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Record Information
StatusExpected but not Quantified
Creation Date2008-09-26 14:11:48 UTC
Update Date2022-03-07 02:51:02 UTC
Secondary Accession Numbers
  • HMDB10712
Metabolite Identification
Common NameGalactosylceramide (d18:1/24:1(15Z))
DescriptionGalactosylceramides (GalCer) are non-acidic monoglycosphingolipids, i.e. a sphingolipid with one carbohydrate moiety attached to a ceramide unit. They are an intermediate in sphingolipid metabolism and is the second to last step in the synthesis of digalactosylceramidesulfate. GalCer is generated from ceramide via the enzyme UDP-galactose ceramide galactosyltransferase [EC:]. It can be converted to digalactosylceramide via the enzyme glycosyltransferases [EC 2.4.1.-]. Galactosylceramide is the principal glycosphingolipid in brain tissue, hence the trivial name "cerebroside", which was first conferred on it in 1874. Galactosylceramides are found in all nervous tissues, but they can amount to 2% of the dry weight of grey matter and 12% of white matter. They are major constituents of oligodendrocytes. Synthesis of galactosylceramide takes place on the lumenal surface of the endoplasmic reticulum, although it has free access to the cytosolic surface by an energy-independent flip-flop process. GalCer sits in the extracellular leaflet of cell membranes in nanometer sized domains or rafts. The local clustering of GalCer within rafts is thought to facilitate the initial adhesion of certain viruses, including HIV-1 and bacteria to cells through multivalent interactions between receptor proteins and GalCer. A defect in the degradation of cerbrosides leads to a disorder called Krabbe disease. Krabbe disease (also known as globoid cell leukodystrophy or galactosylceramide lipidosis) is a rare, often fatal degenerative disorder that affects the myelin sheath of the nervous system. Krabbe disease is caused by mutations in the GALC gene, which causes a deficiency of galactosylceramidase. Infants with Krabbe disease are normal at birth. Symptoms begin between the ages of 3 and 6 months with irritability, fevers, limb stiffness, seizures, feeding difficulties, vomiting, and slowing of mental and motor development. There are also juvenile- and adult-onset cases of Krabbe disease, which have similar symptoms but slower progression. In infants, the disease is generally fatal before age 2. Patients with late-onset Krabbe disease tend to have a slower progression of the disease and live significantly longer.Cerebrosides are glycosphingolipids. There are four types of glycosphingolipids, the cerebrosides, sulfatides, globosides and gangliosides. Cerebrosides have a single sugar group linked to ceramide. The most common are galactocerebrosides (containing galactose), the least common are glucocerebrosides (containing glucose). Galactocerebrosides are found predominantly in neuronal cell membranes. In contrast glucocerebrosides are not normally found in membranes. Instead, they are typically intermediates in the synthesis or degradation of more complex glycosphingolipids. Galactocerebrosides are synthesized from ceramide and UDP-galactose. Excess lysosomal accumulation of glucocerebrosides is found in Gaucher disease.
