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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:42:28 UTC
Update Date2022-03-07 02:52:56 UTC
HMDB IDHMDB0031350
Secondary Accession Numbers
  • HMDB31350
Metabolite Identification
Common NameOleoside dimethyl ester
DescriptionOleoside 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. Based on a literature review a small amount of articles have been published on Oleoside dimethyl ester.
Structure
Data?1563862113
Synonyms
ValueSource
(-)-Oleoside dimethyl esterHMDB
Secologanoside 7-methyl esterHMDB
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 acidGenerator
Chemical FormulaC18H26O11
Average Molecular Weight418.3924
Monoisotopic Molecular Weight418.147511674
IUPAC Namemethyl (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 Namemethyl (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 Number30164-95-5
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 KeyKYVUMEGNMQDSHO-YWEYNIOJSA-N
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene glycosides
Direct ParentTerpene 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 FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility31240 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility6.17 g/LALOGPS
logP-0.74ALOGPS
logP-1.3ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)4.94ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area161.21 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity94.89 m³·mol⁻¹ChemAxon
Polarizability41.29 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+195.54131661259
DarkChem[M-H]-189.11831661259
DeepCCS[M+H]+199.32130932474
DeepCCS[M-H]-196.96430932474
DeepCCS[M-2H]-231.07330932474
DeepCCS[M+Na]+206.57230932474
AllCCS[M+H]+196.732859911
AllCCS[M+H-H2O]+194.432859911
AllCCS[M+NH4]+198.932859911
AllCCS[M+Na]+199.532859911
AllCCS[M-H]-194.132859911
AllCCS[M+Na-2H]-194.732859911
AllCCS[M+HCOO]-195.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Oleoside dimethyl esterCOC(=O)CC1\C(=C\C)C(OC2OC(CO)C(O)C(O)C2O)OC=C1C(=O)OC3899.4Standard polar33892256
Oleoside dimethyl esterCOC(=O)CC1\C(=C\C)C(OC2OC(CO)C(O)C(O)C2O)OC=C1C(=O)OC2844.1Standard non polar33892256
Oleoside dimethyl esterCOC(=O)CC1\C(=C\C)C(OC2OC(CO)C(O)C(O)C2O)OC=C1C(=O)OC3094.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Oleoside dimethyl ester,1TMS,isomer #1C/C=C1\C(OC2OC(CO[Si](C)(C)C)C(O)C(O)C2O)OC=C(C(=O)OC)C1CC(=O)OC2959.6Semi standard non polar33892256
Oleoside dimethyl ester,1TMS,isomer #2C/C=C1\C(OC2OC(CO)C(O[Si](C)(C)C)C(O)C2O)OC=C(C(=O)OC)C1CC(=O)OC2968.9Semi standard non polar33892256
Oleoside dimethyl ester,1TMS,isomer #3C/C=C1\C(OC2OC(CO)C(O)C(O[Si](C)(C)C)C2O)OC=C(C(=O)OC)C1CC(=O)OC2959.1Semi standard non polar33892256
Oleoside dimethyl ester,1TMS,isomer #4C/C=C1\C(OC2OC(CO)C(O)C(O)C2O[Si](C)(C)C)OC=C(C(=O)OC)C1CC(=O)OC2967.4Semi standard non polar33892256
Oleoside dimethyl ester,2TMS,isomer #1C/C=C1\C(OC2OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C2O)OC=C(C(=O)OC)C1CC(=O)OC2946.5Semi standard non polar33892256
Oleoside dimethyl ester,2TMS,isomer #2C/C=C1\C(OC2OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C2O)OC=C(C(=O)OC)C1CC(=O)OC2943.3Semi standard non polar33892256
Oleoside dimethyl ester,2TMS,isomer #3C/C=C1\C(OC2OC(CO[Si](C)(C)C)C(O)C(O)C2O[Si](C)(C)C)OC=C(C(=O)OC)C1CC(=O)OC2941.2Semi standard non polar33892256
Oleoside dimethyl ester,2TMS,isomer #4C/C=C1\C(OC2OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O)OC=C(C(=O)OC)C1CC(=O)OC2963.9Semi standard non polar33892256
Oleoside dimethyl ester,2TMS,isomer #5C/C=C1\C(OC2OC(CO)C(O[Si](C)(C)C)C(O)C2O[Si](C)(C)C)OC=C(C(=O)OC)C1CC(=O)OC2958.6Semi standard non polar33892256
Oleoside dimethyl ester,2TMS,isomer #6C/C=C1\C(OC2OC(CO)C(O)C(O[Si](C)(C)C)C2O[Si](C)(C)C)OC=C(C(=O)OC)C1CC(=O)OC2933.8Semi standard non polar33892256
Oleoside dimethyl ester,3TMS,isomer #1C/C=C1\C(OC2OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O)OC=C(C(=O)OC)C1CC(=O)OC2920.5Semi standard non polar33892256
Oleoside dimethyl ester,3TMS,isomer #2C/C=C1\C(OC2OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C2O[Si](C)(C)C)OC=C(C(=O)OC)C1CC(=O)OC2898.8Semi standard non polar33892256
Oleoside dimethyl ester,3TMS,isomer #3C/C=C1\C(OC2OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C2O[Si](C)(C)C)OC=C(C(=O)OC)C1CC(=O)OC2895.6Semi standard non polar33892256
Oleoside dimethyl ester,3TMS,isomer #4C/C=C1\C(OC2OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O[Si](C)(C)C)OC=C(C(=O)OC)C1CC(=O)OC2892.4Semi standard non polar33892256
Oleoside dimethyl ester,4TMS,isomer #1C/C=C1\C(OC2OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O[Si](C)(C)C)OC=C(C(=O)OC)C1CC(=O)OC2855.5Semi standard non polar33892256
Oleoside dimethyl ester,1TBDMS,isomer #1C/C=C1\C(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C2O)OC=C(C(=O)OC)C1CC(=O)OC3176.2Semi standard non polar33892256
