NP-MRD: Showing NP-Card for [3S-(3alpha,3aalpha,5abeta,9bbeta)]-3a,5,5a,7,8,9b-Hexahydro-3,5a,9-trimethylnaphtho[1,2-b]furan-2,6(3H,4H)-dione (NP0059534)

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Record Information

Version

2.0

Created at

2022-04-28 04:45:23 UTC

Updated at

2022-04-28 04:45:23 UTC

NP-MRD ID

NP0059534

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[3S-(3alpha,3aalpha,5abeta,9bbeta)]-3a,5,5a,7,8,9b-Hexahydro-3,5a,9-trimethylnaphtho[1,2-b]furan-2,6(3H,4H)-dione

Description

Gracilin 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. [3S-(3alpha,3aalpha,5abeta,9bbeta)]-3a,5,5a,7,8,9b-Hexahydro-3,5a,9-trimethylnaphtho[1,2-b]furan-2,6(3H,4H)-dione is found in Artemisia afra, Artemisia barrelieri, Artemisia fragrans, Artemisia gmelinii, Artemisia gracilescens, Artemisia granatensis , Artemisia hanseniana, Artemisia herba-alba, Artemisia maritima, Artemisia santolinifolia, Artemisia taurica, Artemisia tenuisecta, Artemisia vestita , Delphinium gracile and Dioscorea communis. [3S-(3alpha,3aalpha,5abeta,9bbeta)]-3a,5,5a,7,8,9b-Hexahydro-3,5a,9-trimethylnaphtho[1,2-b]furan-2,6(3H,4H)-dione was first documented in 2002 (PMID: 12227201). Based on a literature review a significant number of articles have been published on Gracilin (PMID: 19601607) (PMID: 31729596) (PMID: 27822214) (PMID: 26356268) (PMID: 18788476) (PMID: 31387354).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
   -1.2208    2.7884    0.0461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5518    1.3400    0.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6365    0.3876   -0.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7179    0.7101   -0.4132 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3179    1.8375    0.1911 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6826    1.6731   -0.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5262    2.5862    0.0810 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9725    0.2564   -0.3644 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1874   -0.2662    0.3608 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6992   -0.3659    0.0861 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2782   -1.6336   -0.5379 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0169   -2.0309    0.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0635   -1.0250    0.1079 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0011   -1.4453   -1.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8989   -1.0627    1.3600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6302   -1.7424    2.3195 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0962   -0.2123    1.3738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9523    1.0359    0.5544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9581    3.2387    1.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1408    3.2969   -0.3090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4693    2.9792   -0.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8623    0.8234   -1.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1649    0.1579   -1.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1144   -0.1718    1.4563 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2600   -1.3457    0.1163 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0724    0.2305   -0.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6724   -0.3733    1.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0228   -2.4274   -0.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9622   -1.4293   -1.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3218   -2.9841   -0.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3176   -2.2488    1.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1295   -0.5670   -1.6781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9859   -1.7613   -0.6621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5063   -2.2254   -1.6566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9476   -0.8437    0.9913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3803    0.0435    2.4175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5273    0.8924   -0.3843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4294    1.8844    1.0835 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18  2  1  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  4 10  1  0
  3 13  1  0
  9 24  1  0
  9 25  1  0
  9 26  1  0
  8 23  1  6
 10 27  1  1
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  6
M  END


  Mrv1652304282206452D          

 18 20  0  0  1  0            999 V2000
    1.9878    2.2242    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5978    1.4972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0325    0.7959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8571    0.8217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2470    1.5487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8124    2.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2024    2.9770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6425    0.0689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7732    1.4714    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3386    2.1727    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7286    2.8997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5532    2.9254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4626    1.9760    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5232    1.1532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2244    0.7186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2406    0.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0926    2.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3778    2.9512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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
  1  6  1  0  0  0  0
  6  7  2  0  0  0  0
  3  8  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
  1 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 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
 13 17  1  1  0  0  0
  1 18  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0059534

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@@H]2CC[C@@]3(C)C(=O)CCC(C)=C3[C@H]2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-8-4-5-11(16)15(3)7-6-10-9(2)14(17)18-13(10)12(8)15/h9-10,13H,4-7H2,1-3H3/t9-,10-,13-,15-/m0/s1

> <INCHI_KEY>
RSDQBPGKMDFRHH-MJVIGCOGSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.322

> <EXACT_MASS>
248.141244504

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
27.26219091841123

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,3aS,5aR,9bS)-3,5a,9-trimethyl-2H,3H,3aH,4H,5H,5aH,6H,7H,8H,9bH-naphtho[1,2-b]furan-2,6-dione

> <ALOGPS_LOGP>
2.56

> <JCHEM_LOGP>
2.6033532213333337

> <ALOGPS_LOGS>
-2.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.784543984570657

