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Record Information
Version1.0
Creation Date2016-07-13 19:41:19 UTC
Update Date2016-07-20 21:03:09 UTC
LmdbLMDB00052
Secondary Accession NumbersNone
Metabolite Identification
Common NameGlycerol 3-phosphate
DescriptionGlycerol 3-phosphate is a chemical intermediate in the glycolysis metabolic pathway. It is commonly confused with the similarly named glycerate 3-phosphate or glyceraldehyde 3-phosphate. Glycerol 3-phosphate is produced from glycerol, the triose sugar backbone of triglycerides and glycerophospholipids, by the enzyme glycerol kinase. Glycerol 3-phospate may then be converted by dehydrogenation to dihydroxyacetone phosphate (DHAP) by the enzyme glycerol-3-phosphate dehydrogenase. DHAP can then be rearranged into glyceraldehyde 3-phosphate (GA3P) by triose phosphate isomerase (TIM), and feed into glycolysis. The glycerol 3-phosphate shuttle is used to rapidly regenerate NAD+ in the brain and skeletal muscle cells of mammals (wikipedia).
Structure
Thumb
Synonyms
ValueSource
(R)-Glycerol 1-phosphateChEBI
D-(Glycerol 1-phosphate)ChEBI
D-Glycerol 1-phosphateChEBI
Glycerol-3-phosphateChEBI
Glycerophosphoric acidChEBI
L-(Glycerol 3-phosphate)ChEBI
Phosphoric acid mono-((R)-2,3-dihydroxy-propyl) esterChEBI
Phosphorsaeure-mono-((R)-2,3-dihydroxy-propylester)ChEBI
sn-GLYCEROL-3-phosphATEChEBI
sn-Gro-1-pChEBI
(R)-Glycerol 1-phosphoric acidGenerator
D-(Glycerol 1-phosphoric acid)Generator
D-Glycerol 1-phosphoric acidGenerator
Glycerol-3-phosphoric acidGenerator
GlycerophosphateGenerator
L-(Glycerol 3-phosphoric acid)Generator
Phosphate mono-((R)-2,3-dihydroxy-propyl) esterGenerator
sn-GLYCEROL-3-phosphoric acidGenerator
Glycerol 3-phosphoric acidGenerator
1-(Dihydrogen phosphate) glycerolHMDB
1-GlycerophosphateHMDB
1-GlycerophosphorateHMDB
1-Glycerophosphoric acidHMDB
3-GlycerophosphateHMDB
a-GlycerophosphateHMDB
a-GlycerophosphorateHMDB
a-Glycerophosphoric acidHMDB
a-PhosphoglycerolHMDB
alpha-GlycerophosphateHMDB
alpha-GlycerophosphorateHMDB
alpha-Glycerophosphoric acidHMDB
alpha-PhosphoglycerolHMDB
Dihydrogen a-glycerophosphateHMDB
DL-a-Glycerol phosphateHMDB
DL-a-GlycerophosphateHMDB
DL-a-GlycerophosphorateHMDB
DL-a-Glycerophosphoric acidHMDB
DL-a-Glyceryl phosphateHMDB
DL-alpha-Glycerol phosphateHMDB
DL-alpha-GlycerophosphateHMDB
DL-alpha-GlycerophosphorateHMDB
DL-alpha-Glycerophosphoric acidHMDB
DL-alpha-Glyceryl phosphateHMDB
DL-Glycerol 1-phosphateHMDB
DL-Glycerol 3-phosphateHMDB
Glycerol 1-phosphateHMDB
Glycerol a-phosphateHMDB
Glycerol monophosphateHMDB
GlycerophosphorateHMDB
Glycerophosphoric acid IHMDB
Glyceryl phosphateHMDB
sn-Glycerol 3-phosphateHMDB
1-PhosphoglycerolHMDB
alpha-Glycerophosphoric acid, (DL)-isomerHMDB
alpha-Glycerophosphoric acid, (R)-isomerHMDB
alpha-Glycerophosphoric acid, (S)-isomerHMDB
alpha-Glycerophosphoric acid, 1,2,3-propanetriol-1-(18)O,3-(dihydrogen phosphate)-labeledHMDB
alpha-Glycerophosphoric acid, 1,2,3-propanetriol-2-(18)O,3-(dihydrogen phosphate)-labeledHMDB
alpha-Glycerophosphoric acid, fe saltHMDB
alpha-Glycerophosphoric acid, fe(+3) salt (3:2)HMDB
alpha-Glycerophosphoric acid, calcium saltHMDB
alpha-Glycerophosphoric acid, disodium saltHMDB
alpha-Glycerophosphoric acid, disodium salt (+-)-isomerHMDB
alpha-Glycerophosphoric acid, disodium salt hexahydrate(+-)-isomerHMDB
alpha-Glycerophosphoric acid, monocalcium saltHMDB
alpha-Glycerophosphoric acid, monocalcium salt (S)-isomerHMDB
alpha-Glycerophosphoric acid, monomagnesium saltHMDB
alpha-Glycerophosphoric acid, sodium saltHMDB
Disodium glycerophosphateHMDB
Sodium glycerophosphateHMDB
Chemical FormulaC3H9O6P
Average Molecular Weight172.0737
Monoisotopic Molecular Weight172.013674532
IUPAC Name[(2R)-2,3-dihydroxypropoxy]phosphonic acid
Traditional Name3-phosphoglycerol
CAS Registry Number57-03-4
SMILES
OC[C@@H](O)COP(O)(O)=O
InChI Identifier
InChI=1S/C3H9O6P/c4-1-3(5)2-9-10(6,7)8/h3-5H,1-2H2,(H2,6,7,8)/t3-/m1/s1
