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Record Information

Version

2.0

Creation Date

2012-07-30 14:55:27 -0600

Update Date

2015-06-03 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

MOL SDF PDB SMILES InChI

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]oxy)phosphinic 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

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoinositols

Direct Parent

Glycerophosphoinositols

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 Framework

Aliphatic homomonocyclic compounds

External Descriptors

sn-glycerol 3-phosphates (CHEBI:18321 )
myo-inositol monophosphate derivative (CHEBI:18321 )

Physical Properties

State:

Not Available

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	40.9 g/L	ALOGPS
logP	-2.5	ALOGPS
logP	-4.8	ChemAxon
logS	-0.91	ALOGPS
pKa (Strongest Acidic)	1.83	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	197.37 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	63.38 m³·mol⁻¹	ChemAxon
Polarizability	28.8 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

Adenosine triphosphate + Water + Sn-Glycero-3-phospho-1-inositol > ADP + Sn-Glycero-3-phospho-1-inositol + Hydrogen ion + Phosphate
Adenosine triphosphate + Water + Sn-Glycero-3-phospho-1-inositol > ADP + Sn-Glycero-3-phospho-1-inositol + Hydrogen ion + Phosphate
Sn-Glycero-3-phospho-1-inositol + Water > Glycerol 3-phosphate + Hydrogen ion + Inositol

SMPDB Pathways:

Not Available

KEGG Pathways:

Not Available

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0300-5496000000-84efb8ec050f4c9f17b7	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive	splash10-0g30-1304039000-ea70d488eb876065d7d3	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_4_66) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("Glycerophosphoinositol,4TBDMS,#66" TMS) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00tr-5729000000-77cf10de08bfe9a0d966	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-9332000000-6c7d50102de3918a31da	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-06tb-9600000000-165e7d287c38c605bdf0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-1139000000-6f6dad972f38a9d35095	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056r-9583000000-d901449da6faa456e564	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9100000000-6eb59ff75ccaecb4ec40	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0009000000-b246d9d30677ca93576a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-057i-6759000000-fc8aae06d678cd5fd195	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9200000000-e143d85aa39afab46064	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a6r-4902000000-65aa1c251a257777fec9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01r2-9550000000-6361d6accd269b0452bc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006x-5910000000-b78145321ee1bd5d8d8c	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Not Available

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	18321
HMDB ID	HMDB0011649
Pubchem Compound ID	6857358
Kegg ID	C01225
ChemSpider ID	28184592
Wikipedia ID	Not Available
BioCyc ID	CPD-541
EcoCyc ID	CPD-541

Enzymes

Protein Details

1. Glycerophosphoryl diester phosphodiesterase

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.

Protein Details

2. sn-glycerol-3-phosphate import ATP-binding protein UgpC

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).

Protein Details

3. Glycerophosphoryl diester phosphodiesterase_

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.

Protein Details

4. sn-glycerol-3-phosphate transport system permease protein ugpA

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

Protein Details

5. sn-glycerol-3-phosphate transport system permease protein ugpE

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

Protein Details

6. sn-glycerol-3-phosphate-binding periplasmic protein ugpB

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

Protein Details

1. sn-glycerol-3-phosphate import ATP-binding protein UgpC

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).

Protein Details

2. sn-glycerol-3-phosphate transport system permease protein ugpA

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

Protein Details

3. sn-glycerol-3-phosphate transport system permease protein ugpE

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

Protein Details

4. Outer membrane protein N

General function:: Involved in transporter activity
Specific function:: Non-specific porin
Gene Name:: ompN
Uniprot ID:: P77747
Molecular weight:: 41220

Protein Details

5. Outer membrane pore protein E

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

Protein Details

6. Outer membrane protein F

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

Protein Details

7. sn-glycerol-3-phosphate-binding periplasmic protein ugpB

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

Protein Details

8. Outer membrane protein C

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

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Sn-Glycero-3-phospho-1-inositol (M2MDB001754)

Structure for #<Compound:0xa4dd0c44>

Enzymes

Reactions

Reactions

Reactions

Transporters

Reactions