NP-MRD: Showing NP-Card for Praeroside I (NP0063236)

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Record Information

Version

2.0

Created at

2022-04-28 07:41:42 UTC

Updated at

2022-04-28 07:41:42 UTC

NP-MRD ID

NP0063236

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Praeroside I

Description

Rutaretin 1'-O-[6-O-(4-hydroxy-3-methoxybenzoyl-beta-D-glucopyranoside] belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. Praeroside I is found in Peucedanum praeruptorum. Based on a literature review very few articles have been published on Rutaretin 1'-O-[6-O-(4-hydroxy-3-methoxybenzoyl-beta-D-glucopyranoside].

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282209412D          

 41 45  0  0  1  0            999 V2000
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.7812    1.1104    0.0000 C   0  0  0  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
    5.4957    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 O   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  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  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
    2.6378    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.1712    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9962    1.5229    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  0  0  0  0
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  9 10  2  0  0  0  0
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  1 11  2  0  0  0  0
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  9 15  1  0  0  0  0
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 21 37  1  6  0  0  0
 20 38  1  1  0  0  0
 19 39  1  6  0  0  0
 16 40  1  0  0  0  0
 16 41  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282209412D          

 41 45  0  0  1  0            999 V2000
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   -0.1712    0.0940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    0.6979    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  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  1  7  1  0  0  0  0
  2  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  1 11  2  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 15  1  0  0  0  0
 14 16  1  1  0  0  0
 16 17  1  0  0  0  0
 18 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 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
 18 23  1  0  0  0  0
 22 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 28 33  1  0  0  0  0
 31 34  1  0  0  0  0
 30 35  1  0  0  0  0
 35 36  1  0  0  0  0
 21 37  1  6  0  0  0
 20 38  1  1  0  0  0
 19 39  1  6  0  0  0
 16 40  1  0  0  0  0
 16 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0063236

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC(=C1)C(=O)OC[C@H]1O[C@@H](OC(C)(C)[C@@H]2CC3=C(O2)C(O)=C2OC(=O)C=CC2=C3)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H30O13/c1-28(2,18-10-14-8-12-5-7-19(30)40-24(12)23(34)25(14)39-18)41-27-22(33)21(32)20(31)17(38-27)11-37-26(35)13-4-6-15(29)16(9-13)36-3/h4-9,17-18,20-22,27,29,31-34H,10-11H2,1-3H3/t17-,18+,20-,21+,22-,27+/m1/s1

> <INCHI_KEY>
BWOIWJCVUMZWKV-FCOZARIJSA-N

> <FORMULA>
C28H30O13

> <MOLECULAR_WEIGHT>
574.535

> <EXACT_MASS>
574.168641026

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
57.43626676863321

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({2-[(2S)-9-hydroxy-7-oxo-2H,3H,7H-furo[3,2-g]chromen-2-yl]propan-2-yl}oxy)oxan-2-yl]methyl 4-hydroxy-3-methoxybenzoate

> <ALOGPS_LOGP>
1.64

> <JCHEM_LOGP>
2.3420559009999993

> <ALOGPS_LOGS>
-3.24

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.732433588249119

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.983783866527949

> <JCHEM_PKA_STRONGEST_BASIC>
-3.499019453131395

> <JCHEM_POLAR_SURFACE_AREA>
190.67

> <JCHEM_REFRACTIVITY>
139.00119999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.28e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({2-[(2S)-9-hydroxy-7-oxo-2H,3H-furo[3,2-g]chromen-2-yl]propan-2-yl}oxy)oxan-2-yl]methyl 4-hydroxy-3-methoxybenzoate

