NP-MRD: Showing NP-Card for [3aR-(3aalpha,4aalpha,7alpha,8abeta,9aalpha)]-Decahydro-7-hydroxy-8a-methyl-3,5-bis(methylene)-naphtho[2,3-b]furan-2(3H)-one (NP0051919)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-27 23:07:18 UTC

Updated at

2022-04-27 23:07:18 UTC

NP-MRD ID

NP0051919

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[3aR-(3aalpha,4aalpha,7alpha,8abeta,9aalpha)]-Decahydro-7-hydroxy-8a-methyl-3,5-bis(methylene)-naphtho[2,3-b]furan-2(3H)-one

Description

Ivalin 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. [3aR-(3aalpha,4aalpha,7alpha,8abeta,9aalpha)]-Decahydro-7-hydroxy-8a-methyl-3,5-bis(methylene)-naphtho[2,3-b]furan-2(3H)-one is found in Aldama canescens, Carpesium abrotanoides, Carpesium faberi, Carpesium macrocephalum, Carpesium spp., Centaurea cadmea, Dittrichia graveolens, Geigeria aspera, Greenmaniella resinosa, Inula anatolica, Inula sp., Iva imbricata, Iva microcephala, Klasea latifolia, Ondetia linearis, Sphagneticola trilobata, Viguiera linearis, Wedelia spp. and Zaluzania spp.. [3aR-(3aalpha,4aalpha,7alpha,8abeta,9aalpha)]-Decahydro-7-hydroxy-8a-methyl-3,5-bis(methylene)-naphtho[2,3-b]furan-2(3H)-one was first documented in 2017 (PMID: 30428197). Based on a literature review a significant number of articles have been published on Ivalin (PMID: 31617781) (PMID: 31207352) (PMID: 34063007) (PMID: 33477743) (PMID: 33328532) (PMID: 32708381).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
    3.9837   -1.5837    0.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3104   -0.4715    0.2309 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5781    0.6224    1.1533 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5870    0.6949    1.8980 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5177    1.5429    1.0430 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8627    1.3500   -0.2036 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4913    1.8680   -0.2654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5970    0.9050    0.0867 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5880    0.7192    1.5854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9447    1.3881   -0.3978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9906    0.4866    0.1947 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2458    0.8662   -0.3333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7391   -0.9661   -0.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4814   -1.2882   -0.7016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3775   -2.4094   -1.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3194   -0.3807   -0.6537 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9124   -0.9792   -0.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0653   -0.0938   -0.4768 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6493   -2.3015   -0.7087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8953   -1.8147    0.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4907    1.9224   -0.9496 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3932    2.7406    0.4450 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2544    2.2651   -1.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2906    1.4648    2.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4205    1.0049    2.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8975   -0.2697    1.9173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9598    1.3416   -1.5060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1172    2.4095   -0.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0418    0.7119    1.2931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9416    0.2808    0.0818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7141   -1.5213    0.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6370   -1.4092   -0.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2156   -3.0807   -1.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4747   -2.6825   -1.9024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0776   -0.0755   -1.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9047   -0.9801    1.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1021   -1.9951   -0.4444 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2325   -0.2823   -1.5723 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  1
  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
  2 18  1  0
 18 17  1  0
 17 16  1  0
 16 14  1  0
 14 15  2  3
 14 13  1  0
 13 11  1  0
 11 12  1  0
 11 10  1  0
 16  8  1  0
 10  8  1  0
 18  6  1  0
  9 24  1  0
  9 25  1  0
  9 26  1  0
  7 22  1  0
  7 23  1  0
  6 21  1  6
  1 19  1  0
  1 20  1  0
 18 38  1  6
 17 36  1  0
 17 37  1  0
 16 35  1  6
 15 33  1  0
 15 34  1  0
 13 31  1  0
 13 32  1  0
 11 29  1  1
 12 30  1  0
 10 27  1  0
 10 28  1  0
M  END


  Mrv1652304282201072D          

 18 20  0  0  1  0            999 V2000
    4.7812    1.1104    0.0000 C   0  0  1  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
    5.4957    0.6979    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  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
  1 18  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0051919

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]12C[C@H]3OC(=O)C(=C)[C@H]3C[C@H]1C(=C)C[C@H](O)C2

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-8-4-10(16)6-15(3)7-13-11(5-12(8)15)9(2)14(17)18-13/h10-13,16H,1-2,4-7H2,3H3/t10-,11+,12-,13+,15+/m0/s1

> <INCHI_KEY>
OVIILQQKQPCQTF-GGAZOKNXSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.322

> <EXACT_MASS>
248.141244504

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
26.949385529112096

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,4aS,7S,8aR,9aR)-7-hydroxy-8a-methyl-3,5-dimethylidene-dodecahydronaphtho[2,3-b]furan-2-one

> <ALOGPS_LOGP>
1.96

> <JCHEM_LOGP>
1.9712567949999997

> <ALOGPS_LOGS>
-2.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.845244997401377

