NP-MRD: Showing NP-Card for methyl (4s,5z,6s)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate (NP0203856)

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Record Information

Version

2.0

Created at

2022-09-04 23:25:08 UTC

Updated at

2022-09-04 23:25:08 UTC

NP-MRD ID

NP0203856

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Oleoside dimethylester 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,5z,6s)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate is found in Olea europaea. Oleoside dimethylester is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

Oleoside dimethylester
  Mrv1652309251702342D          

 29 30  0  0  1  0            999 V2000
    4.2365   -0.9034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655   -0.9034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -3.3783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -2.5534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655   -2.5534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    0.3341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -1.3159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    2.8092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3318    2.2860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799    2.8092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3318    0.8572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -2.5534    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5220   -2.1408    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9509   -2.1408    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5220   -1.3159    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9509   -1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655   -0.0784    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8075   -0.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799    1.1592    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3799    0.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655    1.5717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944    1.5717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    1.1592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944   -0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655    2.3967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9194    1.5717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944   -0.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    3.6341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1570    2.2860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 15  1  0  0  0  0
  1 16  1  0  0  0  0
  2 16  1  0  0  0  0
 17  2  1  6  0  0  0
 12  3  1  1  0  0  0
 13  4  1  6  0  0  0
 14  5  1  6  0  0  0
  6 17  1  0  0  0  0
  6 23  1  0  0  0  0
  7 18  1  0  0  0  0
  8 25  1  0  0  0  0
  8 28  1  0  0  0  0
  9 26  1  0  0  0  0
  9 29  1  0  0  0  0
 10 25  2  0  0  0  0
 11 26  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 18  1  1  0  0  0
 17 20  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  1  0  0  0
 20 24  2  0  0  0  0
 21 23  2  0  0  0  0
 21 25  1  0  0  0  0
 22 26  1  0  0  0  0
 24 27  1  0  0  0  0
M  END

     RDKit          3D

 55 56  0  0  0  0  0  0  0  0999 V2000
   -0.1264   -0.6333   -2.6853 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2068   -0.3030   -2.1462 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3512   -0.0544   -0.8524 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2680   -0.0499    0.1468 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7592    0.8101   -0.1143 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0410    0.2972    0.0314 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6701    0.8696    1.1534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6586    0.0270    1.6087 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1613   -1.1092    2.4710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2760   -1.8841    2.8646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4627   -0.5747    0.4755 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7862   -0.6647    0.8779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3835    0.4423   -0.6551 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2621    0.1357   -1.6802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9301    0.4354   -1.1571 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7403    1.6439   -1.8456 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8406    0.4143    1.3852 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6885    1.5034    1.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6717    1.4824    0.4404 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6102    2.5416    0.2855 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5340    2.4888   -0.5710 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5740    3.6988    1.0616 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5078    4.7410    0.9001 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    0.2681   -0.4326 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3915   -0.8275    0.3734 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4867   -2.1259   -0.2919 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0822   -2.3213   -1.4561 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0446   -3.2373    0.3491 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1335   -4.4964   -0.3046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6344   -1.3066   -1.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6863    0.2454   -2.9981 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0345   -1.2483   -3.6181 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0744   -0.2542   -2.8355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0656   -1.0856    0.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9393   -0.7738    0.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3931    0.5889    2.2537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5001   -1.8123    1.9363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7069   -0.7370    3.4100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0108   -1.2463    3.0461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1277   -1.5686    0.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4119   -0.8125    0.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6111    1.4406   -0.2331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5528    0.9276   -2.1880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8499   -0.4224   -1.8615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3043    2.3291   -1.2525 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6207    2.3882    1.9590 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0040    5.5484    0.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3968    4.4369    0.3113 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7957    5.2169    1.8624 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4092    0.5179   -1.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7437   -0.9457    1.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3826   -0.4993    0.7988 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0385   -5.0440   -0.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1716   -4.3103   -1.3913 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2114   -5.0911   -0.0583 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  6
 16 45  1  0
 18 46  1  0
 23 47  1  0
 23 48  1  0
 23 49  1  0
M  END