Chemical FormulaC48H91NO8
Average Molecular Weight810.238
Monoisotopic Molecular Weight809.674468893
IUPAC Name(15Z)-N-[(4Z)-3-hydroxy-1-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadec-4-en-2-yl]tetracos-15-enamide
Traditional Name(15Z)-N-[(4Z)-3-hydroxy-1-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadec-4-en-2-yl]tetracos-15-enamide
CAS Registry NumberNot Available
InChI Identifier
Chemical Taxonomy
Description Belongs to the class of organic compounds known as glycosyl-n-acylsphingosines. Glycosyl-N-acylsphingosines are compounds containing a sphingosine linked to a simple glucosyl moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
Sub ClassGlycosphingolipids
Direct ParentGlycosyl-N-acylsphingosines
Alternative Parents
  • Glycosyl-n-acylsphingosine
  • Fatty acyl glycoside
  • Fatty acyl glycoside of mono- or disaccharide
  • Alkyl glycoside
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Fatty amide
  • Fatty acyl
  • Monosaccharide
  • N-acyl-amine
  • Oxane
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Alcohol
  • Organic oxygen compound
  • Organic nitrogen compound
  • Primary alcohol
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Not AvailableNot Available
Physical Properties
Experimental Molecular Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Water Solubility0.00024 g/LALOGPS
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 Count40ChemAxon
Refractivity236.11 m³·mol⁻¹ChemAxon
Polarizability103.52 ųChemAxon
Number of Rings1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference

Predicted Kovats Retention Indices


MetaboliteSMILESKovats RI ValueColumn TypeReference
Galactosylceramide (d18:1/24:1(15Z))CCCCCCCCCCCCC\C=C/C(O)C(CO[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)NC(=O)CCCCCCCCCCCCC\C=C/CCCCCCCC4032.7Standard polar33892256
Galactosylceramide (d18:1/24:1(15Z))CCCCCCCCCCCCC\C=C/C(O)C(CO[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)NC(=O)CCCCCCCCCCCCC\C=C/CCCCCCCC5338.0Standard non polar33892256
Galactosylceramide (d18:1/24:1(15Z))CCCCCCCCCCCCC\C=C/C(O)C(CO[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)NC(=O)CCCCCCCCCCCCC\C=C/CCCCCCCC6208.5Semi standard non polar33892256

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Galactosylceramide (d18:1/24:1(15Z)) GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Galactosylceramide (d18:1/24:1(15Z)) GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Galactosylceramide (d18:1/24:1(15Z)) GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Galactosylceramide (d18:1/24:1(15Z)) GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Galactosylceramide (d18:1/24:1(15Z)) GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Galactosylceramide (d18:1/24:1(15Z)) GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galactosylceramide (d18:1/24:1(15Z)) 10V, Negative-QTOFsplash10-0a4i-0000000090-f50e2b4ec00e9f49c1fe2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galactosylceramide (d18:1/24:1(15Z)) 20V, Negative-QTOFsplash10-0a4i-7210104790-bdf0c08b1ba9b4e32f672021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galactosylceramide (d18:1/24:1(15Z)) 40V, Negative-QTOFsplash10-0a4i-9415320000-a289b61abf581d8881ad2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galactosylceramide (d18:1/24:1(15Z)) 10V, Positive-QTOFsplash10-03di-2002009560-655411d55f2feb31a3de2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galactosylceramide (d18:1/24:1(15Z)) 20V, Positive-QTOFsplash10-01q9-2100009310-662ca4397c6119825e932021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galactosylceramide (d18:1/24:1(15Z)) 40V, Positive-QTOFsplash10-0006-9500004000-9ff06df0fe9afa39b9ea2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue Locations
  • All Tissues
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 IDFDB027862
KNApSAcK IDNot Available
Chemspider ID24765748