InChI KeyAWUCVROLDVIAJX-GSVOUGTGSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as glycerophosphates. Glycerophosphates are compounds containing a glycerol linked to a phosphate group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphates
Direct ParentGlycerophosphates
Alternative Parents
Substituents
  • Sn-glycerol-3-phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Secondary alcohol
  • 1,2-diol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.8ALOGPS
logP-2ChemAxon
logS-0.75ALOGPS
pKa (Strongest Acidic)1.51ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.39 m³·mol⁻¹ChemAxon
Polarizability13.58 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uea-0932000000-726f422c76a193edf232View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uea-0932000000-726f422c76a193edf232View in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0zgj-1976000000-019de1fa6314b95ef7feView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ot-9300000000-a435ec7fb966f8ddc1a2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0230-9080000000-9f48133c7a08fb549acdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-9200000000-bf06c1d1e56cb8853243View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kr-9200000000-ffce45222cab00a0c302View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001j-9000000000-7689cca8f9c9a12d9e75View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0902000000-00e3a7e1ee10fbd8b03eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-1a40c90fd2eb656ddf5cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0002-9000000000-f9bc5f552db38767c437View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0002-0920000000-72f8b96355726dd3a5b1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0901000000-2c3a8ed438d7ca0fa049View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-a3549fb5ec2675fbf615View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0002-9000000000-096e2ba9a6ef6fd20d88View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0002-0930000000-171708905bad289d6031View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0925110000-c1ced10d34f533b3fa1fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0900000000-4ee8a36492a451beda75View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-9000000000-de2aacfb81476c7755e5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0900000000-dd342482ade09e9ce749View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0fkc-0917520000-d61e6034525ac5f7588dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-9000000000-d537d3f23f3d9a789c20View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0900000000-2f1ca45b50402f6e62dfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0009000000-5606781224d6ab5caed3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0pi0-1900000000-75b6ed57a4c9cd6378b4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0a59-6900000000-1c46fbda1468f6fd803cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0a5c-9400000000-305e9a2554d8c3274f32View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-007o-9000000000-d11ad04a048c3dca25deView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-00mo-9000000000-7b779b4be184b5b26b6aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-5900000000-297dbde751110233eca5View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Milk
  • Plasma
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
Cerebrospinal Fluid (CSF)Detected but not QuantifiedNot ApplicableNot AvailableOvine details
FecesDetected but not QuantifiedNot ApplicableNot AvailableOvine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • Kurt J. Boudonck,...
details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableOvine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
DrugBank IDDB02515
HMDB IDHMDB0000126
FooDB IDFDB021800
Phenol Explorer IDNot Available
KNApSAcK IDC00007288
BiGG ID137383
BioCyc IDGLYCEROL-3P
METLIN ID5161
PDB IDNot Available
Wikipedia LinkGlycerol 3-phosphate
Chemspider ID388308
ChEBI ID15978
PubChem Compound ID439162
Kegg Compound IDC00093
YMDB IDYMDB00073
ECMDB IDECMDB00126
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available