NP-MRD: Showing NP-Card for (2s)-1-(acetyloxy)-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate (NP0305798)

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Record Information

Version

2.0

Created at

2022-09-10 21:53:57 UTC

Updated at

2022-09-10 21:53:57 UTC

NP-MRD ID

NP0305798

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-1-(acetyloxy)-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate

Description

Regaloside I belongs to the class of organic compounds known as glycosyldiacylglycerols. These are diacylglycerols that carry a saccharide moiety linked to the glycerol. (2s)-1-(acetyloxy)-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate is found in Lilium auratum. Based on a literature review very few articles have been published on Regaloside I.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102223532D          

 31 32  0  0  1  0            999 V2000
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    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   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.0125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -8.2500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -8.6625    0.0000 C   0  0  0  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
    0.7145   -8.6625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -9.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -8.2500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -4.5375    0.0000 O   0  0  0  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
    1.4289   -3.3000    0.0000 O   0  0  0  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
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  0  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   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  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
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  1  0  0  0
  6 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 25 31  1  0  0  0  0
M  END

     RDKit          3D

 57 58  0  0  0  0  0  0  0  0999 V2000
    0.3214    3.8702   -3.7084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3508    2.9507   -2.7220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1405    3.4823   -1.9272 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1423    1.6254   -2.6642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6357    0.6307   -1.8487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2638    0.6532   -0.3973 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9889    1.5659    0.4385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3589    1.4976    0.2999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9523    0.3133    0.7087 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6752   -0.2012   -0.3199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4630   -1.2953    0.0240 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0657   -1.8360   -1.2438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1026   -2.2427   -2.1595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5930   -0.7392    0.8677 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.5061   -1.7221    1.2326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9915   -0.1636    2.1029 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0132    0.5077    2.7942 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8240    0.7257    1.8949 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0134    0.6795    3.0287 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1301    0.6086   -0.3214 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9216   -0.4012    0.0771 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4090   -1.4568    0.4364 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3677   -0.2517    0.0852 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1816   -1.2258    0.4718 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6341   -1.1270    0.4984 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3431   -0.0269    0.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7387   -0.0404    0.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4489   -1.1412    0.6242 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8435   -1.0968    0.6679 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7275   -2.2558    0.9955 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3503   -2.2324    0.9281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4486    4.6034   -4.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6379    3.2486   -4.5658 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1627    4.3575   -3.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2820   -0.3470   -2.3331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7631    0.5150   -1.9673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5418   -0.3974   -0.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7349    2.6390    0.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7371    1.2472    1.5413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2044   -0.4255    1.0586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9012   -2.0650    0.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7522   -2.6973   -1.0484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7078   -1.0286   -1.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2938   -2.5245   -1.6779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0788    0.0543    0.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0013   -2.0429    0.4255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6988   -1.0152    2.7668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8162    1.4697    2.7345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1788    1.7727    1.7975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8614   -0.2247    3.3631 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8040    0.6711   -0.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6763   -2.1363    0.7789 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8090    0.8487   -0.2071 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2655    0.8566   -0.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2496   -0.7759    1.5320 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2746   -3.1363    1.3367 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7856   -3.1219    1.2249 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  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
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
  6 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 28 30  1  0
 30 31  2  0
 18  9  1  0
 31 25  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  1
  7 38  1  0
  7 39  1  0
  9 40  1  1
 11 41  1  1
 12 42  1  0
 12 43  1  0
 13 44  1  0
 14 45  1  6
 15 46  1  0
 16 47  1  1
 17 48  1  0
 18 49  1  6
 19 50  1  0
 23 51  1  0
 24 52  1  0
 26 53  1  0
 27 54  1  0
 29 55  1  0
 30 56  1  0
 31 57  1  0
M  END


  Mrv1652309102223532D          

 31 32  0  0  1  0            999 V2000
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    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   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.0125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -8.2500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -8.6625    0.0000 C   0  0  0  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
    0.7145   -8.6625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -9.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -8.2500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -4.5375    0.0000 O   0  0  0  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
    1.4289   -3.3000    0.0000 O   0  0  0  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
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  0  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   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  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
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  1  0  0  0
  6 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 25 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0305798

