NP-MRD: Showing NP-Card for (2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl octanoate (NP0255625)

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Record Information

Version

2.0

Created at

2022-09-07 20:10:46 UTC

Updated at

2022-09-07 20:10:47 UTC

NP-MRD ID

NP0255625

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl octanoate

Description

CHEMBL227838 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. (2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl octanoate is found in Morinda citrifolia. Based on a literature review very few articles have been published on CHEMBL227838.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072222102D          

 32 33  0  0  1  0            999 V2000
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    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
    8.5737   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5737   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0026   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0026   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -6.6000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.5737   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -7.8375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0026   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -7.8375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4315   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -8.6625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.4315   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -9.0750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0026   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -8.6625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.5737   -9.0750    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  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  1  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 22 31  1  0  0  0  0
 31 32  1  1  0  0  0
M  END

     RDKit          3D

 68 69  0  0  0  0  0  0  0  0999 V2000
    6.6838    2.8000    0.6846 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2225    2.8324    1.0145 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9477    2.3689    2.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4146    0.9602    2.6641 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7479   -0.0305    1.7562 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2324   -0.0105    1.9783 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6534   -1.0254    1.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1726   -1.1112    1.1430 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6059   -0.3728    1.9880 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3981   -1.9404    0.3859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0087   -2.0590    0.4536 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3408   -3.3231    0.8348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1317   -4.3089   -0.0842 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3059   -4.6463   -0.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2746   -5.6822   -1.3334 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9319   -4.0336   -1.3111 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2849   -4.2621   -0.9854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7657   -2.6518   -1.8691 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7012   -2.6684   -2.7810 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6338   -1.5807   -0.8368 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8075   -0.8734   -0.5918 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7212    0.4864   -0.8893 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0680    1.1525    0.2604 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3340    2.4728    0.1861 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6303    2.7211    0.9730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9779    4.0672    0.9452 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3975    3.1272   -1.1307 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2085    3.8081   -1.4248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7653    2.2352   -2.2792 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9952    2.5648   -2.8430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8140    0.7763   -1.8978 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6882    0.0253   -3.0600 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2463    3.0538    1.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9833    1.8041    0.2667 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8636    3.5470   -0.1312 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6179    2.2713    0.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9062    3.9090    0.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8892    2.5004    2.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5132    3.0242    3.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5033    0.8838    2.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0997    0.6807    3.7102 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9719    0.1580    0.6805 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1583   -1.0352    1.9782 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8189    0.9888    1.8602 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0759   -0.3326    3.0282 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1460   -1.9980    1.2530 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8965   -0.7630   -0.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4184   -1.3605    1.2452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5685   -5.2550    0.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7645   -5.0777    0.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8832   -3.8416   -0.8495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3008   -6.4343   -1.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6727   -4.7927   -2.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5280   -3.8078   -0.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6740   -2.4471   -2.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6562   -3.5647   -3.2142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9175   -0.8265   -1.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7236    0.7738   -1.2758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5500    3.0137    0.7966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5655    2.3297    1.9986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4371    2.1542    0.4516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8784    4.1253    1.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1889    3.9322   -1.0905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8872    4.1394   -0.5264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0030    2.3256   -3.0796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8837    2.9384   -3.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7806    0.6049   -1.3790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1569    0.5604   -3.7011 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  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 20 11  1  0
 31 22  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  2 37  1  0
  3 38  1  0
  3 39  1  0
  4 40  1  0
  4 41  1  0
  5 42  1  0
  5 43  1  0
  6 44  1  0
  6 45  1  0
  7 46  1  0
  7 47  1  0
 11 48  1  1
 13 49  1  1
 14 50  1  0
 14 51  1  0
 15 52  1  0
 16 53  1  6
 17 54  1  0
 18 55  1  6
 19 56  1  0
 20 57  1  6
 22 58  1  6
 24 59  1  1
 25 60  1  0
 25 61  1  0
 26 62  1  0
 27 63  1  1
 28 64  1  0
 29 65  1  6
 30 66  1  0
 31 67  1  1
 32 68  1  0
M  END


  Mrv1652309072222102D          

 32 33  0  0  1  0            999 V2000
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    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
    8.5737   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5737   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0026   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0026   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -6.6000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.5737   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -7.8375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0026   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -7.8375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4315   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -8.6625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.4315   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -9.0750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0026   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -8.6625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.5737   -9.0750    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  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  1  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 22 31  1  0  0  0  0
 31 32  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0255625

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCC(=O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H36O12/c1-2-3-4-5-6-7-12(23)31-20-18(16(27)14(25)11(9-22)30-20)32-19-17(28)15(26)13(24)10(8-21)29-19/h10-11,13-22,24-28H,2-9H2,1H3/t10-,11-,13-,14-,15+,16+,17-,18-,19+,20+/m1/s1

> <INCHI_KEY>
PKTOHQWFHRKNMN-SYVJZRHHSA-N

> <FORMULA>
C20H36O12

> <MOLECULAR_WEIGHT>
468.496

> <EXACT_MASS>
468.220676599

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
48.24409352174429

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-1.3388702813333344

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.70034217281539

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.089726411891592

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083576692681

> <JCHEM_POLAR_SURFACE_AREA>
195.6

> <JCHEM_REFRACTIVITY>
105.12010000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.003 -11.550   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.003 -10.010   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      13.337 -12.320   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      14.670 -10.010   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      16.004  -9.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.004  -7.700   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      17.338  -6.930   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      17.338 -10.010   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      18.672  -9.240   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      17.338 -11.550   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      18.672 -12.320   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      16.004 -12.320   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      16.004 -13.860   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      17.338 -14.630   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      18.672 -13.860   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      20.005 -14.630   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      21.339 -13.860   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      21.339 -12.320   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      20.005 -16.170   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      21.339 -16.940   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      18.672 -16.940   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      18.672 -18.480   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      17.338 -16.170   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      16.004 -16.940   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                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   20                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   11   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   31                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   22   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₆O₁₂

Average Mass

468.4960 Da

Monoisotopic Mass

468.22068 Da

IUPAC Name

(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl octanoate

Traditional Name

(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl octanoate

CAS Registry Number

Not Available

SMILES

CCCCCCCC(=O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C20H36O12/c1-2-3-4-5-6-7-12(23)31-20-18(16(27)14(25)11(9-22)30-20)32-19-17(28)15(26)13(24)10(8-21)29-19/h10-11,13-22,24-28H,2-9H2,1H3/t10-,11-,13-,14-,15+,16+,17-,18-,19+,20+/m1/s1

InChI Key

PKTOHQWFHRKNMN-SYVJZRHHSA-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
Morinda citrifolia	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
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Primary 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	-1.3	ChemAxon
pKa (Strongest Acidic)	12.09	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	195.6 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	105.12 m³·mol⁻¹	ChemAxon
Polarizability	48.24 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

C00057670

Chemspider ID

17613606

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16680920

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl octanoate (NP0255625)

MOL for NP0255625 ((2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl octanoate)

3D MOL for NP0255625 ((2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl octanoate)

3D SDF for NP0255625 ((2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl octanoate)

3D-SDF for NP0255625 ((2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl octanoate)

PDB for NP0255625 ((2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl octanoate)

3D PDB for NP0255625 ((2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl octanoate)

SMILES for NP0255625 ((2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl octanoate)

INCHI for NP0255625 ((2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl octanoate)

Structure for NP0255625 ((2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl octanoate)

3D Structure for NP0255625 ((2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl octanoate)