> <JCHEM_PKA_STRONGEST_BASIC>
-6.9661119436428764

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
67.73910000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.46e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,3aS,5aR,9bS)-3,5a,9-trimethyl-3H,3aH,4H,5H,7H,8H,9bH-naphtho[1,2-b]furan-2,6-dione

> <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       3.711   4.152   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.983   2.795   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.794   1.486   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.333   1.534   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.061   2.891   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.250   4.200   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.978   5.557   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.066   0.129   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.443   2.747   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.632   4.056   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.360   5.413   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.899   5.461   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.863   3.689   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.977   2.153   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.286   1.341   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.449   1.571   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.040   4.683   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.439   5.509   0.000  0.00  0.00           C+0
CONECT    1    2    6   12   18                                             
CONECT    2    1    3    9                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    3                                                            
CONECT    9    2   10   16                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11    1                                                       
CONECT   13   10   14   17                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    9                                                       
CONECT   17   13                                                            
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

(3S,3aS,5aR,9bS)-3,5a,9-trimethyl-2H,3H,3aH,4H,5H,5aH,6H,7H,8H,9bH-naphtho[1,2-b]furan-2,6-dione

Traditional Name

(3S,3aS,5aR,9bS)-3,5a,9-trimethyl-3H,3aH,4H,5H,7H,8H,9bH-naphtho[1,2-b]furan-2,6-dione

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@@H]2CC[C@@]3(C)C(=O)CCC(C)=C3[C@H]2OC1=O

InChI Identifier

InChI=1S/C15H20O3/c1-8-4-5-11(16)15(3)7-6-10-9(2)14(17)18-13(10)12(8)15/h9-10,13H,4-7H2,1-3H3/t9-,10-,13-,15-/m0/s1

InChI Key

RSDQBPGKMDFRHH-MJVIGCOGSA-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
Artemisia afra	LOTUS Database	35616633
Artemisia barrelieri	LOTUS Database	35616633
Artemisia fragrans	Plant	KNApSAcK
Artemisia gmelinii	LOTUS Database	35616633
Artemisia gracilescens	LOTUS Database	35616633
Artemisia granatensis	Plant	KNApSAcK
Artemisia hanseniana	Plant	KNApSAcK
Artemisia herba-alba	LOTUS Database	35616633
Artemisia maritima	LOTUS Database	35616633
Artemisia santolinifolia	LOTUS Database	35616633
Artemisia taurica	Plant	KNApSAcK
Artemisia tenuisecta	LOTUS Database	35616633
Artemisia vestita	Plant	KNApSAcK
Delphinium gracile	LOTUS Database	35616633
Dioscorea communis	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
Cyclohexenone
Gamma butyrolactone
Tetrahydrofuran
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
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	2.56	ALOGPS
logP	2.6	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	19.78	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	67.74 m³·mol⁻¹	ChemAxon
Polarizability	27.26 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