Oleoside dimethylester
  Mrv1652309251702342D          

 29 30  0  0  1  0            999 V2000
    4.2365   -0.9034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655   -0.9034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -3.3783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -2.5534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655   -2.5534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    0.3341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -1.3159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    2.8092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3318    2.2860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799    2.8092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3318    0.8572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -2.5534    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5220   -2.1408    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9509   -2.1408    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5220   -1.3159    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9509   -1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655   -0.0784    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8075   -0.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799    1.1592    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3799    0.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655    1.5717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944    1.5717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    1.1592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944   -0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655    2.3967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9194    1.5717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944   -0.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    3.6341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1570    2.2860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 15  1  0  0  0  0
  1 16  1  0  0  0  0
  2 16  1  0  0  0  0
 17  2  1  6  0  0  0
 12  3  1  1  0  0  0
 13  4  1  6  0  0  0
 14  5  1  6  0  0  0
  6 17  1  0  0  0  0
  6 23  1  0  0  0  0
  7 18  1  0  0  0  0
  8 25  1  0  0  0  0
  8 28  1  0  0  0  0
  9 26  1  0  0  0  0
  9 29  1  0  0  0  0
 10 25  2  0  0  0  0
 11 26  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 18  1  1  0  0  0
 17 20  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  1  0  0  0
 20 24  2  0  0  0  0
 21 23  2  0  0  0  0
 21 25  1  0  0  0  0
 22 26  1  0  0  0  0
 24 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0203856

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C[C@H]1\C(=C\C)[C@H](OC2O[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-VQQRNZRFSA-N

> <FORMULA>
C18H26O11

> <MOLECULAR_WEIGHT>
418.3924

> <EXACT_MASS>
418.147511674

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
41.11486998167791

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.74

> <JCHEM_LOGP>
-1.2947279233333333

> <ALOGPS_LOGS>
-1.83

> <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>
161.21

> <JCHEM_REFRACTIVITY>
94.8888

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.17e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (4S,5Z,6S)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(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                                 25-SEP-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Oleoside dimethylester                            
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-SEP-17         0                                  
HETATM    1  O   UNK     0       7.908  -1.686   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      10.576  -1.686   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       7.908  -6.306   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       5.241  -4.766   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      10.576  -4.766   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       9.242   0.624   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       3.907  -2.456   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       9.242   5.244   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      15.553   4.267   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      11.909   5.244   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      15.553   1.600   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.908  -4.766   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.574  -3.996   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.242  -3.996   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.574  -2.456   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.242  -2.456   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.576  -0.146   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.241  -1.686   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.909   2.164   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.909   0.624   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.576   2.934   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.243   2.934   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.242   2.164   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.243  -0.146   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.576   4.474   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.783   2.934   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.243  -1.686   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.242   6.784   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      17.093   4.267   0.000  0.00  0.00           C+0
CONECT    1   15   16                                                       
CONECT    2   16   17                                                       
CONECT    3   12                                                            
CONECT    4   13                                                            
CONECT    5   14                                                            
CONECT    6   17   23                                                       
CONECT    7   18                                                            
CONECT    8   25   28                                                       
CONECT    9   26   29                                                       
CONECT   10   25                                                            
CONECT   11   26                                                            
CONECT   12    3   13   14                                                  
CONECT   13    4   12   15                                                  
CONECT   14    5   12   16                                                  
CONECT   15    1   13   18                                                  
CONECT   16    1    2   14                                                  
CONECT   17    2    6   20                                                  
CONECT   18    7   15                                                       
CONECT   19   20   21   22                                                  
CONECT   20   17   19   24                                                  
CONECT   21   19   23   25                                                  
CONECT   22   19   26                                                       
CONECT   23    6   21                                                       
CONECT   24   20   27                                                       
CONECT   25    8   10   21                                                  
CONECT   26    9   11   22                                                  
CONECT   27   24                                                            
CONECT   28    8                                                            
CONECT   29    9                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   60    0
END

View in JSmol

Synonyms

Value	Source
Methyl (2S,4S)-3-ethylidene-4-(2-methoxy-2-oxoethyl)-2-{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylic acid	Generator

Chemical Formula

C₁₈H₂₆O₁₁

Average Mass

418.3924 Da

Monoisotopic Mass

418.14751 Da

IUPAC Name

methyl (2S,3Z,4S)-3-ethylidene-4-(2-methoxy-2-oxoethyl)-2-{[(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,5Z,6S)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(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](OC2O[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-VQQRNZRFSA-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
Olea europaea	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	-0.74	ALOGPS
logP	-1.3	ChemAxon
logS	-1.8	ALOGPS
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	41.11 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

6476722

PDB ID

Not Available

ChEBI ID

140131

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (4s,5z,6s)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate (NP0203856)

MOL for NP0203856 (methyl (4s,5z,6s)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

3D MOL for NP0203856 (methyl (4s,5z,6s)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

3D SDF for NP0203856 (methyl (4s,5z,6s)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

3D-SDF for NP0203856 (methyl (4s,5z,6s)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

PDB for NP0203856 (methyl (4s,5z,6s)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

3D PDB for NP0203856 (methyl (4s,5z,6s)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

SMILES for NP0203856 (methyl (4s,5z,6s)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

INCHI for NP0203856 (methyl (4s,5z,6s)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

Structure for NP0203856 (methyl (4s,5z,6s)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

3D Structure for NP0203856 (methyl (4s,5z,6s)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)