NP-MRD: Showing NP-Card for (2r,3s,4r,5r,6s)-6-{4-[(s)-cyano(hydroxy)methyl]phenoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate (NP0177239)

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Record Information

Version

2.0

Created at

2022-09-03 15:02:59 UTC

Updated at

2022-09-03 15:02:59 UTC

NP-MRD ID

NP0177239

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3s,4r,5r,6s)-6-{4-[(s)-cyano(hydroxy)methyl]phenoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Description

(2R,3S,4R,5R,6S)-6-{4-[(S)-cyano(hydroxy)methyl]phenoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. (2r,3s,4r,5r,6s)-6-{4-[(s)-cyano(hydroxy)methyl]phenoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate is found in Nandina domestica. Based on a literature review very few articles have been published on (2R,3S,4R,5R,6S)-6-{4-[(S)-cyano(hydroxy)methyl]phenoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032217032D          

 34 36  0  0  1  0            999 V2000
    2.1434   -4.5375    0.0000 N   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  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
    3.5724   -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
    4.2868   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -9.0750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -10.3125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -11.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -9.9000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289  -11.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579  -14.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579  -12.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -9.0750    0.0000 C   0  0  2  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
    2.1434   -8.6625    0.0000 C   0  0  1  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
    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
  1  2  3  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
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 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
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 21 28  1  0  0  0  0
 15 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 10 31  1  0  0  0  0
 31 32  1  1  0  0  0
  8 33  1  0  0  0  0
 33 34  2  0  0  0  0
  5 34  1  0  0  0  0
M  END

     RDKit          3D

 57 59  0  0  0  0  0  0  0  0999 V2000
    9.2220    2.9062    0.9275 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1421    1.7652    0.7609 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0348    0.3396    0.5283 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.5027   -0.3912    1.6390 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5981   -0.0750    0.3578 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6172    0.8598    0.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2837    0.4603   -0.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9167   -0.8557    0.0412 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6402   -1.3095   -0.1017 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4642   -0.5880   -0.3429 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5850   -0.6871    0.7373 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5413    0.2017    0.4810 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1960    0.5732    1.7469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7476   -0.5350    2.3649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3698   -0.5580   -0.4882 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6023    0.0804   -0.5949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7842   -0.4807   -0.2039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7575   -1.6413    0.2809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0835    0.2158   -0.3267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2084   -0.3478    0.0585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5209    0.2571   -0.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7462    1.5168   -0.5273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0432    2.0463   -0.5801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1115    1.3042   -0.1251 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4013    1.8206   -0.1734 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8993    0.0560    0.3749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9985   -0.6672    0.8260 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6133   -0.4494    0.4191 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3804   -0.6723   -1.7793 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2790   -1.6091   -2.5801 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8250   -0.9666   -1.6477 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5480   -0.3814   -2.7154 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9135   -1.7784    0.2746 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2326   -1.4003    0.4308 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6262    0.0255   -0.3422 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9384   -0.0880    2.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8681    1.9064    0.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5470    1.2290   -0.2114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7141    0.4869   -0.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8969    1.0963   -0.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9161    1.3915    1.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5798    0.9721    2.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8543   -0.3926    3.3526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4733   -1.5767   -0.0467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1358    1.2103   -0.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1190   -1.3559    0.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9437    2.1161   -0.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2474    3.0282   -0.9686 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5759    2.7438   -0.5411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9107   -1.5968    1.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4866   -1.4340    0.8190 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2840    0.3046   -2.3397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5629   -2.4095   -2.0769 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9693   -2.0619   -1.7765 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0177    0.3915   -3.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6932   -2.8357    0.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0060   -2.1602    0.6160 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  2  0
  5 34  1  0
 34 33  2  0
  5  3  1  0
  3  4  1  0
  3  2  1  0
  2  1  3  0
 10 31  1  0
 31 32  1  0
 31 29  1  0
 29 30  1  0
 29 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
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 22 23  1  0
 23 24  2  0
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 26 28  2  0
 15 12  1  0
 28 21  1  0
 33  8  1  0
 14 43  1  0
 13 41  1  0
 13 42  1  0
 12 40  1  6
 10 39  1  6
  7 38  1  0
  6 37  1  0
 34 57  1  0
 33 56  1  0
  3 35  1  6
  4 36  1  0
 31 54  1  6
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 29 52  1  6
 30 53  1  0
 15 44  1  1
 19 45  1  0
 20 46  1  0
 22 47  1  0
 23 48  1  0
 25 49  1  0
 27 50  1  0
 28 51  1  0
M  END


  Mrv1652309032217032D          

 34 36  0  0  1  0            999 V2000
    2.1434   -4.5375    0.0000 N   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  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
    3.5724   -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
    4.2868   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -9.0750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -10.3125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -11.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7145  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4289  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1434  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579  -12.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -9.0750    0.0000 C   0  0  2  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
    2.1434   -8.6625    0.0000 C   0  0  1  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
    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
  1  2  3  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  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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 29 30  1  6  0  0  0
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  8 33  1  0  0  0  0
 33 34  2  0  0  0  0
  5 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0177239

