NP-MRD: Showing NP-Card for (-)-3-O-beta-D-Glucopyranosylfagomine (NP0082965)

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Record Information

Version

2.0

Created at

2022-04-29 04:01:47 UTC

Updated at

2022-04-29 04:01:47 UTC

NP-MRD ID

NP0082965

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-3-O-beta-D-Glucopyranosylfagomine

Description

(2S,3R,4S,5R,6R)-2-{[(2R,3R,4R)-3-hydroxy-2-(hydroxymethyl)piperidin-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. (-)-3-O-beta-D-Glucopyranosylfagomine is found in Xanthocercis zambesiaca. Based on a literature review very few articles have been published on (2S,3R,4S,5R,6R)-2-{[(2R,3R,4R)-3-hydroxy-2-(hydroxymethyl)piperidin-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 44 45  0  0  0  0  0  0  0  0999 V2000
   -5.8252    0.2272    0.2786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6585    0.3749    1.0267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4850   -0.1394    0.2294 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2988    0.5548   -1.0075 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5819   -0.3270   -1.9069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7185   -1.2686   -1.1287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1091   -0.6421    0.1064 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1815    0.2927   -0.3007 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1042    0.0195    0.0929 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8965   -0.1938   -0.9913 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0698    0.4993   -1.0362 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8629    0.0252   -2.2391 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1351   -1.3414   -2.1418 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8270    0.2092    0.2567 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7129   -1.1857    0.4565 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683    0.9392    1.3484 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3227    0.3016    2.5582 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6099    1.0599    1.0532 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3320    2.3558    0.6517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1878   -0.0420    1.0027 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3181   -0.7070    2.1968 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6895   -0.5961   -0.2901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7876   -0.1371    1.9785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5568    1.4738    1.2217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6803   -1.2386    0.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1771    0.9251   -1.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3467   -0.9399   -2.4616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0001    0.2693   -2.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8458   -1.5293   -1.7941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2051   -2.2477   -0.9134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6618   -1.4734    0.6929 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0638   -0.9478    0.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9452    1.5984   -1.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2388    0.2416   -3.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8306    0.5569   -2.3322 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3461   -1.8653   -2.4877 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8822    0.5001    0.1973 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7864   -1.3157    1.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5396    1.9592    1.4184 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3983    0.9942    3.2756 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0631    0.9079    2.0221 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3536    2.4917    0.5079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9325    1.0275    1.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1411   -1.6671    2.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
  7 20  1  0
 20 21  1  0
 20  3  1  0
 18  9  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  6
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  1
  9 32  1  1
 11 33  1  6
 12 34  1  0
 12 35  1  0
 13 36  1  0
 14 37  1  6
 15 38  1  0
 16 39  1  1
 17 40  1  0
 18 41  1  1
 19 42  1  0
 20 43  1  1
 21 44  1  0
M  END


  Mrv1652304292206012D          

 21 22  0  0  1  0            999 V2000
   -0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0000   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   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  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  1  6  0  0  0
  7  8  1  0  0  0  0
  4  9  1  1  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  1  0  0  0
 14 17  1  6  0  0  0
 17 18  1  0  0  0  0
  3 19  1  1  0  0  0
  2 20  1  6  0  0  0
  1 21  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0082965

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1NCC[C@@H](O[C@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C12H23NO8/c14-3-5-8(16)6(1-2-13-5)20-12-11(19)10(18)9(17)7(4-15)21-12/h5-19H,1-4H2/t5-,6-,7-,8-,9+,10+,11-,12+/m1/s1

> <INCHI_KEY>
ZFBSYXPXCAAPOU-IYDDCBTQSA-N

> <FORMULA>
C12H23NO8

> <MOLECULAR_WEIGHT>
309.315

> <EXACT_MASS>
309.142366705

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
29.529299158368758

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5R,6R)-2-{[(2R,3R,4R)-3-hydroxy-2-(hydroxymethyl)piperidin-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-2.38

> <JCHEM_LOGP>
-3.966284147666667

> <ALOGPS_LOGS>
-0.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.050163728398989

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.189743850131393

> <JCHEM_PKA_STRONGEST_BASIC>
8.929362711186677

> <JCHEM_POLAR_SURFACE_AREA>
151.87

> <JCHEM_REFRACTIVITY>
67.89059999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.31e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5R,6R)-2-{[(2R,3R,4R)-3-hydroxy-2-(hydroxymethyl)piperidin-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <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      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       2.667  -9.240   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.667 -12.320   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2    6   21                                                  
CONECT    2    1    3   20                                                  
CONECT    3    2    4   19                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    4   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   10   16                                                  
CONECT   16   15                                                            
CONECT   17   14   18                                                       
CONECT   18   17                                                            
CONECT   19    3                                                            
CONECT   20    2                                                            
CONECT   21    1                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₂₃NO₈

Average Mass

309.3150 Da

Monoisotopic Mass

309.14237 Da

IUPAC Name

(2S,3R,4S,5R,6R)-2-{[(2R,3R,4R)-3-hydroxy-2-(hydroxymethyl)piperidin-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

(2S,3R,4S,5R,6R)-2-{[(2R,3R,4R)-3-hydroxy-2-(hydroxymethyl)piperidin-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

OC[C@H]1NCC[C@@H](O[C@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@@H]1O

InChI Identifier

InChI=1S/C12H23NO8/c14-3-5-8(16)6(1-2-13-5)20-12-11(19)10(18)9(17)7(4-15)21-12/h5-19H,1-4H2/t5-,6-,7-,8-,9+,10+,11-,12+/m1/s1

InChI Key

ZFBSYXPXCAAPOU-IYDDCBTQSA-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
Xanthocercis zambesiaca	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

Hexose monosaccharide
O-glycosyl compound
Piperidine
Oxane
Monosaccharide
Secondary alcohol
1,2-aminoalcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Secondary amine
Polyol
Secondary aliphatic amine
Acetal
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Primary alcohol
Organonitrogen compound
Amine
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	-2.4	ALOGPS
logP	-4	ChemAxon
logS	-0.13	ALOGPS
pKa (Strongest Acidic)	12.19	ChemAxon
pKa (Strongest Basic)	8.93	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	151.87 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	67.89 m³·mol⁻¹	ChemAxon
Polarizability	29.53 Å³	ChemAxon
Number of Rings	2	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

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METLIN ID

Not Available

PubChem Compound

162845022

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (-)-3-O-beta-D-Glucopyranosylfagomine (NP0082965)

MOL for NP0082965 ((-)-3-O-beta-D-Glucopyranosylfagomine)

3D MOL for NP0082965 ((-)-3-O-beta-D-Glucopyranosylfagomine)

3D SDF for NP0082965 ((-)-3-O-beta-D-Glucopyranosylfagomine)

3D-SDF for NP0082965 ((-)-3-O-beta-D-Glucopyranosylfagomine)

PDB for NP0082965 ((-)-3-O-beta-D-Glucopyranosylfagomine)

3D PDB for NP0082965 ((-)-3-O-beta-D-Glucopyranosylfagomine)

SMILES for NP0082965 ((-)-3-O-beta-D-Glucopyranosylfagomine)

INCHI for NP0082965 ((-)-3-O-beta-D-Glucopyranosylfagomine)

Structure for NP0082965 ((-)-3-O-beta-D-Glucopyranosylfagomine)

3D Structure for NP0082965 ((-)-3-O-beta-D-Glucopyranosylfagomine)