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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-13 02:07:10 UTC
HMDB IDHMDB00126
Secondary Accession Numbers
  • HMDB02722
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
Glycerophosphoric acidKegg
D-Glycerol 1-phosphateKegg
GlycerophosphateGenerator
Glycerol 3-phosphoric acidGenerator
D-Glycerol 1-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
sn-gro-1-PHMDB
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 KeyInChIKey=AWUCVROLDVIAJX-GSVOUGTGSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as glycerophosphates. These 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
  • Organic phosphate
  • Saccharide
  • Secondary alcohol
  • 1,2-diol
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Glycerolipid metabolism
  • Component of Glycerophospholipid metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • 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
Water Solubility30.6 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.39 m3·mol-1ChemAxon
Polarizability13.58 Å3ChemAxon
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-MSNot Available
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, PositiveNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biofluid Locations
  • Blood
  • Saliva
  • Urine
Tissue Location
  • Prostate
Pathways
NameSMPDB LinkKEGG Link
D-glyceric aciduraSMP00529Not Available
Familial lipoprotein lipase deficiencySMP00530Not Available
Glycerol Kinase DeficiencySMP00187Not Available
Glycerol Phosphate ShuttleSMP00124Not Available
Glycerolipid MetabolismSMP00039map00561
Mitochondrial Electron Transport ChainSMP00355map00190
Phospholipid BiosynthesisSMP00025map00564
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified30.0 +/- 3.0 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
SalivaDetected and Quantified13.48 +/- 7.10 uMAdult (>18 years old)FemaleNormal details
SalivaDetected and Quantified5.30 +/- 2.20 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified6.33 +/- 3.24 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected and Quantified14.80 +/- 11.37 uMAdult (>18 years old)MaleAlzheimer's disease details
SalivaDetected and Quantified18.18 +/- 11.57 uMAdult (>18 years old)MaleFrontotemporal lobe dementia details
SalivaDetected and Quantified19.83 +/- 10.17 uMAdult (>18 years old)BothLewy body disease details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021800
KNApSAcK IDNot Available
Chemspider ID388308
KEGG Compound IDC00093
BioCyc IDGLYCEROL-3P
BiGG ID137383
Wikipedia LinkGlycerol 3-phosphate
NuGOwiki LinkHMDB00126
Metagene LinkHMDB00126
METLIN ID5161
PubChem Compound439162
PDB IDG3P
ChEBI ID15978
References
Synthesis Reference Rios-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. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. [19212411 ]
  2. Slomiany BL, Piotrowski J, Mojtahed H, Slomiany A: Ebrotidine effect on the proteolytic and lipolytic activities of Helicobacter pylori. Gen Pharmacol. 1992 Mar;23(2):203-6. [1639232 ]
  3. Guminski T: Some glycolytic enzymes in normal cerebrospinal fluid, brain tissue and blood plasma of infants. Clin Chim Acta. 1976 Aug 16;71(1):61-6. [134854 ]

Enzymes

General function:
Involved in calcium ion binding
Specific function:
Not Available
Gene Name:
GPD2
Uniprot ID:
P43304
Molecular weight:
80851.99
Reactions
Glycerol 3-phosphate + a quinone → Dihydroxyacetone phosphate + a quinoldetails
Glycerol 3-phosphate + FAD → Dihydroxyacetone phosphate + FADHdetails
General function:
Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:
Key enzyme in the regulation of glycerol uptake and metabolism (By similarity).
Gene Name:
GK2
Uniprot ID:
Q14410
Molecular weight:
60593.32
Reactions
Adenosine triphosphate + Glycerol → ADP + Glycerol 3-phosphatedetails
General function:
Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:
Key enzyme in the regulation of glycerol uptake and metabolism.
Gene Name:
GK
Uniprot ID:
P32189
Molecular weight:
57488.675
Reactions
Adenosine triphosphate + Glycerol → ADP + Glycerol 3-phosphatedetails
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
GPD1
Uniprot ID:
P21695
Molecular weight:
37567.4
Reactions
Glycerol 3-phosphate + NAD → Dihydroxyacetone phosphate + NADHdetails
Glycerol 3-phosphate + NAD → Dihydroxyacetone phosphate + NADH + Hydrogen Iondetails
General function:
Involved in acyltransferase activity
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:
Q9HCL2
Molecular weight:
93793.895
Reactions
Acyl-CoA + Glycerol 3-phosphate → Coenzyme A + 1-acyl-sn-glycerol 3-phosphatedetails
Acyl-[acyl-carrier protein] + Glycerol 3-phosphate → 1-Acyl-sn-glycerol 3-phosphate + Acyl-carrier proteindetails
General function:
Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:
Key enzyme in the regulation of glycerol uptake and metabolism.
