NP-MRD: Showing NP-Card for [(2r,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(s)-cyano(phenyl)methoxy]oxan-2-yl]methyl acetate (NP0296642)

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Record Information

Version

2.0

Created at

2022-09-10 06:20:51 UTC

Updated at

2022-09-10 06:20:51 UTC

NP-MRD ID

NP0296642

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2r,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(s)-cyano(phenyl)methoxy]oxan-2-yl]methyl acetate

Description

ZINC77312669 belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group. [(2r,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(s)-cyano(phenyl)methoxy]oxan-2-yl]methyl acetate is found in Prunus yedoensis. Based on a literature review very few articles have been published on ZINC77312669.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102208202D          

 33 34  0  0  1  0            999 V2000
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  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   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  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   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  3  0  0  0  0
 10 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
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 24 29  1  0  0  0  0
  6 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
M  END

     RDKit          3D

 58 59  0  0  0  0  0  0  0  0999 V2000
   -4.3797    4.0422    1.8118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9078    3.7735    1.8964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1966    4.5015    2.6212 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3418    2.7351    1.1828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9580    2.4319    1.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7337    1.2314    0.3098 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6257    0.9210    0.3345 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9805   -0.0076   -0.6107 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3340   -0.3082   -0.4296 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1165    0.0044   -1.5117 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7060   -1.2523   -1.9996 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1702   -2.2437   -2.3771 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2432    0.9120   -1.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0834    2.0192   -0.3440 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1215    2.8609   -0.0073 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3724    2.6043   -0.4838 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5928    1.5111   -1.2953 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5290    0.6781   -1.6199 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2267   -1.3038   -0.4086 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4617   -2.2275   -1.4225 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1000   -3.4364   -1.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3072   -4.3624   -2.3702 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4851   -3.7130   -0.0751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2365   -1.0939   -0.1809 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8498   -2.2898    0.2266 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8748   -2.9188   -0.4663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4249   -4.1788    0.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2961   -2.4144   -1.5165 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4724    0.0303    0.8183 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8724    0.2121    0.8853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5685    0.0485    2.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0457    0.2344    2.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8830   -0.2683    3.0848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7700    4.2698    2.8080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5960    4.8936    1.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9102    3.1490    1.3894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3447    3.2876    0.8744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6498    2.1602    2.2483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0347    1.4602   -0.7225 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8320    0.4251   -1.6021 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5807    0.4442   -2.3637 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0740    2.2221    0.0377 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9004    3.7086    0.6342 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2100    3.2314   -0.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5852    1.2732   -1.6973 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7063   -0.1639   -2.2471 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6511   -1.7480    0.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9626   -3.9098   -3.1537 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7703   -5.3096   -2.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3459   -4.5830   -2.8495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7171   -0.7664   -1.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9780   -5.0430   -0.4470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5402   -4.1551   -0.0343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2023   -4.2412    1.1686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0399   -0.2460    1.8031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2231    0.8056    3.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5888   -0.7076    2.2409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4380    0.8100    1.3315 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  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  3  0
 10 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  8 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 19 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 24 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  2  0
 29  6  1  0
 18 13  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  6
  8 40  1  6
 10 41  1  6
 14 42  1  0
 15 43  1  0
 16 44  1  0
 17 45  1  0
 18 46  1  0
 19 47  1  1
 22 48  1  0
 22 49  1  0
 22 50  1  0
 24 51  1  6
 27 52  1  0
 27 53  1  0
 27 54  1  0
 29 55  1  1
 32 56  1  0
 32 57  1  0
 32 58  1  0
M  END


  Mrv1652309102208202D          

 33 34  0  0  1  0            999 V2000
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  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   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  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   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  3  0  0  0  0
 10 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
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 24 29  1  0  0  0  0
  6 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0296642