> <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       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.591   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.925   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      10.259   4.383   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       7.591   4.383   0.000  0.00  0.00           O+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  O   UNK     0       4.924   5.923   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.320   2.843   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.860   2.843   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.630   1.509   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.860   0.175   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.630  -1.158   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.170  -1.158   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.940   0.175   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -4.170   1.509   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -6.480   0.175   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -7.250   1.509   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -8.790   1.509   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -9.560   0.175   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -9.560   2.843   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -11.100   2.843   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -11.870   4.177   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -11.100   5.510   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -9.560   5.510   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -8.790   4.177   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0     -11.870   6.844   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0     -13.410   4.177   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0     -14.180   5.510   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -4.940  -2.492   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -1.860  -2.492   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -0.320   0.175   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -0.320   4.383   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -0.320   1.303   0.000  0.00  0.00           C+0
CONECT    1    2    7   11                                                  
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    1                                                       
CONECT    8    2    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10    1   12                                                  
CONECT   12   11                                                            
CONECT   13   10   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14    9                                                       
CONECT   16   14   17   40   41                                             
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20   39                                                  
CONECT   20   19   21   38                                                  
CONECT   21   20   22   37                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22   18                                                       
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   35                                                  
CONECT   31   30   32   34                                                  
CONECT   32   31   33                                                       
CONECT   33   32   28                                                       
CONECT   34   31                                                            
CONECT   35   30   36                                                       
CONECT   36   35                                                            
CONECT   37   21                                                            
CONECT   38   20                                                            
CONECT   39   19                                                            
CONECT   40   16                                                            
CONECT   41   16                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

View in JSmol

Synonyms

Value	Source
Rutaretin 1'-O-[6-O-(4-hydroxy-3-methoxybenzoyl-b-D-glucopyranoside]	Generator
Rutaretin 1'-O-[6-O-(4-hydroxy-3-methoxybenzoyl-β-D-glucopyranoside]	Generator

Chemical Formula

C₂₈H₃₀O₁₃

Average Mass

574.5350 Da

Monoisotopic Mass

574.16864 Da

IUPAC Name

[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({2-[(2S)-9-hydroxy-7-oxo-2H,3H,7H-furo[3,2-g]chromen-2-yl]propan-2-yl}oxy)oxan-2-yl]methyl 4-hydroxy-3-methoxybenzoate

Traditional Name

[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({2-[(2S)-9-hydroxy-7-oxo-2H,3H-furo[3,2-g]chromen-2-yl]propan-2-yl}oxy)oxan-2-yl]methyl 4-hydroxy-3-methoxybenzoate

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=CC(=C1)C(=O)OC[C@H]1O[C@@H](OC(C)(C)[C@@H]2CC3=C(O2)C(O)=C2OC(=O)C=CC2=C3)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C28H30O13/c1-28(2,18-10-14-8-12-5-7-19(30)40-24(12)23(34)25(14)39-18)41-27-22(33)21(32)20(31)17(38-27)11-37-26(35)13-4-6-15(29)16(9-13)36-3/h4-9,17-18,20-22,27,29,31-34H,10-11H2,1-3H3/t17-,18+,20-,21+,22-,27+/m1/s1

InChI Key

BWOIWJCVUMZWKV-FCOZARIJSA-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
Peucedanum praeruptorum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable tannin
Furanocoumarin
Linear furanocoumarin
Psoralen
P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
Coumarin
Glycosyl compound
M-methoxybenzoic acid or derivatives
O-glycosyl compound
Benzoate ester
Benzopyran
Methoxyphenol
1-benzopyran
Benzoic acid or derivatives
Coumaran
Anisole
Phenoxy compound
Benzoyl
Methoxybenzene
Phenol ether
Pyranone
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyran
Oxane
Benzenoid
Monosaccharide
Monocyclic benzene moiety
Heteroaromatic compound
Secondary alcohol
Lactone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Polyol
Organoheterocyclic compound
Acetal
Oxacycle
Carboxylic acid derivative
Ether
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Alcohol
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	1.64	ALOGPS
logP	2.34	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	8.98	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	190.67 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	139 m³·mol⁻¹	ChemAxon
Polarizability	57.44 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

101421057

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Praeroside I (NP0063236)

MOL for NP0063236 (Praeroside I)

3D MOL for NP0063236 (Praeroside I)

3D SDF for NP0063236 (Praeroside I)

3D-SDF for NP0063236 (Praeroside I)

PDB for NP0063236 (Praeroside I)

3D PDB for NP0063236 (Praeroside I)

SMILES for NP0063236 (Praeroside I)

INCHI for NP0063236 (Praeroside I)

Structure for NP0063236 (Praeroside I)

3D Structure for NP0063236 (Praeroside I)