NP-MRD: Showing NP-Card for 4-[(1r,3as,3br,5ar,7s,9ar,9bs,11ar)-3a-hydroxy-9a-(hydroxymethyl)-11a-methyl-7-{[(3r,4r,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one (NP0195585)

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Record Information

Version

2.0

Created at

2022-09-04 13:28:25 UTC

Updated at

2022-09-04 13:28:25 UTC

NP-MRD ID

NP0195585

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[(1r,3as,3br,5ar,7s,9ar,9bs,11ar)-3a-hydroxy-9a-(hydroxymethyl)-11a-methyl-7-{[(3r,4r,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one

Description

Frugoside belongs to the class of organic compounds known as cardenolide glycosides and derivatives. Cardenolide glycosides and derivatives are compounds containing a carbohydrate glycosidically bound to the cardenolide moiety. 4-[(1r,3as,3br,5ar,7s,9ar,9bs,11ar)-3a-hydroxy-9a-(hydroxymethyl)-11a-methyl-7-{[(3r,4r,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one is found in Asclepias curassavica, Asclepias incarnata, Asclepias tuberosa, Calotropis gigantea, Calotropis procera, Danaus plexippus and Gomphocarpus sinaicus. 4-[(1r,3as,3br,5ar,7s,9ar,9bs,11ar)-3a-hydroxy-9a-(hydroxymethyl)-11a-methyl-7-{[(3r,4r,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one was first documented in 2013 (PMID: 24012528). Based on a literature review a small amount of articles have been published on Frugoside (PMID: 33493345) (PMID: 31248223) (PMID: 27173346) (PMID: 24678783).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042215282D          

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M  END

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M  END


  Mrv1652309042215282D          

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    5.2939   -0.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0646   -0.0646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7474    0.3984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7742    1.2229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3987   -0.1080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1184   -0.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168   -2.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340   -2.7639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826   -2.2576    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4850   -3.0585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705   -2.4028    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5902   -3.1787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781   -3.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -2.6932    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4342   -2.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6582   -3.7596    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1539   -3.6143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9385   -4.5355    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4067   -5.1662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7507   -4.6807    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0310   -5.4566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 18 23  1  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 15 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 12 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 31 30  1  6  0  0  0
  9 31  1  0  0  0  0
 31 32  1  0  0  0  0
  6 32  1  0  0  0  0
  4 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
 35 36  1  6  0  0  0
 35 37  1  0  0  0  0
  2 37  1  0  0  0  0
 37 38  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0195585

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1OC(O[C@H]2CC[C@@]3(CO)[C@H](CC[C@@H]4[C@@H]3CC[C@]3(C)[C@H](CC[C@]43O)C3=CC(=O)OC3)C2)[C@H](O)[C@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C29H44O9/c1-15-23(32)24(33)25(34)26(37-15)38-18-5-9-28(14-30)17(12-18)3-4-21-20(28)6-8-27(2)19(7-10-29(21,27)35)16-11-22(31)36-13-16/h11,15,17-21,23-26,30,32-35H,3-10,12-14H2,1-2H3/t15-,17-,18+,19-,20+,21-,23-,24-,25-,26?,27-,28-,29+/m1/s1

> <INCHI_KEY>
WPVGSIBYLZQSIK-VEZJFPMXSA-N

> <FORMULA>
C29H44O9

> <MOLECULAR_WEIGHT>
536.662

> <EXACT_MASS>
536.298532997

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
57.80259527341782

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[(1S,2R,5S,7R,10R,11S,14R,15R)-11-hydroxy-2-(hydroxymethyl)-15-methyl-5-{[(3R,4R,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2,5-dihydrofuran-2-one

> <JCHEM_LOGP>
1.0626577513333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.224383119900558

