Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:51:53 UTC
Update Date2024-04-30 19:33:24 UTC
Metabolite IDMMDBc0000648
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
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
Molecular FormulaC9H19O11P
Average Mass334.2143
Monoisotopic Mass334.066497962
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 NumberNot Available
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