NP-MRD: Showing NP-Card for methyl (4s,5e,6s)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate (NP0260470)

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Record Information

Version

2.0

Created at

2022-09-08 02:39:16 UTC

Updated at

2022-09-08 02:39:16 UTC

NP-MRD ID

NP0260470

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (4s,5e,6s)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate

Description

Dimethyloleoside belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. methyl (4s,5e,6s)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate is found in Fraxinus americana, Fraxinus excelsior, Jasminum grandiflorum, Jasminum sambac, Ligustrum lucidum, Olea europaea, Syringa persica and Syringa vulgaris. Based on a literature review very few articles have been published on Dimethyloleoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082204392D          

 29 30  0  0  1  0            999 V2000
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -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
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3789    0.3412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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  1  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  1  0  0  0
  4 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 19 24  1  0  0  0  0
  3 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END

     RDKit          3D

 55 56  0  0  0  0  0  0  0  0999 V2000
   -0.9957   -0.2931   -2.8358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1070   -0.1796   -1.6911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6357    0.0074   -0.4979 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1952    0.1452    0.7365 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3529   -0.6067    0.5494 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4473    0.2338    0.7431 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2636    0.2912   -0.3747 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4283    0.9693   -0.0483 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0304    1.4999   -1.3347 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3279    0.4653   -2.2152 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3476   -0.0973    0.5615 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3798    0.5223    1.2446 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5233   -1.0159    1.4516 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2246   -2.2207    0.8592 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2487   -0.3262    1.8916 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5519    0.6914    2.8130 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5281   -0.3781    1.8161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7488   -1.0520    1.7202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5480   -0.8599    0.6931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7864   -1.5482    0.5832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1218   -2.3570    1.5001 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6919   -1.4217   -0.4578 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8967   -2.1644   -0.4571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0810    0.0979   -0.3346 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6777    1.4542   -0.2004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1574    1.4247   -0.0286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6940    1.2252    1.1069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0582    1.6074   -1.0668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4632    1.5755   -0.8810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7513    0.4919   -2.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3416   -0.1870   -3.7615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4140   -1.3351   -2.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9700   -0.2428   -1.7792 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4186    1.1953    0.9815 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0926    1.2736    0.9868 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2390    1.7797    0.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2936    2.1549   -1.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9344    2.1091   -1.1435 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6650    0.4331   -2.9583 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7346   -0.6959   -0.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1508   -0.0724    1.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1257   -1.2074    2.3616 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0260   -2.5393    0.3767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6521   -1.0671    2.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4941    0.6202    3.0479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9679   -1.7219    2.5387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7152   -3.2118   -0.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3986   -2.1408   -1.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6183   -1.7286    0.2706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5075   -0.3301   -1.2736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2200    2.1226    0.5373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5317    2.0261   -1.1687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8319    0.6348   -1.3313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6594    1.4767    0.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9690    2.4722   -1.2618 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 28  1  0
 28 26  1  0
 26 27  2  0
 26 25  1  0
 25 24  1  0
 24  3  1  0
  3  2  2  0
  2  1  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
  4 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 19 24  1  0
 15  6  1  0
 29 53  1  0
 29 54  1  0
 29 55  1  0
 25 51  1  0
 25 52  1  0
 24 50  1  6
  2 33  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 34  1  1
  6 35  1  1
  8 36  1  1
  9 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  6
 12 41  1  0
 13 42  1  1
 14 43  1  0
 15 44  1  1
 16 45  1  0
 18 46  1  0
 23 47  1  0
 23 48  1  0
 23 49  1  0
M  END


  Mrv1652309082204392D          

 29 30  0  0  1  0            999 V2000
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -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
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3789    0.3412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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  1  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  1  0  0  0
  4 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 19 24  1  0  0  0  0
  3 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0260470

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C[C@H]1\C(=C/C)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C1C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C18H26O11/c1-4-8-9(5-12(20)25-2)10(16(24)26-3)7-27-17(8)29-18-15(23)14(22)13(21)11(6-19)28-18/h4,7,9,11,13-15,17-19,21-23H,5-6H2,1-3H3/b8-4+/t9-,11+,13+,14-,15+,17-,18-/m0/s1

> <INCHI_KEY>
KYVUMEGNMQDSHO-PVCIXGPPSA-N

> <FORMULA>
C18H26O11

> <MOLECULAR_WEIGHT>
418.395

> <EXACT_MASS>
418.147511657

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
40.52443079146824

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-1.2947279233333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.19855385936313

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.206586036403378

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810849052288235

> <JCHEM_POLAR_SURFACE_AREA>
161.20999999999998

> <JCHEM_REFRACTIVITY>
94.88879999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.707   0.637   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5   17                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    6   16                                                  
CONECT   16   15                                                            
CONECT   17    4   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22                                                            
CONECT   24   19    3   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₂₆O₁₁

Average Mass

418.3950 Da

Monoisotopic Mass

418.14751 Da

IUPAC Name

methyl (2S,3E,4S)-3-ethylidene-4-(2-methoxy-2-oxoethyl)-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate

Traditional Name

methyl (4S,5E,6S)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C[C@H]1\C(=C/C)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C1C(=O)OC

InChI Identifier

InChI=1S/C18H26O11/c1-4-8-9(5-12(20)25-2)10(16(24)26-3)7-27-17(8)29-18-15(23)14(22)13(21)11(6-19)28-18/h4,7,9,11,13-15,17-19,21-23H,5-6H2,1-3H3/b8-4+/t9-,11+,13+,14-,15+,17-,18-/m0/s1

InChI Key

KYVUMEGNMQDSHO-PVCIXGPPSA-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
Fraxinus americana	LOTUS Database	35616633
Fraxinus excelsior	LOTUS Database	35616633
Jasminum grandiflorum	LOTUS Database	35616633
Jasminum sambac	LOTUS Database	35616633
Ligustrum lucidum	LOTUS Database	35616633
Olea europaea	LOTUS Database	35616633
Syringa persica	LOTUS Database	35616633
Syringa vulgaris	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Glycosyl compound
Secoiridoid-skeleton
O-glycosyl compound
Monocyclic monoterpenoid
Monoterpenoid
Sugar acid
Dicarboxylic acid or derivatives
Monosaccharide
Oxane
Vinylogous ester
Enoate ester
Methyl ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
Polyol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Acetal
Primary alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Carbonyl group
Organooxygen compound
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)	12.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	161.21 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	94.89 m³·mol⁻¹	ChemAxon
Polarizability	40.52 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

8963462

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10788149

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-methoxy-2-oxoethyl)-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate (NP0260470)

MOL for NP0260470 (methyl (4s,5e,6s)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

3D MOL for NP0260470 (methyl (4s,5e,6s)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

3D SDF for NP0260470 (methyl (4s,5e,6s)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

3D-SDF for NP0260470 (methyl (4s,5e,6s)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

PDB for NP0260470 (methyl (4s,5e,6s)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

3D PDB for NP0260470 (methyl (4s,5e,6s)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

SMILES for NP0260470 (methyl (4s,5e,6s)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

INCHI for NP0260470 (methyl (4s,5e,6s)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

Structure for NP0260470 (methyl (4s,5e,6s)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

3D Structure for NP0260470 (methyl (4s,5e,6s)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)