inositol phosphomannosylinositol phosphoceramide (YMDB00713)

Identification
YMDB IDYMDB00713
Nameinositol phosphomannosylinositol phosphoceramide
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionInositol phosphomannosylinositol phosphoceramide is an intermediate in the sphingolipid metabolism pathway. Sphingolipids are essential components of the plasma membrane in all eukaryotic cells. S. cerevisiae cells make three complex sphingolipids: inositol-phosphoceramide (IPC), mannose-inositol-phosphoceramide (MIPC), and mannosyl-diinositol-phosphorylceramide (M(IP)2C). [Biocyc SPHINGOLIPID-SYN-PWY]
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • Mannose-(inositol phosphate)2-ceramide
  • MIP2C
CAS numberNot Available
WeightAverage: 1358.5628
Monoisotopic: 1357.765206073
InChI KeyLLRAWGAIAQKMSU-DBQPHHGNSA-N
InChIInChI=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)49(71)50(72)58(56(60)78)86-62-55(77)54(76)57(44(39-64)85-62)87-91(82,83)89-59-51(73)47(69)46(68)48(70)52(59)74/h41-60,62,64-78H,3-40H2,1-2H3,(H,63,79)(H,80,81)(H,82,83)/t41-,42+,43?,44+,45-,46-,47-,48+,49-,50-,51+,52+,53+,54+,55-,56+,57+,58+,59-,60-,62-/m0/s1
IUPAC Name{[(2S,3S,4R)-3,4-dihydroxy-2-(2-hydroxyhexacosanamido)octadecyl]oxy}({[(1S,2R,3R,4S,5S,6R)-3-{[(2S,3S,4R,5S,6R)-3,4-dihydroxy-5-{[hydroxy({[(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy})phosphoryl]oxy}-6-(hydroxymethyl)oxan-2-yl]oxy}-2,4,5,6-tetrahydroxycyclohexyl]oxy})phosphinic acid
Traditional IUPAC Name[(2S,3S,4R)-3,4-dihydroxy-2-(2-hydroxyhexacosanamido)octadecyl]oxy[(1S,2R,3R,4S,5S,6R)-3-{[(2S,3S,4R,5S,6R)-3,4-dihydroxy-5-({hydroxy[(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxyphosphoryl}oxy)-6-(hydroxymethyl)oxan-2-yl]oxy}-2,4,5,6-tetrahydroxycyclohexyl]oxyphosphinic acid
Chemical FormulaC62H121NO26P2
SMILESCCCCCCCCCCCCCCCCCCCCCCCCC(O)C(=O)N[C@@H](COP(O)(=O)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O[C@@H]2O[C@H](CO)[C@@H](OP(O)(=O)O[C@H]3[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@H]3O)[C@H](O)[C@@H]2O)[C@H]1O)[C@H](O)[C@H](O)CCCCCCCCCCCCCC
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
  • Hexose phosphate
  • Fatty acyl glycoside of mono- or disaccharide
  • Fatty acyl glycoside
  • Hexose monosaccharide
  • Alkyl glycoside
  • O-glycosyl compound
  • Glycosyl compound
  • Monosaccharide phosphate
  • Phosphoethanolamine
  • Dialkyl phosphate
  • Cyclohexanol
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • N-acyl-amine
  • Monosaccharide
  • Fatty amide
  • Cyclitol or derivatives
  • Cyclic alcohol
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid derivative
  • Acetal
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.046 g/LALOGPS
logP3.87ALOGPS
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
Polarizability151.5 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Golgi
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG Reactions
mannosylinositol phosphorylceramide + 1D-myo-inositol 1-phosphate ↔ inositol phosphomannosylinositol phosphoceramide
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0225019107-db21634e68cbbbaa2db8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000f-0112309002-e026ed053909067695d8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0nmm-1925334003-345f3f8a8e15287055b2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a71-0039002102-42fe3696a108151215daJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004s-5159204003-f150f1d3bcff43ff265eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-7192400102-fd052c9b120578b450e2JSpectraViewer
MSMass Spectrum (Electron Ionization)Not AvailableJSpectraViewer
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Albuquerque, C. P., Smolka, M. B., Payne, S. H., Bafna, V., Eng, J., Zhou, H. (2008). "A multidimensional chromatography technology for in-depth phosphoproteome analysis." Mol Cell Proteomics 7:1389-1396.18407956
  • Smolka, M. B., Albuquerque, C. P., Chen, S. H., Zhou, H. (2007). "Proteome-wide identification of in vivo targets of DNA damage checkpoint kinases." Proc Natl Acad Sci U S A 104:10364-10369.17563356
  • Funato, K., Vallee, B., Riezman, H. (2002). "Biosynthesis and trafficking of sphingolipids in the yeast Saccharomyces cerevisiae." Biochemistry 41:15105-15114.12484746
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID53005
HMDB IDNot Available
Pubchem Compound IDNot Available
Kegg IDNot Available
ChemSpider ID23107105
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Inositolphosphotransferase 1
General function:
Involved in catalytic activity
Specific function:
Catalyzes the addition of a phosphorylinositol group onto mannosyl phosphorylinositol ceramide to form mannosyl diphosphorylinositol ceramide
Gene Name:
IPT1
Uniprot ID:
P38954
Molecular weight:
60872.69922
Reactions