass

232.3230 Da

Monoisotopic Mass

232.14633 Da

IUPAC Name

(3aR,4aS,8aR,9aR)-8a-methyl-3,5-dimethylidene-dodecahydronaphtho[2,3-b]furan-2-one

Traditional Name

isoalantolactone

CAS Registry Number

Not Available

SMILES

C[C@]12CCCC(=C)[C@@H]1C[C@H]1[C@@H](C2)OC(=O)C1=C

InChI Identifier

InChI=1S/C15H20O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h11-13H,1-2,4-8H2,3H3/t11-,12+,13-,15-/m1/s1

InChI Key

CVUANYCQTOGILD-QVHKTLOISA-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
Abutilon indicum	Plant	KNApSAcK
Ambrosia artemisioides	LOTUS Database	35616633
Artemisia feddei	LOTUS Database	35616633
Bidens subalternans	LOTUS Database	35616633
Carpesium longifolium	Plant	KNApSAcK
Carpesium macrocephalum	LOTUS Database	35616633
Craspedia glauca	LOTUS Database	35616633
Eupatorium cannabinum	LOTUS Database	35616633
Eupatorium quadrangulare	LOTUS Database	35616633
Flourensia riparia	LOTUS Database	35616633
Flourensia riparia Grisebach	Plant	KNApSAcK
Hypochoeris cretensis	Plant	KNApSAcK
Inula grandis	Plant	KNApSAcK
Inula helenium	Plant	KNApSAcK
Inula henium	Plant	KNApSAcK
Inula japonica	Plant	KNApSAcK
Inula magnifica	LOTUS Database	35616633
Inula racemosa	Plant	KNApSAcK
Inula royleana	Plant	KNApSAcK
Inula salicina	Plant	KNApSAcK
Liatris cylindrica	Plant	KNApSAcK
Ratibida columnaris	LOTUS Database	35616633
Rudbeckia mollis	LOTUS Database	35616633
Saussurea costus	Plant	KNApSAcK
Telekia speciosa	Plant	KNApSAcK
Trilophozia quinquedentata	LOTUS Database	35616633
Tritomaria quinquedentata (Huds.)	Plant	KNApSAcK
Xanthium canadense Mill.	Plant	KNApSAcK
Xanthium indicum	LOTUS Database	35616633
Xanthium strumarium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Eudesmanolides, secoeudesmanolides, and derivatives

Alternative Parents

Substituents

Eudesmanolide
Sesquiterpenoid
Naphthofuran
Gamma butyrolactone
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

sesquiterpene lactone (CHEBI:5981 )
eudesmane sesquiterpenoid (CHEBI:5981 )
Eudesmane sesquiterpenoids (C09484 )
Eudesmanes (C09484 )

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	3.15	ALOGPS
logP	3.36	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	66.2 m³·mol⁻¹	ChemAxon
Polarizability	26.09 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

