NP-MRD: Showing NP-Card for (+)-Argeloside O (NP0077881)

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Record Information

Version

1.0

Created at

2022-04-28 23:01:43 UTC

Updated at

2022-04-28 23:01:43 UTC

NP-MRD ID

NP0077881

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Argeloside O

Description

(2R)-2-[(1R)-3-methoxy-3-oxo-1-{[(1S,2R,7S,10R,11S,14R,15R,16R,19S)-10,14,16-trimethyl-17,20,21-trioxahexacyclo[14.4.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,¹⁹]Henicos-4-en-7-yl]oxy}propoxy]propanoic acid belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. (+)-Argeloside O is found in Solenostemma argel . Based on a literature review very few articles have been published on (2R)-2-[(1R)-3-methoxy-3-oxo-1-{[(1S,2R,7S,10R,11S,14R,15R,16R,19S)-10,14,16-trimethyl-17,20,21-trioxahexacyclo[14.4.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,¹⁹]Henicos-4-en-7-yl]oxy}propoxy]propanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292201012D          

 37 42  0  0  1  0            999 V2000
    5.1125   -3.0641    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3980   -3.4766    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6835   -3.0641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9691   -3.4766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9691   -4.3016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6835   -4.7141    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3980   -4.3016    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1125   -4.7141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7879   -2.3808    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3211   -1.7535    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6902   -2.2960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5401   -5.9516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6033   -8.0141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1112   -9.2516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
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  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
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  1 13  1  6  0  0  0
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  1 17  1  0  0  0  0
 12 18  1  6  0  0  0
 10 19  1  6  0  0  0
  6 20  1  0  0  0  0
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  5 23  1  0  0  0  0
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 25 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
  6 37  1  6  0  0  0
M  END

     RDKit          3D

 77 82  0  0  0  0  0  0  0  0999 V2000
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 31 71  1  0
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M  END


  Mrv1652304292201012D          

 37 42  0  0  1  0            999 V2000
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    4.3980   -3.4766    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.1112   -9.2516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2546   -7.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2546   -8.0141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9190   -8.7678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9691   -8.4266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9691   -9.2516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3980   -5.1266    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  1  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  1 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  1  0  0  0
  1 17  1  0  0  0  0
 12 18  1  6  0  0  0
 10 19  1  6  0  0  0
  6 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  5 23  1  0  0  0  0
 22 24  1  6  0  0  0
 25 24  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 25 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
  6 37  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0077881

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C[C@@H](O[C@H](C)C(O)=O)O[C@H]1CC[C@]2(C)[C@H]3CC[C@]4(C)[C@@H]5[C@H]6CO[C@]5(C)O[C@@]4(O6)[C@@H]3CC=C2C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H40O9/c1-15(24(30)31)34-22(13-21(29)32-5)35-17-8-10-25(2)16(12-17)6-7-19-18(25)9-11-26(3)23-20-14-33-27(23,4)37-28(19,26)36-20/h6,15,17-20,22-23H,7-14H2,1-5H3,(H,30,31)/t15-,17+,18+,19-,20-,22+,23+,25+,26-,27-,28+/m1/s1

> <INCHI_KEY>
LAGKFZXTTOABAX-JGGUGFFYSA-N

> <FORMULA>
C28H40O9

> <MOLECULAR_WEIGHT>
520.619

> <EXACT_MASS>
520.267232868

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
55.85111952648397

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-[(1R)-3-methoxy-3-oxo-1-{[(1S,2R,7S,10R,11S,14R,15R,16R,19S)-10,14,16-trimethyl-17,20,21-trioxahexacyclo[14.4.1.0^{1,14}.0^{2,11}.0^{5,10}.0^{15,19}]henicos-4-en-7-yl]oxy}propoxy]propanoic acid

