NP-MRD: Showing NP-Card for 1-O-Cinnamoyl-beta-D-gentiobiose (NP0085613)

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Record Information

Version

2.0

Created at

2022-04-29 06:07:30 UTC

Updated at

2022-04-29 06:07:31 UTC

NP-MRD ID

NP0085613

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-O-Cinnamoyl-beta-D-gentiobiose

Description

1-O-trans-Cinnamoyl-6-O-beta-D-glucopyranosyl-beta-D-glucopyranose belongs to the class of organic compounds known as o-cinnamoyl glycosides. These are o-glycoside derivatives of cinnamic acid. Cinnamic acid is an aromatic compound containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid. 1-O-Cinnamoyl-beta-D-gentiobiose is found in Physalis peruviana . Based on a literature review very few articles have been published on 1-O-trans-Cinnamoyl-6-O-beta-D-glucopyranosyl-beta-D-glucopyranose.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292208072D          

 33 35  0  0  1  0            999 V2000
    4.2868   -4.9500    0.0000 O   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
    5.0013   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -7.8375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    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
    6.4302   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -9.0750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -8.6625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8592   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -9.0750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2881   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -9.9000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2881  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592  -10.3125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  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  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  6  0  0  0
  5 12  1  1  0  0  0
 12 13  1  0  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 26 31  1  0  0  0  0
 23 32  2  0  0  0  0
 21 33  1  0  0  0  0
 14 33  1  0  0  0  0
M  END

     RDKit          3D

 61 63  0  0  0  0  0  0  0  0999 V2000
    2.3496   -1.4778    2.9263 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8126   -0.8534    1.9426 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2604   -0.9149    1.6544 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7993   -0.2869    0.6462 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2148   -0.2960    0.2937 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6443    0.4227   -0.8108 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9514    0.4822   -1.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8880   -0.2305   -0.4861 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5201   -0.9599    0.6171 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1737   -0.9876    1.0028 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9409   -0.1322    1.1690 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5342   -0.0739    1.4509 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2291   -0.5531    0.4174 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6840    0.4329   -0.4606 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0343   -0.2721   -1.7436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0056   -1.2215   -1.5257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1777   -0.6633   -1.1222 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5685   -1.0235    0.1582 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7045   -0.4159    0.6004 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4925   -1.2535    1.5876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7016   -1.5285    2.7136 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6405    0.0555   -0.4649 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2521    1.2994   -0.9527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6243   -0.9274   -1.5972 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0870   -2.1819   -1.2064 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2342   -0.9771   -2.1582 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1272   -0.0467   -3.1726 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4163    1.4628   -0.6787 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0367    2.3342   -1.6633 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5279    2.2618    0.6049 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8183    2.7989    0.7101 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2128    1.3665    1.7849 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1050    1.5002    2.2010 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8976   -1.4980    2.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1020    0.2914    0.0253 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8773    0.9703   -1.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2671    1.0534   -2.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9280   -0.2091   -0.7839 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2317   -1.5192    1.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8590   -1.5525    1.8651 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3187   -0.6861    2.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5509    0.9865   -0.0942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0847   -0.7093   -2.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3667    0.5308   -2.4461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0862    0.4353   -1.1084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3882    0.5022    1.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3461   -0.6429    1.9502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7938   -2.2243    1.1650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3388   -1.7394    3.4430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6603    0.1220   -0.0342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7908    2.0328   -0.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3045   -0.5741   -2.3999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3576   -2.8569   -1.2063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0416   -2.0223   -2.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1305   -0.5263   -4.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3735    0.9710   -0.9431 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2812    2.1113   -2.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1801    3.1181    0.6161 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4031    2.2549    0.1459 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8756    1.6435    2.6499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3536    2.4571    2.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  1  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 12 32  1  0
 32 33  1  0
 32 30  1  0
 30 31  1  0
 30 28  1  0
 28 29  1  0
 17 26  1  0
 26 27  1  0
 26 24  1  0
 24 25  1  0
 24 22  1  0
 22 23  1  0
 22 19  1  0
 28 14  1  0
 10  5  1  0
 21 49  1  0
 20 47  1  0
 20 48  1  0
 19 46  1  1
 17 45  1  1
 15 43  1  0
 15 44  1  0
 14 42  1  1
 12 41  1  1
  3 34  1  0
  4 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 32 60  1  1
 33 61  1  0
 30 58  1  6
 31 59  1  0
 28 56  1  6
 29 57  1  0
 26 54  1  6
 27 55  1  0
 24 52  1  6
 25 53  1  0
 22 50  1  1
 23 51  1  0
M  END


  Mrv1652304292208072D          

 33 35  0  0  1  0            999 V2000
    4.2868   -4.9500    0.0000 O   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
    5.0013   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -7.8375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    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
    6.4302   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -9.0750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -8.6625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8592   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -9.0750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2881   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -9.9000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2881  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592  -10.3125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  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  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  6  0  0  0
  5 12  1  1  0  0  0
 12 13  1  0  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 26 31  1  0  0  0  0
 23 32  2  0  0  0  0
 21 33  1  0  0  0  0
 14 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0085613