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.182632280316325

> <JCHEM_PKA_STRONGEST_BASIC>
0.26970059575976135

> <JCHEM_POLAR_SURFACE_AREA>
145.91

> <JCHEM_REFRACTIVITY>
136.2849

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
4-[(1S,2R,5S,7R,10R,11S,14R,15R)-11-hydroxy-2-(hydroxymethyl)-15-methyl-5-{[(3R,4R,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.777  -7.831   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.261  -7.560   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.737  -6.112   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.221  -5.841   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.698  -4.392   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.182  -4.121   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.341  -2.673   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.857  -2.402   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.850  -3.579   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.373  -2.131   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.380  -0.953   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.366  -3.308   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.889  -1.859   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.405  -1.588   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.398  -2.766   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.069  -1.380   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.937  -2.816   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.882  -1.600   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.454  -0.121   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.728   0.744   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.779   2.283   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      11.944  -0.202   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      11.421  -1.650   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.365  -4.295   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.090  -5.159   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.874  -4.214   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.505  -5.709   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.358  -4.485   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.835  -5.934   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.319  -6.205   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.326  -5.027   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.810  -5.298   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.229  -7.018   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.287  -6.747   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -1.752  -8.466   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -0.759  -9.644   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -3.268  -8.737   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -3.791 -10.186   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   37                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   33                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   32                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   12   31                                             
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   28                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   26                                             
CONECT   16   15                                                            
CONECT   17   15   18   24                                                  
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   18                                                       
CONECT   24   17   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   15   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   12   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30    9   32                                                  
CONECT   32   31    6                                                       
CONECT   33    4   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35    2   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   86    0
END

View in JSmol

Synonyms

Value	Source
Cannogenol-3-O-beta-D-allomethyloside	MeSH

Chemical Formula

C₂₉H₄₄O₉

Average Mass

536.6620 Da

Monoisotopic Mass

536.29853 Da

IUPAC Name

4-[(1S,2R,5S,7R,10R,11S,14R,15R)-11-hydroxy-2-(hydroxymethyl)-15-methyl-5-{[(3R,4R,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2,5-dihydrofuran-2-one

Traditional Name

4-[(1S,2R,5S,7R,10R,11S,14R,15R)-11-hydroxy-2-(hydroxymethyl)-15-methyl-5-{[(3R,4R,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-5H-furan-2-one

CAS Registry Number

Not Available

SMILES

C[C@H]1OC(O[C@H]2CC[C@@]3(CO)[C@H](CC[C@@H]4[C@@H]3CC[C@]3(C)[C@H](CC[C@]43O)C3=CC(=O)OC3)C2)[C@H](O)[C@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C29H44O9/c1-15-23(32)24(33)25(34)26(37-15)38-18-5-9-28(14-30)17(12-18)3-4-21-20(28)6-8-27(2)19(7-10-29(21,27)35)16-11-22(31)36-13-16/h11,15,17-21,23-26,30,32-35H,3-10,12-14H2,1-2H3/t15-,17-,18+,19-,20+,21-,23-,24-,25-,26?,27-,28-,29+/m1/s1

InChI Key

WPVGSIBYLZQSIK-VEZJFPMXSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Asclepias curassavica	LOTUS Database	35616633
Asclepias incarnata	LOTUS Database	35616633
Asclepias tuberosa	LOTUS Database	35616633
Calotropis gigantea	LOTUS Database	35616633
Calotropis procera	LOTUS Database	35616633
Danaus plexippus	LOTUS Database	35616633
Gomphocarpus sinaicus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cardenolide glycosides and derivatives. Cardenolide glycosides and derivatives are compounds containing a carbohydrate glycosidically bound to the cardenolide moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Cardenolide glycosides and derivatives

Alternative Parents

Substituents

Cardanolide-glycoside
Steroidal glycoside
19-hydroxysteroid
14-hydroxysteroid
Hydroxysteroid
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
2-furanone
Monosaccharide
Oxane
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Oxacycle
Organoheterocyclic compound
Organic oxide
Organic oxygen compound
Primary alcohol
Alcohol
Hydrocarbon derivative
Carbonyl group
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	1.06	ChemAxon
pKa (Strongest Acidic)	7.18	ChemAxon
pKa (Strongest Basic)	0.27	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	145.91 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	136.28 m³·mol⁻¹	ChemAxon
Polarizability	57.8 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00032985