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@H](CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)OC(=O)\C=C\C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O11/c1-11(22)28-9-14(30-16(24)7-4-12-2-5-13(23)6-3-12)10-29-20-19(27)18(26)17(25)15(8-21)31-20/h2-7,14-15,17-21,23,25-27H,8-10H2,1H3/b7-4+/t14-,15-,17-,18+,19-,20-/m1/s1

> <INCHI_KEY>
CPSJADJRZYHWCV-OXHLYYAYSA-N

> <FORMULA>
C20H26O11

> <MOLECULAR_WEIGHT>
442.417

> <EXACT_MASS>
442.147511657

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
44.11727818172565

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-1-(acetyloxy)-3-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_LOGP>
-0.43839886166666664

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.211457109535411

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.397919461030263

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810834223250477

> <JCHEM_POLAR_SURFACE_AREA>
172.21

> <JCHEM_REFRACTIVITY>
103.6295

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-1-(acetyloxy)-3-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -6.160   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334  -8.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667 -10.780   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334 -11.550   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.334 -13.090   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.667 -13.860   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.667 -15.400   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001 -16.170   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.001 -17.710   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334 -16.170   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.334 -17.710   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.000 -15.400   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.334 -16.170   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.334 -13.090   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.001  -8.470   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.667  -6.160   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.335  -6.160   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      10.669  -1.540   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       9.336  -3.850   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   20                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    9   19                                                  
CONECT   19   18                                                            
CONECT   20    6   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   31                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   25                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₆O₁₁

Average Mass

442.4170 Da

Monoisotopic Mass

442.14751 Da

IUPAC Name

(2S)-1-(acetyloxy)-3-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

Traditional Name

(2S)-1-(acetyloxy)-3-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@H](CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)OC(=O)\C=C\C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C20H26O11/c1-11(22)28-9-14(30-16(24)7-4-12-2-5-13(23)6-3-12)10-29-20-19(27)18(26)17(25)15(8-21)31-20/h2-7,14-15,17-21,23,25-27H,8-10H2,1H3/b7-4+/t14-,15-,17-,18+,19-,20-/m1/s1

InChI Key

CPSJADJRZYHWCV-OXHLYYAYSA-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
Lilium auratum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glycosyldiacylglycerols. These are diacylglycerols that carry a saccharide moiety linked to the glycerol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerolipids

Sub Class

Glycosylglycerols

Direct Parent

Glycosyldiacylglycerols

Alternative Parents

Substituents

Glycosyldiacylglycerol
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
Coumaric acid ester
Hydroxycinnamic acid or derivatives
Hexose monosaccharide
Cinnamic acid ester
Cinnamic acid or derivatives
Coumaric acid or derivatives
Glycosyl compound
O-glycosyl compound
Styrene
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Oxane
Monosaccharide
Monocyclic benzene moiety
Benzenoid
Dicarboxylic acid or derivatives
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Polyol
Primary alcohol
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen compound
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	ChemAxon
pKa (Strongest Acidic)	9.4	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	172.21 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	103.63 m³·mol⁻¹	ChemAxon
Polarizability	44.12 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

14542292

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-1-(acetyloxy)-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate (NP0305798)

MOL for NP0305798 ((2s)-1-(acetyloxy)-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D MOL for NP0305798 ((2s)-1-(acetyloxy)-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D SDF for NP0305798 ((2s)-1-(acetyloxy)-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D-SDF for NP0305798 ((2s)-1-(acetyloxy)-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

PDB for NP0305798 ((2s)-1-(acetyloxy)-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D PDB for NP0305798 ((2s)-1-(acetyloxy)-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

SMILES for NP0305798 ((2s)-1-(acetyloxy)-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

INCHI for NP0305798 ((2s)-1-(acetyloxy)-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

Structure for NP0305798 ((2s)-1-(acetyloxy)-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D Structure for NP0305798 ((2s)-1-(acetyloxy)-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)