Glucosylceramide (d18:1/25:0) (CHEM035837)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 06:42:37 UTC
Update Date2016-11-09 01:21:23 UTC
Accession NumberCHEM035837
Identification
Common NameGlucosylceramide (d18:1/25:0)
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
N-[(2S,3R,4E)-3-Hydroxy-1-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadec-4-en-2-yl]pentacosanimidateHMDB
1-O-b-D-Glucopyranosyl-ceramideHMDB
1-O-beta-delta-Glucopyranosyl-ceramideHMDB
Ganglioside GL1aHMDB
Gaucher cerebrosideHMDB
GLC-beta1->1'cerHMDB
GlcCeramideHMDB
GlucocerebrosideHMDB
GlucosylceramideHMDB
Chemical FormulaC49H95NO8
Average Molecular Mass826.281 g/mol
Monoisotopic Mass825.706 g/mol
CAS Registry NumberNot Available
IUPAC NameN-[(2S,3R,4E)-3-hydroxy-1-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadec-4-en-2-yl]pentacosanamide
Traditional NameN-[(2S,3R,4E)-3-hydroxy-1-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadec-4-en-2-yl]pentacosanamide
SMILESCCCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@H](O)\C=C\CCCCCCCCCCCCC
InChI IdentifierInChI=1S/C49H95NO8/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-25-27-29-31-33-35-37-39-45(53)50-42(41-57-49-48(56)47(55)46(54)44(40-51)58-49)43(52)38-36-34-32-30-28-26-16-14-12-10-8-6-4-2/h36,38,42-44,46-49,51-52,54-56H,3-35,37,39-41H2,1-2H3,(H,50,53)/b38-36+/t42-,43+,44+,46+,47-,48+,49+/m0/s1
InChI KeyRIGGIBNQNREJCL-ZVFXBQQRSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as asparagine and derivatives. Asparagine and derivatives are compounds containing asparagine or a derivative thereof resulting from reaction of asparagine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAsparagine and derivatives
Alternative Parents
Substituents
  • Asparagine or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Medium-chain fatty acid
  • Amino fatty acid
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Fatty acid
  • Fatty amide
  • N-acyl-amine
  • Carboxamide group
  • Amino acid
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Organooxygen compound
  • Primary aliphatic amine
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Organonitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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 Solubility0.00016 g/LALOGPS
logP9.28ALOGPS
logP13.1ChemAxon
logS-6.7ALOGPS
pKa (Strongest Acidic)12.18ChemAxon
pKa (Strongest Basic)0.019ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area148.71 ŲChemAxon
Rotatable Bond Count42ChemAxon
Refractivity239.6 m³·mol⁻¹ChemAxon
Polarizability107.72 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000000090-7614609a57153d7c0e93Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-5110103690-aed41a948520f3a16d64Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-9242612000-6c4a5c955a5bc7183026Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056s-5100007190-7a0e0eaac242d6f153a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-6200109340-8e363e26988e21fd6005Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000x-9141002000-1076b035f22d54a38628Spectrum
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 IDHMDB0004979
FooDB IDFDB023566
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDGLUCOSYL_CERAMIDE
METLIN ID7232
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID16744964
ChEBI IDNot Available
PubChem Compound ID20057360
Kegg Compound IDC01190
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Harzer K, Massenkeil G, Frohlich E: Concurrent increase of cholesterol, sphingomyelin and glucosylceramide in the spleen from non-neurologic Niemann-Pick type C patients but also patients possibly affected with other lipid trafficking disorders. FEBS Lett. 2003 Feb 27;537(1-3):177-81.
2. Hara A, Kitazawa N, Taketomi T: Abnormalities of glycosphingolipids in mucopolysaccharidosis type III B. J Lipid Res. 1984 Feb;25(2):175-84.
3. Beutler E: Gaucher disease. Blood Rev. 1988 Mar;2(1):59-70.
4. Kaye EM, Ullman MD, Wilson ER, Barranger JA: Type 2 and type 3 Gaucher disease: a morphological and biochemical study. Ann Neurol. 1986 Aug;20(2):223-30.
5. Conradi NG, Kalimo H, Sourander P: Reactions of vessel walls and brain parenchyma to the accumulation of Gaucher cells in the Norrbottnian type (type III) of Gaucher disease. Acta Neuropathol. 1988;75(4):385-90.
6. Adar T, Ben-Ami R, Elstein D, Zimran A, Berliner S, Yedgar S, Barshtein G: Aggregation of red blood cells in patients with Gaucher disease. Br J Haematol. 2006 Aug;134(4):432-7. Epub 2006 Jul 10.
7. Smith RL, Hutchins GM, Sack GH Jr, Ridolfi RL: Unusual cardiac, renal and pulmonary involvement in Gaucher's disease. Intersitial glucocerebroside accumulation, pulmonary hypertension and fatal bone marrow embolization. Am J Med. 1978 Aug;65(2):352-60.
8. Dolen EG, Berdon WE, Ruzal-Shapiro C: "Cold bone scans" as a sign of hemorrhagic infarcts of the spine in Gaucher's disease. Pediatr Radiol. 1997 Jun;27(6):514-6.
9. Daniels LB, Coyle PJ, Glew RH, Radin NS, Labow RS: Brain glucocerebrosidase in Gaucher's disease. Arch Neurol. 1982 Sep;39(9):550-6.
10. Stirnemann J, Belmatoug N: [Adult Gaucher disease]. Rev Med Interne. 2001 Dec;22 Suppl 3:374s-383s.
11. Dawson G, Kruski AW, Scanu AM: Distribution of glycosphingolipids in the serum lipoproteins of normal human subjects and patients with hypo- and hyperlipidemias. J Lipid Res. 1976 Mar;17(2):125-31.
