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inositol-P-ceramide C (C26) (YMDB00712)

Identification
YMDB IDYMDB00712
Nameinositol-P-ceramide C (C26)
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Descriptioninositol-P-ceramide C (C26), also known as ins-1-pcer(t18:0/2-OH-26:0) or ipc t18:0/26:0(2oh), 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. inositol-P-ceramide C (C26) is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • inositol-P-ceramide
  • inositol-P-ceramide C (C26)
  • InsPCer
  • InsPCer-3 (C26)
  • InsPCer-C (C26)
  • IPC
  • IPC-3 (C26)
  • IPC-C (C26)
  • Inositol-1-phospho-N-(2-hydroxyhexacosanoyl)phytosphingosine
  • Ins-1-pcer(t18:0/2-OH-26:0)
  • IPC t18:0/26:0(2oh)
CAS numberNot Available
WeightAverage: 954.3017
Monoisotopic: 953.693228803
InChI KeyPMXMKGYRVPAIJJ-XBBDMFFLSA-N
InChIInChI=1S/C50H100NO13P/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-25-26-28-30-32-34-36-38-42(53)50(60)51-40(39-63-65(61,62)64-49-47(58)45(56)44(55)46(57)48(49)59)43(54)41(52)37-35-33-31-29-27-16-14-12-10-8-6-4-2/h40-49,52-59H,3-39H2,1-2H3,(H,51,60)(H,61,62)/t40-,41+,42?,43-,44-,45-,46+,47+,48+,49-/m0/s1
IUPAC Name{[(2S,3S,4R)-3,4-dihydroxy-2-(2-hydroxyhexacosanamido)octadecyl]oxy}({[(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy})phosphinic acid
Traditional IUPAC Name[(2S,3S,4R)-3,4-dihydroxy-2-(2-hydroxyhexacosanamido)octadecyl]oxy[(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxyphosphinic acid
Chemical FormulaC50H100NO13P
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]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
  • Phosphoethanolamine
  • Dialkyl phosphate
  • Cyclohexanol
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • N-acyl-amine
  • Monosaccharide
  • Fatty amide
  • Cyclitol or derivatives
  • Cyclic alcohol
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Polyol
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00086 g/LALOGPS
logP7.12ALOGPS
logP10.56ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)1.84ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area246.7 ŲChemAxon
Rotatable Bond Count45ChemAxon
Refractivity256.55 m³·mol⁻¹ChemAxon
Polarizability116.88 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Golgi
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG Reactions
1D-myo-inositol 1-phosphate + N-(24-hydroxytetracosanoyl)sphinganine ↔ inositol-P-ceramide C (C26)
1D-myo-inositol 1-phosphate + N-(26-hydroxyhexacosanoyl)sphinganine ↔ inositol-P-ceramide C (C26)
N-(24-Hydroxytetracosanoyl)phytosphingosine + 1D-myo-inositol 1-phosphate ↔ inositol-P-ceramide C (C26)
N-(26-Hydroxyhexacosanyl)phytosphingosine + 1D-myo-inositol 1-phosphate ↔ inositol-P-ceramide C (C26)
inositol-P-ceramide C (C26) + Guanosine diphosphate mannose ↔ mannosylinositol phosphorylceramide
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052f-0121059103-979adb94344549e413ccJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-0135819000-194c4e5482e8b7a75b5aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-1935211000-a5a58c85f84534d011ddJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pb9-0094011208-5ce036adaececea4a95cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6r-4195002002-f5be503ee3ee4233e1d8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9011000000-77c5751bc3e95678fa38JSpectraViewer
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
  • Dickson, R. C., Nagiec, E. E., Wells, G. B., Nagiec, M. M., Lester, R. L. (1997). "Synthesis of mannose-(inositol-P)2-ceramide, the major sphingolipid in Saccharomyces cerevisiae, requires the IPT1 (YDR072c) gene." J Biol Chem 272:29620-29625.9368028
  • Nagiec, M. M., Nagiec, E. E., Baltisberger, J. A., Wells, G. B., Lester, R. L., Dickson, R. C. (1997). "Sphingolipid synthesis as a target for antifungal drugs. Complementation of the inositol phosphorylceramide synthase defect in a mutant strain of Saccharomyces cerevisiae by the AUR1 gene." J Biol Chem 272:9809-9817.9092515
  • Dickson, R. C., Sumanasekera, C., Lester, R. L. (2006). "Functions and metabolism of sphingolipids in Saccharomyces cerevisiae." Prog Lipid Res 45:447-465.16730802
  • Funato, K., Vallee, B., Riezman, H. (2002). "Biosynthesis and trafficking of sphingolipids in the yeast Saccharomyces cerevisiae." Biochemistry 41:15105-15114.12484746
  • Reggiori, F., Conzelmann, A. (1998). "Biosynthesis of inositol phosphoceramides and remodeling of glycosylphosphatidylinositol anchors in Saccharomyces cerevisiae are mediated by different enzymes." J Biol Chem 273:30550-30559.9804825
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID53004
HMDB IDNot Available
Pubchem Compound ID44224058
Kegg IDNot Available
ChemSpider ID24765754
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Mannosyl phosphorylinositol ceramide synthase regulatory protein CSG2
General function:
Involved in enzyme regulator activity
Specific function:
Required for calcium regulation. May regulate calcium accumulation by a non-vacuole organelle. Also regulates the activity of CSH1 and SUR1 during mannosyl phosphorylinositol ceramide synthesis
Gene Name:
CSG2
Uniprot ID:
P35206
Molecular weight:
45441.60156
Reactions
Protein Details
2. Inositol phosphorylceramide synthase
General function:
Involved in catalytic activity
Specific function:
Catalyzes the addition of a phosphorylinositol group onto ceramide to form inositol phosphorylceramide, an essential step in sphingolipid biosynthesis
Gene Name:
AUR1
Uniprot ID:
P36107
Molecular weight:
45192.80078
Reactions