> <JCHEM_PKA_STRONGEST_BASIC>
-1.1168890619543812

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
67.8669

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.11e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ivalin

> <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       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
HETATM   18  O   UNK     0      10.259   1.303   0.000  0.00  0.00           O+0
CONECT    1    2    7   18                                                  
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                                                            
CONECT   18    1                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₃

Average Mass

248.3220 Da

Monoisotopic Mass

248.14124 Da

IUPAC Name

(3aR,4aS,7S,8aR,9aR)-7-hydroxy-8a-methyl-3,5-dimethylidene-dodecahydronaphtho[2,3-b]furan-2-one

Traditional Name

ivalin

CAS Registry Number

Not Available

SMILES

C[C@@]12C[C@H]3OC(=O)C(=C)[C@H]3C[C@H]1C(=C)C[C@H](O)C2

InChI Identifier

InChI=1S/C15H20O3/c1-8-4-10(16)6-15(3)7-13-11(5-12(8)15)9(2)14(17)18-13/h10-13,16H,1-2,4-7H2,3H3/t10-,11+,12-,13+,15+/m0/s1

InChI Key

OVIILQQKQPCQTF-GGAZOKNXSA-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
Aldama canescens	LOTUS Database	35616633
Carpesium abrotanoides	LOTUS Database	35616633
Carpesium faberi	LOTUS Database	35616633
Carpesium macrocephalum	LOTUS Database	35616633
Carpesium spp.	Plant	KNApSAcK
Centaurea cadmea	LOTUS Database	35616633
Dittrichia graveolens	LOTUS Database	35616633
Geigeria aspera	LOTUS Database	35616633
Greenmaniella resinosa	LOTUS Database	35616633
Inula anatolica	Plant	KNApSAcK
Inula sp.	Plant	KNApSAcK
Iva imbricata	Plant	KNApSAcK
Iva microcephala	Plant	KNApSAcK
Klasea latifolia	LOTUS Database	35616633
Ondetia linearis	Plant	KNApSAcK
Sphagneticola trilobata	LOTUS Database	35616633
Viguiera linearis	LOTUS Database	35616633
Wedelia spp.	Plant	KNApSAcK
Zaluzania spp.	Plant	KNApSAcK

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
Cyclic alcohol
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

eudesmane sesquiterpenoid (CHEBI:6077 )
Eudesmanes (C09488 )

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	1.96	ALOGPS
logP	1.97	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	18.85	ChemAxon
pKa (Strongest Basic)	-1.1	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	67.87 m³·mol⁻¹	ChemAxon
Polarizability	26.95 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

C00003310

Chemspider ID

58663

KEGG Compound ID

C09488

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

65156

PDB ID

Not Available

ChEBI ID

6077

Good Scents ID

rw1434941

References

General References

Fouche G, Ackerman LGJ, Venter EA, Mathe YZ, Liles DC, Botha CJ: Sesquiterpene lactones from Geigeria aspera Harv. and their cytotoxicity. Nat Prod Res. 2021 Jul;35(14):2353-2359. doi: 10.1080/14786419.2019.1675068. Epub 2019 Oct 16. [PubMed:31617781 ]
Botha CJ, Venter EA, Ferreira GCH, Phaswane RM, Clift SJ: Geigerin-induced disorganization of desmin, an intermediate filament of the cytoskeleton, in a murine myoblast cell line (C2C12). Toxicon. 2019 Sep;167:162-167. doi: 10.1016/j.toxicon.2019.06.014. Epub 2019 Jun 14. [PubMed:31207352 ]
Karpinski TM, Ozarowski M, Seremak-Mrozikiewicz A, Wolski H, Adamczak A: Plant Preparations and Compounds with Activities against Biofilms Formed by Candida spp. J Fungi (Basel). 2021 May 5;7(5). pii: jof7050360. doi: 10.3390/jof7050360. [PubMed:34063007 ]
Shah MD, Tani K, Yong YS, Ching FF, Shaleh SRM, Vairappan CS, Venmathi Maran BA: Antiparasitic Potential of Chromatographic Fractions of Nephrolepis biserrata and Liquid Chromatography-Quadrupole Time-of-Flight-Mass Spectrometry Analysis. Molecules. 2021 Jan 19;26(2). pii: molecules26020499. doi: 10.3390/molecules26020499. [PubMed:33477743 ]
Shah MD, Venmathi Maran BA, Haron FK, Ransangan J, Ching FF, Shaleh SRM, Shapawi R, Yong YS, Ohtsuka S: Antiparasitic potential of Nephrolepis biserrata methanol extract against the parasitic leech Zeylanicobdella arugamensis (Hirudinea) and LC-QTOF analysis. Sci Rep. 2020 Dec 16;10(1):22091. doi: 10.1038/s41598-020-79094-4. [PubMed:33328532 ]
Botha CJ, Mathe YZ, Ferreira GCH, Venter EA: Cytotoxicity of the Sesquiterpene Lactones, Ivalin and Parthenolide in Murine Muscle Cell Lines and Their Effect on Desmin, a Cytoskeletal Intermediate Filament. Toxins (Basel). 2020 Jul 18;12(7). pii: toxins12070459. doi: 10.3390/toxins12070459. [PubMed:32708381 ]
Han Z, Liu FY, Lin SQ, Zhang CY, Ma JH, Guo C, Jia FJ, Zhang Q, Xie WD, Li X: Ivalin Induces Mitochondria-Mediated Apoptosis Associated with the NF-kappaB Activation in Human Hepatocellular Carcinoma SMMC-7721 Cells. Molecules. 2019 Oct 22;24(20). pii: molecules24203809. doi: 10.3390/molecules24203809. [PubMed:31652659 ]
Liu F, Lin S, Zhang C, Ma J, Han Z, Jia F, Xie W, Li X: The Novel Nature Microtubule Inhibitor Ivalin Induces G2/M Arrest and Apoptosis in Human Hepatocellular Carcinoma SMMC-7721 Cells In Vitro. Medicina (Kaunas). 2019 Aug 12;55(8). pii: medicina55080470. doi: 10.3390/medicina55080470. [PubMed:31409007 ]
Ma JH, Qi J, Liu FY, Lin SQ, Zhang CY, Xie WD, Zhang HY, Li X: Ivalin Inhibits Proliferation, Migration and Invasion by Suppressing Epithelial Mesenchymal Transition in Breast Cancer Cells. Nutr Cancer. 2018 Nov-Dec;70(8):1330-1338. doi: 10.1080/01635581.2018.1539185. Epub 2018 Nov 21. [PubMed:30463445 ]
Ivanova V, Trendafilova A, Todorova M, Danova K, Dimitrov D: Phytochemical Profile of Inula britannica from Bulgaria. Nat Prod Commun. 2017 Feb;12(2):153-154. [PubMed:30428197 ]

