NP-MRD: Showing NP-Card for (2s)-2-phenyl-2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile (NP0205979)

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Record Information

Version

2.0

Created at

2022-09-05 02:03:03 UTC

Updated at

2022-09-05 02:03:03 UTC

NP-MRD ID

NP0205979

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-phenyl-2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile

Description

[(AlphaS)-alpha-Cyanobenzyl]6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranoside belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group. (2s)-2-phenyl-2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile is found in Passiflora edulis. Based on a literature review very few articles have been published on [(alphaS)-alpha-Cyanobenzyl]6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052204032D          

 31 33  0  0  1  0            999 V2000
   -3.5724   -2.8875    0.0000 C   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
   -2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -8.2500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   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
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0013   -3.7125    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  1  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  3  0  0  0  0
 11 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
  9 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
  7 24  1  0  0  0  0
 24 25  1  6  0  0  0
  4 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
  2 30  1  0  0  0  0
 30 31  1  1  0  0  0
M  END

     RDKit          3D

 58 60  0  0  0  0  0  0  0  0999 V2000
   -5.8221   -0.8626    0.6306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7150    0.1676    0.5405 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8217   -0.0795    1.5723 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6636    0.6844    1.4685 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7835    0.1963    0.5269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5461   -0.1520    1.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3072   -0.6661   -0.0632 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5666   -1.0503    0.3320 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2773   -1.4149   -0.8044 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6433   -1.4360   -0.6137 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3241   -0.5275   -1.4119 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3236   -1.2753   -2.1675 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1246   -1.8527   -2.7710 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0315    0.4199   -0.5068 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7300   -0.0578    0.5883 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4018    0.7505    1.4609 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4019    2.1197    1.2659 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7135    2.6203    0.1823 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0285    1.7851   -0.7059 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7176   -2.7231   -1.2913 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5270   -3.3392   -2.2373 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3352   -2.4353   -1.8388 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3311   -3.5851   -2.2353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4677   -1.7499   -0.7580 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5616   -1.1488   -1.3815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0103    2.1039    1.1133 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2223    2.9744    1.8703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4492    2.4507    1.3870 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7400    2.3291    2.7369 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3323    1.5271    0.6116 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5381    1.9855   -0.6882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9454   -1.4361   -0.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8134   -0.3850    0.8724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6461   -1.5893    1.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2085    0.0456   -0.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1625    0.6829    2.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1290    0.7792    1.5102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6631   -0.9274    1.8707 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4116    0.1736   -0.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0552   -0.6468   -1.5787 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6781    0.0606   -2.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7650   -1.1317    0.7929 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9371    0.3349    2.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9405    2.7411    1.9693 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7199    3.7044    0.0373 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4988    2.2077   -1.5449 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5678   -3.4066   -0.4141 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1189   -4.2069   -2.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4556   -1.7047   -2.6603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1897   -4.2966   -1.5821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8778   -2.5099   -0.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2099   -0.3583   -1.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7961    2.2763    0.0365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4996    3.8911    1.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6143    3.4778    1.0025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1811    1.4575    2.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3518    1.4562    1.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3095    1.5520   -1.1183 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  3  0
 11 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  9 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
  4 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 30  2  1  0
 24  7  1  0
 19 14  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  6
  4 36  1  1
  6 37  1  0
  6 38  1  0
  7 39  1  6
  9 40  1  6
 11 41  1  6
 15 42  1  0
 16 43  1  0
 17 44  1  0
 18 45  1  0
 19 46  1  0
 20 47  1  1
 21 48  1  0
 22 49  1  6
 23 50  1  0
 24 51  1  1
 25 52  1  0
 26 53  1  6
 27 54  1  0
 28 55  1  6
 29 56  1  0
 30 57  1  1
 31 58  1  0
M  END


  Mrv1652309052204032D          

 31 33  0  0  1  0            999 V2000
   -3.5724   -2.8875    0.0000 C   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
   -2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -8.2500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   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
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0013   -3.7125    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  1  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  3  0  0  0  0
 11 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
  9 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
  7 24  1  0  0  0  0
 24 25  1  6  0  0  0
  4 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
  2 30  1  0  0  0  0
 30 31  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0205979

