NP-MRD: Showing NP-Card for (-)-Ptilosaponoside B (NP0081467)

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Record Information

Version

2.0

Created at

2022-04-29 02:28:30 UTC

Updated at

2022-04-29 02:28:30 UTC

NP-MRD ID

NP0081467

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Ptilosaponoside B

Description

[(2R,3R,4S,5R,6R)-2-{[(1S,2S,5S,6R,7R,10S,11S,14R,15S)-14-ethenyl-5-hydroxy-2-(hydroxymethyl)-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-6-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxidanesulfonic acid belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton. (-)-Ptilosaponoside B is found in Ptilocaulis spiculifer. Based on a literature review very few articles have been published on [(2R,3R,4S,5R,6R)-2-{[(1S,2S,5S,6R,7R,10S,11S,14R,15S)-14-ethenyl-5-hydroxy-2-(hydroxymethyl)-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-6-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxidanesulfonic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292204282D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304292204282D          

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    4.3177   -5.3296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1298   -5.4748    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.9419   -5.6200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9846   -6.2869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2750   -4.6627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6935   -5.0391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1965   -2.2259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4798   -1.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0117   -0.3836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3959   -2.1305    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6762   -1.3546    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1444   -0.7239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5008   -1.3814    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7301   -2.1739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0473   -2.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0071   -0.7301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8244   -0.8429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0361   -0.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  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
  6 11  1  0  0  0  0
 11 12  1  6  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 13 18  1  0  0  0  0
 17 19  1  6  0  0  0
 19 20  1  0  0  0  0
 16 21  1  1  0  0  0
 15 22  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  2  0  0  0  0
 23 26  1  0  0  0  0
 14 27  1  1  0  0  0
 10 28  1  6  0  0  0
  7 29  1  6  0  0  0
 29 30  1  0  0  0  0
  3 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
  1 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 31 36  1  6  0  0  0
 34 37  1  6  0  0  0
 37 38  2  0  0  0  0
 32 39  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0081467

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]12CC[C@H]3[C@@H](CC[C@H]4[C@@H](O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](OS(O)(=O)=O)[C@H]5O)[C@@H](O)CC[C@]34CO)[C@@H]1CC[C@@H]2C=C

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O11S/c1-3-14-4-6-16-15-5-7-18-23(19(30)9-11-27(18,13-29)17(15)8-10-26(14,16)2)37-25-22(32)24(38-39(33,34)35)21(31)20(12-28)36-25/h3,14-25,28-32H,1,4-13H2,2H3,(H,33,34,35)/t14-,15-,16-,17-,18-,19-,20+,21+,22+,23+,24-,25-,26-,27-/m0/s1

> <INCHI_KEY>
KTFHNNJQQWKFQS-XSQKZGFSSA-N

> <FORMULA>
C27H44O11S

> <MOLECULAR_WEIGHT>
576.7

> <EXACT_MASS>
576.260433411

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
60.30261341229465

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3R,4S,5R,6R)-2-{[(1S,2S,5S,6R,7R,10S,11S,14R,15S)-14-ethenyl-5-hydroxy-2-(hydroxymethyl)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-6-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxidanesulfonic acid