Showing NP-Card for [3aR-(3aalpha,4aalpha,7alpha,8abeta,9aalpha)]-Decahydro-7-hydroxy-8a-methyl-3,5-bis(methylene)-naphtho[2,3-b]furan-2(3H)-one (NP0051919)

MOL for NP0051919 ([3aR-(3aalpha,4aalpha,7alpha,8abeta,9aalpha)]-Decahydro-7-hydroxy-8a-methyl-3,5-bis(methylene)-naphtho[2,3-b]furan-2(3H)-one)

3D MOL for NP0051919 ([3aR-(3aalpha,4aalpha,7alpha,8abeta,9aalpha)]-Decahydro-7-hydroxy-8a-methyl-3,5-bis(methylene)-naphtho[2,3-b]furan-2(3H)-one)

3D SDF for NP0051919 ([3aR-(3aalpha,4aalpha,7alpha,8abeta,9aalpha)]-Decahydro-7-hydroxy-8a-methyl-3,5-bis(methylene)-naphtho[2,3-b]furan-2(3H)-one)

3D-SDF for NP0051919 ([3aR-(3aalpha,4aalpha,7alpha,8abeta,9aalpha)]-Decahydro-7-hydroxy-8a-methyl-3,5-bis(methylene)-naphtho[2,3-b]furan-2(3H)-one)

PDB for NP0051919 ([3aR-(3aalpha,4aalpha,7alpha,8abeta,9aalpha)]-Decahydro-7-hydroxy-8a-methyl-3,5-bis(methylene)-naphtho[2,3-b]furan-2(3H)-one)

3D PDB for NP0051919 ([3aR-(3aalpha,4aalpha,7alpha,8abeta,9aalpha)]-Decahydro-7-hydroxy-8a-methyl-3,5-bis(methylene)-naphtho[2,3-b]furan-2(3H)-one)

SMILES for NP0051919 ([3aR-(3aalpha,4aalpha,7alpha,8abeta,9aalpha)]-Decahydro-7-hydroxy-8a-methyl-3,5-bis(methylene)-naphtho[2,3-b]furan-2(3H)-one)

INCHI for NP0051919 ([3aR-(3aalpha,4aalpha,7alpha,8abeta,9aalpha)]-Decahydro-7-hydroxy-8a-methyl-3,5-bis(methylene)-naphtho[2,3-b]furan-2(3H)-one)

Structure for NP0051919 ([3aR-(3aalpha,4aalpha,7alpha,8abeta,9aalpha)]-Decahydro-7-hydroxy-8a-methyl-3,5-bis(methylene)-naphtho[2,3-b]furan-2(3H)-one)

3D Structure for NP0051919 ([3aR-(3aalpha,4aalpha,7alpha,8abeta,9aalpha)]-Decahydro-7-hydroxy-8a-methyl-3,5-bis(methylene)-naphtho[2,3-b]furan-2(3H)-one)