NP-MRD: Showing NP-Card for 1,4-bis[(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl] (2r)-2-(2-methylpropyl)-2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-phenylprop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}butanedioate (NP0191817)

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Record Information

Version

2.0

Created at

2022-09-04 08:53:22 UTC

Updated at

2022-09-04 08:53:22 UTC

NP-MRD ID

NP0191817

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,4-bis[(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl] (2r)-2-(2-methylpropyl)-2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-phenylprop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}butanedioate

Description

Gymnoside VI 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. 1,4-bis[(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl] (2r)-2-(2-methylpropyl)-2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-phenylprop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}butanedioate is found in Gymnadenia conopsea. Based on a literature review very few articles have been published on Gymnoside VI.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042210532D          

 72 77  0  0  1  0            999 V2000
   -6.7388    2.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.7810    0.4497    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.7810   -0.3753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0665   -0.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3128   -1.1234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0665   -1.6128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7810   -2.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7810   -2.8503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0665   -3.2628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0665   -4.0878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.6389   -5.3253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2099   -5.3253    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.2099   -4.5003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4955   -4.0878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2193   -5.5805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3908   -6.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1754   -6.6424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5440   -1.5035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9856   -0.1445    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -7.5656    0.1948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.9741    1.3410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8026    2.1479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4157    2.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2003    2.4450    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  -12.3719    1.6381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1565    1.3831    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  -13.3280    0.5762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.1126    0.3212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -13.7696    1.9352    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  -14.5542    1.6802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5980    2.7421    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  -14.2111    3.2942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8134    2.9971    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  -12.6419    3.8040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0180    2.4029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4049    1.8509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  1  0  0  0
 14 27  1  0  0  0  0
 27 28  2  0  0  0  0
 11 28  1  0  0  0  0
  5 29  1  6  0  0  0
 30 29  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 39 44  1  0  0  0  0
 32 45  1  0  0  0  0
 45 46  1  6  0  0  0
 45 47  1  0  0  0  0
 47 48  1  1  0  0  0
 47 49  1  0  0  0  0
 30 49  1  0  0  0  0
 49 50  1  6  0  0  0
  5 51  1  0  0  0  0
 51 52  2  0  0  0  0
 51 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  2  0  0  0  0
 56 57  1  0  0  0  0
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 58 59  1  0  0  0  0
 60 59  1  6  0  0  0
 60 61  1  0  0  0  0
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 62 63  1  6  0  0  0
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 62 65  1  0  0  0  0
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 65 67  1  0  0  0  0
 67 68  1  6  0  0  0
 67 69  1  0  0  0  0
 60 69  1  0  0  0  0
 69 70  1  1  0  0  0
 58 71  1  0  0  0  0
 71 72  2  0  0  0  0
 55 72  1  0  0  0  0
M  END

     RDKit          3D

134139  0  0  0  0  0  0  0  0999 V2000
   -4.4130   -3.0074    0.1656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6713   -4.0729   -0.5393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7124   -5.1154   -1.0097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8567   -3.7463   -1.7225 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4756    0.5510   -1.7926 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.9213    6.7004    4.6512 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9645    5.3545    5.0169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6014    7.0735    4.0636 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4020    8.4526    4.2151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5140    6.6062    2.6523 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7122    5.4608    2.6341 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5025    5.0340   -1.4078 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.5845   -1.2628   -1.1401 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7377   -5.7601   -4.3294 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2660   -6.7136   -3.3971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3749   -5.2790   -5.1828 C   0  0  2  0  0  0  0  0  0  0  0  0
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    3.2888    4.8367    0.5126 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6584   -0.5844    1.5699 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6832   -1.5723    1.4155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3566   -3.4857    0.5837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7299   -2.1667   -0.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309042210532D          

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M  END
> <DATABASE_ID>
NP0191817

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C[C@](CC(=O)OCC1=CC=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C=C1)(O[C@@H]1O[C@H](COC(=O)\C=C\C2=CC=CC=C2)[C@@H](O)[C@H](O)[C@H]1O)C(=O)OCC1=CC=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C49H62O23/c1-25(2)18-49(48(63)66-23-28-10-15-30(16-11-28)68-46-43(61)40(58)37(55)32(21-51)70-46,72-47-44(62)41(59)38(56)33(71-47)24-65-34(52)17-12-26-6-4-3-5-7-26)19-35(53)64-22-27-8-13-29(14-9-27)67-45-42(60)39(57)36(54)31(20-50)69-45/h3-17,25,31-33,36-47,50-51,54-62H,18-24H2,1-2H3/b17-12+/t31-,32-,33-,36-,37-,38-,39+,40+,41+,42-,43-,44-,45-,46-,47+,49-/m1/s1

