25-Acetylvulgaroside (CHEM034478)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 04:56:49 UTC
Update Date2016-11-09 01:21:08 UTC
Accession NumberCHEM034478
Identification
Common Name25-Acetylvulgaroside
ClassSmall Molecule
Description25-Acetylvulgaroside is found in fruits. 25-Acetylvulgaroside is a constituent of Cydonia vulgaris (quince).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-{1-hydroxy-2-[2-hydroxy-2-(hydroxymethyl)-4b,8,8,10a-tetramethyl-tetradecahydrophenanthren-1-yl]ethyl}-5-oxo-2,5-dihydrofuran-2-yl acetic acidHMDB
Chemical FormulaC27H42O7
Average Molecular Mass478.618 g/mol
Monoisotopic Mass478.293 g/mol
CAS Registry Number172616-88-5
IUPAC Name3-{1-hydroxy-2-[2-hydroxy-2-(hydroxymethyl)-4b,8,8,10a-tetramethyl-tetradecahydrophenanthren-1-yl]ethyl}-5-oxo-2,5-dihydrofuran-2-yl acetate
Traditional Name3-{1-hydroxy-2-[2-hydroxy-2-(hydroxymethyl)-4b,8,8,10a-tetramethyl-decahydrophenanthren-1-yl]ethyl}-5-oxo-2H-furan-2-yl acetate
SMILESCC(=O)OC1OC(=O)C=C1C(O)CC1C(O)(CO)CCC2C1(C)CCC1C(C)(C)CCCC21C
InChI IdentifierInChI=1S/C27H42O7/c1-16(29)33-23-17(13-22(31)34-23)18(30)14-21-26(5)11-7-19-24(2,3)9-6-10-25(19,4)20(26)8-12-27(21,32)15-28/h13,18-21,23,28,30,32H,6-12,14-15H2,1-5H3
InChI KeyQNZZHRCSGTYEAW-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
  • 18-hydroxysteroid
  • 13-hydroxysteroid
  • Hydroxysteroid
  • 17-hydroxysteroid
  • 16-hydroxysteroid
  • Steroid
  • Hydrophenanthrene
  • Phenanthrene
  • Acylal
  • 2-furanone
  • Dicarboxylic acid or derivatives
  • 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
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Primary alcohol
  • 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 Solubility0.012 g/LALOGPS
logP2.78ALOGPS
logP3.23ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)1.9ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity126.32 m³·mol⁻¹ChemAxon
Polarizability52.72 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ot-1111900000-076a5ef68b23dd0efa60Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-005l-2100019000-5e83f421f3532978b523Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0409-1000900000-662e1ef7002378f92e13Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0j4l-2203900000-daf790c9eb74d341b728Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kk-4569600000-bae1626ac9f761423774Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002f-3100900000-45dd0bdb7069a847bbf9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052f-8507900000-489ae74fcc126ba169a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9007300000-947a12f34be271b8e6f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000900000-f143bb723ddb0d8c09dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kf-3202900000-a20115206cc6107a415aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0016-8943200000-16c29eb0090754893588Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052r-3000900000-ee416e5dd82e3d000fd7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9001200000-63f542d2cd17bf5123b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4j-9102600000-01e4e95360b51b2539deSpectrum
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 IDHMDB0041365
FooDB IDFDB021290
Phenol Explorer IDNot Available
KNApSAcK IDC00054369
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35015159
ChEBI ID169802
PubChem Compound ID85163499
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