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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2009-02-03 09:40:25 UTC
Update Date2022-09-22 18:34:20 UTC
HMDB IDHMDB0011649
Secondary Accession Numbers
  • HMDB11649
Metabolite Identification
Common NameGlycerophosphoinositol
DescriptionGlycerophosphoinositol (CAS: 16824-65-0), also known as 1-(sn-glycero-3-phospho)-1D-myo-inositol, is produced through deacylation by phospholipase B of the essential phospholipid phosphatidylinositol. Glycerophosphoinositols are ubiquitous phosphoinositide metabolites involved in the control of several cell functions. They exert their actions both intracellularly and by rapidly equilibrating across the plasma membrane. Their transport is mediated by the Glut2 transporter, the human ortholog of GIT1 (PMID: 17141226 ). Glycerophosphoinositol is a substrate for glycerophosphoinositol inositolphosphodiesterase (EC 3.1.4.43) and is involved in the following reaction: 1-(sn-glycero-3-phospho)-1D-myo-inositol + H2O = glycerol + 1D-myo-inositol 1-phosphate. It is also a substrate for glycerophosphoinositol glycerophosphodiesterase (EC 3.1.4.44) which catalyzes the chemical reaction: 1-(sn-glycero-3-phospho)-1D-myo-inositol + H2O = myo-inositol + sn-glycerol 3-phosphate.
Structure
Thumb
Synonyms
ValueSource
3-PhosphoglyceroinositolChEBI
GlyerophosphoinositolChEBI
GroPInsChEBI
sn-Glycero-3-phospho-1-inositolChEBI
1-(sn-Glycero-3-phospho)-1D-myo-inositolKegg
GlycerophosphoinositolHMDB
alpha-Glycerophosphoryl inositolHMDB
alpha-GlycerophosphorylinositolHMDB
α-Glycerophosphoryl inositolHMDB
α-GlycerophosphorylinositolHMDB
Chemical FormulaC9H19O11P
Average Molecular Weight334.2143
Monoisotopic Molecular Weight334.066497962
IUPAC Name[(2R)-2,3-dihydroxypropoxy]({[(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy})phosphinic acid
Traditional Name(2R)-2,3-dihydroxypropoxy([(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy)phosphinic acid
CAS Registry Number129830-95-1
SMILES
OC[C@@H](O)COP(O)(=O)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O
InChI Identifier
InChI=1S/C9H19O11P/c10-1-3(11)2-19-21(17,18)20-9-7(15)5(13)4(12)6(14)8(9)16/h3-16H,1-2H2,(H,17,18)/t3-,4-,5-,6+,7-,8-,9-/m1/s1
InChI KeyBMVUIWJCUQSHLZ-UJGXJMNGSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as glycerophosphoinositols. These are lipids containing a glycerol moiety carrying a phosphoinositol at the 3-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoinositols
Direct ParentGlycerophosphoinositols
Alternative Parents
Substituents
  • Glycerophosphoinositol
  • Inositol phosphate
  • Cyclohexanol
  • Dialkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Cyclitol or derivatives
  • Cyclic alcohol
  • Secondary alcohol
  • Polyol
  • Primary alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
Process
Role
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
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB011624
KNApSAcK IDNot Available
Chemspider ID28184592
KEGG Compound IDC01225
BioCyc IDCPD-541
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID18321
Food Biomarker OntologyNot Available
VMH IDM02911
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Mariggio S, Iurisci C, Sebastia J, Patton-Vogt J, Corda D: Molecular characterization of a glycerophosphoinositol transporter in mammalian cells. FEBS Lett. 2006 Dec 22;580(30):6789-96. Epub 2006 Nov 27. [PubMed:17141226 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
  7. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
  8. Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
  9. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in glycerophosphodiester phosphodiesterase activity
Specific function:
Has glycerophosphoinositol phosphodiesterase activity. Has little or no activity towards glycerophosphocholine. GDE1 activity can be modulated by G-protein signaling pathways (By similarity).
Gene Name:
GDE1
Uniprot ID:
Q9NZC3
Molecular weight:
37718.04
Reactions
Glycerophosphoinositol + Water → myo-Inositol + Glycerol 3-phosphatedetails
General function:
Involved in glycerophosphodiester phosphodiesterase activity
Specific function:
Has glycerophosphoinositol inositolphosphodiesterase activity and specifically hydrolyzes glycerophosphoinositol, with no activity for other substrates such as glycerophosphoinositol 4-phosphate, glycerophosphocholine, glycerophosphoethanolamine, and glycerophosphoserine. Accelerates the program of osteoblast differentiation and growth. May play a role in remodeling of the actin cytoskeleton (By similarity).
Gene Name:
GDPD2
Uniprot ID:
Q9HCC8
Molecular weight:
52185.905
Reactions
Glycerophosphoinositol + Water → Glycerol + myo-Inositol 6-phosphatedetails