> <INCHI_KEY>
VCCBFXCFLIEPOV-RVDSMONLSA-N

> <FORMULA>
C49H62O23

> <MOLECULAR_WEIGHT>
1019.012

> <EXACT_MASS>
1018.368188256

> <JCHEM_ACCEPTOR_COUNT>
20

> <JCHEM_ATOM_COUNT>
134

> <JCHEM_AVERAGE_POLARIZABILITY>
103.26693674044232

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,4-bis[(4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl] (2R)-2-(2-methylpropyl)-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-phenylprop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}butanedioate

> <JCHEM_LOGP>
0.4337572033333317

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.193902937141482

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.748604424433479

> <JCHEM_PKA_STRONGEST_BASIC>
-3.648395345629174

> <JCHEM_POLAR_SURFACE_AREA>
356.81000000000006

> <JCHEM_REFRACTIVITY>
242.25709999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
24

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
1,4-bis[(4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl] (2R)-2-(2-methylpropyl)-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-phenylprop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}butanedioate

> <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     -12.579   4.913   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -12.103   3.449   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -10.597   3.128   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -13.134   2.304   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -12.658   0.839   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -12.658  -0.701   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -11.324  -1.471   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -9.917  -2.097   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0     -11.324  -3.011   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0     -12.658  -3.781   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -12.658  -5.321   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -11.324  -6.091   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -11.324  -7.631   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -12.658  -8.401   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0     -12.658  -9.941   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0     -13.992 -10.711   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0     -13.992 -12.251   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0     -15.325 -13.021   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -15.325 -14.561   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0     -16.659 -15.331   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0     -16.659 -12.251   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0     -17.993 -13.021   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0     -16.659 -10.711   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0     -17.993  -9.941   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0     -15.325  -9.941   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0     -15.325  -8.401   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0     -13.992  -7.631   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -13.992  -6.091   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0     -11.193   1.315   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0     -10.049   0.285   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0     -10.369  -1.221   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -9.225  -2.252   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -9.545  -3.758   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -8.400  -4.789   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -8.720  -6.295   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0     -10.185  -6.771   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -7.576  -7.326   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -7.896  -8.832   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -6.752  -9.862   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -5.287  -9.386   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -4.143 -10.417   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -4.463 -11.923   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -5.927 -12.399   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -7.072 -11.369   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -7.760  -1.776   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      -6.615  -2.807   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      -7.440  -0.270   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      -5.975   0.206   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      -8.584   0.761   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      -8.264   2.267   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0     -14.122   0.364   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0     -14.443  -1.143   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0     -15.267   1.394   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0     -16.732   0.918   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0     -17.876   1.949   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0     -19.341   1.473   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0     -20.485   2.503   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0     -20.165   4.010   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0     -21.309   5.040   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0     -22.774   4.564   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0     -23.094   3.058   0.000  0.00  0.00           O+0
HETATM   62  C   UNK     0     -24.559   2.582   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0     -24.879   1.075   0.000  0.00  0.00           C+0
HETATM   64  O   UNK     0     -26.344   0.600   0.000  0.00  0.00           O+0
HETATM   65  C   UNK     0     -25.703   3.612   0.000  0.00  0.00           C+0
HETATM   66  O   UNK     0     -27.168   3.136   0.000  0.00  0.00           O+0
HETATM   67  C   UNK     0     -25.383   5.119   0.000  0.00  0.00           C+0
HETATM   68  O   UNK     0     -26.527   6.149   0.000  0.00  0.00           O+0
HETATM   69  C   UNK     0     -23.918   5.595   0.000  0.00  0.00           C+0
HETATM   70  O   UNK     0     -23.598   7.101   0.000  0.00  0.00           O+0
HETATM   71  C   UNK     0     -18.700   4.485   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0     -17.556   3.455   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   29   51                                             
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   28                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   27                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   25                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   16   26                                                  
CONECT   26   25                                                            
CONECT   27   14   28                                                       
CONECT   28   27   11                                                       
CONECT   29    5   30                                                       
CONECT   30   29   31   49                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   45                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40   44                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   39                                                       
CONECT   45   32   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47   30   50                                                  
CONECT   50   49                                                            
CONECT   51    5   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   56   72                                                  
CONECT   56   55   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57   59   71                                                  
CONECT   59   58   60                                                       
CONECT   60   59   61   69                                                  
CONECT   61   60   62                                                       
CONECT   62   61   63   65                                                  
CONECT   63   62   64                                                       
CONECT   64   63                                                            
CONECT   65   62   66   67                                                  
CONECT   66   65                                                            
CONECT   67   65   68   69                                                  
CONECT   68   67                                                            
CONECT   69   67   60   70                                                  
CONECT   70   69                                                            
CONECT   71   58   72                                                       
CONECT   72   71   55                                                       
MASTER        0    0    0    0    0    0    0    0   72    0  154    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₉H₆₂O₂₃