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC=C(C=C2)[C@H](O)C#N)[C@H](O)[C@@H](O)[C@@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C23H23NO10/c24-10-17(28)13-3-5-14(6-4-13)32-23-21(31)20(30)22(18(11-25)33-23)34-19(29)8-2-12-1-7-15(26)16(27)9-12/h1-9,17-18,20-23,25-28,30-31H,11H2/b8-2+/t17-,18-,20-,21-,22-,23-/m1/s1

> <INCHI_KEY>
OTBWOFBYEYFNNC-IDSCLJDSSA-N

> <FORMULA>
C23H23NO10

> <MOLECULAR_WEIGHT>
473.434

> <EXACT_MASS>
473.132195945

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
46.19091223277952

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3S,4R,5R,6S)-6-{4-[(S)-cyano(hydroxy)methyl]phenoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <JCHEM_LOGP>
0.8089111710000003

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.616409669508597

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.20707551942252

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981816496359672

> <JCHEM_POLAR_SURFACE_AREA>
189.92999999999998

> <JCHEM_REFRACTIVITY>
115.3379

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4R,5R,6S)-6-{4-[(S)-cyano(hydroxy)methyl]phenoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  N   UNK     0       4.001  -8.470   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002 -13.860   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668 -14.630   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.668 -16.170   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.335 -16.940   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335 -18.480   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.001 -19.250   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001 -20.790   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.335 -21.560   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.667 -18.480   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.334 -19.250   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.334 -20.790   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.667 -21.560   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.000 -21.560   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000 -23.100   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.334 -23.870   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.334 -25.410   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.667 -26.180   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.001 -25.410   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -5.335 -26.180   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -4.001 -23.870   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -5.335 -23.100   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -2.667 -23.100   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667 -16.940   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.334 -16.170   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.001 -16.170   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.001 -14.630   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   34                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   33                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   31                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   29                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   28                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   21                                                       
CONECT   29   15   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   10   32                                                  
CONECT   32   31                                                            
CONECT   33    8   34                                                       
CONECT   34   33    5                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Value	Source
(2R,3S,4R,5R,6S)-6-{4-[(S)-cyano(hydroxy)methyl]phenoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₂₃H₂₃NO₁₀

Average Mass

473.4340 Da

Monoisotopic Mass

473.13220 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=CC=C(C=C2)[C@H](O)C#N)[C@H](O)[C@@H](O)[C@@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C23H23NO10/c24-10-17(28)13-3-5-14(6-4-13)32-23-21(31)20(30)22(18(11-25)33-23)34-19(29)8-2-12-1-7-15(26)16(27)9-12/h1-9,17-18,20-23,25-28,30-31H,11H2/b8-2+/t17-,18-,20-,21-,22-,23-/m1/s1

InChI Key

OTBWOFBYEYFNNC-IDSCLJDSSA-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
Nandina domestica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hexose monosaccharide
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
O-glycosyl compound
Phenol ether
Phenoxy compound
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Monocyclic benzene moiety
Fatty acyl
Monosaccharide
Benzenoid
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Alpha-hydroxynitrile
Cyanohydrin
Secondary alcohol
Carbonitrile
Nitrile
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Acetal
Primary alcohol
Organic oxide
Alcohol
Organopnictogen compound
Hydrocarbon derivative
Carbonyl group
Aromatic alcohol
Organic nitrogen compound
Organonitrogen 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	0.81	ChemAxon
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	189.93 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	115.34 m³·mol⁻¹	ChemAxon
Polarizability	46.19 Å³	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

163195479

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3s,4r,5r,6s)-6-{4-[(s)-cyano(hydroxy)methyl]phenoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate (NP0177239)

MOL for NP0177239 ((2r,3s,4r,5r,6s)-6-{4-[(s)-cyano(hydroxy)methyl]phenoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D MOL for NP0177239 ((2r,3s,4r,5r,6s)-6-{4-[(s)-cyano(hydroxy)methyl]phenoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D SDF for NP0177239 ((2r,3s,4r,5r,6s)-6-{4-[(s)-cyano(hydroxy)methyl]phenoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D-SDF for NP0177239 ((2r,3s,4r,5r,6s)-6-{4-[(s)-cyano(hydroxy)methyl]phenoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

PDB for NP0177239 ((2r,3s,4r,5r,6s)-6-{4-[(s)-cyano(hydroxy)methyl]phenoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D PDB for NP0177239 ((2r,3s,4r,5r,6s)-6-{4-[(s)-cyano(hydroxy)methyl]phenoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

SMILES for NP0177239 ((2r,3s,4r,5r,6s)-6-{4-[(s)-cyano(hydroxy)methyl]phenoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

INCHI for NP0177239 ((2r,3s,4r,5r,6s)-6-{4-[(s)-cyano(hydroxy)methyl]phenoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

Structure for NP0177239 ((2r,3s,4r,5r,6s)-6-{4-[(s)-cyano(hydroxy)methyl]phenoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D Structure for NP0177239 ((2r,3s,4r,5r,6s)-6-{4-[(s)-cyano(hydroxy)methyl]phenoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)