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@H]1O[C@@H](O[C@H](C#N)C2=CC=CC=C2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H25NO10/c1-12(24)28-11-18-19(29-13(2)25)20(30-14(3)26)21(31-15(4)27)22(33-18)32-17(10-23)16-8-6-5-7-9-16/h5-9,17-22H,11H2,1-4H3/t17-,18-,19-,20+,21-,22-/m1/s1

> <INCHI_KEY>
QTSUMWNLKZZILY-WHVWYTALSA-N

> <FORMULA>
C22H25NO10

> <MOLECULAR_WEIGHT>
463.439

> <EXACT_MASS>
463.147846009

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
45.68680157473983

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(2R,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(S)-cyano(phenyl)methoxy]oxan-2-yl]methyl acetate

> <JCHEM_LOGP>
0.947450507

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.004974353799305

> <JCHEM_PKA_STRONGEST_BASIC>
-4.136415696898174

> <JCHEM_POLAR_SURFACE_AREA>
147.45000000000002

> <JCHEM_REFRACTIVITY>
106.70240000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(S)-cyano(phenyl)methoxy]oxan-2-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       6.668  -3.850   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   29                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   19                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19    8   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   19   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   24    6   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₅NO₁₀

Average Mass

463.4390 Da

Monoisotopic Mass

463.14785 Da

IUPAC Name

[(2R,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(S)-cyano(phenyl)methoxy]oxan-2-yl]methyl acetate

Traditional Name

[(2R,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(S)-cyano(phenyl)methoxy]oxan-2-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@H]1O[C@@H](O[C@H](C#N)C2=CC=CC=C2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O

InChI Identifier

InChI=1S/C22H25NO10/c1-12(24)28-11-18-19(29-13(2)25)20(30-14(3)26)21(31-15(4)27)22(33-18)32-17(10-23)16-8-6-5-7-9-16/h5-9,17-22H,11H2,1-4H3/t17-,18-,19-,20+,21-,22-/m1/s1

InChI Key

QTSUMWNLKZZILY-WHVWYTALSA-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
Prunus yedoensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Cyanogenic glycosides

Alternative Parents

Substituents

Cyanogenic glycoside
Tetracarboxylic acid or derivatives
O-glycosyl compound
Monocyclic benzene moiety
Monosaccharide
Oxane
Benzenoid
Carboxylic acid ester
Oxacycle
Nitrile
Carbonitrile
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic 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	0.95	ChemAxon
pKa (Strongest Acidic)	15	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	147.45 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	106.7 m³·mol⁻¹	ChemAxon
Polarizability	45.69 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

107442502

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

96367559

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(2r,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(s)-cyano(phenyl)methoxy]oxan-2-yl]methyl acetate (NP0296642)

MOL for NP0296642 ([(2r,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(s)-cyano(phenyl)methoxy]oxan-2-yl]methyl acetate)

3D MOL for NP0296642 ([(2r,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(s)-cyano(phenyl)methoxy]oxan-2-yl]methyl acetate)

3D SDF for NP0296642 ([(2r,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(s)-cyano(phenyl)methoxy]oxan-2-yl]methyl acetate)

3D-SDF for NP0296642 ([(2r,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(s)-cyano(phenyl)methoxy]oxan-2-yl]methyl acetate)

PDB for NP0296642 ([(2r,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(s)-cyano(phenyl)methoxy]oxan-2-yl]methyl acetate)

3D PDB for NP0296642 ([(2r,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(s)-cyano(phenyl)methoxy]oxan-2-yl]methyl acetate)

SMILES for NP0296642 ([(2r,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(s)-cyano(phenyl)methoxy]oxan-2-yl]methyl acetate)

INCHI for NP0296642 ([(2r,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(s)-cyano(phenyl)methoxy]oxan-2-yl]methyl acetate)

Structure for NP0296642 ([(2r,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(s)-cyano(phenyl)methoxy]oxan-2-yl]methyl acetate)

3D Structure for NP0296642 ([(2r,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(s)-cyano(phenyl)methoxy]oxan-2-yl]methyl acetate)