Chemspider ID

107771

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

120728

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang H, Zhang H, Fan K, Zhang D, Hu A, Zeng X, Liu YL, Tan G, Wang H: Frugoside delays osteoarthritis progression via inhibiting miR-155-modulated synovial macrophage M1 polarization. Rheumatology (Oxford). 2021 Oct 2;60(10):4899-4909. doi: 10.1093/rheumatology/keab018. [PubMed:33493345 ]
Song IS, Jeong YJ, Kim JE, Shin J, Jang SW: Frugoside Induces Mitochondria-Mediated Apoptotic Cell Death through Inhibition of Sulfiredoxin Expression in Melanoma Cells. Cancers (Basel). 2019 Jun 19;11(6):854. doi: 10.3390/cancers11060854. [PubMed:31248223 ]
Gurung AB, Ali MA, Bhattacharjee A, AbulFarah M, Al-Hemaid F, Abou-Tarboush FM, Al-Anazi KM, Al-Anazi FS, Lee J: Molecular docking of the anticancer bioactive compound proceraside with macromolecules involved in the cell cycle and DNA replication. Genet Mol Res. 2016 May 9;15(2). doi: 10.4238/gmr.15027829. [PubMed:27173346 ]
Ibrahim SR, Mohamed GA, Shaala LA, Moreno L, Banuls Y, Kiss R, Youssef DT: Proceraside A, a new cardiac glycoside from the root barks of Calotropis procera with in vitro anticancer effects. Nat Prod Res. 2014;28(17):1322-7. doi: 10.1080/14786419.2014.901323. Epub 2014 Mar 31. [PubMed:24678783 ]
Kadiyala M, Ponnusankar S, Elango K: Calotropis gigantiea (L.) R. Br (Apocynaceae): a phytochemical and pharmacological review. J Ethnopharmacol. 2013 Oct 28;150(1):32-50. doi: 10.1016/j.jep.2013.08.045. Epub 2013 Sep 6. [PubMed:24012528 ]
LOTUS database [Link]

Showing NP-Card for 4-[(1r,3as,3br,5ar,7s,9ar,9bs,11ar)-3a-hydroxy-9a-(hydroxymethyl)-11a-methyl-7-{[(3r,4r,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one (NP0195585)

MOL for NP0195585 (4-[(1r,3as,3br,5ar,7s,9ar,9bs,11ar)-3a-hydroxy-9a-(hydroxymethyl)-11a-methyl-7-{[(3r,4r,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

3D MOL for NP0195585 (4-[(1r,3as,3br,5ar,7s,9ar,9bs,11ar)-3a-hydroxy-9a-(hydroxymethyl)-11a-methyl-7-{[(3r,4r,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

3D SDF for NP0195585 (4-[(1r,3as,3br,5ar,7s,9ar,9bs,11ar)-3a-hydroxy-9a-(hydroxymethyl)-11a-methyl-7-{[(3r,4r,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

3D-SDF for NP0195585 (4-[(1r,3as,3br,5ar,7s,9ar,9bs,11ar)-3a-hydroxy-9a-(hydroxymethyl)-11a-methyl-7-{[(3r,4r,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

PDB for NP0195585 (4-[(1r,3as,3br,5ar,7s,9ar,9bs,11ar)-3a-hydroxy-9a-(hydroxymethyl)-11a-methyl-7-{[(3r,4r,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

3D PDB for NP0195585 (4-[(1r,3as,3br,5ar,7s,9ar,9bs,11ar)-3a-hydroxy-9a-(hydroxymethyl)-11a-methyl-7-{[(3r,4r,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

SMILES for NP0195585 (4-[(1r,3as,3br,5ar,7s,9ar,9bs,11ar)-3a-hydroxy-9a-(hydroxymethyl)-11a-methyl-7-{[(3r,4r,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

INCHI for NP0195585 (4-[(1r,3as,3br,5ar,7s,9ar,9bs,11ar)-3a-hydroxy-9a-(hydroxymethyl)-11a-methyl-7-{[(3r,4r,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

Structure for NP0195585 (4-[(1r,3as,3br,5ar,7s,9ar,9bs,11ar)-3a-hydroxy-9a-(hydroxymethyl)-11a-methyl-7-{[(3r,4r,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

3D Structure for NP0195585 (4-[(1r,3as,3br,5ar,7s,9ar,9bs,11ar)-3a-hydroxy-9a-(hydroxymethyl)-11a-methyl-7-{[(3r,4r,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)