NP-MRD: Showing NP-Card for (2s,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 (2e)-3-phenylprop-2-enoate (NP0185312)

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Record Information

Version

2.0

Created at

2022-09-04 00:41:04 UTC

Updated at

2022-09-04 00:41:04 UTC

NP-MRD ID

NP0185312

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,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 (2e)-3-phenylprop-2-enoate

Description

GLEDITSCHIASIDE A 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. (2s,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 (2e)-3-phenylprop-2-enoate is found in Picea neoveitchii. Based on a literature review very few articles have been published on GLEDITSCHIASIDE A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042202412D          

 32 34  0  0  1  0            999 V2000
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  2  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  1  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    0.0000 C   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
    0.0000   -7.4250    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
    1.4289   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    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
    3.5724   -6.1875    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
    4.2868   -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
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -8.6625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -9.0750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0000   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -8.6625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2868   -4.9500    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
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 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
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
  7 25  1  0  0  0  0
 25 26  1  6  0  0  0
  4 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
  2 31  1  0  0  0  0
 31 32  1  1  0  0  0
M  END

     RDKit          3D

 60 62  0  0  0  0  0  0  0  0999 V2000
   -1.9582    2.5187   -0.1084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5721    2.0394    1.2024 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8292    0.9555    1.6323 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6307   -0.1986    1.7624 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8282   -1.2058    2.2301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8242   -2.3572    1.4772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3506   -2.1255    0.0582 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0518   -1.6275    0.1442 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3968   -1.2644   -1.1248 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5788   -0.5108   -0.9400 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7074    0.7726   -1.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7971    1.3332   -2.0568 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9656    1.4907   -1.1975 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9509    0.9286   -0.5381 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2402    1.5557   -0.2538 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579    0.7840    0.4655 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3911    1.3122    0.7680 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7102    2.5957    0.3595 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7977    3.3377   -0.3449 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5479    2.8232   -0.6602 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7070   -2.5811   -1.8498 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2566   -2.3710   -3.0903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6167   -3.2874   -2.0170 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4857   -4.5239   -2.6184 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3808   -3.3931   -0.7387 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7068   -3.7159   -1.0726 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6926    0.1790    2.8053 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2779   -0.9332    3.3669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7103    1.0312    2.0541 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6494    0.1261    1.5284 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0089    1.7276    0.9329 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6644    2.9605    0.7244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7612    2.8982   -0.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5201    1.6449   -0.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2082    3.3146    0.0850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5050    2.9066    1.9195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1815   -0.4164    0.8433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1811   -3.0944    1.9999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8452   -2.8395    1.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9502   -1.3758   -0.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3822   -0.7270   -1.6852 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1023    2.5053   -1.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7580   -0.0873   -0.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9088   -0.2211    0.7856 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0942    0.7271    1.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6818    3.0087    0.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0053    4.3319   -0.6781 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8290    3.4130   -1.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3188   -3.1872   -1.1664 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7676   -1.5217   -3.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2310   -2.6477   -2.7141 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4881   -4.7513   -2.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9818   -4.2635   -0.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9401   -3.2463   -1.9140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2453    0.8665    3.5779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3178   -0.7815    4.3528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2474    1.7182    2.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8811   -0.5830    2.2007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1085    1.1866   -0.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4328    2.8459    0.1228 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
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 10 11  1  0
 11 12  2  0
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 13 14  2  0
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 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  9 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
  4 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 31  2  1  0
 25  7  1  0
 20 15  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  1
  4 37  1  6
  6 38  1  0
  6 39  1  0
  7 40  1  6
  9 41  1  6
 13 42  1  0
 14 43  1  0
 16 44  1  0
 17 45  1  0
 18 46  1  0
 19 47  1  0
 20 48  1  0
 21 49  1  1
 22 50  1  0
 23 51  1  6
 24 52  1  0
 25 53  1  1
 26 54  1  0
 27 55  1  1
 28 56  1  0
 29 57  1  1
 30 58  1  0
 31 59  1  6
 32 60  1  0
M  END


