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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2009-01-27 10:53:45 UTC
Update Date2022-11-30 19:04:01 UTC
HMDB IDHMDB0011594
Secondary Accession Numbers
  • HMDB0004871
  • HMDB04871
  • HMDB11594
Metabolite Identification
Common NameLacCer(d18:1/22:0)
DescriptionLacCer(d18:1/22:0) is a lactosylceramide or LacCer. Lactosylceramides are the most important and abundant of the diosylceramides. Lactosylceramides (LacCer) were originally called 'cytolipin H'. It is found in small amounts only in most animal tissues, but it has a number of significant biological functions and it is of great importance as the biosynthetic precursor of most of the neutral oligoglycosylceramides, sulfatides and gangliosides. In animal tissues, biosynthesis of lactosylceramide involves addition of the second monosaccharides unit (galactose) as its nucleotide derivative to monoglucosylceramide, catalysed by a specific beta-1,4-galactosyltransferase on the lumenal side of the Golgi apparatus. The glucosylceramide precursor must first cross from the cytosolic side of the membrane, possibly via the action of a flippase. The lactosylceramide produced can be further glycosylated or transferred to the plasma membrane. Lactosylceramide may assist in stabilizing the plasma membrane and activating receptor molecules in the special micro-domains or rafts, as with the cerebrosides. It may also have its own specialized function in the immunological system in that it is known to bind to specific bacteria. In addition, it is believed that a number of pro-inflammatory factors activate lactosylceramide synthase to generate lactosylceramide, which in turn activates "oxygen-sensitive" signalling pathways that affect such cellular processes as proliferation, adhesion, migration and angiogenesis. Dysfunctions in these pathways can affect several diseases of the cardiovascular system, cancer and inflammatory states, so lactosylceramide metabolism is a potential target for new therapeutic treatments. beta-D-Galactosyl-1,4-beta-D-glucosylceramide is the second to last step in the synthesis of N-Acylsphingosine and is converted. from Glucosylceramide via the enzyme beta-1,4-galactosyltransferase 6(EC:2.4.1.-). It can be converted to Glucosylceramide via the enzyme beta-galactosidase (EC:3.2.1.23).
Structure
Data?1592001378
Synonyms
ValueSource
β-LacCerChEBI
CDHHMDB
LacCer d18:1/22:0HMDB
LacCer(d18:1/22:0)HMDB
LactosylceramideHMDB
Lactosylceramide (d18:1,C22:0)HMDB
Lactosylceramide (d18:1/22:0)HMDB
Lactosylceramide(d18:1/22:0)HMDB
N-(Docosanoyl)-1-beta-lactosyl-4-sphingenineHMDB
N-(Docosanoyl)-1-beta-lactosyl-D-erythro-sphingosineHMDB
N-(Docosanoyl)-1-beta-lactosyl-D-sphingosineHMDB
N-(Docosanoyl)-1-beta-lactosyl-erythro-4-sphingenineHMDB
N-(Docosanoyl)-1-beta-lactosyl-sphing-4-enineHMDB
N-(Docosanoyl)-1-beta-lactosyl-sphingenineHMDB
N-(Docosanoyl)-1-beta-lactosyl-sphingosineHMDB
N-(Docosanoyl)-1-β-lactosyl-4-sphingenineHMDB
N-(Docosanoyl)-1-β-lactosyl-D-erythro-sphingosineHMDB
N-(Docosanoyl)-1-β-lactosyl-D-sphingosineHMDB
N-(Docosanoyl)-1-β-lactosyl-erythro-4-sphingenineHMDB
N-(Docosanoyl)-1-β-lactosyl-sphing-4-enineHMDB
N-(Docosanoyl)-1-β-lactosyl-sphingenineHMDB
N-(Docosanoyl)-1-β-lactosyl-sphingosineHMDB
N-[(2S,3R,4E)-1-{[4-O-(b-D-galactopyranosyl)-b-D-glucopyranosyl]oxy}-3-hydroxyoctadec-4-en-2-yl]docosanamideHMDB
N-[(2S,3R,4E)-1-{[4-O-(beta-D-galactopyranosyl)-beta-D-glucopyranosyl]oxy}-3-hydroxyoctadec-4-en-2-yl]docosanamideHMDB
N-[(2S,3R,4E)-1-{[4-O-(β-D-galactopyranosyl)-β-D-glucopyranosyl]oxy}-3-hydroxyoctadec-4-en-2-yl]docosanamideHMDB
b-D-Galactosyl-(1->4)-b-D-glucosyl-N-(docosanoyl)sphingosineHMDB
b-LacCerHMDB
b-Lactosyl-N-(docosanoyl)sphingosineHMDB
b-LactosylceramideHMDB
