NP-MRD: Showing NP-Card for (-)-Coelovirin A (NP0076340)

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Record Information

Version

2.0

Created at

2022-04-28 21:29:26 UTC

Updated at

2022-04-28 21:29:26 UTC

NP-MRD ID

NP0076340

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Coelovirin A

Description

(2S,3R,4R)-2,3-dihydroxy-4-methyl-3-{[(4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methoxy]carbonyl}hexanoic acid 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. (-)-Coelovirin A is found in Gymnadenia conopsea. Based on a literature review very few articles have been published on (2S,3R,4R)-2,3-dihydroxy-4-methyl-3-{[(4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methoxy]carbonyl}hexanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282223292D          

 33 34  0  0  1  0            999 V2000
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1599    1.9520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3349    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9224    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849    0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0000   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0000   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 11  9  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 12 16  1  6  0  0  0
 11 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 11 21  1  6  0  0  0
  2 22  1  0  0  0  0
 23 22  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  1  0  0  0
 27 30  1  6  0  0  0
 26 31  1  1  0  0  0
 25 32  1  6  0  0  0
 32 33  1  0  0  0  0
M  END

     RDKit          3D

 63 64  0  0  0  0  0  0  0  0999 V2000
    6.2078   -0.3889   -2.1822 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7432   -0.9651   -0.8999 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8404   -1.0458    0.2282 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6222   -1.6749    1.4249 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0555    0.0533    0.7843 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3636   -0.6376    1.8923 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9771    0.6479   -0.0115 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2372    1.4479   -0.9336 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6257    0.3782    0.1897 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6295    1.0033   -0.6351 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2770    0.5897   -0.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0358   -0.2967    0.7526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -0.6281    1.0299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4029   -0.0801    0.2935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6650   -0.4796    0.6551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8785   -0.0983    0.1021 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7186    0.5054    1.0371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0015    0.6857    0.5944 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.9539   -0.1182    1.4558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8310    0.3339    2.7778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2097    0.4615   -0.8680 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.7473    1.5768   -1.5812 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6517   -0.8195   -1.3927 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.6236   -1.8002   -1.6034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5256   -1.3364   -0.4973 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5683   -1.9776   -1.2845 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1058    0.7916   -0.7076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7910    1.1061   -0.9646 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7940    1.1289    1.5472 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7501    1.8155    2.2640 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4061    2.1731    0.7039 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9346    3.3687    0.6736 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5068    1.9983   -0.1127 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4195    0.7092   -2.2840 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8208   -0.8241   -3.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1540   -0.6097   -2.3815 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0095   -2.0559   -1.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7594   -0.5493   -0.7408 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1088   -1.9064   -0.0041 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4388   -1.0130    1.7333 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0753   -2.5997    1.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9294   -1.9618    2.2173 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9281   -1.3908    1.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7654    2.0994   -0.5918 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7943    0.6685   -1.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8011   -0.7190    1.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5113   -1.3270    1.8389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7784    0.6223   -0.7336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2638    1.7666    0.7929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0227    0.0978    1.1751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8247   -1.2014    1.3576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4301   -0.1908    3.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3267    0.4582   -1.0360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6881    1.3519   -2.5446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1406   -0.5723   -2.3694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3937   -2.2520   -2.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8731   -2.0521    0.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5191   -2.9558   -1.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9286    1.2267   -1.2907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5923    1.8029   -1.7682 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4791    0.7694    2.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3446    2.4659    1.6222 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5527    2.4235   -1.0328 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
  3  5  1  0
  5  6  1  1
  5 29  1  0
 29 30  1  0
 29 31  1  0
 31 33  1  0
 31 32  2  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 14 27  1  0
 27 28  2  0
 28 11  1  0
 25 16  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  0
  2 38  1  0
  3 39  1  6
  4 40  1  0
  4 41  1  0
  4 42  1  0
  6 43  1  0
 29 61  1  1
 30 62  1  0
 33 63  1  0
 10 44  1  0
 10 45  1  0
 12 46  1  0
 13 47  1  0
 16 48  1  6
 18 49  1  6
 19 50  1  0
 19 51  1  0
 20 52  1  0
 21 53  1  1
 22 54  1  0
 23 55  1  6
 24 56  1  0
 25 57  1  1
 26 58  1  0
 27 59  1  0
 28 60  1  0
M  END


  Mrv1652304282223292D          

 33 34  0  0  1  0            999 V2000
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1599    1.9520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3349    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9224    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849    0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0000   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0000   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 11  9  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 12 16  1  6  0  0  0
 11 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 11 21  1  6  0  0  0
  2 22  1  0  0  0  0
 23 22  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  1  0  0  0
 27 30  1  6  0  0  0
 26 31  1  1  0  0  0
 25 32  1  6  0  0  0
 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0076340