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](O[C@H](C#N)C3=CC=CC=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H27NO10/c1-9-13(22)15(24)17(26)19(29-9)28-8-12-14(23)16(25)18(27)20(31-12)30-11(7-21)10-5-3-2-4-6-10/h2-6,9,11-20,22-27H,8H2,1H3/t9-,11+,12+,13-,14+,15+,16-,17+,18+,19+,20+/m0/s1

> <INCHI_KEY>
QSPJUYWAUZTHLP-JPHMQOHFSA-N

> <FORMULA>
C20H27NO10

> <MOLECULAR_WEIGHT>
441.433

> <EXACT_MASS>
441.163496073

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
43.50424975595712

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-phenyl-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile

> <JCHEM_LOGP>
-1.5409768133333328

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.442487083672741

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.915919532124308

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6121823516836606

> <JCHEM_POLAR_SURFACE_AREA>
182.08999999999997

> <JCHEM_REFRACTIVITY>
100.96600000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-phenyl-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -4.001 -10.010   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.334 -11.550   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       2.667 -15.400   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.334 -16.170   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -4.001 -14.630   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -6.668 -11.550   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -9.336 -10.010   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -9.336  -6.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   30                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   26                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   24                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   20                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20    9   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22    7   25                                                  
CONECT   25   24                                                            
CONECT   26    4   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28    2   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Value	Source
[(AlphaS)-a-cyanobenzyl]6-O-(a-L-rhamnopyranosyl)-b-D-glucopyranoside	Generator
[(AlphaS)-α-cyanobenzyl]6-O-(α-L-rhamnopyranosyl)-β-D-glucopyranoside	Generator

Chemical Formula

C₂₀H₂₇NO₁₀

Average Mass

441.4330 Da

Monoisotopic Mass

441.16350 Da

IUPAC Name

(2S)-2-phenyl-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile

Traditional Name

(2S)-2-phenyl-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](O[C@H](C#N)C3=CC=CC=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C20H27NO10/c1-9-13(22)15(24)17(26)19(29-9)28-8-12-14(23)16(25)18(27)20(31-12)30-11(7-21)10-5-3-2-4-6-10/h2-6,9,11-20,22-27H,8H2,1H3/t9-,11+,12+,13-,14+,15+,16-,17+,18+,19+,20+/m0/s1

InChI Key

QSPJUYWAUZTHLP-JPHMQOHFSA-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
Passiflora edulis	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
Disaccharide
O-glycosyl compound
Monocyclic benzene moiety
Oxane
Benzenoid
Secondary alcohol
Polyol
Nitrile
Carbonitrile
Acetal
Organoheterocyclic compound
Oxacycle
Alcohol
Organonitrogen compound
Cyanide
Organopnictogen compound
Organic nitrogen compound
Hydrocarbon derivative
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	-1.5	ChemAxon
pKa (Strongest Acidic)	11.92	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	182.09 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	100.97 m³·mol⁻¹	ChemAxon
Polarizability	43.5 Å³	ChemAxon
Number of Rings	3	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

101785493

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-2-phenyl-2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile (NP0205979)

MOL for NP0205979 ((2s)-2-phenyl-2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile)

3D MOL for NP0205979 ((2s)-2-phenyl-2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile)

3D SDF for NP0205979 ((2s)-2-phenyl-2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile)

3D-SDF for NP0205979 ((2s)-2-phenyl-2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile)

PDB for NP0205979 ((2s)-2-phenyl-2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile)

3D PDB for NP0205979 ((2s)-2-phenyl-2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile)

SMILES for NP0205979 ((2s)-2-phenyl-2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile)

INCHI for NP0205979 ((2s)-2-phenyl-2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile)

Structure for NP0205979 ((2s)-2-phenyl-2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile)

3D Structure for NP0205979 ((2s)-2-phenyl-2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile)