NP-MRD: Showing NP-Card for methyl (4s,5e,6s)-5-ethylidene-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[(9e)-octadec-9-enoyloxy]methyl}oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate (NP0224765)

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Record Information

Version

2.0

Created at

2022-09-06 03:16:52 UTC

Updated at

2022-09-06 03:16:52 UTC

NP-MRD ID

NP0224765

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (4s,5e,6s)-5-ethylidene-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[(9e)-octadec-9-enoyloxy]methyl}oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate

Description

Jaspolyanoside belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety. methyl (4s,5e,6s)-5-ethylidene-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[(9e)-octadec-9-enoyloxy]methyl}oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate is found in Jasminum polyanthum. Based on a literature review very few articles have been published on Jaspolyanoside.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062205162D          

 56 58  0  0  1  0            999 V2000
    2.6289   -3.8962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4215   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6197   -4.9258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4123   -5.1547    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0068   -4.5826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7994   -4.8114    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3939   -4.2394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1865   -4.4682    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7810   -3.8962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1681   -3.5530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9700   -2.7521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9608   -3.7818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1589   -4.5826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9516   -4.8114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5460   -4.2394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3387   -4.4682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9331   -3.8962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7258   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3203   -3.5530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1129   -3.7818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7074   -3.2097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5000   -3.4386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0945   -2.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8871   -3.0953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4816   -2.5233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2742   -2.7521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8687   -2.1801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6613   -2.4089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3847   -5.2691    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1773   -5.4979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7902   -5.8411    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9884   -6.6420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9976   -5.6123    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4031   -6.1843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6105   -5.9555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0160   -6.5275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2234   -6.2987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6289   -6.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8363   -6.6420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8271   -7.6716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2326   -8.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0252   -5.4979    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2326   -5.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0344   -4.4682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1791   -3.6560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2418   -4.2394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0436   -3.4386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2510   -3.2097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0528   -2.4089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7398   -2.1801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9380   -1.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3435   -0.8072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5416   -0.0064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4491   -1.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6473   -1.8369    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
  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
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  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  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  8 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  0  0  0  0
  6 34  1  0  0  0  0
 34 35  1  1  0  0  0
  4 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
 38 43  1  0  0  0  0
  3 43  1  0  0  0  0
 43 44  1  1  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 45 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
 51 52  1  0  0  0  0
 52 53  2  0  0  0  0
 53 54  1  0  0  0  0
 53 55  1  0  0  0  0
 55 56  2  0  0  0  0
 50 56  1  0  0  0  0
M  END


  Mrv1652309062205162D          

 56 58  0  0  1  0            999 V2000
    2.6289   -3.8962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4215   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6197   -4.9258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4123   -5.1547    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0068   -4.5826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7994   -4.8114    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3939   -4.2394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1865   -4.4682    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7810   -3.8962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1681   -3.5530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9700   -2.7521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9608   -3.7818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1589   -4.5826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9516   -4.8114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5460   -4.2394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3387   -4.4682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9331   -3.8962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7258   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3203   -3.5530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1129   -3.7818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7074   -3.2097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5000   -3.4386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0945   -2.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8871   -3.0953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4816   -2.5233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2742   -2.7521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8687   -2.1801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6613   -2.4089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3847   -5.2691    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1773   -5.4979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7902   -5.8411    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9884   -6.6420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9976   -5.6123    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4031   -6.1843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6105   -5.9555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0160   -6.5275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2234   -6.2987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6289   -6.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8363   -6.6420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8271   -7.6716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2326   -8.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0252   -5.4979    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2326   -5.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0344   -4.4682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1791   -3.6560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2418   -4.2394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0436   -3.4386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2510   -3.2097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0528   -2.4089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7398   -2.1801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9380   -1.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3435   -0.8072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5416   -0.0064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4491   -1.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6473   -1.8369    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
  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
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  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  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  8 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  0  0  0  0
  6 34  1  0  0  0  0
 34 35  1  1  0  0  0
  4 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
 38 43  1  0  0  0  0
  3 43  1  0  0  0  0
 43 44  1  1  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 45 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
 51 52  1  0  0  0  0
 52 53  2  0  0  0  0
 53 54  1  0  0  0  0
 53 55  1  0  0  0  0
 55 56  2  0  0  0  0
 50 56  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0224765

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCC\C=C\CCCCCCCC(=O)OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@@H](CC(=O)OCCC3=CC=C(O)C=C3)\C2=C/C)C(=O)OC)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C43H64O13/c1-4-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-36(45)53-29-35-38(47)39(48)40(49)43(55-35)56-42-32(5-2)33(34(28-54-42)41(50)51-3)27-37(46)52-26-25-30-21-23-31(44)24-22-30/h5,12-13,21-24,28,33,35,38-40,42-44,47-49H,4,6-11,14-20,25-27,29H2,1-3H3/b13-12+,32-5+/t33-,35+,38+,39-,40+,42-,43-/m0/s1

> <INCHI_KEY>
MWUYCBORLRLZMO-NSCVCSAUSA-N

> <FORMULA>
C43H64O13

> <MOLECULAR_WEIGHT>
788.972

> <EXACT_MASS>
788.434692121

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
120

> <JCHEM_AVERAGE_POLARIZABILITY>
89.88627957988115

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2S,3E,4S)-3-ethylidene-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-{[(9E)-octadec-9-enoyloxy]methyl}oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate

> <JCHEM_LOGP>
7.863110652999998

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.208948874343342

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.50288410778719

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6490875505670557

> <JCHEM_POLAR_SURFACE_AREA>
187.51

> <JCHEM_REFRACTIVITY>
210.14730000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
28

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (4S,5E,6S)-5-ethylidene-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-{[(9E)-octadec-9-enoyloxy]methyl}oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       4.907  -7.273   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.387  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.757  -9.195   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.236  -9.622   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       9.346  -8.554   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      10.826  -8.981   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      11.935  -7.914   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      13.415  -8.341   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.525  -7.273   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      16.004  -7.700   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      17.114  -6.632   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      16.744  -5.137   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      18.593  -7.059   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.963  -8.554   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.443  -8.981   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      21.553  -7.914   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      23.032  -8.341   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      24.142  -7.273   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      25.621  -7.700   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      26.731  -6.632   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      28.211  -7.059   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      29.320  -5.992   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      30.800  -6.419   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      31.910  -5.351   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      33.389  -5.778   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      34.499  -4.710   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      35.979  -5.137   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      37.088  -4.069   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      38.568  -4.497   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.785  -9.836   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      15.264 -10.263   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      12.675 -10.903   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      13.045 -12.398   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      11.196 -10.476   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      10.086 -11.544   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       8.606 -11.117   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       7.497 -12.185   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.017 -11.758   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       4.907 -12.825   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       3.428 -12.398   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       5.277 -14.320   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       4.167 -15.388   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       5.647 -10.263   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       4.167  -9.836   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       3.798  -8.341   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       4.068  -6.825   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0       2.318  -7.914   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0       1.948  -6.419   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       0.469  -5.992   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       0.099  -4.497   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      -1.381  -4.069   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      -1.751  -2.575   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      -0.641  -1.507   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      -1.011  -0.012   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0       0.838  -1.934   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       1.208  -3.429   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   43                                                  
CONECT    4    3    5   36                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   34                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   30                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30    8   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32    6   35                                                  
CONECT   35   34                                                            
CONECT   36    4   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39   43                                                  
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41                                                            
CONECT   43   38    3   44                                                  
CONECT   44   43   45                                                       
CONECT   45   44   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51   56                                                  
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53   56                                                       
CONECT   56   55   50                                                       
MASTER        0    0    0    0    0    0    0    0   56    0  116    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₃H₆₄O₁₃

Average Mass

788.9720 Da

Monoisotopic Mass

788.43469 Da

IUPAC Name

methyl (2S,3E,4S)-3-ethylidene-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-{[(9E)-octadec-9-enoyloxy]methyl}oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate

Traditional Name

methyl (4S,5E,6S)-5-ethylidene-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-{[(9E)-octadec-9-enoyloxy]methyl}oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate

CAS Registry Number

Not Available

SMILES

CCCCCCCC\C=C\CCCCCCCC(=O)OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@@H](CC(=O)OCCC3=CC=C(O)C=C3)\C2=C/C)C(=O)OC)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C43H64O13/c1-4-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-36(45)53-29-35-38(47)39(48)40(49)43(55-35)56-42-32(5-2)33(34(28-54-42)41(50)51-3)27-37(46)52-26-25-30-21-23-31(44)24-22-30/h5,12-13,21-24,28,33,35,38-40,42-44,47-49H,4,6-11,14-20,25-27,29H2,1-3H3/b13-12+,32-5+/t33-,35+,38+,39-,40+,42-,43-/m0/s1

InChI Key

MWUYCBORLRLZMO-NSCVCSAUSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Jasminum polyanthum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Saccharolipids

Sub Class

Not Available

Direct Parent

Saccharolipids

Alternative Parents

Substituents

Saccharolipid
Terpene glycoside
Glycosyl compound
Secoiridoid-skeleton
O-glycosyl compound
Aromatic monoterpenoid
Monocyclic monoterpenoid
Monoterpenoid
Tyrosol derivative
Tricarboxylic acid or derivatives
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Sugar acid
Monocyclic benzene moiety
Fatty acyl
Monosaccharide
Oxane
Benzenoid
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous ester
Secondary alcohol
Carboxylic acid ester
Acetal
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Oxacycle
Organic oxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	7.86	ChemAxon
pKa (Strongest Acidic)	9.5	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	187.51 Å²	ChemAxon
Rotatable Bond Count	28	ChemAxon
Refractivity	210.15 m³·mol⁻¹	ChemAxon
Polarizability	89.89 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

102063090

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (4s,5e,6s)-5-ethylidene-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[(9e)-octadec-9-enoyloxy]methyl}oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate (NP0224765)

MOL for NP0224765 (methyl (4s,5e,6s)-5-ethylidene-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[(9e)-octadec-9-enoyloxy]methyl}oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

3D MOL for NP0224765 (methyl (4s,5e,6s)-5-ethylidene-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[(9e)-octadec-9-enoyloxy]methyl}oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

3D SDF for NP0224765 (methyl (4s,5e,6s)-5-ethylidene-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[(9e)-octadec-9-enoyloxy]methyl}oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

3D-SDF for NP0224765 (methyl (4s,5e,6s)-5-ethylidene-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[(9e)-octadec-9-enoyloxy]methyl}oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

PDB for NP0224765 (methyl (4s,5e,6s)-5-ethylidene-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[(9e)-octadec-9-enoyloxy]methyl}oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

3D PDB for NP0224765 (methyl (4s,5e,6s)-5-ethylidene-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[(9e)-octadec-9-enoyloxy]methyl}oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

SMILES for NP0224765 (methyl (4s,5e,6s)-5-ethylidene-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[(9e)-octadec-9-enoyloxy]methyl}oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

INCHI for NP0224765 (methyl (4s,5e,6s)-5-ethylidene-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[(9e)-octadec-9-enoyloxy]methyl}oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

Structure for NP0224765 (methyl (4s,5e,6s)-5-ethylidene-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[(9e)-octadec-9-enoyloxy]methyl}oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

3D Structure for NP0224765 (methyl (4s,5e,6s)-5-ethylidene-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[(9e)-octadec-9-enoyloxy]methyl}oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)