ergosteryl 3-beta-D-glucoside (YMDB00777)

Identification
YMDB IDYMDB00777
Nameergosteryl 3-beta-D-glucoside
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Descriptionergosteryl 3-beta-D-glucoside belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton. ergosteryl 3-beta-D-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
  • Ergosteryl 3-b-D-glucoside
  • Ergosteryl 3-β-D-glucoside
CAS numberNot Available
WeightAverage: 558.789
Monoisotopic: 558.39203946
InChI KeyMKZPNGBJJJZJMI-GBLVNJONSA-N
InChIInChI=1S/C34H54O6/c1-19(2)20(3)7-8-21(4)25-11-12-26-24-10-9-22-17-23(13-15-33(22,5)27(24)14-16-34(25,26)6)39-32-31(38)30(37)29(36)28(18-35)40-32/h7-10,19-21,23,25-32,35-38H,11-18H2,1-6H3/b8-7+/t20-,21+,23-,25+,26-,27-,28+,29+,30-,31+,32+,33-,34+/m0/s1
IUPAC Name(2R,3R,4S,5S,6R)-2-{[(1S,2R,5S,11R,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-7,9-dien-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
Traditional IUPAC Nameergosteryl 3-β-D-glucoside
Chemical FormulaC34H54O6
SMILESOC[C@H]1O[C@@H](O[C@H]2CC[C@@]3(C)C(=CC=C4[C@]5([H])CC[C@]([H])([C@H](C)\C=C\[C@H](C)C(C)C)[C@@]5(C)CC[C@]34[H])C2)[C@H](O)[C@@H](O)[C@@H]1O
Chemical Taxonomy
Description belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroidal glycosides
Direct ParentSteroidal glycosides
Alternative Parents
Substituents
  • Diterpene glycoside
  • Ergostane-skeleton
  • Steroidal glycoside
  • Diterpenoid
  • Delta-5-steroid
  • Delta-7-steroid
  • Terpene glycoside
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Monosaccharide
  • Oxane
  • Secondary alcohol
  • Polyol
  • Oxacycle
  • Acetal
  • Organoheterocyclic compound
  • Primary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.0065 g/LALOGPS
logP5.45ALOGPS
logP4.86ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)12.21ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area99.38 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity159.54 m³·mol⁻¹ChemAxon
Polarizability67.11 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG Reactions
Uridine diphosphate glucose + ergosterol → Uridine 5'-diphosphate + ergosteryl 3-beta-D-glucoside + hydron
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_4_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-054n-2009050000-617edb35974d1aeecd29JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-3119000000-4e682984edc756a5cab9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01qa-6449000000-e61772c6448dbec9d34aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4j-1208090000-1fa416f442a61bdd4f7cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-1209010000-37723240e12156728d89JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002e-4009000000-e23c5e1abf1ee4706923JSpectraViewer
MSMass Spectrum (Electron Ionization)Not AvailableJSpectraViewer
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Warnecke, D., Erdmann, R., Fahl, A., Hube, B., Muller, F., Zank, T., Zahringer, U., Heinz, E. (1999). "Cloning and functional expression of UGT genes encoding sterol glucosyltransferases from Saccharomyces cerevisiae, Candida albicans, Pichia pastoris, and Dictyostelium discoideum." J Biol Chem 274:13048-13059.10224056
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID52973
HMDB IDNot Available
Pubchem Compound ID44176397
Kegg IDNot Available
ChemSpider ID23107093
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Sterol 3-beta-glucosyltransferase
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
May be involved in decane metabolism and autophagy. Involved in the biosynthesis of sterol glucoside
Gene Name:
ATG26
Uniprot ID:
Q06321
Molecular weight:
136053.0
Reactions
UDP-glucose + a sterol → UDP + a sterol 3-beta-D-glucoside.