12. Erickson JS, Radin NS: N-hexyl-O-glucosyl sphingosine, an inhibitor of glucosyl ceramide -glucosidase. J Lipid Res. 1973 Mar;14(2):133-7.
13. Deguchi H, Bouma BN, Middeldorp S, Lee YM, Griffin JH: Decreased plasma sensitivity to activated protein C by oral contraceptives is associated with decreases in plasma glucosylceramide. J Thromb Haemost. 2005 May;3(5):935-8.
14. Shoenfeld Y, Gallant LA, Shaklai M, Livni E, Djaldetti M, Pinkhas J: Gaucher's disease: a disease with chronic stimulation of the immune system. Arch Pathol Lab Med. 1982 Aug;106(8):388-91.
15. Ohashi T: [Gene therapy for Gaucher disease]. Nihon Rinsho. 1995 Dec;53(12):3089-94.
16. Ringden O, Groth CG, Erikson A, Granqvist S, Mansson JE, Sparrelid E: Ten years' experience of bone marrow transplantation for Gaucher disease. Transplantation. 1995 Mar 27;59(6):864-70.
17. Nilsson O, Mansson JE, Hakansson G, Svennerholm L: The occurrence of psychosine and other glycolipids in spleen and liver from the three major types of Gaucher's disease. Biochim Biophys Acta. 1982 Sep 14;712(3):453-63.
18. Eto Y, Ida H: [Molecular studies of Gaucher disease]. Rinsho Byori. 1996 Apr;44(4):327-34.
19. Nishimura RN, Barranger JA: Neurologic complications of Gaucher's disease, type 3. Arch Neurol. 1980 Feb;37(2):92-3.
20. Naito M, Takahashi K, Hojo H: An ultrastructural and experimental study on the development of tubular structures in the lysosomes of Gaucher cells. Lab Invest. 1988 May;58(5):590-8.
21. Mariani G, Filocamo M, Giona F, Villa G, Amendola A, Erba P, Buffoni F, Copello F, Pierini A, Minichilli F, Gatti R, Brady RO: Severity of bone marrow involvement in patients with Gaucher's disease evaluated by scintigraphy with 99mTc-sestamibi. J Nucl Med. 2003 Aug;44(8):1253-62.
22. Soffer D, Yamanaka T, Wenger DA, Suzuki K, Suzuki K: Central nervous system involvement in adult-onset Gaucher's disease. Acta Neuropathol. 1980;49(1):1-6.
23. Dann K, Althaus C, Kersten A, vom Dahl S, Sundmacher R: [Uveitis masquerade syndrome in Gaucher disease. Causal treatment by alglucerase substitution therapy]. Klin Monbl Augenheilkd. 1998 Dec;213(6):358-61.
24. Conradi NG, Sourander P, Nilsson O, Svennerholm L, Erikson A: Neuropathology of the Norrbottnian type of Gaucher disease. Morphological and biochemical studies. Acta Neuropathol. 1984;65(2):99-109.
25. Beutler E: Gaucher disease: new molecular approaches to diagnosis and treatment. Science. 1992 May 8;256(5058):794-9.
26. Owada M, Sakiyama T, Kitagawa T: Neuropathic Gaucher's disease with normal 4-methylumbelliferyl-beta-glucosidase activity in the liver. Pediatr Res. 1977 May;11(5):641-6.
27. Ohashi T: [Gaucher disease]. Nihon Rinsho. 1995 Dec;53(12):2943-6.
28. Starzl TE, Demetris AJ, Trucco M, Ricordi C, Ildstad S, Terasaki PI, Murase N, Kendall RS, Kocova M, Rudert WA, et al.: Chimerism after liver transplantation for type IV glycogen storage disease and type 1 Gaucher's disease. N Engl J Med. 1993 Mar 18;328(11):745-9.
29. Nilsson O, Svennerholm L: Accumulation of glucosylceramide and glucosylsphingosine (psychosine) in cerebrum and cerebellum in infantile and juvenile Gaucher disease. J Neurochem. 1982 Sep;39(3):709-18.
30. Liu Y, Suzuki K, Reed JD, Grinberg A, Westphal H, Hoffmann A, Doring T, Sandhoff K, Proia RL: Mice with type 2 and 3 Gaucher disease point mutations generated by a single insertion mutagenesis procedure. Proc Natl Acad Sci U S A. 1998 Mar 3;95(5):2503-8.
31. Poll LW, Maas M, Terk MR, Roca-Espiau M, Bembi B, Ciana G, Weinreb NJ: Response of Gaucher bone disease to enzyme replacement therapy. Br J Radiol. 2002;75 Suppl 1:A25-36.
32. Campbell PE, Harris CM, Harris CM, Sirimanna T, Vellodi A: A model of neuronopathic Gaucher disease. J Inherit Metab Dis. 2003;26(7):629-39.
33. Pilz H, Heipertz R: [Differential diagnosis of congenital lipidoses by lipid analyses of body fluids, biopsy and autopsy tissue]. Fortschr Neurol Psychiatr Grenzgeb. 1975 Nov;43(11):602-17.
34. Schaison G, Caubel I, Belmatoug N, Billette de Villemeur T, Saudubray JM: [French results of enzyme replacement therapy in Gaucher's disease]. Bull Acad Natl Med. 2002;186(5):851-61; discussion 861-3.
35. Hollak CE, Boot RG, Poorthuis BJ, Aerts JM: [From gene to disease; Gaucher disease]. Ned Tijdschr Geneeskd. 2005 Sep 24;149(39):2163-6.
36. Nilsson O, Grabowski GA, Ludman MD, Desnick RJ, Svennerholm L: Glycosphingolipid studies of visceral tissues and brain from type 1 Gaucher disease variants. Clin Genet. 1985 May;27(5):443-50.