Oleoside dimethyl ester,1TBDMS,isomer #2C/C=C1\C(OC2OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C2O)OC=C(C(=O)OC)C1CC(=O)OC3202.4Semi standard non polar33892256
Oleoside dimethyl ester,1TBDMS,isomer #3C/C=C1\C(OC2OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C2O)OC=C(C(=O)OC)C1CC(=O)OC3191.4Semi standard non polar33892256
Oleoside dimethyl ester,1TBDMS,isomer #4C/C=C1\C(OC2OC(CO)C(O)C(O)C2O[Si](C)(C)C(C)(C)C)OC=C(C(=O)OC)C1CC(=O)OC3198.6Semi standard non polar33892256
Oleoside dimethyl ester,2TBDMS,isomer #1C/C=C1\C(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C2O)OC=C(C(=O)OC)C1CC(=O)OC3375.9Semi standard non polar33892256
Oleoside dimethyl ester,2TBDMS,isomer #2C/C=C1\C(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C2O)OC=C(C(=O)OC)C1CC(=O)OC3381.9Semi standard non polar33892256
Oleoside dimethyl ester,2TBDMS,isomer #3C/C=C1\C(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C2O[Si](C)(C)C(C)(C)C)OC=C(C(=O)OC)C1CC(=O)OC3376.8Semi standard non polar33892256
Oleoside dimethyl ester,2TBDMS,isomer #4C/C=C1\C(OC2OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C2O)OC=C(C(=O)OC)C1CC(=O)OC3402.7Semi standard non polar33892256
Oleoside dimethyl ester,2TBDMS,isomer #5C/C=C1\C(OC2OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C2O[Si](C)(C)C(C)(C)C)OC=C(C(=O)OC)C1CC(=O)OC3402.1Semi standard non polar33892256
Oleoside dimethyl ester,2TBDMS,isomer #6C/C=C1\C(OC2OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C)OC=C(C(=O)OC)C1CC(=O)OC3389.9Semi standard non polar33892256
Oleoside dimethyl ester,3TBDMS,isomer #1C/C=C1\C(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C2O)OC=C(C(=O)OC)C1CC(=O)OC3591.3Semi standard non polar33892256
Oleoside dimethyl ester,3TBDMS,isomer #2C/C=C1\C(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C2O[Si](C)(C)C(C)(C)C)OC=C(C(=O)OC)C1CC(=O)OC3574.5Semi standard non polar33892256
Oleoside dimethyl ester,3TBDMS,isomer #3C/C=C1\C(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C)OC=C(C(=O)OC)C1CC(=O)OC3578.5Semi standard non polar33892256
Oleoside dimethyl ester,3TBDMS,isomer #4C/C=C1\C(OC2OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C)OC=C(C(=O)OC)C1CC(=O)OC3580.3Semi standard non polar33892256
Oleoside dimethyl ester,4TBDMS,isomer #1C/C=C1\C(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C)OC=C(C(=O)OC)C1CC(=O)OC3790.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Oleoside dimethyl ester GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kg9-6409200000-11262ee5471390675baa2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oleoside dimethyl ester GC-MS (3 TMS) - 70eV, Positivesplash10-01b9-2583059000-8e6b42abbe303bbf36e92017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oleoside dimethyl ester GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleoside dimethyl ester 10V, Positive-QTOFsplash10-07e0-0973300000-bb39fd472b5fe839723a2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleoside dimethyl ester 20V, Positive-QTOFsplash10-0bvr-0970000000-9bac481efae3abe54d222016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleoside dimethyl ester 40V, Positive-QTOFsplash10-002k-4910000000-bcf786108b1a8bb4f1192016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleoside dimethyl ester 10V, Negative-QTOFsplash10-066r-1394400000-092f7553eb76dffcac0f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleoside dimethyl ester 20V, Negative-QTOFsplash10-074i-2493000000-22ed019237cec8cea6822016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleoside dimethyl ester 40V, Negative-QTOFsplash10-074l-5950000000-106277dbe29ec20751902016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleoside dimethyl ester 10V, Negative-QTOFsplash10-014i-0595700000-b4e6e8a828a72063d9002021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleoside dimethyl ester 20V, Negative-QTOFsplash10-00or-1739100000-ad216f04d4472989ba2e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleoside dimethyl ester 40V, Negative-QTOFsplash10-000w-2920000000-d49403b323fe52c4a0c62021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleoside dimethyl ester 10V, Positive-QTOFsplash10-052b-0970100000-7a8f3d442efadecc600c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleoside dimethyl ester 20V, Positive-QTOFsplash10-069s-0930000000-f1ece553b991001d9e552021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleoside dimethyl ester 40V, Positive-QTOFsplash10-0002-4902000000-89359b8aaabebcf37f052021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003414
KNApSAcK IDC00033266
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14038297
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1825801
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.