NP-MRD: Showing NP-Card for Oleoside dimethyl ester (NP0046151)

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Record Information

Version

2.0

Created at

2022-03-17 19:49:18 UTC

Updated at

2022-03-17 19:49:18 UTC

NP-MRD ID

NP0046151

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Oleoside dimethyl ester

Description

Oleoside dimethyl ester 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. Oleoside dimethyl ester is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Oleoside dimethyl ester has been detected, but not quantified in, several different foods, such as fats and oils, herbs and spices, olives, and pomes. Oleoside dimethyl ester is found in Fraxinus americana, Fraxinus excelsior , Jasminum grandiflorum , Ligustrum lucidum and Syringa afghanica. This could make oleoside dimethyl ester a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061305532D          

 29 30  0  0  0  0            999 V2000
    0.7145    1.2375    0.0000 C   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
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    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
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   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
    3.5724   -0.4125    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
    4.2868    0.0000    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
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   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
    5.0013   -0.4125    0.0000 O   0  0  0  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    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    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    4.9500    0.0000 O   0  0  0  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
    2.8579    0.0000    0.0000 O   0  0  0  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
  4  1  1  0  0  0  0
  8  4  2  0  0  0  0
  9  5  1  0  0  0  0
  9  8  1  0  0  0  0
 10  7  2  0  0  0  0
 10  9  1  0  0  0  0
 11  6  1  0  0  0  0
 12  5  1  0  0  0  0
 13 11  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 10  1  0  0  0  0
 17  8  1  0  0  0  0
 18 15  1  0  0  0  0
 19  6  1  0  0  0  0
 20 12  2  0  0  0  0
 21 13  1  0  0  0  0
 22 14  1  0  0  0  0
 23 15  1  0  0  0  0
 24 16  2  0  0  0  0
 25  2  1  0  0  0  0
 25 12  1  0  0  0  0
 26  3  1  0  0  0  0
 26 16  1  0  0  0  0
 27  7  1  0  0  0  0
 27 17  1  0  0  0  0
 28 11  1  0  0  0  0
 28 18  1  0  0  0  0
 29 17  1  0  0  0  0
 29 18  1  0  0  0  0
M  END


  Mrv0541 05061305532D          

 29 30  0  0  0  0            999 V2000
    0.7145    1.2375    0.0000 C   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
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    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
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   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
    3.5724   -0.4125    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
    4.2868    0.0000    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
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   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
    5.0013   -0.4125    0.0000 O   0  0  0  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    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    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    4.9500    0.0000 O   0  0  0  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
    2.8579    0.0000    0.0000 O   0  0  0  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
  4  1  1  0  0  0  0
  8  4  2  0  0  0  0
  9  5  1  0  0  0  0
  9  8  1  0  0  0  0
 10  7  2  0  0  0  0
 10  9  1  0  0  0  0
 11  6  1  0  0  0  0
 12  5  1  0  0  0  0
 13 11  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 10  1  0  0  0  0
 17  8  1  0  0  0  0
 18 15  1  0  0  0  0
 19  6  1  0  0  0  0
 20 12  2  0  0  0  0
 21 13  1  0  0  0  0
 22 14  1  0  0  0  0
 23 15  1  0  0  0  0
 24 16  2  0  0  0  0
 25  2  1  0  0  0  0
 25 12  1  0  0  0  0
 26  3  1  0  0  0  0
 26 16  1  0  0  0  0
 27  7  1  0  0  0  0
 27 17  1  0  0  0  0
 28 11  1  0  0  0  0
 28 18  1  0  0  0  0
 29 17  1  0  0  0  0
 29 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046151

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CC1\C(=C\C)C(OC2OC(CO)C(O)C(O)C2O)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-

> <INCHI_KEY>
KYVUMEGNMQDSHO-YWEYNIOJSA-N

> <FORMULA>
C18H26O11

> <MOLECULAR_WEIGHT>
418.3924

> <EXACT_MASS>
418.147511674

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
41.290440700299484

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (3Z)-3-ethylidene-4-(2-methoxy-2-oxoethyl)-2-{[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>
12.206649151336707

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.9408775563446685

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810849052288235

> <JCHEM_POLAR_SURFACE_AREA>
161.20999999999998

> <JCHEM_REFRACTIVITY>
94.88879999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.17e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.335   9.240   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       2.667   9.240   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2   25                                                            
CONECT    3   26                                                            
CONECT    4    1    8                                                       
CONECT    5    9   12                                                       
CONECT    6   11   19                                                       
CONECT    7   10   27                                                       
CONECT    8    4    9   17                                                  
CONECT    9    5    8   10                                                  
CONECT   10    7    9   16                                                  
CONECT   11    6   13   28                                                  
CONECT   12    5   20   25                                                  
CONECT   13   11   14   21                                                  
CONECT   14   13   15   22                                                  
CONECT   15   14   18   23                                                  
CONECT   16   10   24   26                                                  
CONECT   17    8   27   29                                                  
CONECT   18   15   28   29                                                  
CONECT   19    6                                                            
CONECT   20   12                                                            
CONECT   21   13                                                            
CONECT   22   14                                                            
CONECT   23   15                                                            
CONECT   24   16                                                            
CONECT   25    2   12                                                       
CONECT   26    3   16                                                       
CONECT   27    7   17                                                       
CONECT   28   11   18                                                       
CONECT   29   17   18                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   60    0
END

View in JSmol

Synonyms

Value	Source
(-)-Oleoside dimethyl ester	HMDB
Secologanoside 7-methyl ester	HMDB
Methyl 3-ethylidene-4-(2-methoxy-2-oxoethyl)-2-{[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 (3Z)-3-ethylidene-4-(2-methoxy-2-oxoethyl)-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate

Traditional Name

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

CAS Registry Number

30164-95-5

SMILES

COC(=O)CC1\C(=C\C)C(OC2OC(CO)C(O)C(O)C2O)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-

InChI Key

KYVUMEGNMQDSHO-YWEYNIOJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Fraxinus americana	Plant	KNApSAcK
Fraxinus excelsior	Plant	KNApSAcK
Jasminum grandiflorum	Plant	KNApSAcK
Ligustrum lucidum	Plant	KNApSAcK
Olea europaea	FooDB	PHENOL EXPLORER
Syringa afghanica	Plant	KNApSAcK

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)	4.94	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	41.29 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

HMDB0031350

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB003414

KNApSAcK ID

C00033266

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

14038297

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Oleoside dimethyl ester (NP0046151)

MOL for NP0046151 (Oleoside dimethyl ester)

3D MOL for NP0046151 (Oleoside dimethyl ester)

3D SDF for NP0046151 (Oleoside dimethyl ester)

3D-SDF for NP0046151 (Oleoside dimethyl ester)

PDB for NP0046151 (Oleoside dimethyl ester)

3D PDB for NP0046151 (Oleoside dimethyl ester)

SMILES for NP0046151 (Oleoside dimethyl ester)

INCHI for NP0046151 (Oleoside dimethyl ester)

Structure for NP0046151 (Oleoside dimethyl ester)

3D Structure for NP0046151 (Oleoside dimethyl ester)