Average Mass

1019.0120 Da

Monoisotopic Mass

1018.36819 Da

IUPAC Name

1,4-bis[(4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl] (2R)-2-(2-methylpropyl)-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-phenylprop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}butanedioate

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(C)C[C@](CC(=O)OCC1=CC=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C=C1)(O[C@@H]1O[C@H](COC(=O)\C=C\C2=CC=CC=C2)[C@@H](O)[C@H](O)[C@H]1O)C(=O)OCC1=CC=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C=C1

InChI Identifier

InChI=1S/C49H62O23/c1-25(2)18-49(48(63)66-23-28-10-15-30(16-11-28)68-46-43(61)40(58)37(55)32(21-51)70-46,72-47-44(62)41(59)38(56)33(71-47)24-65-34(52)17-12-26-6-4-3-5-7-26)19-35(53)64-22-27-8-13-29(14-9-27)67-45-42(60)39(57)36(54)31(20-50)69-45/h3-17,25,31-33,36-47,50-51,54-62H,18-24H2,1-2H3/b17-12+/t31-,32-,33-,36-,37-,38-,39+,40+,41+,42-,43-,44-,45-,46-,47+,49-/m1/s1

InChI Key

VCCBFXCFLIEPOV-RVDSMONLSA-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
Gymnadenia conopsea	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

Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
Phenolic glycoside
Alkyl glycoside
Cinnamic acid ester
Cinnamic acid or derivatives
O-glycosyl compound
Benzyloxycarbonyl
Tricarboxylic acid or derivatives
Styrene
Phenoxy compound
Phenol ether
Sugar acid
Fatty acid ester
Oxane
Benzenoid
Monosaccharide
Fatty acyl
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Acetal
Carboxylic acid derivative
Oxacycle
Polyol
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Primary 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	0.43	ChemAxon
pKa (Strongest Acidic)	11.75	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	356.81 Å²	ChemAxon
Rotatable Bond Count	24	ChemAxon
Refractivity	242.26 m³·mol⁻¹	ChemAxon
Polarizability	103.27 Å³	ChemAxon
Number of Rings	6	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

C00030443

Chemspider ID

9775305

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11600548

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1,4-bis[(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl] (2r)-2-(2-methylpropyl)-2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-phenylprop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}butanedioate (NP0191817)

MOL for NP0191817 (1,4-bis[(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl] (2r)-2-(2-methylpropyl)-2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-phenylprop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}butanedioate)

3D MOL for NP0191817 (1,4-bis[(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl] (2r)-2-(2-methylpropyl)-2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-phenylprop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}butanedioate)

3D SDF for NP0191817 (1,4-bis[(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl] (2r)-2-(2-methylpropyl)-2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-phenylprop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}butanedioate)

3D-SDF for NP0191817 (1,4-bis[(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl] (2r)-2-(2-methylpropyl)-2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-phenylprop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}butanedioate)

PDB for NP0191817 (1,4-bis[(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl] (2r)-2-(2-methylpropyl)-2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-phenylprop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}butanedioate)

3D PDB for NP0191817 (1,4-bis[(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl] (2r)-2-(2-methylpropyl)-2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-phenylprop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}butanedioate)

SMILES for NP0191817 (1,4-bis[(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl] (2r)-2-(2-methylpropyl)-2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-phenylprop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}butanedioate)

INCHI for NP0191817 (1,4-bis[(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl] (2r)-2-(2-methylpropyl)-2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-phenylprop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}butanedioate)

Structure for NP0191817 (1,4-bis[(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl] (2r)-2-(2-methylpropyl)-2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-phenylprop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}butanedioate)

3D Structure for NP0191817 (1,4-bis[(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl] (2r)-2-(2-methylpropyl)-2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-phenylprop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}butanedioate)