  Mrv1652309042202412D          

 32 34  0  0  1  0            999 V2000
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  2  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  1  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    0.0000 C   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
    0.0000   -7.4250    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
    1.4289   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    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
    3.5724   -6.1875    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
    4.2868   -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
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -8.6625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -9.0750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0000   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -8.6625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2868   -4.9500    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
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
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 14 15  1  0  0  0  0
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 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
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 19 20  2  0  0  0  0
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 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
  7 25  1  0  0  0  0
 25 26  1  6  0  0  0
  4 27  1  0  0  0  0
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  2 31  1  0  0  0  0
 31 32  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0185312

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[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/C21H28O11/c1-10-14(23)16(25)18(27)20(30-10)29-9-12-15(24)17(26)19(28)21(31-12)32-13(22)8-7-11-5-3-2-4-6-11/h2-8,10,12,14-21,23-28H,9H2,1H3/b8-7+/t10-,12+,14-,15+,16+,17-,18+,19+,20+,21-/m0/s1

> <INCHI_KEY>
BVUBTNCZSYXLNC-SWQDJAIOSA-N

> <FORMULA>
C21H28O11

> <MOLECULAR_WEIGHT>
456.444

> <EXACT_MASS>
456.163161722

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
44.94902086375471

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,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 (2E)-3-phenylprop-2-enoate

> <JCHEM_LOGP>
-0.6225741789999999

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.437615121794831

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.909801655157237

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6121823516836606

> <JCHEM_POLAR_SURFACE_AREA>
175.36999999999998

> <JCHEM_REFRACTIVITY>
106.36070000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,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 (2E)-3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -4.001 -10.010   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.667 -12.320   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334 -14.630   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.000 -13.860   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.667 -13.860   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.001 -16.170   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334 -16.170   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.667 -16.940   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.000 -16.940   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.000 -18.480   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.334 -16.170   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.667 -16.940   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -5.335 -13.860   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -8.002 -12.320   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -8.002  -9.240   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   27                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   25                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   21                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
CONECT   21    9   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23    7   26                                                  
CONECT   26   25                                                            
CONECT   27    4   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29    2   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₈O₁₁

Average Mass

456.4440 Da

Monoisotopic Mass

456.16316 Da

IUPAC Name

(2S,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 (2E)-3-phenylprop-2-enoate

Traditional Name

(2S,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 (2E)-3-phenylprop-2-enoate

CAS Registry Number

Not Available

SMILES

C[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/C21H28O11/c1-10-14(23)16(25)18(27)20(30-10)29-9-12-15(24)17(26)19(28)21(31-12)32-13(22)8-7-11-5-3-2-4-6-11/h2-8,10,12,14-21,23-28H,9H2,1H3/b8-7+/t10-,12+,14-,15+,16+,17-,18+,19+,20+,21-/m0/s1

InChI Key

BVUBTNCZSYXLNC-SWQDJAIOSA-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
Picea neoveitchii	LOTUS Database	35616633

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
Fatty acyl
Benzenoid
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Polyol
Acetal
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen 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	-0.62	ChemAxon
pKa (Strongest Acidic)	11.91	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	175.37 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	106.36 m³·mol⁻¹	ChemAxon
Polarizability	44.95 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	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

31145224

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

76319177

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,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 (2e)-3-phenylprop-2-enoate (NP0185312)

MOL for NP0185312 ((2s,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 (2e)-3-phenylprop-2-enoate)

3D MOL for NP0185312 ((2s,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 (2e)-3-phenylprop-2-enoate)

3D SDF for NP0185312 ((2s,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 (2e)-3-phenylprop-2-enoate)

3D-SDF for NP0185312 ((2s,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 (2e)-3-phenylprop-2-enoate)

PDB for NP0185312 ((2s,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 (2e)-3-phenylprop-2-enoate)

3D PDB for NP0185312 ((2s,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 (2e)-3-phenylprop-2-enoate)

SMILES for NP0185312 ((2s,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 (2e)-3-phenylprop-2-enoate)

INCHI for NP0185312 ((2s,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 (2e)-3-phenylprop-2-enoate)

Structure for NP0185312 ((2s,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 (2e)-3-phenylprop-2-enoate)

3D Structure for NP0185312 ((2s,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 (2e)-3-phenylprop-2-enoate)