KEGG Compound IDC02686
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480656
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Wang J, Guillaume J, Pauwels N, Van Calenbergh S, Van Rhijn I, Zajonc DM: Crystal structures of bovine CD1d reveal altered alphaGalCer presentation and a restricted A' pocket unable to bind long-chain glycolipids. PLoS One. 2012;7(10):e47989. doi: 10.1371/journal.pone.0047989. Epub 2012 Oct 23. [PubMed:23110152 ]
  2. Okamoto Y, Fujikawa A, Kurosaki M, Yamasaki K, Sakurai D, Horiguchi S, Nakayama T: Nasal submucosal administration of antigen-presenting cells induces effective immunological responses in cancer immunotherapy. Adv Otorhinolaryngol. 2011;72:149-52. doi: 10.1159/000324775. Epub 2011 Aug 18. [PubMed:21865716 ]
  3. Lopez-Sagaseta J, Kung JE, Savage PB, Gumperz J, Adams EJ: The molecular basis for recognition of CD1d/alpha-galactosylceramide by a human non-Valpha24 T cell receptor. PLoS Biol. 2012;10(10):e1001412. doi: 10.1371/journal.pbio.1001412. Epub 2012 Oct 23. [PubMed:23109910 ]
  4. Tonti E, Fedeli M, Napolitano A, Iannacone M, von Andrian UH, Guidotti LG, Abrignani S, Casorati G, Dellabona P: Follicular helper NKT cells induce limited B cell responses and germinal center formation in the absence of CD4(+) T cell help. J Immunol. 2012 Apr 1;188(7):3217-22. doi: 10.4049/jimmunol.1103501. Epub 2012 Feb 29. [PubMed:22379027 ]
  5. Freigang S, Landais E, Zadorozhny V, Kain L, Yoshida K, Liu Y, Deng S, Palinski W, Savage PB, Bendelac A, Teyton L: Scavenger receptors target glycolipids for natural killer T cell activation. J Clin Invest. 2012 Nov;122(11):3943-54. doi: 10.1172/JCI62267. Epub 2012 Oct 15. [PubMed:23064364 ]
  6. Yang JQ, Kim PJ, Singh RR: Brief treatment with iNKT cell ligand alpha-galactosylceramide confers a long-term protection against lupus. J Clin Immunol. 2012 Feb;32(1):106-13. doi: 10.1007/s10875-011-9590-y. Epub 2011 Oct 15. [PubMed:22002593 ]
  7. Patel O, Pellicci DG, Uldrich AP, Sullivan LC, Bhati M, McKnight M, Richardson SK, Howell AR, Mallevaey T, Zhang J, Bedel R, Besra GS, Brooks AG, Kjer-Nielsen L, McCluskey J, Porcelli SA, Gapin L, Rossjohn J, Godfrey DI: Vbeta2 natural killer T cell antigen receptor-mediated recognition of CD1d-glycolipid antigen. Proc Natl Acad Sci U S A. 2011 Nov 22;108(47):19007-12. doi: 10.1073/pnas.1109066108. Epub 2011 Nov 7. [PubMed:22065767 ]
  8. Detre C, Keszei M, Garrido-Mesa N, Kis-Toth K, Castro W, Agyemang AF, Veerapen N, Besra GS, Carroll MC, Tsokos GC, Wang N, Leadbetter EA, Terhorst C: SAP expression in invariant NKT cells is required for cognate help to support B-cell responses. Blood. 2012 Jul 5;120(1):122-9. doi: 10.1182/blood-2011-11-395913. Epub 2012 May 21. [PubMed:22613797 ]
  9. Tyznik AJ, Farber E, Girardi E, Birkholz A, Li Y, Chitale S, So R, Arora P, Khurana A, Wang J, Porcelli SA, Zajonc DM, Kronenberg M, Howell AR: Glycolipids that elicit IFN-gamma-biased responses from natural killer T cells. Chem Biol. 2011 Dec 23;18(12):1620-30. doi: 10.1016/j.chembiol.2011.10.015. [PubMed:22195564 ]
  10. Nagy L: Would eating carrots protect your liver? A new role involving NKT cells for retinoic acid in hepatitis. Eur J Immunol. 2012 Jul;42(7):1677-80. doi: 10.1002/eji.201242705. [PubMed:22806070 ]
  11. Choi DH, Kim KS, Yang SH, Chung DH, Song B, Sprent J, Cho JH, Sung YC: Dendritic cell internalization of alpha-galactosylceramide from CD8 T cells induces potent antitumor CD8 T-cell responses. Cancer Res. 2011 Dec 15;71(24):7442-51. doi: 10.1158/0008-5472.CAN-11-1459. Epub 2011 Oct 25. [PubMed:22028323 ]
  12. Yu ED, Girardi E, Wang J, Mac TT, Yu KO, Van Calenbergh S, Porcelli SA, Zajonc DM: Structural basis for the recognition of C20:2-alphaGalCer by the invariant natural killer T cell receptor-like antibody L363. J Biol Chem. 2012 Jan 6;287(2):1269-78. doi: 10.1074/jbc.M111.308783. Epub 2011 Nov 22. [PubMed:22110136 ]