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](OC(=O)\C=C\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/C21H28O12/c22-8-11-14(24)16(26)18(28)20(31-11)30-9-12-15(25)17(27)19(29)21(32-12)33-13(23)7-6-10-4-2-1-3-5-10/h1-7,11-12,14-22,24-29H,8-9H2/b7-6+/t11-,12-,14-,15-,16+,17+,18-,19-,20-,21+/m1/s1

> <INCHI_KEY>
VFNCMPJNJCOCMS-KLZQJKIXSA-N

> <FORMULA>
C21H28O12

> <MOLECULAR_WEIGHT>
472.443

> <EXACT_MASS>
472.158076342

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
45.52842702715012

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl (2E)-3-phenylprop-2-enoate

> <ALOGPS_LOGP>
-0.91

> <JCHEM_LOGP>
-1.669484145666667

> <ALOGPS_LOGS>
-1.64

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.426171799607022

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.903057228718861

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083422322401

> <JCHEM_POLAR_SURFACE_AREA>
195.59999999999997

> <JCHEM_REFRACTIVITY>
107.9044

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.08e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl (2E)-3-phenylprop-2-enoate

> <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  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      10.669 -12.320   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336 -14.630   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.336 -16.170   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.002 -13.860   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.668 -14.630   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.668 -11.550   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      12.003 -14.630   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      12.003 -16.170   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.337 -16.940   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.670 -16.170   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      14.670 -14.630   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      16.004 -16.940   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      17.338 -16.170   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      16.004 -18.480   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      17.338 -19.250   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      14.670 -19.250   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      14.670 -20.790   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      16.004 -21.560   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.004 -23.100   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      17.338 -23.870   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      17.338 -25.410   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      18.672 -26.180   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      18.672 -27.720   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      17.338 -28.490   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      16.004 -27.720   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      16.004 -26.180   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      17.338 -20.790   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      13.337 -18.480   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    3   11                                                  
CONECT   11   10                                                            
CONECT   12    5   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   33                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   33                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   32                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   26                                                       
CONECT   32   23                                                            
CONECT   33   21   14                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Value	Source
1-O-trans-Cinnamoyl-6-O-b-D-glucopyranosyl-b-D-glucopyranose	Generator
1-O-trans-Cinnamoyl-6-O-β-D-glucopyranosyl-β-D-glucopyranose	Generator

Chemical Formula

C₂₁H₂₈O₁₂

Average Mass

472.4430 Da

Monoisotopic Mass

472.15808 Da

IUPAC Name

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl (2E)-3-phenylprop-2-enoate

Traditional Name

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl (2E)-3-phenylprop-2-enoate

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](OC(=O)\C=C\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/C21H28O12/c22-8-11-14(24)16(26)18(28)20(31-11)30-9-12-15(25)17(27)19(29)21(32-12)33-13(23)7-6-10-4-2-1-3-5-10/h1-7,11-12,14-22,24-29H,8-9H2/b7-6+/t11-,12-,14-,15-,16+,17+,18-,19-,20-,21+/m1/s1

InChI Key

VFNCMPJNJCOCMS-KLZQJKIXSA-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
Physalis peruviana	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-cinnamoyl glycosides. These are o-glycoside derivatives of cinnamic acid. Cinnamic acid is an aromatic compound containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Cinnamic acid esters

Direct Parent

O-cinnamoyl glycosides

Alternative Parents

Substituents

O-cinnamoyl glycoside
Disaccharide
Glycosyl compound
O-glycosyl compound
Styrene
Fatty acid ester
Monocyclic benzene moiety
Oxane
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Acetal
Polyol
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Primary alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Alcohol
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	-0.91	ALOGPS
logP	-1.7	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	11.9	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	195.6 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	107.9 m³·mol⁻¹	ChemAxon
Polarizability	45.53 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

C00055537

Chemspider ID

103883986

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101999893

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 1-O-Cinnamoyl-beta-D-gentiobiose (NP0085613)

MOL for NP0085613 (1-O-Cinnamoyl-beta-D-gentiobiose)

3D MOL for NP0085613 (1-O-Cinnamoyl-beta-D-gentiobiose)

3D SDF for NP0085613 (1-O-Cinnamoyl-beta-D-gentiobiose)

3D-SDF for NP0085613 (1-O-Cinnamoyl-beta-D-gentiobiose)

PDB for NP0085613 (1-O-Cinnamoyl-beta-D-gentiobiose)

3D PDB for NP0085613 (1-O-Cinnamoyl-beta-D-gentiobiose)

SMILES for NP0085613 (1-O-Cinnamoyl-beta-D-gentiobiose)

INCHI for NP0085613 (1-O-Cinnamoyl-beta-D-gentiobiose)

Structure for NP0085613 (1-O-Cinnamoyl-beta-D-gentiobiose)

3D Structure for NP0085613 (1-O-Cinnamoyl-beta-D-gentiobiose)