Mannosyl-inositol-phosphorylceramide (CHEM040741)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 00:30:18 UTC
Update Date2016-11-09 01:22:19 UTC
Accession NumberCHEM040741
Identification
Common NameMannosyl-inositol-phosphorylceramide
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
MIPCHMDB
N-[3,4-Dihydroxy-1-({hydroxy[(2,3,5,6-tetrahydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexyl)oxy]phosphoryl}oxy)octadecan-2-yl]-2-hydroxyhexacosanimidateGenerator
Chemical FormulaC56H110NO18P
Average Molecular Mass1116.442 g/mol
Monoisotopic Mass1115.746 g/mol
CAS Registry NumberNot Available
IUPAC Name{[3,4-dihydroxy-2-(2-hydroxyhexacosanamido)octadecyl]oxy}[(2,3,5,6-tetrahydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexyl)oxy]phosphinic acid
Traditional Name[3,4-dihydroxy-2-(2-hydroxyhexacosanamido)octadecyl]oxy(2,3,5,6-tetrahydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexyl)oxyphosphinic acid
SMILESCCCCCCCCCCCCCCCCCCCCCCCCC(O)C(=O)NC(COP(O)(=O)OC1C(O)C(O)C(OC2OC(CO)C(O)C(O)C2O)C(O)C1O)C(O)C(O)CCCCCCCCCCCCCC
InChI IdentifierInChI=1S/C56H110NO18P/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-25-26-28-30-32-34-36-38-43(60)55(69)57-41(45(61)42(59)37-35-33-31-29-27-16-14-12-10-8-6-4-2)40-72-76(70,71)75-54-50(66)48(64)53(49(65)51(54)67)74-56-52(68)47(63)46(62)44(39-58)73-56/h41-54,56,58-68H,3-40H2,1-2H3,(H,57,69)(H,70,71)
InChI KeyZKFACHLEPWMTPW-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phosphosphingolipids. These are sphingolipids with a structure based on a sphingoid base that is attached to a phosphate head group. They differ from phosphonospingolipids which have a phosphonate head group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSphingolipids
Sub ClassPhosphosphingolipids
Direct ParentPhosphosphingolipids
Alternative Parents
Substituents
  • Sphingoid-1-phosphate or derivatives
  • Inositol phosphate
  • Fatty acyl glycoside
  • Fatty acyl glycoside of mono- or disaccharide
  • Alkyl glycoside
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Monosaccharide phosphate
  • Phosphoethanolamine
  • Cyclohexanol
  • Dialkyl phosphate
  • Cyclitol or derivatives
  • Fatty amide
  • Fatty acyl
  • Alkyl phosphate
  • Monosaccharide
  • N-acyl-amine
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Cyclic alcohol
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Polyol
  • Carboxylic acid derivative
  • Oxacycle
  • Acetal
  • Organoheterocyclic compound
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Primary alcohol
  • Alcohol
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic 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 Solubility0.0035 g/LALOGPS
logP5.83ALOGPS
logP8.79ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)1.84ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area325.85 ŲChemAxon
Rotatable Bond Count48ChemAxon
Refractivity288.96 m³·mol⁻¹ChemAxon
Polarizability132.43 ųChemAxon
Number of Rings2ChemAxon
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, Negativesplash10-03di-1900000001-8bc77ebed061f49fa60fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-9801100203-01178bd97d0ee804b678Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00g3-9040200012-4a9b7465f5d2f65de19eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-8300004901-44b4b8733dc14cfbb72fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9702013418-8394e4348d76e61255a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9202000000-38219942978be63df0dfSpectrum
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 IDHMDB0012257
FooDB IDFDB028896
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDMIPC
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID24765756
ChEBI IDNot Available
PubChem Compound ID25246093
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Hechtberger P, Daum G: Intracellular transport of inositol-containing sphingolipids in the yeast, Saccharomyces cerevisiae. FEBS Lett. 1995 Jun 26;367(2):201-4.
2. Beeler TJ, Fu D, Rivera J, Monaghan E, Gable K, Dunn TM: SUR1 (CSG1/BCL21), a gene necessary for growth of Saccharomyces cerevisiae in the presence of high Ca2+ concentrations at 37 degrees C, is required for mannosylation of inositolphosphorylceramide. Mol Gen Genet. 1997 Aug;255(6):570-9.
3. Abeijon C, Yanagisawa K, Mandon EC, Hausler A, Moremen K, Hirschberg CB, Robbins PW: Guanosine diphosphatase is required for protein and sphingolipid glycosylation in the Golgi lumen of Saccharomyces cerevisiae. J Cell Biol. 1993 Jul;122(2):307-23.
4. Hechtberger P, Zinser E, Saf R, Hummel K, Paltauf F, Daum G: Characterization, quantification and subcellular localization of inositol-containing sphingolipids of the yeast, Saccharomyces cerevisiae. Eur J Biochem. 1994 Oct 15;225(2):641-9.
5. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78.
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.
7. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
8. 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.
9. 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.
10. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
11. Phospholipids Handbook
12. The lipid handbook with CD-ROM