  13. Kim YJ, Han SH, Kang HW, Lee JM, Kim YS, Seo JH, Seong YK, Ko HJ, Choi TH, Moon C, Kang CY: NKT ligand-loaded, antigen-expressing B cells function as long-lasting antigen presenting cells in vivo. Cell Immunol. 2011;270(2):135-44. doi: 10.1016/j.cellimm.2011.04.006. Epub 2011 Apr 22. [PubMed:21741036 ]
  14. Chen Q, Ross AC: All-trans-retinoic acid and the glycolipid alpha-galactosylceramide combined reduce breast tumor growth and lung metastasis in a 4T1 murine breast tumor model. Nutr Cancer. 2012;64(8):1219-27. doi: 10.1080/01635581.2012.718404. [PubMed:23163850 ]
  15. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  16. 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 ]
  17. 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 ]
  18. 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 ]
  19. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
  20. Ghosh S, Strum JC, Bell RM: Lipid biochemistry: functions of glycerolipids and sphingolipids in cellular signaling. FASEB J. 1997 Jan;11(1):45-50. [PubMed:9034165 ]
  21. Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
  22. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Only showing the first 10 proteins. There are 70 proteins in total.


General function:
Involved in galactosylceramidase activity
Specific function:
Hydrolyzes the galactose ester bonds of galactosylceramide, galactosylsphingosine, lactosylceramide, and monogalactosyldiglyceride. Enzyme with very low activity responsible for the lysosomal catabolism of galactosylceramide, a major lipid in myelin, kidney and epithelial cells of small intestine and colon.
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in exo-alpha-sialidase activity
Specific function:
Hydrolyzes sialylated compounds.
Gene Name:
Uniprot ID:
Molecular weight:
Not Available
General function:
Involved in galactosylceramide sulfotransferase activity
Specific function:
Catalyzes the sulfation of membrane glycolipids. Seems to prefer beta-glycosides at the non-reducing termini of sugar chains attached to a lipid moiety. Catalyzes the synthesis of galactosylceramide sulfate (sulfatide), a major lipid component of the myelin sheath and of monogalactosylalkylacylglycerol sulfate (seminolipid), present in spermatocytes (By similarity). Also acts on lactosylceramide, galactosyl 1-alkyl-2-sn-glycerol and galactosyl diacylglycerol (in vitro).
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in catalytic activity
Specific function:
Hydrolyzes cerebroside sulfate.
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in exo-alpha-sialidase activity
Specific function:
May function in lysosomal catabolism of sialylated glycoconjugates. Has sialidase activity towards synthetic substrates, such as 2'-(4-methylumbelliferyl)-alpha-D-N-acetylneuraminic acid (4-MU-NANA or 4MU-NeuAc). Has a broad substrate specificity being active on glycoproteins, oligosaccharides and sialylated glycolipids.
Gene Name:
Uniprot ID:
Molecular weight:
Not Available
General function:
Involved in catalytic activity
Specific function:
May be essential for the correct composition of cartilage and bone matrix during development. Has no activity toward steroid sulfates
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Catalyzes the formation of some glycolipid via the addition of N-acetylgalactosamine (GalNAc) in alpha-1,3-linkage to some substrate. Glycolipids probably serve for adherence of some pathogens
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in N-acetylglucosaminylphosphatidylinositol de
Specific function:
Involved in the second step of GPI biosynthesis. De-N-acetylation of N-acetylglucosaminyl-phosphatidylinositol.
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
Uniprot ID:
Molecular weight:
Not Available

Only showing the first 10 proteins. There are 70 proteins in total.