NP-MRD: Showing NP-Card for butyl (3r)-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}butanoate (NP0184661)

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Record Information

Version

2.0

Created at

2022-09-03 23:50:39 UTC

Updated at

2022-09-03 23:50:39 UTC

NP-MRD ID

NP0184661

Secondary Accession Numbers

None

Natural Product Identification

Common Name

butyl (3r)-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}butanoate

Description

3-O-(alpha-l-arabinopyranosyl-(1->6)-beta-d-glucopyranosyl) butyl 3r-hydroxybutanoate belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. butyl (3r)-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}butanoate is found in Physalis peruviana. Based on a literature review very few articles have been published on 3-o-(alpha-l-arabinopyranosyl-(1->6)-beta-d-glucopyranosyl) butyl 3r-hydroxybutanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309042201502D          

 31 32  0  0  1  0            999 V2000
   -3.5724   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -8.2500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -9.0750    0.0000 C   0  0  0  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   -8.2500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -8.2500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -5.7750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.0125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -9.0750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013   -9.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -9.4875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -9.0750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -9.4875    0.0000 O   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  1  0  0  0
 14 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 12 30  1  0  0  0  0
 30 31  1  1  0  0  0
M  END

     RDKit          3D

 65 66  0  0  0  0  0  0  0  0999 V2000
    8.6679    1.1621    0.9924 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7166    1.3333   -0.1966 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6795   -0.0156   -0.9040 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7506    0.1291   -2.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4766    0.4915   -1.6115 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7117   -0.2775   -0.7746 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1108   -1.3822   -0.3636 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3838    0.2709   -0.3819 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6432   -0.6850    0.5475 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5332   -0.8532    1.7793 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4964   -0.0578    0.9561 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3227   -0.7826    0.6412 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4005    0.0312   -0.1877 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6312   -0.5342   -0.5998 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4917    0.6217   -0.9449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7438    0.4877   -1.3935 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7014    0.0785   -0.5668 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2879   -1.0921   -1.1227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3051   -0.7638   -1.9943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5432   -0.4360   -1.1406 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.4207    0.3380   -1.8689 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0336    0.3511    0.0527 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.0137    1.1696    0.5966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8453    1.1417   -0.4546 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4731    2.0818    0.4768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1575   -1.4792    0.3829 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3965   -2.7177    0.3227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8780   -0.9913    1.8106 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2154    0.3342    1.9188 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3489   -1.1379    1.9408 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0947   -2.4890    2.2420 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6469    0.0893    1.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7133    1.3804    0.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3827    1.8463    1.8161 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6966    1.5838    0.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1258    2.0647   -0.9036 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7099   -0.2376   -1.2746 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3243   -0.8257   -0.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0865    0.9665   -2.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6784   -0.8208   -2.6706 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7676    0.4778   -1.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5478    1.2314    0.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4784   -1.6512    0.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0300   -0.5001    2.7007 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4774   -0.3159    1.6954 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7621   -1.9323    1.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6969   -1.7096    0.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4501   -1.1047   -1.5657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4557    1.4058   -0.0968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9551    1.2545   -1.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4619   -0.0988    0.4942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0730    0.0295   -2.7041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5361   -1.6804   -2.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9608   -1.4202   -0.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2418    1.2771   -1.6999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6499   -0.3823    0.7887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2288    0.8078    1.4949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0139    1.6162   -1.4243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2520    2.9572    0.0442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1667   -1.8342    0.3353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6873   -3.2039   -0.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3396   -1.6470    2.5593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4399    0.9095    2.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0554   -0.5179    2.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6673   -2.8316    2.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
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 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 14 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 30 12  1  0
 24 17  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  6
 10 44  1  0
 10 45  1  0
 10 46  1  0
 12 47  1  6
 14 48  1  6
 15 49  1  0
 15 50  1  0
 17 51  1  1
 19 52  1  0
 19 53  1  0
 20 54  1  1
 21 55  1  0
 22 56  1  1
 23 57  1  0
 24 58  1  6
 25 59  1  0
 26 60  1  1
 27 61  1  0
 28 62  1  1
 29 63  1  0
 30 64  1  1
 31 65  1  0
M  END

  Mrv1652309042201502D          

 31 32  0  0  1  0            999 V2000
   -3.5724   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -8.2500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -9.0750    0.0000 C   0  0  0  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   -8.2500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -8.2500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -5.7750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.0125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -9.0750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013   -9.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -9.4875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -9.0750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -9.4875    0.0000 O   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  1  0  0  0
 14 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 12 30  1  0  0  0  0
 30 31  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0184661

