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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:21:51 UTC
Update Date2021-09-16 15:29:06 UTC
HMDB IDHMDB0012256
Secondary Accession Numbers
  • HMDB12256
Metabolite Identification
Common NameMannosyl-diinositol-phosphorylceramide
DescriptionMannosyl-diinositol-phosphorylceramide, also known as mannose-(inositol phosphate)2-ceramide or MIP2C, 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. Mannosyl-diinositol-phosphorylceramide is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1582753034
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 Weight1358.5628
Monoisotopic Molecular Weight1357.765206073
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
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCCCCCCCCC(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 Identifier
InChI=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
Ontology
Disposition

Biological location

Source

Route of exposure

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 Solubility0.041 g/LALOGPS
logP10(3.9) g/LALOGPS
logP10(5.78) g/LChemAxon
logS10(-4.5) g/LALOGPS
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mannosyl-diinositol-phosphorylceramide 10V, Negative-QTOFsplash10-0a4i-0019000001-e51571852d6ce59ac01d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mannosyl-diinositol-phosphorylceramide 20V, Negative-QTOFsplash10-0pbi-2078412009-5ad70623ae2c53971ac82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mannosyl-diinositol-phosphorylceramide 40V, Negative-QTOFsplash10-004r-9060100002-26f44cf3dea0eca0095f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mannosyl-diinositol-phosphorylceramide 10V, Positive-QTOFsplash10-0006-3627002901-55857243da7743279efa2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mannosyl-diinositol-phosphorylceramide 20V, Positive-QTOFsplash10-03di-1292001102-6f23f4a14343cd953ab92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mannosyl-diinositol-phosphorylceramide 40V, Positive-QTOFsplash10-0006-9452000000-2173e885b4cee1f787d52021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028895
KNApSAcK IDNot Available
Chemspider ID24765755
KEGG Compound IDNot Available
BioCyc IDMIP2C
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound25244686
PDB IDNot Available
ChEBI IDNot Available
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. Hechtberger P, Daum G: Intracellular transport of inositol-containing sphingolipids in the yeast, Saccharomyces cerevisiae. FEBS Lett. 1995 Jun 26;367(2):201-4. [PubMed:7796921 ]
  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. [PubMed:16527275 ]
  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. [PubMed:9368039 ]
  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. [PubMed:7957179 ]
  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. [PubMed:17240982 ]
  6. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
  11. 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 ]
  12. Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
  13. 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 59 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 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 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 phosphatidylinositol N-acetylglucosaminyltransferase activity
Specific function:
Part of the complex catalyzing the transfer of N-acetylglucosamine from UDP-N-acetylglucosamine to phosphatidylinositol, the first step of GPI biosynthesis.
Gene Name:
PIGQ
Uniprot ID:
Q9BRB3
Molecular weight:
65343.25
General function:
Involved in biosynthetic process
Specific function:
Necessary for the synthesis of N-acetylglucosaminyl-phosphatidylinositol, the very early intermediate in GPI-anchor biosynthesis.
Gene Name:
PIGA
Uniprot ID:
P37287
Molecular weight:
54126.065
General function:
Involved in phosphatidylinositol N-acetylglucosaminyltr
Specific function:
Part of the complex catalyzing the transfer of N-acetylglucosamine from UDP-N-acetylglucosamine to phosphatidylinositol, the first step of GPI biosynthesis.
Gene Name:
PIGH
Uniprot ID:
Q14442
Molecular weight:
21080.415
General function:
Involved in phosphatidylinositol N-acetylglucosaminyltr
Specific function:
Part of the complex catalyzing the transfer of N-acetylglucosamine from UDP-N-acetylglucosamine to phosphatidylinositol, the first step of GPI biosynthesis.
Gene Name:
PIGP
Uniprot ID:
P57054
Molecular weight:
18089.055
General function:
Involved in phosphatidylinositol N-acetylglucosaminyltransferase activity
Specific function:
Part of the complex catalyzing the transfer of N-acetylglucosamine from UDP-N-acetylglucosamine to phosphatidylinositol, the first step of GPI biosynthesis.
Gene Name:
PIGC
Uniprot ID:
Q92535
Molecular weight:
33582.18

Only showing the first 10 proteins. There are 59 proteins in total.