24,25-Diacetylvulgaroside (CHEM034479)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 04:56:50 UTC
Update Date2016-11-09 01:21:08 UTC
Accession NumberCHEM034479
Identification
Common Name24,25-Diacetylvulgaroside
ClassSmall Molecule
Description24,25-Diacetylvulgaroside is found in fruits. 24,25-Diacetylvulgaroside is a constituent of Cydonia vulgaris (quince).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(1-{2-[2-(acetyloxy)-5-oxo-2,5-dihydrofuran-3-yl]-2-hydroxyethyl}-2-hydroxy-4b,8,8,10a-tetramethyl-tetradecahydrophenanthren-2-yl)methyl acetic acidHMDB
Chemical FormulaC29H44O8
Average Molecular Mass520.655 g/mol
Monoisotopic Mass520.304 g/mol
CAS Registry Number172616-87-4
IUPAC Name(1-{2-[2-(acetyloxy)-5-oxo-2,5-dihydrofuran-3-yl]-2-hydroxyethyl}-2-hydroxy-4b,8,8,10a-tetramethyl-tetradecahydrophenanthren-2-yl)methyl acetate
Traditional Name(1-{2-[2-(acetyloxy)-5-oxo-2H-furan-3-yl]-2-hydroxyethyl}-2-hydroxy-4b,8,8,10a-tetramethyl-decahydrophenanthren-2-yl)methyl acetate
SMILESCC(=O)OCC1(O)CCC2C(C)(CCC3C(C)(C)CCCC23C)C1CC(O)C1=CC(=O)OC1OC(C)=O
InChI IdentifierInChI=1S/C29H44O8/c1-17(30)35-16-29(34)13-9-22-27(5)11-7-10-26(3,4)21(27)8-12-28(22,6)23(29)15-20(32)19-14-24(33)37-25(19)36-18(2)31/h14,20-23,25,32,34H,7-13,15-16H2,1-6H3
InChI KeyCQEKWFACITVTKT-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cheilanthane sesterterpenoids. These are sesterterpnoids with a structure based on the cheilanthane backbone. Cheilanthane is a tricyclic compound consisting of a tetradecahydrophenanthrene ring system that carries two methyl groups at the 1-position, one methyl group at the 4a-,7-, and 8a-positions, as well as a 3-methylpentyl group at the 8-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesterterpenoids
Direct ParentCheilanthane sesterterpenoids
Alternative Parents
Substituents
  • Cheilanthane sesterterpenoid
  • 13-hydroxysteroid
  • Hydroxysteroid
  • 16-hydroxysteroid
  • Steroid
  • Hydrophenanthrene
  • Phenanthrene
  • Tricarboxylic acid or derivatives
  • Acylal
  • 2-furanone
  • Cyclic alcohol
  • Dihydrofuran
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tertiary alcohol
  • Lactone
  • Carboxylic acid ester
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0028 g/LALOGPS
logP3.41ALOGPS
logP3.67ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)1.9ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area119.36 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity135.47 m³·mol⁻¹ChemAxon
Polarizability57.15 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-2225930000-38afdf530ec5da59bb34Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-052e-2010039000-dedaac5b8d7aea4fd4e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0itc-1000940000-48d7328bf43d6a3f6e3aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-0302910000-9e11295414c11f1d05bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-4545910000-67bc3ed77dce981ce297Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05ox-8200980000-dcde5b6ea0d8cfbc5926Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-9300510000-06181be4568de7e11377Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000300000-482bb7114ddbc2f8e5bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05q9-1000900000-15d51cda95d2359df4bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000110000-f1dd59c17bea49e0e797Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9200000000-1476561a028b2d49c38eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03mi-0000940000-8f44e584effc33e576fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-3911540000-429b7eb4cba186b2d321Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-008c-5923100000-c06e65e90caea8dad333Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0041366
FooDB IDFDB021291
Phenol Explorer IDNot Available
KNApSAcK IDC00054368
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35015160
ChEBI ID175926
PubChem Compound ID85261348
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
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.
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.
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.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
6. The lipid handbook with CD-ROM