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCOC(=O)C[C@@H](C)O[C@@H]1O[C@H](CO[C@@H]2OC[C@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C19H34O12/c1-3-4-5-27-12(21)6-9(2)30-19-17(26)15(24)14(23)11(31-19)8-29-18-16(25)13(22)10(20)7-28-18/h9-11,13-20,22-26H,3-8H2,1-2H3/t9-,10+,11-,13+,14-,15+,16-,17-,18+,19-/m1/s1

> <INCHI_KEY>
MLIAQAVEASULJH-UYQTUCCPSA-N

> <FORMULA>
C19H34O12

> <MOLECULAR_WEIGHT>
454.469

> <EXACT_MASS>
454.205026535

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
46.11084967309857

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
butyl (3R)-3-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}butanoate

> <JCHEM_LOGP>
-1.8285492780000008

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.461955610883454

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.928090163433657

> <JCHEM_PKA_STRONGEST_BASIC>
-3.526580404084756

> <JCHEM_POLAR_SURFACE_AREA>
184.6

> <JCHEM_REFRACTIVITY>
100.97090000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
butyl (3R)-3-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}butanoate

> <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      -6.668 -14.630   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335 -15.400   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001 -14.630   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667 -15.400   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.334 -14.630   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.000 -15.400   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000 -16.940   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667 -15.400   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667 -16.940   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001 -14.630   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.335 -15.400   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.668 -14.630   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.002 -15.400   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336 -14.630   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.336 -13.090   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.669 -10.780   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.337 -10.780   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      14.670 -10.010   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      13.337 -12.320   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      14.670 -13.090   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      12.003 -13.090   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      12.003 -14.630   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.002 -16.940   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       9.336 -17.710   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.668 -17.710   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.668 -19.250   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       5.335 -16.940   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.001 -17.710   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   30                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   26                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   17   25                                                  
CONECT   25   24                                                            
CONECT   26   14   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   12   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END

View in JSmol

Synonyms

Value	Source
3-O-(a-L-Arabinopyranosyl-(1->6)-b-D-glucopyranosyl) butyl 3R-hydroxybutanoate	Generator
3-O-(a-L-Arabinopyranosyl-(1->6)-b-D-glucopyranosyl) butyl 3R-hydroxybutanoic acid	Generator
3-O-(alpha-L-Arabinopyranosyl-(1->6)-beta-D-glucopyranosyl) butyl 3R-hydroxybutanoic acid	Generator
3-O-(Α-L-arabinopyranosyl-(1->6)-β-D-glucopyranosyl) butyl 3R-hydroxybutanoate	Generator
3-O-(Α-L-arabinopyranosyl-(1->6)-β-D-glucopyranosyl) butyl 3R-hydroxybutanoic acid	Generator

Chemical Formula

C₁₉H₃₄O₁₂

Average Mass

454.4690 Da

Monoisotopic Mass

454.20503 Da

IUPAC Name

butyl (3R)-3-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}butanoate

Traditional Name

butyl (3R)-3-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}butanoate

CAS Registry Number

Not Available

SMILES

CCCCOC(=O)C[C@@H](C)O[C@@H]1O[C@H](CO[C@@H]2OC[C@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C19H34O12/c1-3-4-5-27-12(21)6-9(2)30-19-17(26)15(24)14(23)11(31-19)8-29-18-16(25)13(22)10(20)7-28-18/h9-11,13-20,22-26H,3-8H2,1-2H3/t9-,10+,11-,13+,14-,15+,16-,17-,18+,19-/m1/s1

InChI Key

MLIAQAVEASULJH-UYQTUCCPSA-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
Physalis peruviana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty acyl glycosides of mono- and disaccharides

Alternative Parents

Substituents

Fatty acyl glycoside of mono- or disaccharide
Disaccharide
Glycosyl compound
O-glycosyl compound
Fatty acid ester
Oxane
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Acetal
Carboxylic acid derivative
Polyol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic 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	-1.8	ChemAxon
pKa (Strongest Acidic)	11.93	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	184.6 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	100.97 m³·mol⁻¹	ChemAxon
Polarizability	46.11 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

113371230

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25080004

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for butyl (3r)-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}butanoate (NP0184661)

MOL for NP0184661 (butyl (3r)-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}butanoate)

3D MOL for NP0184661 (butyl (3r)-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}butanoate)

3D SDF for NP0184661 (butyl (3r)-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}butanoate)

3D-SDF for NP0184661 (butyl (3r)-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}butanoate)

PDB for NP0184661 (butyl (3r)-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}butanoate)

3D PDB for NP0184661 (butyl (3r)-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}butanoate)

SMILES for NP0184661 (butyl (3r)-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}butanoate)

INCHI for NP0184661 (butyl (3r)-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}butanoate)

Structure for NP0184661 (butyl (3r)-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}butanoate)

3D Structure for NP0184661 (butyl (3r)-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}butanoate)