NP-MRD: Showing NP-Card for (3s,4as,5r,6s)-5-ethenyl-1-oxo-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl (2s)-2-methylbutanoate (NP0313501)

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Record Information

Version

2.0

Created at

2022-09-11 11:06:01 UTC

Updated at

2022-09-11 11:06:01 UTC

NP-MRD ID

NP0313501

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,4as,5r,6s)-5-ethenyl-1-oxo-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl (2s)-2-methylbutanoate

Description

Dihydrochelonanthoside belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. (3s,4as,5r,6s)-5-ethenyl-1-oxo-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl (2s)-2-methylbutanoate is found in Chelonanthus alatus. Based on a literature review very few articles have been published on Dihydrochelonanthoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112213062D          

 32 34  0  0  1  0            999 V2000
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.0625    0.0000 C   0  0  1  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
   -3.5724   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.8250    0.0000 C   0  0  1  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
   -2.1434    0.4125    0.0000 O   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
   -1.4289    1.6500    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
   -2.1434    2.8875    0.0000 O   0  0  0  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
    0.0000    2.4750    0.0000 C   0  0  2  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
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  1  0  0  0
  4 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 23 31  1  0  0  0  0
 32 31  1  1  0  0  0
 19 32  1  0  0  0  0
  3 32  1  0  0  0  0
M  END

     RDKit          3D

 62 64  0  0  0  0  0  0  0  0999 V2000
   -0.1111    0.8028    2.5523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9330   -0.1283    2.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6279   -1.2750    1.2995 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4711   -1.3502    0.0258 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7023   -0.8062    0.2956 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0565    0.2139   -0.6096 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1878    1.4312   -0.0507 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3839    1.8644    0.4061 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7177    1.4945    1.8362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7822    2.0367    2.6817 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5141    1.6050   -0.5242 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5043    2.5608   -1.5354 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5283    0.2088   -1.0849 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0934   -0.6838   -0.1753 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1655   -0.2530   -1.5179 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9326    0.1014   -2.8533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5747   -2.7837   -0.2194 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3360   -3.4767   -0.2074 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7256   -2.9765    0.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0240   -3.6126    0.3108 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1217   -4.8296    0.1805 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0943   -2.6954    0.4428 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9042   -1.4404   -0.1816 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8772   -0.4972    0.2243 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8227    0.0501   -0.6288 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7966   -0.3264   -1.8250 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8085    1.0369   -0.1131 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6885    0.4307    0.9661 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7219    1.4567   -1.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9325    2.0738   -2.3882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5543   -0.8038    0.0513 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7776   -1.6099    1.0323 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4634    1.6072    3.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9223    0.7898    2.2827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9839   -0.0019    2.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0296   -2.1802    1.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0268   -0.8542   -0.8319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1577    0.2844   -1.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2949    3.0039    0.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7042    1.9546    2.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8515    0.4044    1.9715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1156    1.9477    3.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4730    1.7264    0.0449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3970    2.9124   -1.7431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1845    0.2137   -1.9792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6619   -0.1507    0.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1702   -1.3631   -1.4848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2591   -0.5649   -3.4917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2412   -4.4656   -0.6662 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0834   -1.6068   -1.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2735    1.9058    0.2821 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7669   -0.6479    0.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2417    0.5752    1.9513 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6566    0.9645    0.9241 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2147    0.5380   -1.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4182    2.2062   -0.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9610    2.4575   -1.9920 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5087    2.9275   -2.8095 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7820    1.3267   -3.1891 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6341    0.2652    0.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0035   -0.8975   -0.9364 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3205   -1.6624    1.9816 H   0  0  0  0  0  0  0  0  0  0  0  0
 30 29  1  0
 29 27  1  0
 27 28  1  0
 27 25  1  0
 25 26  2  0
 25 24  1  0
 24 23  1  0
 23 31  1  0
 31 32  1  0
 32  3  1  0
  3  2  1  0
  2  1  2  3
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
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  4 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 19 32  1  0
 15  6  1  0
 30 57  1  0
 30 58  1  0
 30 59  1  0
 29 55  1  0
 29 56  1  0
 27 51  1  1
 28 52  1  0
 28 53  1  0
 28 54  1  0
 23 50  1  6
 31 60  1  0
 31 61  1  0
 32 62  1  1
  3 36  1  1
  2 35  1  0
  1 33  1  0
  1 34  1  0
  4 37  1  6
  6 38  1  6
  8 39  1  1
  9 40  1  0
  9 41  1  0
 10 42  1  0
 11 43  1  1
 12 44  1  0
 13 45  1  6
 14 46  1  0
 15 47  1  6
 16 48  1  0
 18 49  1  0
M  END


  Mrv1652309112213062D          

 32 34  0  0  1  0            999 V2000
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.0625    0.0000 C   0  0  1  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
   -3.5724   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.8250    0.0000 C   0  0  1  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
   -2.1434    0.4125    0.0000 O   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
   -1.4289    1.6500    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
   -2.1434    2.8875    0.0000 O   0  0  0  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
    0.0000    2.4750    0.0000 C   0  0  2  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
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  1  0  0  0
  4 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 23 31  1  0  0  0  0
 32 31  1  1  0  0  0
 19 32  1  0  0  0  0
  3 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0313501

