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Record Information
Version1.0
Creation Date2016-09-30 22:19:54 UTC
Update Date2020-05-21 16:26:16 UTC
BMDB IDBMDB0000126
Secondary Accession Numbers
  • BMDB00126
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 and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Intracellular membrane
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point102 - 104 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000.0 mg/mLNot 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 Locations
  • Cell membrane
  • Cytoplasm
  • Intracellular membrane
  • Mitochondria
Biospecimen Locations
  • Liver
  • Mammary Gland
  • Milk
  • Placenta
  • Prostate Tissue
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
details
MilkDetected and Quantified80 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified97 uMNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
PlacentaExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Prostate TissueExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000126
DrugBank IDDB02515
Phenol Explorer Compound IDNot Available
FooDB IDFDB031180
KNApSAcK IDC00007288
Chemspider ID388308
KEGG Compound IDC00093
BioCyc IDGLYCEROL-3P
BiGG ID137383
Wikipedia LinkGlycerol 3-phosphate
METLIN ID5161
PubChem Compound439162
PDB IDNot Available
ChEBI ID15978
References
Synthesis ReferenceRios-Mercadillo, Victor M.; Whitesides, George M. Enzymic synthesis of sn-glycerol 3-phosphate. Journal of the American Chemical Society (1979), 101(19), 5828-9.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hurtaud C, Lemosquet S, Rulquin H: Effect of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 2. Diets based on grass silage. J Dairy Sci. 2000 Dec;83(12):2952-62. doi: 10.3168/jds.S0022-0302(00)75195-2. [PubMed:11132867 ]
  2. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
  3. Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23. [PubMed:28342601 ]
  4. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.

Enzymes

General function:
Lipid transport and metabolism
Specific function:
Functions in the biosynthesis of the anionic phospholipids phosphatidylglycerol and cardiolipin.
Gene Name:
PGS1
Uniprot ID:
Q2KJ28
Molecular weight:
62732.0
Reactions
Glycerol 3-phosphate + a CDP-diacylglycerol → an L-1-phosphatidylglycerol-phosphate + Cytidine monophosphatedetails
CDP-DG(16:0/18:1(11Z)) + Glycerol 3-phosphate → PGP(16:0/18:1(11Z)) + Cytidine monophosphatedetails
CDP-DG(18:1(9Z)/18:1(9Z)) + Glycerol 3-phosphate → PGP(18:1(9Z)/18:1(9Z)) + Cytidine monophosphatedetails
CDP-DG(18:2(9Z,12Z)/18:2(9Z,12Z)) + Glycerol 3-phosphate → PGP(18:2(9Z,12Z)/18:2(9Z,12Z)) + Cytidine monophosphatedetails
General function:
Energy production and conversion
Specific function:
Not Available
Gene Name:
GPD2
Uniprot ID:
A6QLU1
Molecular weight:
80763.0
Reactions
Glycerol 3-phosphate + Quinone → Dihydroxyacetone phosphate + Hydroquinonedetails
Dihydroxyacetone phosphate + Quinone → Glycerol 3-phosphate + Hydroquinonedetails
Coenzyme Q10 + Glycerol 3-phosphate → Ubiquinol + Dihydroxyacetone phosphatedetails
General function:
Lipid transport and metabolism
Specific function:
Not Available
Gene Name:
GNPAT
Uniprot ID:
A4IF87
Molecular weight:
77664.0
Reactions
Glycerol 3-phosphate + Long-chain fatty acyl-CoA → 1-Acyl-sn-glycerol 3-phosphate + Coenzyme Adetails
Palmityl-CoA + Glycerol 3-phosphate → Coenzyme A + LPA(16:0/0:0)details
Stearoyl-CoA + Glycerol 3-phosphate → Coenzyme A + LPA(18:0/0:0)details
Oleoyl-CoA + Glycerol 3-phosphate → Coenzyme A + LysoPA(18:1(9Z)/0:0)details
Gamma-linolenoyl-CoA + Glycerol 3-phosphate → Coenzyme A + LysoPA(18:3(6Z,9Z,12Z)/0:0)details
Eicosanoyl-CoA + Glycerol 3-phosphate → Coenzyme A + LysoPA(20:0/0:0)details
Gondoyl-CoA + Glycerol 3-phosphate → Coenzyme A + LysoPA(20:1(11Z)/0:0)details
Docosanoyl-CoA + Glycerol 3-phosphate → Coenzyme A + LysoPA(22:0/0:0)details
Erucoyl-CoA + Glycerol 3-phosphate → Coenzyme A + LysoPA(22:1(13Z)/0:0)details
General function:
Energy production and conversion
Specific function:
Has glycerophosphoinositol phosphodiesterase activity. Hydrolyzes lysoglycerophospholipids to produce lysophosphatidic acid (LPA) and the corresponding amines. Has little or no activity towards glycerophosphocholine. GDE1 activity can be modulated by G-protein signaling pathways (By similarity).
Gene Name:
GDE1
Uniprot ID:
Q3T0T0
Molecular weight:
37653.0
Reactions
Citicoline → Glycerol 3-phosphate + Cholinedetails
General function:
Energy production and conversion
Specific function:
Key enzyme in the regulation of glycerol uptake and metabolism.
Gene Name:
GK
Uniprot ID:
Q0IID9
Molecular weight:
61261.0
Reactions
Glycerol + Adenosine triphosphate → Glycerol 3-phosphate + ADPdetails
General function:
Energy production and conversion
Specific function:
Not Available
Gene Name:
GPD1
Uniprot ID:
Q5EA88
Molecular weight:
37648.0
Reactions
Dihydroxyacetone phosphate + NADH → Glycerol 3-phosphate + NADdetails
Glycerol 3-phosphate + NAD → Dihydroxyacetone phosphate + NADHdetails
General function:
Involved in glycerol-3-phosphate O-acyltransferase acti
Specific function:
Converts glycerol-3-phosphate to 1-acyl-sn-glycerol-3-phosphate (lysophosphatidic acid or LPA) by incorporating an acyl moiety at the sn-1 position of the glycerol backbone (By similarity). Active against both saturated and unsaturated long-chain fatty acyl-CoAs (By similarity).
Gene Name:
GPAT4
Uniprot ID:
A3FPG8
Molecular weight:
52055.0
General function:
Transcription
Specific function:
Not Available
Gene Name:
GK5
Uniprot ID:
Q08D86
Molecular weight:
58765.0
General function:
Lipid transport and metabolism
Specific function:
Esterifies acyl-group from acyl-ACP to the sn-1 position of glycerol-3-phosphate, an essential step in glycerolipid biosynthesis.
Gene Name:
GPAM
Uniprot ID:
Q5GJ77
Molecular weight:
93144.0
Reactions
Glycerol 3-phosphate + Palmityl-CoA → LPA(16:0/0:0) + Coenzyme Adetails