Mannosyl-diinositol-phosphorylceramide (CHEM040740)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 00:30:17 UTC
Update Date2016-11-09 01:22:19 UTC
Accession NumberCHEM040740
Identification
Common NameMannosyl-diinositol-phosphorylceramide
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Mannose-(inositol phosphate)2-ceramideHMDB
MIP2cHMDB
N-[1-({[(4-{[3,4-dihydroxy-5-({hydroxy[(2,3,4,5,6-pentahydroxycyclohexyl)oxy]phosphoryl}oxy)-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3,5,6-tetrahydroxycyclohexyl)oxy](hydroxy)phosphoryl}oxy)-3,4-dihydroxyoctadecan-2-yl]-2-hydroxyhexacosanimidateGenerator
Chemical FormulaC62H121NO26P2
Average Molecular Mass1358.563 g/mol
Monoisotopic Mass1357.765 g/mol
CAS Registry NumberNot Available
IUPAC Name{[3,4-dihydroxy-2-(2-hydroxyhexacosanamido)octadecyl]oxy}[(4-{[3,4-dihydroxy-5-({hydroxy[(2,3,4,5,6-pentahydroxycyclohexyl)oxy]phosphoryl}oxy)-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3,5,6-tetrahydroxycyclohexyl)oxy]phosphinic acid
Traditional Name[3,4-dihydroxy-2-(2-hydroxyhexacosanamido)octadecyl]oxy({4-[(3,4-dihydroxy-5-{[hydroxy(2,3,4,5,6-pentahydroxycyclohexyl)oxyphosphoryl]oxy}-6-(hydroxymethyl)oxan-2-yl)oxy]-2,3,5,6-tetrahydroxycyclohexyl}oxy)phosphinic acid
SMILESCCCCCCCCCCCCCCCCCCCCCCCCC(O)C(=O)NC(COP(O)(=O)OC1C(O)C(O)C(OC2OC(CO)C(OP(O)(=O)OC3C(O)C(O)C(O)C(O)C3O)C(O)C2O)C(O)C1O)C(O)C(O)CCCCCCCCCCCCCC
InChI IdentifierInChI=1S/C62H121NO26P2/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(66)61(79)63-41(45(67)42(65)37-35-33-31-29-27-16-14-12-10-8-6-4-2)40-84-90(80,81)88-60-53(75)51(73)58(52(74)54(60)76)86-62-56(78)55(77)57(44(39-64)85-62)87-91(82,83)89-59-49(71)47(69)46(68)48(70)50(59)72/h41-60,62,64-78H,3-40H2,1-2H3,(H,63,79)(H,80,81)(H,82,83)
InChI KeyCPMOABJYWXUZCM-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
  • Hexose phosphate
  • 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 acyl
  • Fatty amide
  • Alkyl phosphate
  • Monosaccharide
  • N-acyl-amine
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Polyol
  • Carboxylic acid derivative
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Alcohol
  • Organic oxide
  • Organic nitrogen compound
  • Primary alcohol
  • 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 Solubility0.041 g/LALOGPS
logP3.9ALOGPS
logP5.78ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)1.51ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count22ChemAxon
Hydrogen Donor Count18ChemAxon
Polar Surface Area462.53 ŲChemAxon
Rotatable Bond Count52ChemAxon
Refractivity331.83 m³·mol⁻¹ChemAxon
Polarizability151.88 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0019000001-e51571852d6ce59ac01dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pbi-2078412009-5ad70623ae2c53971ac8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004r-9060100002-26f44cf3dea0eca0095fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-3627002901-55857243da7743279efaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1292001102-6f23f4a14343cd953ab9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9452000000-2173e885b4cee1f787d5Spectrum
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 IDHMDB0012256
FooDB IDFDB028895
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDMIP2C
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID24765755
ChEBI IDNot Available
PubChem Compound ID25244686
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. Aerts AM, Francois IE, Bammens L, Cammue BP, Smets B, Winderickx J, Accardo S, De Vos DE, Thevissen K: Level of M(IP)2C sphingolipid affects plant defensin sensitivity, oxidative stress resistance and chronological life-span in yeast. FEBS Lett. 2006 Mar 20;580(7):1903-7. Epub 2006 Mar 3.
3. Haak D, Gable K, Beeler T, Dunn T: Hydroxylation of Saccharomyces cerevisiae ceramides requires Sur2p and Scs7p. J Biol Chem. 1997 Nov 21;272(47):29704-10.
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. Lobo DS, Pereira IB, Fragel-Madeira L, Medeiros LN, Cabral LM, Faria J, Bellio M, Campos RC, Linden R, Kurtenbach E: Antifungal Pisum sativum defensin 1 interacts with Neurospora crassa cyclin F related to the cell cycle. Biochemistry. 2007 Jan 30;46(4):987-96.
6. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78.
7. Ghosh S, Strum JC, Bell RM: Lipid biochemistry: functions of glycerolipids and sphingolipids in cellular signaling. FASEB J. 1997 Jan;11(1):45-50.
8. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
9. 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.
10. 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.
11. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
12. Phospholipids Handbook
13. The lipid handbook with CD-ROM