> <ALOGPS_LOGP>
3.17

> <JCHEM_LOGP>
3.9554283983333316

> <ALOGPS_LOGS>
-5.30

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6402946974485544

> <JCHEM_PKA_STRONGEST_BASIC>
-3.704858343053312

> <JCHEM_POLAR_SURFACE_AREA>
109.75000000000001

> <JCHEM_REFRACTIVITY>
130.3515

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.58e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-[(1R)-3-methoxy-3-oxo-1-{[(1S,2R,7S,10R,11S,14R,15R,16R,19S)-10,14,16-trimethyl-17,20,21-trioxahexacyclo[14.4.1.0^{1,14}.0^{2,11}.0^{5,10}.0^{15,19}]henicos-4-en-7-yl]oxy}propoxy]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       9.543  -5.720   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.210  -6.490   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.876  -5.720   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.542  -6.490   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.542  -8.030   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.876  -8.800   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.210  -8.030   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.543  -8.800   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.877  -8.030   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.877  -6.490   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.804  -4.444   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.933  -3.273   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.755  -4.286   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      11.074  -2.123   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      12.439  -2.905   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.176  -4.525   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      11.550  -6.073   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.883  -2.146   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.417  -6.462   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.876 -10.340   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.542 -11.110   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.209 -10.340   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.209  -8.800   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.875 -11.110   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.875 -12.650   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.541 -13.420   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.541 -14.960   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.875 -15.730   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.208 -15.730   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.126 -14.960   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       0.208 -17.270   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.209 -13.420   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.209 -14.960   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       3.582 -16.367   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       5.542 -15.730   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       5.542 -17.270   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.210  -9.570   0.000  0.00  0.00           C+0
CONECT    1    2   10   13   17                                             
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   23                                                  
CONECT    6    5    7   20   37                                             
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    1   11   19                                             
CONECT   11   10   12   16                                                  
CONECT   12   11   13   14   18                                             
CONECT   13   12    1                                                       
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11   17                                                  
CONECT   17   16    1                                                       
CONECT   18   12                                                            
CONECT   19   10                                                            
CONECT   20    6   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22    5                                                       
CONECT   24   22   25                                                       
CONECT   25   24   26   32                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   25   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35                                                            
CONECT   37    6                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   84    0
END

View in JSmol

Synonyms

Value	Source
(2R)-2-[(1R)-3-Methoxy-3-oxo-1-{[(1S,2R,7S,10R,11S,14R,15R,16R,19S)-10,14,16-trimethyl-17,20,21-trioxahexacyclo[14.4.1.0,.0,.0,.0,]henicos-4-en-7-yl]oxy}propoxy]propanoate	Generator

Chemical Formula

C₂₈H₄₀O₉

Average Mass

520.6190 Da

Monoisotopic Mass

520.26723 Da

IUPAC Name

(2R)-2-[(1R)-3-methoxy-3-oxo-1-{[(1S,2R,7S,10R,11S,14R,15R,16R,19S)-10,14,16-trimethyl-17,20,21-trioxahexacyclo[14.4.1.0^{1,14}.0^{2,11}.0^{5,10}.0^{15,19}]henicos-4-en-7-yl]oxy}propoxy]propanoic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)C[C@@H](O[C@H](C)C(O)=O)O[C@H]1CC[C@]2(C)[C@H]3CC[C@]4(C)[C@@H]5[C@H]6CO[C@]5(C)O[C@@]4(O6)[C@@H]3CC=C2C1

InChI Identifier

InChI=1S/C28H40O9/c1-15(24(30)31)34-22(13-21(29)32-5)35-17-8-10-25(2)16(12-17)6-7-19-18(25)9-11-26(3)23-20-14-33-27(23,4)37-28(19,26)36-20/h6,15,17-20,22-23H,7-14H2,1-5H3,(H,30,31)/t15-,17+,18+,19-,20-,22+,23+,25+,26-,27-,28+/m1/s1

InChI Key

LAGKFZXTTOABAX-JGGUGFFYSA-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
Solenostemma argel	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
Furofuran
Ketal
Meta-dioxane
Dicarboxylic acid or derivatives
Methyl ester
Tetrahydrofuran
Carboxylic acid ester
Acetal
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organic oxide
Organic oxygen compound
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	3.17	ALOGPS
logP	3.96	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	3.64	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	109.75 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	130.35 m³·mol⁻¹	ChemAxon
Polarizability	55.85 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	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162982520

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Argeloside O (NP0077881)

MOL for NP0077881 ((+)-Argeloside O)

3D MOL for NP0077881 ((+)-Argeloside O)

3D SDF for NP0077881 ((+)-Argeloside O)

3D-SDF for NP0077881 ((+)-Argeloside O)

PDB for NP0077881 ((+)-Argeloside O)

3D PDB for NP0077881 ((+)-Argeloside O)

SMILES for NP0077881 ((+)-Argeloside O)

INCHI for NP0077881 ((+)-Argeloside O)

Structure for NP0077881 ((+)-Argeloside O)

3D Structure for NP0077881 ((+)-Argeloside O)