Record Information
Version2.0
Creation Date2012-07-30 14:55:27 -0600
Update Date2015-06-03 17:21:13 -0600
Secondary Accession Numbers
  • ECMDB21357
Identification
Name:Sn-Glycero-3-phospho-1-inositol
Description:Sn-glycero-3-phospho-1-inositol is a member of the chemical class known as Inositol Phosphates. These are compounds containing a phosphate group attached to an inositol (or cyclohexanehexol) moiety.
Structure
Thumb
Synonyms:
  • 1-(sn-glycero-3-phospho)-1D-myo-inositol
  • 1-(Sn-glycero-3-Phospho)-1D-myo-inositol
  • 1D-Myo-inositol 1-[(2R)-2,3-dihydroxypropyl hydrogen phosphate]
  • 1D-myo-Inositol 1-[(2R)-2,3-dihydroxypropyl hydrogen phosphoric acid]
  • Sn-glycero-3-Phospho-1-inositol
Chemical Formula:C9H19O11P
Weight:Average: 334.2143
Monoisotopic: 334.066497962
InChI Key:BMVUIWJCUQSHLZ-UJGXJMNGSA-N
InChI: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
CAS number:Not Available
IUPAC Name:[(2R)-2,3-dihydroxypropoxy]({[(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy})phosphinic acid
Traditional IUPAC Name:(2R)-2,3-dihydroxypropoxy[(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxyphosphinic acid
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
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as glycerophosphoinositols. These are lipids containing a glycerol moiety carrying a phosphoinositol at the 3-position.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassGlycerophospholipids
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
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility40.9 mg/mLALOGPS
logP-2.5ALOGPS
logP-4.8ChemAxon
logS-0.91ALOGPS
pKa (Strongest Acidic)1.83ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area197.37 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity63.38 m3·mol-1ChemAxon
Polarizability28.66 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSsplash10-0300-5496000000-84efb8ec050f4c9f17b7View in MoNA
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-0g30-1304039000-ea70d488eb876065d7d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00tr-5729000000-77cf10de08bfe9a0d966View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-9332000000-6c7d50102de3918a31daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06tb-9600000000-165e7d287c38c605bdf0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1139000000-6f6dad972f38a9d35095View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-9583000000-d901449da6faa456e564View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-6eb59ff75ccaecb4ec40View in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID18321
HMDB IDHMDB11649
Pubchem Compound ID6857358
Kegg IDC01225
ChemSpider ID28184592
Wikipedia IDNot Available
BioCyc IDCPD-541
EcoCyc IDCPD-541

Enzymes

General function:
Involved in glycerophosphodiester phosphodiesterase activity
Specific function:
Glycerophosphoryl diester phosphodiesterase hydrolyzes deacylated phospholipids to G3P and the corresponding alcohols
Gene Name:
glpQ
Uniprot ID:
P09394
Molecular weight:
40843
Reactions
A glycerophosphodiester + H(2)O = an alcohol + sn-glycerol 3-phosphate.
General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex UgpABCE involved in sn-glycerol-3-phosphate import. Responsible for energy coupling to the transport system (Probable). Can also transport glycerophosphoryl diesters
Gene Name:
ugpC
Uniprot ID:
P10907
Molecular weight:
39524
Reactions
ATP + H(2)O + glycerol-3-phosphate(Out) = ADP + phosphate + glycerol-3-phosphate(In).
General function:
Involved in glycerophosphodiester phosphodiesterase activity
Specific function:
Glycerophosphoryl diester phosphodiesterase hydrolyzes deacylated phospholipids to G3P and the corresponding alcohols
Gene Name:
ugpQ
Uniprot ID:
P10908
Molecular weight:
27409
Reactions
A glycerophosphodiester + H(2)O = an alcohol + sn-glycerol 3-phosphate.
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for sn-glycerol-3-phosphate; probably responsible for the translocation of the substrate across the membrane
Gene Name:
ugpA
Uniprot ID:
P10905
Molecular weight:
33264
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for sn-glycerol-3-phosphate; probably responsible for the translocation of the substrate across the membrane
Gene Name:
ugpE
Uniprot ID:
P10906
Molecular weight:
31499
General function:
Involved in transporter activity
Specific function:
sn-glycerol-3-phosphate and glycerophosphoryl diester- binding protein interacts with the binding protein-dependent transport system ugpACE
Gene Name:
ugpB
Uniprot ID:
P0AG80
Molecular weight:
48448

Transporters

General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex UgpABCE involved in sn-glycerol-3-phosphate import. Responsible for energy coupling to the transport system (Probable). Can also transport glycerophosphoryl diesters
Gene Name:
ugpC
Uniprot ID:
P10907
Molecular weight:
39524
Reactions
ATP + H(2)O + glycerol-3-phosphate(Out) = ADP + phosphate + glycerol-3-phosphate(In).
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for sn-glycerol-3-phosphate; probably responsible for the translocation of the substrate across the membrane
Gene Name:
ugpA
Uniprot ID:
P10905
Molecular weight:
33264
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for sn-glycerol-3-phosphate; probably responsible for the translocation of the substrate across the membrane
Gene Name:
ugpE
Uniprot ID:
P10906
Molecular weight:
31499
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
sn-glycerol-3-phosphate and glycerophosphoryl diester- binding protein interacts with the binding protein-dependent transport system ugpACE
Gene Name:
ugpB
Uniprot ID:
P0AG80
Molecular weight:
48448
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368