beta-D-Galactosyl-(1->4)-beta-D-glucosyl-N-(docosanoyl)sphingosineHMDB
beta-LacCerHMDB
beta-Lactosyl-N-(docosanoyl)sphingosineHMDB
beta-LactosylceramideHMDB
β-D-Galactosyl-(1->4)-β-D-glucosyl-N-(docosanoyl)sphingosineHMDB
β-Lactosyl-N-(docosanoyl)sphingosineHMDB
β-LactosylceramideHMDB
Chemical FormulaC52H99NO13
Average Molecular Weight946.3414
Monoisotopic Molecular Weight945.711642259
IUPAC NameN-[(2S,3R,4E)-1-{[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]docosanamide
Traditional NameCDH
CAS Registry Number111142-68-8
SMILES
[H][C@@](CO[C@@H]1O[C@H](CO)[C@@H](O[C@]2([H])O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O)(NC(=O)CCCCCCCCCCCCCCCCCCCCC)[C@H](O)\C=C\CCCCCCCCCCCCC
InChI Identifier
InChI=1S/C52H99NO13/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-26-28-30-32-34-36-44(57)53-40(41(56)35-33-31-29-27-25-23-16-14-12-10-8-6-4-2)39-63-51-49(62)47(60)50(43(38-55)65-51)66-52-48(61)46(59)45(58)42(37-54)64-52/h33,35,40-43,45-52,54-56,58-62H,3-32,34,36-39H2,1-2H3,(H,53,57)/b35-33+/t40-,41+,42+,43+,45-,46-,47+,48+,49+,50+,51+,52-/m0/s1
InChI KeyQYWVASPEUXEHSY-NNRNTGNWSA-N
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
ClassSphingolipids
Sub ClassGlycosphingolipids
Direct ParentGlycosyl-N-acylsphingosines
Alternative Parents
Substituents
  • Glycosyl-n-acylsphingosine
  • Fatty acyl glycoside
  • Fatty acyl glycoside of mono- or disaccharide
  • Alkyl glycoside
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Fatty amide
  • N-acyl-amine
  • Oxane
  • Fatty acyl
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Organoheterocyclic compound
  • Polyol
  • Oxacycle
  • Carboxylic acid derivative
  • Acetal
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Organonitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Primary alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
  • beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-N-acylsphingosine (CHEBI:62109 )
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0032 g/LALOGPS
logP7.05ALOGPS
logP9.99ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)11.92ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area227.86 ŲChemAxon
Rotatable Bond Count42ChemAxon
Refractivity258.21 m³·mol⁻¹ChemAxon
Polarizability116.28 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+310.03430932474
DeepCCS[M-H]-308.3130932474
DeepCCS[M-2H]-342.35230932474
DeepCCS[M+Na]+316.36330932474
AllCCS[M+H]+313.732859911
AllCCS[M+H-H2O]+313.932859911
AllCCS[M+NH4]+313.532859911
AllCCS[M+Na]+313.432859911
AllCCS[M-H]-324.532859911
AllCCS[M+Na-2H]-329.132859911
AllCCS[M+HCOO]-334.232859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LacCer(d18:1/22:0) 10V, Positive-QTOFsplash10-00or-0111004809-3d472fd9629198430f932017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LacCer(d18:1/22:0) 20V, Positive-QTOFsplash10-0gb9-0222116912-c8f59a495e4350a4c0cc2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LacCer(d18:1/22:0) 40V, Positive-QTOFsplash10-03dj-1774914752-d7bcdacf6bb987f798e62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LacCer(d18:1/22:0) 10V, Negative-QTOFsplash10-002f-0312004419-e066b9667abc0b46f46f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LacCer(d18:1/22:0) 20V, Negative-QTOFsplash10-03fr-3504043903-eef9aa9b4e5171faba552017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LacCer(d18:1/22:0) 40V, Negative-QTOFsplash10-0059-4902111200-70ea0c13127e2b5893e52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LacCer(d18:1/22:0) 10V, Positive-QTOFsplash10-0feb-2500018905-a33e29571335a1877ac82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LacCer(d18:1/22:0) 20V, Positive-QTOFsplash10-0uxs-3900013301-bdf42a957cb2cb56277c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LacCer(d18:1/22:0) 40V, Positive-QTOFsplash10-01vx-4910021100-8244f0288c2d525ca6002021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LacCer(d18:1/22:0) 10V, Negative-QTOFsplash10-0006-0101000109-77350ecf3f81c1ee5cb52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LacCer(d18:1/22:0) 20V, Negative-QTOFsplash10-06r6-7593003234-65c1a3db4ccd6c3d034e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LacCer(d18:1/22:0) 40V, Negative-QTOFsplash10-06z9-3219020000-0d5f3fd1908f635e38962021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedNewborn (0-30 days old)Not Specified