C00003306

Chemspider ID

66028

KEGG Compound ID

C09484

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Helenin

METLIN ID

Not Available

PubChem Compound

73285

PDB ID

Not Available

ChEBI ID

5981

Good Scents ID

rw1065851

References

General References

Munoz-Tello P, Lin H, Khan P, de Vera IMS, Kamenecka TM, Kojetin DJ: Assessment of NR4A Ligands That Directly Bind and Modulate the Orphan Nuclear Receptor Nurr1. J Med Chem. 2020 Dec 24;63(24):15639-15654. doi: 10.1021/acs.jmedchem.0c00894. Epub 2020 Dec 8. [PubMed:33289551 ]
Song Y, Li X, Liu F, Zhu H, Shen Y: Isoalantolactone alleviates ovalbumininduced asthmatic inflammation by reducing alternatively activated macrophage and STAT6/PPARgamma/KLF4 signals. Mol Med Rep. 2021 Oct;24(4). pii: 701. doi: 10.3892/mmr.2021.12340. Epub 2021 Aug 9. [PubMed:34368878 ]
Kenny CR, Stojakowska A, Furey A, Lucey B: From Monographs to Chromatograms: The Antimicrobial Potential of Inula helenium L. (Elecampane) Naturalised in Ireland. Molecules. 2022 Feb 18;27(4). pii: molecules27041406. doi: 10.3390/molecules27041406. [PubMed:35209195 ]
Wu ZC, Hui XG, Huo L, Sun DX, Peng W, Zhang Y, Li XB, Ma T, Li WH, Liang J, Sun ZQ: Antiproliferative effects of isoalantolactone in human liver cancer cells are mediated through caspase-dependent apoptosis, ROS generation, suppression of cell migration and invasion and targeting Ras/Raf/MEK signalling pathway. Acta Biochim Pol. 2022 Apr 7. pii: 5704. doi: 10.18388/abp.2020_5704. [PubMed:35389600 ]
Wu F, Shao R, Zheng P, Zhang T, Qiu C, Sui H, Li S, Jin L, Pan H, Jin X, Zou P, Cui R, Xie C: Isoalantolactone Enhances the Antitumor Activity of Doxorubicin by Inducing Reactive Oxygen Species and DNA Damage. Front Oncol. 2022 Jan 25;12:813854. doi: 10.3389/fonc.2022.813854. eCollection 2022. [PubMed:35145916 ]
Kim MY, Lee H, Ji SY, Kim SY, Hwangbo H, Park SH, Kim GY, Park C, Leem SH, Hong SH, Choi YH: Induction of Apoptosis by Isoalantolactone in Human Hepatocellular Carcinoma Hep3B Cells through Activation of the ROS-Dependent JNK Signaling Pathway. Pharmaceutics. 2021 Oct 6;13(10). pii: pharmaceutics13101627. doi: 10.3390/pharmaceutics13101627. [PubMed:34683920 ]
Huang H, Li P, Ye X, Zhang F, Lin Q, Wu K, Chen W: Isoalantolactone Increases the Sensitivity of Prostate Cancer Cells to Cisplatin Treatment by Inducing Oxidative Stress. Front Cell Dev Biol. 2021 Apr 20;9:632779. doi: 10.3389/fcell.2021.632779. eCollection 2021. [PubMed:33959604 ]
Liu Y, Meng Q, Jing L, Feng L, Zhou Z, Ni Z: 11, 13-Dehydro Lactone Moiety in Gynecologic Cancer Cells. Iran J Public Health. 2020 Nov;49(11):2103-2110. doi: 10.18502/ijph.v49i11.4726. [PubMed:33680997 ]
Zhang C, Huang L, Xiong J, Xie L, Ying S, Jia Y, Yao Y, Song X, Zeng Z, Yuan J: Isoalantolactone inhibits pancreatic cancer proliferation by regulation of PI3K and Wnt signal pathway. PLoS One. 2021 Mar 4;16(3):e0247752. doi: 10.1371/journal.pone.0247752. eCollection 2021. [PubMed:33661942 ]
Kumar A, Agnihotri VK: NMR based profiling of sesquiterpene lactones in Saussurea lappa roots collected from different location of Western Himalaya. Nat Prod Res. 2022 Jan;36(2):621-624. doi: 10.1080/14786419.2020.1789635. Epub 2020 Jul 13. [PubMed:32657146 ]

Showing NP-Card for Isoalantolactone (NP0051915)

MOL for NP0051915 (Isoalantolactone)

3D MOL for NP0051915 (Isoalantolactone)

3D SDF for NP0051915 (Isoalantolactone)

3D-SDF for NP0051915 (Isoalantolactone)

PDB for NP0051915 (Isoalantolactone)

3D PDB for NP0051915 (Isoalantolactone)

SMILES for NP0051915 (Isoalantolactone)

INCHI for NP0051915 (Isoalantolactone)

Structure for NP0051915 (Isoalantolactone)

3D Structure for NP0051915 (Isoalantolactone)