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@H](C)[C@@](O)([C@H](O)C(O)=O)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/C21H30O12/c1-3-10(2)21(30,17(26)18(27)28)20(29)31-9-11-4-6-12(7-5-11)32-19-16(25)15(24)14(23)13(8-22)33-19/h4-7,10,13-17,19,22-26,30H,3,8-9H2,1-2H3,(H,27,28)/t10-,13-,14-,15+,16-,17-,19-,21-/m1/s1

> <INCHI_KEY>
HXJSMUHQCRYXNT-DTIOYLITSA-N

> <FORMULA>
C21H30O12

> <MOLECULAR_WEIGHT>
474.459

> <EXACT_MASS>
474.173726406

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
46.76807337856228

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4R)-2,3-dihydroxy-4-methyl-3-[(4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl carboxy]hexanoic acid

> <ALOGPS_LOGP>
-0.44

> <JCHEM_LOGP>
-0.7652363580000008

> <ALOGPS_LOGS>
-2.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.266060426388744

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5861475065850517

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092343686494

> <JCHEM_POLAR_SURFACE_AREA>
203.44

> <JCHEM_REFRACTIVITY>
108.03029999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.90e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4R)-2,3-dihydroxy-4-methyl-3-[(4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl carboxy]hexanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      10.669   3.080   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       9.336   0.770   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.898   3.644   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668   4.977   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.358   3.644   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.588   4.977   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.438   0.976   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -0.000 -12.320   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   22                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   17   21                                             
CONECT   12   11   13   16                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   12                                                            
CONECT   17   11   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19                                                            
CONECT   21   11                                                            
CONECT   22    2   23                                                       
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   32                                                  
CONECT   26   25   27   31                                                  
CONECT   27   26   28   30                                                  
CONECT   28   27   23   29                                                  
CONECT   29   28                                                            
CONECT   30   27                                                            
CONECT   31   26                                                            
CONECT   32   25   33                                                       
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

View in JSmol

Synonyms

Value	Source
(2S,3R,4R)-2,3-Dihydroxy-4-methyl-3-{[(4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methoxy]carbonyl}hexanoate	Generator

Chemical Formula

C₂₁H₃₀O₁₂

Average Mass

474.4590 Da

Monoisotopic Mass

474.17373 Da

IUPAC Name

(2S,3R,4R)-2,3-dihydroxy-4-methyl-3-[(4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl carboxy]hexanoic acid

Traditional Name

(2S,3R,4R)-2,3-dihydroxy-4-methyl-3-[(4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl carboxy]hexanoic acid

CAS Registry Number

Not Available

SMILES

CC[C@@H](C)[C@@](O)([C@H](O)C(O)=O)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/C21H30O12/c1-3-10(2)21(30,17(26)18(27)28)20(29)31-9-11-4-6-12(7-5-11)32-19-16(25)15(24)14(23)13(8-22)33-19/h4-7,10,13-17,19,22-26,30H,3,8-9H2,1-2H3,(H,27,28)/t10-,13-,14-,15+,16-,17-,19-,21-/m1/s1

InChI Key

HXJSMUHQCRYXNT-DTIOYLITSA-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
Gymnadenia conopsea	Plant	KNApSAcK

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
Hexose monosaccharide
O-glycosyl compound
Benzyloxycarbonyl
Phenoxy compound
Phenol ether
Fatty acid ester
Beta-hydroxy acid
Fatty acyl
Benzenoid
Oxane
Monosaccharide
Hydroxy acid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Alpha-hydroxy acid
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid
Carboxylic acid derivative
Acetal
Organic oxide
Hydrocarbon derivative
Primary alcohol
Carbonyl group
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	-0.44	ALOGPS
logP	-0.77	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	3.59	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	203.44 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	108.03 m³·mol⁻¹	ChemAxon
Polarizability	46.77 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

154496360

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Coelovirin A (NP0076340)

MOL for NP0076340 ((-)-Coelovirin A)

3D MOL for NP0076340 ((-)-Coelovirin A)

3D SDF for NP0076340 ((-)-Coelovirin A)

3D-SDF for NP0076340 ((-)-Coelovirin A)

PDB for NP0076340 ((-)-Coelovirin A)

3D PDB for NP0076340 ((-)-Coelovirin A)

SMILES for NP0076340 ((-)-Coelovirin A)

INCHI for NP0076340 ((-)-Coelovirin A)

Structure for NP0076340 ((-)-Coelovirin A)

3D Structure for NP0076340 ((-)-Coelovirin A)