> <ALOGPS_LOGP>
-0.42

> <JCHEM_LOGP>
-0.8583544387199593

> <ALOGPS_LOGS>
-2.30

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.240418454752149

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.8264000506539322

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7603193849931715

> <JCHEM_POLAR_SURFACE_AREA>
183.20999999999998

> <JCHEM_REFRACTIVITY>
137.7737

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.88e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3R,4S,5R,6R)-2-{[(1S,2S,5S,6R,7R,10S,11S,14R,15S)-14-ethenyl-5-hydroxy-2-(hydroxymethyl)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-6-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxidanesulfonic 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      -0.620  -1.622   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.097  -3.071   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.090  -4.248   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.567  -5.696   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.949  -5.967   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.942  -4.790   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.419  -3.342   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.412  -2.164   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.928  -2.436   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.451  -3.884   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.458  -5.061   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.981  -6.510   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.497  -6.781   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.021  -8.229   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.536  -8.500   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.529  -7.323   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.006  -5.874   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.490  -5.603   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.999  -4.697   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.475  -3.249   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      10.045  -7.594   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.060  -9.949   0.000  0.00  0.00           O+0
HETATM   23  S   UNK     0       9.576 -10.220   0.000  0.00  0.00           S+0
HETATM   24  O   UNK     0      11.092 -10.491   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       9.305 -11.736   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       9.847  -8.704   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       5.028  -9.406   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       5.967  -4.155   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.896  -1.893   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.888  -0.716   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -2.606  -3.977   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -3.129  -2.529   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.136  -1.351   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -4.668  -2.579   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -5.096  -4.058   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -3.822  -4.922   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -5.613  -1.363   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -7.139  -1.573   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -3.801  -1.143   0.000  0.00  0.00           C+0
CONECT    1    2   33                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4   31                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    2    8   29                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   28                                                  
CONECT   11   10    6   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   27                                                  
CONECT   15   14   16   22                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   13                                                       
CONECT   19   17   20                                                       
CONECT   20   19                                                            
CONECT   21   16                                                            
CONECT   22   15   23                                                       
CONECT   23   22   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23                                                            
CONECT   27   14                                                            
CONECT   28   10                                                            
CONECT   29    7   30                                                       
CONECT   30   29                                                            
CONECT   31    3   32   36                                                  
CONECT   32   31   33   34   39                                             
CONECT   33   32    1                                                       
CONECT   34   32   35   37                                                  
CONECT   35   34   36                                                       
CONECT   36   35   31                                                       
CONECT   37   34   38                                                       
CONECT   38   37                                                            
CONECT   39   32                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Value	Source
[(2R,3R,4S,5R,6R)-2-{[(1S,2S,5S,6R,7R,10S,11S,14R,15S)-14-ethenyl-5-hydroxy-2-(hydroxymethyl)-15-methyltetracyclo[8.7.0.0,.0,]heptadecan-6-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxidanesulfonate	Generator
[(2R,3R,4S,5R,6R)-2-{[(1S,2S,5S,6R,7R,10S,11S,14R,15S)-14-ethenyl-5-hydroxy-2-(hydroxymethyl)-15-methyltetracyclo[8.7.0.0,.0,]heptadecan-6-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxidanesulphonate	Generator
[(2R,3R,4S,5R,6R)-2-{[(1S,2S,5S,6R,7R,10S,11S,14R,15S)-14-ethenyl-5-hydroxy-2-(hydroxymethyl)-15-methyltetracyclo[8.7.0.0,.0,]heptadecan-6-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxidanesulphonic acid	Generator

Chemical Formula

C₂₇H₄₄O₁₁S

Average Mass

576.7000 Da

Monoisotopic Mass

576.26043 Da

IUPAC Name

[(2R,3R,4S,5R,6R)-2-{[(1S,2S,5S,6R,7R,10S,11S,14R,15S)-14-ethenyl-5-hydroxy-2-(hydroxymethyl)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-6-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxidanesulfonic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@@]12CC[C@H]3[C@@H](CC[C@H]4[C@@H](O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](OS(O)(=O)=O)[C@H]5O)[C@@H](O)CC[C@]34CO)[C@@H]1CC[C@@H]2C=C

InChI Identifier

InChI=1S/C27H44O11S/c1-3-14-4-6-16-15-5-7-18-23(19(30)9-11-27(18,13-29)17(15)8-10-26(14,16)2)37-25-22(32)24(38-39(33,34)35)21(31)20(12-28)36-25/h3,14-25,28-32H,1,4-13H2,2H3,(H,33,34,35)/t14-,15-,16-,17-,18-,19-,20+,21+,22+,23+,24-,25-,26-,27-/m0/s1

InChI Key

KTFHNNJQQWKFQS-XSQKZGFSSA-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
Ptilocaulis spiculifer	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Steroidal glycosides

Alternative Parents

Substituents

Steroidal glycoside
Progestogin-skeleton
Pregnane-skeleton
19-hydroxysteroid
3-beta-hydroxysteroid
Hydroxysteroid
3-hydroxysteroid
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Sulfuric acid ester
Alkyl sulfate
Sulfate-ester
Sulfuric acid monoester
Oxane
Monosaccharide
Organic sulfuric acid or derivatives
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
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	-0.42	ALOGPS
logP	-0.86	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	-1.8	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	183.21 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	137.77 m³·mol⁻¹	ChemAxon
Polarizability	60.3 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	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

163104786

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Ptilosaponoside B (NP0081467)

MOL for NP0081467 ((-)-Ptilosaponoside B)

3D MOL for NP0081467 ((-)-Ptilosaponoside B)

3D SDF for NP0081467 ((-)-Ptilosaponoside B)

3D-SDF for NP0081467 ((-)-Ptilosaponoside B)

PDB for NP0081467 ((-)-Ptilosaponoside B)

3D PDB for NP0081467 ((-)-Ptilosaponoside B)

SMILES for NP0081467 ((-)-Ptilosaponoside B)

INCHI for NP0081467 ((-)-Ptilosaponoside B)

Structure for NP0081467 ((-)-Ptilosaponoside B)

3D Structure for NP0081467 ((-)-Ptilosaponoside B)