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)C(=O)O[C@@H]1C[C@H]2[C@@H](C=C)[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)OC=C2C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O11/c1-4-9(3)18(26)30-14-6-11-10(5-2)20(28-8-12(11)19(27)31-14)32-21-17(25)16(24)15(23)13(7-22)29-21/h5,8-11,13-17,20-25H,2,4,6-7H2,1,3H3/t9-,10+,11-,13+,14-,15+,16-,17+,20-,21-/m0/s1

> <INCHI_KEY>
HIELOUVZQFFFGL-JTCLUIBCSA-N

> <FORMULA>
C21H30O11

> <MOLECULAR_WEIGHT>
458.46

> <EXACT_MASS>
458.178811786

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
45.87361360185788

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,4aS,5R,6S)-5-ethenyl-1-oxo-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,3H,4H,4aH,5H,6H-pyrano[3,4-c]pyran-3-yl (2S)-2-methylbutanoate

> <JCHEM_LOGP>
0.4070960626666662

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.198719032298811

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.207016193590828

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810847615592513

> <JCHEM_POLAR_SURFACE_AREA>
161.20999999999998

> <JCHEM_REFRACTIVITY>
105.54219999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4aS,5R,6S)-5-ethenyl-1-oxo-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3H,4H,4aH,5H,6H-pyrano[3,4-c]pyran-3-yl (2S)-2-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.667  -1.540   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.001  -3.850   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.335  -6.160   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -6.668  -3.850   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -8.002  -1.540   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -4.001   0.770   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.667   3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.001   5.390   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.334   5.390   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.334   5.390   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.667   3.080   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.668   5.390   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   32                                                  
CONECT    4    3    5   17                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    6   16                                                  
CONECT   16   15                                                            
CONECT   17    4   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   32                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   31                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29                                                            
CONECT   31   23   32                                                       
CONECT   32   31   19    3                                                  
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₃₀O₁₁

Average Mass

458.4600 Da

Monoisotopic Mass

458.17881 Da

IUPAC Name

(3S,4aS,5R,6S)-5-ethenyl-1-oxo-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,3H,4H,4aH,5H,6H-pyrano[3,4-c]pyran-3-yl (2S)-2-methylbutanoate

Traditional Name

(3S,4aS,5R,6S)-5-ethenyl-1-oxo-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3H,4H,4aH,5H,6H-pyrano[3,4-c]pyran-3-yl (2S)-2-methylbutanoate

CAS Registry Number

Not Available

SMILES

CC[C@H](C)C(=O)O[C@@H]1C[C@H]2[C@@H](C=C)[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)OC=C2C(=O)O1

InChI Identifier

InChI=1S/C21H30O11/c1-4-9(3)18(26)30-14-6-11-10(5-2)20(28-8-12(11)19(27)31-14)32-21-17(25)16(24)15(23)13(7-22)29-21/h5,8-11,13-17,20-25H,2,4,6-7H2,1,3H3/t9-,10+,11-,13+,14-,15+,16-,17+,20-,21-/m0/s1

InChI Key

HIELOUVZQFFFGL-JTCLUIBCSA-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
Irlbachia alata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

Hexose monosaccharide
O-glycosyl compound
Delta valerolactone
Fatty acid ester
Delta_valerolactone
Acylal
Fatty acyl
Oxane
Dicarboxylic acid or derivatives
Monosaccharide
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Lactone
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Polyol
Acetal
Carbonyl group
Primary alcohol
Hydrocarbon derivative
Alcohol
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	0.41	ChemAxon
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	161.21 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	105.54 m³·mol⁻¹	ChemAxon
Polarizability	45.87 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

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

101678880

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s,4as,5r,6s)-5-ethenyl-1-oxo-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl (2s)-2-methylbutanoate (NP0313501)

MOL for NP0313501 ((3s,4as,5r,6s)-5-ethenyl-1-oxo-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl (2s)-2-methylbutanoate)

3D MOL for NP0313501 ((3s,4as,5r,6s)-5-ethenyl-1-oxo-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl (2s)-2-methylbutanoate)

3D SDF for NP0313501 ((3s,4as,5r,6s)-5-ethenyl-1-oxo-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl (2s)-2-methylbutanoate)

3D-SDF for NP0313501 ((3s,4as,5r,6s)-5-ethenyl-1-oxo-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl (2s)-2-methylbutanoate)

PDB for NP0313501 ((3s,4as,5r,6s)-5-ethenyl-1-oxo-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl (2s)-2-methylbutanoate)

3D PDB for NP0313501 ((3s,4as,5r,6s)-5-ethenyl-1-oxo-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl (2s)-2-methylbutanoate)

SMILES for NP0313501 ((3s,4as,5r,6s)-5-ethenyl-1-oxo-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl (2s)-2-methylbutanoate)

INCHI for NP0313501 ((3s,4as,5r,6s)-5-ethenyl-1-oxo-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl (2s)-2-methylbutanoate)

Structure for NP0313501 ((3s,4as,5r,6s)-5-ethenyl-1-oxo-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl (2s)-2-methylbutanoate)

3D Structure for NP0313501 ((3s,4as,5r,6s)-5-ethenyl-1-oxo-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl (2s)-2-methylbutanoate)