NP-MRD: Showing NP-Card for (2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2s,3ar,4r,4's,5'r,6s,7ar)-4'-(benzoyloxy)-3a,4-dihydroxy-5'-methyl-3-oxo-tetrahydro-4h-spiro[1-benzofuran-2,2'-oxane]-6-carboxylate (NP0230934)

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Record Information

Version

2.0

Created at

2022-09-06 11:33:28 UTC

Updated at

2022-09-06 11:33:28 UTC

NP-MRD ID

NP0230934

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2s,3ar,4r,4's,5'r,6s,7ar)-4'-(benzoyloxy)-3a,4-dihydroxy-5'-methyl-3-oxo-tetrahydro-4h-spiro[1-benzofuran-2,2'-oxane]-6-carboxylate

Description

Phyllaemblicin A belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. (2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2s,3ar,4r,4's,5'r,6s,7ar)-4'-(benzoyloxy)-3a,4-dihydroxy-5'-methyl-3-oxo-tetrahydro-4h-spiro[1-benzofuran-2,2'-oxane]-6-carboxylate is found in Phyllanthus emblica. (2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2s,3ar,4r,4's,5'r,6s,7ar)-4'-(benzoyloxy)-3a,4-dihydroxy-5'-methyl-3-oxo-tetrahydro-4h-spiro[1-benzofuran-2,2'-oxane]-6-carboxylate was first documented in 2009 (PMID: 19374435). Based on a literature review very few articles have been published on phyllaemblicin A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062213332D          

 41 45  0  0  1  0            999 V2000
    5.1735    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3485    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9360   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1110   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6985    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1110    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9360    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3485    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1735    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5860    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5860    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1735    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5860    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4110    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8235    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4110    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2136   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  2  1  1  6  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
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  7  8  1  6  0  0  0
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  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
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 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
  5 17  1  6  0  0  0
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
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 21 22  2  0  0  0  0
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 26 27  1  6  0  0  0
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 29 30  1  1  0  0  0
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 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
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 36 38  1  0  0  0  0
 18 38  1  0  0  0  0
 38 39  1  1  0  0  0
 38 40  1  0  0  0  0
  5 40  1  0  0  0  0
 40 41  2  0  0  0  0
M  END

     RDKit          3D

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   10.7761    0.3153   -1.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2565    1.5911   -1.0960 C   0  0  0  0  0  0  0  0  0  0  0  0
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 34 70  1  0
M  END


  Mrv1652309062213332D          

 41 45  0  0  1  0            999 V2000
    5.1735    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3485    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9360   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1110   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6985    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1110    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9360    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -1.4289   -1.6500    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
   -2.1434   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  1  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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5152    1.6455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2136    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4685    1.8646    0.0000 O   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  0  0  0  0
  4  5  1  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  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
  5 17  1  6  0  0  0
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 24 23  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  1  0  0  0  0
 26 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 24 33  1  0  0  0  0
 33 34  1  1  0  0  0
 20 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  1  0  0  0
 36 38  1  0  0  0  0
 18 38  1  0  0  0  0
 38 39  1  1  0  0  0
 38 40  1  0  0  0  0
  5 40  1  0  0  0  0
 40 41  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0230934

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CO[C@@]2(C[C@@H]1OC(=O)C1=CC=CC=C1)O[C@@H]1C[C@H](C[C@@H](O)[C@]1(O)C2=O)C(=O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H34O14/c1-12-11-37-26(9-15(12)38-22(33)13-5-3-2-4-6-13)25(35)27(36)17(29)7-14(8-18(27)41-26)23(34)40-24-21(32)20(31)19(30)16(10-28)39-24/h2-6,12,14-21,24,28-32,36H,7-11H2,1H3/t12-,14+,15+,16-,17-,18-,19-,20+,21-,24+,26+,27-/m1/s1

> <INCHI_KEY>
VWVDXHBJGQKCJA-NLWJZKKESA-N

> <FORMULA>
C27H34O14

> <MOLECULAR_WEIGHT>
582.555

> <EXACT_MASS>
582.194855775

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
56.11173204882414

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2S,3aR,4R,4'S,5'R,6S,7aR)-4'-(benzoyloxy)-3a,4-dihydroxy-5'-methyl-3-oxo-hexahydro-3H-spiro[1-benzofuran-2,2'-oxane]-6-carboxylate

> <JCHEM_LOGP>
-0.21361147466666605

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.22409012178307

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.067621184934655

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981093679233121

> <JCHEM_POLAR_SURFACE_AREA>
218.73999999999998

> <JCHEM_REFRACTIVITY>
132.12520000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2S,3aR,4R,4'S,5'R,6S,7aR)-4'-(benzoyloxy)-3a,4-dihydroxy-5'-methyl-3-oxo-tetrahydro-4H-spiro[1-benzofuran-2,2'-oxane]-6-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       9.657   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.117   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.347  -0.564   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.807  -0.564   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.037   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.807   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.347   2.104   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.117   3.437   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.657   3.437   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      10.427   2.104   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      10.427   4.771   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.657   6.105   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.427   7.438   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.967   7.438   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.737   6.105   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.967   4.771   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.132  -0.476   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       2.828   3.072   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       4.132   2.016   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       4.608   3.481   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   17   40                                             
CONECT    6    5    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17    5   18                                                       
CONECT   18   17   19   38                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   35                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   33                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   24   34                                                  
CONECT   34   33                                                            
CONECT   35   20   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   18   39   40                                             
CONECT   39   38                                                            
CONECT   40   38    5   41                                                  
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₄O₁₄