C00013081

Chemspider ID

183539

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

211707

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Rateb ME, Houssen WE, Schumacher M, Harrison WT, Diederich M, Ebel R, Jaspars M: Bioactive diterpene derivatives from the marine sponge Spongionella sp. J Nat Prod. 2009 Aug;72(8):1471-6. doi: 10.1021/np900233c. [PubMed:19601607 ]
Gegunde S, Alfonso A, Alonso E, Alvarino R, Botana LM: Gracilin-Derivatives as Lead Compounds for Anti-inflammatory Effects. Cell Mol Neurobiol. 2020 May;40(4):603-615. doi: 10.1007/s10571-019-00758-5. Epub 2019 Nov 15. [PubMed:31729596 ]
Sanchez JA, Alfonso A, Rodriguez I, Alonso E, Cifuentes JM, Bermudez R, Rateb ME, Jaspars M, Houssen WE, Ebel R, Tabudravu J, Botana LM: Spongionella Secondary Metabolites, Promising Modulators of Immune Response through CD147 Receptor Modulation. Front Immunol. 2016 Oct 24;7:452. doi: 10.3389/fimmu.2016.00452. eCollection 2016. [PubMed:27822214 ]
Sanchez JA, Alfonso A, Leiros M, Alonso E, Rateb ME, Jaspars M, Houssen WE, Ebel R, Botana LM: Spongionella Secondary Metabolites Regulate Store Operated Calcium Entry Modulating Mitochondrial Functioning in SH-SY5Y Neuroblastoma Cells. Cell Physiol Biochem. 2015;37(2):779-92. doi: 10.1159/000430395. Epub 2015 Sep 11. [PubMed:26356268 ]
Nirmal N, Praba GO, Velmurugan D: Modeling studies on phospholipase A2-inhibitor complexes. Indian J Biochem Biophys. 2008 Aug;45(4):256-62. [PubMed:18788476 ]
Alvarino R, Alonso E, Abbasov ME, Chaheine CM, Conner ML, Romo D, Alfonso A, Botana LM: Gracilin A Derivatives Target Early Events in Alzheimer's Disease: in Vitro Effects on Neuroinflammation and Oxidative Stress. ACS Chem Neurosci. 2019 Sep 18;10(9):4102-4111. doi: 10.1021/acschemneuro.9b00329. Epub 2019 Aug 23. [PubMed:31387354 ]
Abbasov ME, Alvarino R, Chaheine CM, Alonso E, Sanchez JA, Conner ML, Alfonso A, Jaspars M, Botana LM, Romo D: Simplified immunosuppressive and neuroprotective agents based on gracilin A. Nat Chem. 2019 Apr;11(4):342-350. doi: 10.1038/s41557-019-0230-0. Epub 2019 Mar 22. [PubMed:30903037 ]
Sanchez JA, Alfonso A, Leiros M, Alonso E, Rateb ME, Jaspars M, Houssen WE, Ebel R, Tabudravu J, Botana LM: Identification of Spongionella compounds as cyclosporine A mimics. Pharmacol Res. 2016 May;107:407-414. doi: 10.1016/j.phrs.2016.03.029. Epub 2016 Apr 1. [PubMed:27041481 ]
Leiros M, Alonso E, Rateb ME, Houssen WE, Ebel R, Jaspars M, Alfonso A, Botana LM: Gracilins: Spongionella-derived promising compounds for Alzheimer disease. Neuropharmacology. 2015 Jun;93:285-93. doi: 10.1016/j.neuropharm.2015.02.015. Epub 2015 Feb 24. [PubMed:25724081 ]
Liu HW, Hu K, Zhao QC, Cui CB, Kobayashi H, Yao XS: Bioactive saponins from Dioscorea futschauensis. Pharmazie. 2002 Aug;57(8):570-2. [PubMed:12227201 ]

Showing NP-Card for [3S-(3alpha,3aalpha,5abeta,9bbeta)]-3a,5,5a,7,8,9b-Hexahydro-3,5a,9-trimethylnaphtho[1,2-b]furan-2,6(3H,4H)-dione (NP0059534)

MOL for NP0059534 ([3S-(3alpha,3aalpha,5abeta,9bbeta)]-3a,5,5a,7,8,9b-Hexahydro-3,5a,9-trimethylnaphtho[1,2-b]furan-2,6(3H,4H)-dione)

3D MOL for NP0059534 ([3S-(3alpha,3aalpha,5abeta,9bbeta)]-3a,5,5a,7,8,9b-Hexahydro-3,5a,9-trimethylnaphtho[1,2-b]furan-2,6(3H,4H)-dione)

3D SDF for NP0059534 ([3S-(3alpha,3aalpha,5abeta,9bbeta)]-3a,5,5a,7,8,9b-Hexahydro-3,5a,9-trimethylnaphtho[1,2-b]furan-2,6(3H,4H)-dione)

3D-SDF for NP0059534 ([3S-(3alpha,3aalpha,5abeta,9bbeta)]-3a,5,5a,7,8,9b-Hexahydro-3,5a,9-trimethylnaphtho[1,2-b]furan-2,6(3H,4H)-dione)

PDB for NP0059534 ([3S-(3alpha,3aalpha,5abeta,9bbeta)]-3a,5,5a,7,8,9b-Hexahydro-3,5a,9-trimethylnaphtho[1,2-b]furan-2,6(3H,4H)-dione)

3D PDB for NP0059534 ([3S-(3alpha,3aalpha,5abeta,9bbeta)]-3a,5,5a,7,8,9b-Hexahydro-3,5a,9-trimethylnaphtho[1,2-b]furan-2,6(3H,4H)-dione)

SMILES for NP0059534 ([3S-(3alpha,3aalpha,5abeta,9bbeta)]-3a,5,5a,7,8,9b-Hexahydro-3,5a,9-trimethylnaphtho[1,2-b]furan-2,6(3H,4H)-dione)

INCHI for NP0059534 ([3S-(3alpha,3aalpha,5abeta,9bbeta)]-3a,5,5a,7,8,9b-Hexahydro-3,5a,9-trimethylnaphtho[1,2-b]furan-2,6(3H,4H)-dione)

Structure for NP0059534 ([3S-(3alpha,3aalpha,5abeta,9bbeta)]-3a,5,5a,7,8,9b-Hexahydro-3,5a,9-trimethylnaphtho[1,2-b]furan-2,6(3H,4H)-dione)

3D Structure for NP0059534 ([3S-(3alpha,3aalpha,5abeta,9bbeta)]-3a,5,5a,7,8,9b-Hexahydro-3,5a,9-trimethylnaphtho[1,2-b]furan-2,6(3H,4H)-dione)