Premature neonates
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028307
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52921641
PDB IDNot Available
ChEBI ID62109
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  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. [PubMed:16902246 ]
  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. [PubMed:17374880 ]
  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. [PubMed:20044567 ]
  5. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
  6. 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 ]
  7. Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
  8. 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 66 proteins in total.

Enzymes

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:
GALC
Uniprot ID:
P54803
Molecular weight:
77062.86
General function:
Involved in exo-alpha-sialidase activity
Specific function:
Catalyzes the removal of sialic acid (N-acetylneuramic acid) moities from glycoproteins and glycolipids. To be active, it is strictly dependent on its presence in the multienzyme complex. Appears to have a preference for alpha 2-3 and alpha 2-6 sialyl linkage.
Gene Name:
NEU1
Uniprot ID:
Q99519
Molecular weight:
Not Available
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:
GBGT1
Uniprot ID:
Q8N5D6
Molecular weight:
40126.9
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:
PIGL
Uniprot ID:
Q9Y2B2
Molecular weight:
28530.965
General function:
Involved in sialyltransferase activity
Specific function:
Catalyzes the formation of ganglioside GM3 (alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1, 4-beta-D-glucosylceramide).
Gene Name:
ST3GAL5
Uniprot ID:
Q9UNP4
Molecular weight:
45584.69
General function:
Involved in hydrolase activity
Specific function:
Converts sphingomyelin to ceramide. Also has phospholipase C activities toward 1,2-diacylglycerolphosphocholine and 1,2-diacylglycerolphosphoglycerol. Isoform 2 and isoform 3 have lost catalytic activity.
Gene Name:
SMPD1
Uniprot ID:
P17405
Molecular weight:
69935.53
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Catalyzes the first glycosylation step in glycosphingolipid biosynthesis, the transfer of glucose to ceramide. May also serve as a "flippase".
Gene Name:
UGCG
Uniprot ID:
Q16739
Molecular weight:
44853.255
General function:
Involved in beta-N-acetylhexosaminidase activity
Specific function:
Responsible for the degradation of GM2 gangliosides, and a variety of other molecules containing terminal N-acetyl hexosamines, in the brain and other tissues.
Gene Name:
HEXB
Uniprot ID:
P07686
Molecular weight:
Not Available
General function:
Involved in beta-N-acetylhexosaminidase activity
Specific function:
Responsible for the degradation of GM2 gangliosides, and a variety of other molecules containing terminal N-acetyl hexosamines, in the brain and other tissues. The form B is active against certain oligosaccharides. The form S has no measurable activity.
Gene Name:
HEXA
Uniprot ID:
P06865
Molecular weight:
Not Available
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Involved in the biosynthesis of gangliosides GM2, GD2 and GA2.
Gene Name:
B4GALNT1
Uniprot ID:
Q00973
Molecular weight:
58881.78

Only showing the first 10 proteins. There are 66 proteins in total.