Average Mass

582.5550 Da

Monoisotopic Mass

582.19486 Da

IUPAC Name

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2S,3aR,4R,4'S,5'R,6S,7aR)-4'-(benzoyloxy)-3a,4-dihydroxy-5'-methyl-3-oxo-hexahydro-3H-spiro[1-benzofuran-2,2'-oxane]-6-carboxylate

Traditional Name

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2S,3aR,4R,4'S,5'R,6S,7aR)-4'-(benzoyloxy)-3a,4-dihydroxy-5'-methyl-3-oxo-tetrahydro-4H-spiro[1-benzofuran-2,2'-oxane]-6-carboxylate

CAS Registry Number

Not Available

SMILES

C[C@@H]1CO[C@@]2(C[C@@H]1OC(=O)C1=CC=CC=C1)O[C@@H]1C[C@H](C[C@@H](O)[C@]1(O)C2=O)C(=O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C27H34O14/c1-12-11-37-26(9-15(12)38-22(33)13-5-3-2-4-6-13)25(35)27(36)17(29)7-14(8-18(27)41-26)23(34)40-24-21(32)20(31)19(30)16(10-28)39-24/h2-6,12,14-21,24,28-32,36H,7-11H2,1H3/t12-,14+,15+,16-,17-,18-,19-,20+,21-,24+,26+,27-/m1/s1

InChI Key

VWVDXHBJGQKCJA-NLWJZKKESA-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
Phyllanthus emblica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty acyl glycosides of mono- and disaccharides

Alternative Parents

Substituents

Fatty acyl glycoside of mono- or disaccharide
Benzoate ester
Benzofuran
Benzoic acid or derivatives
Benzoyl
Ketal
Monocyclic benzene moiety
Benzenoid
Dicarboxylic acid or derivatives
3-furanone
Monosaccharide
Oxane
Cyclic alcohol
Tetrahydrofuran
Tertiary alcohol
Ketone
Secondary alcohol
Carboxylic acid ester
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Polyol
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Primary alcohol
Organooxygen 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	-0.21	ChemAxon
pKa (Strongest Acidic)	11.07	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	218.74 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	132.13 m³·mol⁻¹	ChemAxon
Polarizability	56.11 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

C00046852

Chemspider ID

24619068

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

45268814

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liu Q, Wang YF, Chen RJ, Zhang MY, Wang YF, Yang CR, Zhang YJ: Anti-coxsackie virus B3 norsesquiterpenoids from the roots of Phyllanthus emblica. J Nat Prod. 2009 May 22;72(5):969-72. doi: 10.1021/np800792d. [PubMed:19374435 ]
LOTUS database [Link]

Showing NP-Card for (2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2s,3ar,4r,4's,5'r,6s,7ar)-4'-(benzoyloxy)-3a,4-dihydroxy-5'-methyl-3-oxo-tetrahydro-4h-spiro[1-benzofuran-2,2'-oxane]-6-carboxylate (NP0230934)

MOL for NP0230934 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2s,3ar,4r,4's,5'r,6s,7ar)-4'-(benzoyloxy)-3a,4-dihydroxy-5'-methyl-3-oxo-tetrahydro-4h-spiro[1-benzofuran-2,2'-oxane]-6-carboxylate)

3D MOL for NP0230934 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2s,3ar,4r,4's,5'r,6s,7ar)-4'-(benzoyloxy)-3a,4-dihydroxy-5'-methyl-3-oxo-tetrahydro-4h-spiro[1-benzofuran-2,2'-oxane]-6-carboxylate)

3D SDF for NP0230934 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2s,3ar,4r,4's,5'r,6s,7ar)-4'-(benzoyloxy)-3a,4-dihydroxy-5'-methyl-3-oxo-tetrahydro-4h-spiro[1-benzofuran-2,2'-oxane]-6-carboxylate)

3D-SDF for NP0230934 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2s,3ar,4r,4's,5'r,6s,7ar)-4'-(benzoyloxy)-3a,4-dihydroxy-5'-methyl-3-oxo-tetrahydro-4h-spiro[1-benzofuran-2,2'-oxane]-6-carboxylate)

PDB for NP0230934 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2s,3ar,4r,4's,5'r,6s,7ar)-4'-(benzoyloxy)-3a,4-dihydroxy-5'-methyl-3-oxo-tetrahydro-4h-spiro[1-benzofuran-2,2'-oxane]-6-carboxylate)

3D PDB for NP0230934 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2s,3ar,4r,4's,5'r,6s,7ar)-4'-(benzoyloxy)-3a,4-dihydroxy-5'-methyl-3-oxo-tetrahydro-4h-spiro[1-benzofuran-2,2'-oxane]-6-carboxylate)

SMILES for NP0230934 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2s,3ar,4r,4's,5'r,6s,7ar)-4'-(benzoyloxy)-3a,4-dihydroxy-5'-methyl-3-oxo-tetrahydro-4h-spiro[1-benzofuran-2,2'-oxane]-6-carboxylate)

INCHI for NP0230934 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2s,3ar,4r,4's,5'r,6s,7ar)-4'-(benzoyloxy)-3a,4-dihydroxy-5'-methyl-3-oxo-tetrahydro-4h-spiro[1-benzofuran-2,2'-oxane]-6-carboxylate)

Structure for NP0230934 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2s,3ar,4r,4's,5'r,6s,7ar)-4'-(benzoyloxy)-3a,4-dihydroxy-5'-methyl-3-oxo-tetrahydro-4h-spiro[1-benzofuran-2,2'-oxane]-6-carboxylate)

3D Structure for NP0230934 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2s,3ar,4r,4's,5'r,6s,7ar)-4'-(benzoyloxy)-3a,4-dihydroxy-5'-methyl-3-oxo-tetrahydro-4h-spiro[1-benzofuran-2,2'-oxane]-6-carboxylate)