Gene Name:
GK3P
Uniprot ID:
Q14409
Molecular weight:
Not Available
Reactions
Adenosine triphosphate + Glycerol → ADP + Glycerol 3-phosphatedetails
General function:
Involved in acyltransferase activity
Specific function:
Esterifies acyl-group from acyl-ACP to the sn-1 position of glycerol-3-phosphate, an essential step in glycerolipid biosynthesis. Active against both saturated and unsaturated long-chain fatty acyl-CoAs.
Gene Name:
AGPAT6
Uniprot ID:
Q86UL3
Molecular weight:
52070.605
Reactions
Acyl-CoA + Glycerol 3-phosphate → Coenzyme A + 1-acyl-sn-glycerol 3-phosphatedetails
Acyl-[acyl-carrier protein] + Glycerol 3-phosphate → 1-Acyl-sn-glycerol 3-phosphate + Acyl-carrier proteindetails
General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
Functions in the biosynthesis of the anionic phospholipids phosphatidylglycerol and cardiolipin (By similarity).
Gene Name:
PGS1
Uniprot ID:
Q32NB8
Molecular weight:
62729.745
Reactions
CDP-diacylglycerol + Glycerol 3-phosphate → Cytidine monophosphate + 3(3-sn-phosphatidyl)-sn-glycerol 1-phosphatedetails
CDP-diacylglycerol + Glycerol 3-phosphate → Cytidine monophosphate + Phosphatidylglycerophosphatedetails
General function:
Involved in oxidoreductase activity
Specific function:
Plays a role in regulating cardiac sodium current; decreased enzymatic activity with resulting increased levels of glycerol 3-phosphate activating the DPD1L-dependent SCN5A phosphorylation pathway, may ultimately lead to decreased sodium current; cardiac sodium current may also be reduced due to alterations of NAD(H) balance induced by DPD1L.
Gene Name:
GPD1L
Uniprot ID:
Q8N335
Molecular weight:
38418.44
Reactions
Glycerol 3-phosphate + NAD → Dihydroxyacetone phosphate + NADHdetails
Glycerol 3-phosphate + NAD → Dihydroxyacetone phosphate + NADH + Hydrogen Iondetails
General function:
Involved in acyltransferase activity
Specific function:
Esterifies acyl-group from acyl-ACP to the sn-1 position of glycerol-3-phosphate, an essential step in glycerolipid biosynthesis. Overexpression activates the mTOR pathway.
Gene Name:
AGPAT9
Uniprot ID:
Q53EU6
Molecular weight:
48704.805
Reactions
Acyl-CoA + Glycerol 3-phosphate → Coenzyme A + 1-acyl-sn-glycerol 3-phosphatedetails
Acyl-[acyl-carrier protein] + Glycerol 3-phosphate → 1-Acyl-sn-glycerol 3-phosphate + Acyl-carrier proteindetails
General function:
Involved in acyltransferase activity
Specific function:
Not Available
Gene Name:
DKFZp451B1115
Uniprot ID:
Q86T70
Molecular weight:
93735.9
General function:
Involved in glycerophosphodiester phosphodiesterase activity
Specific function:
Has glycerophosphoinositol phosphodiesterase activity. Has little or no activity towards glycerophosphocholine. GDE1 activity can be modulated by G-protein signaling pathways (By similarity).
Gene Name:
GDE1
Uniprot ID:
Q9NZC3
Molecular weight:
37718.04
Reactions
1-(sn-Glycero-3-phospho)-1D-myo-inositol + Water → Myoinositol + Glycerol 3-phosphatedetails
General function:
Involved in acyltransferase activity
Specific function:
Esterifies acyl-group from acyl-ACP to the sn-1 position of glycerol-3-phosphate, an essential step in glycerolipid biosynthesis (By similarity).
Gene Name:
GPAT2
Uniprot ID:
Q6NUI2
Molecular weight:
87834.5
Reactions
Acyl-CoA + Glycerol 3-phosphate → Coenzyme A + 1-acyl-sn-glycerol 3-phosphatedetails
Acyl-[acyl-carrier protein] + Glycerol 3-phosphate → 1-Acyl-sn-glycerol 3-phosphate + Acyl-carrier proteindetails
General function:
Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:
Not Available
Gene Name:
GK5
Uniprot ID:
Q6ZS86
Molecular weight:
59155.64
Reactions
Adenosine triphosphate + Glycerol → ADP + Glycerol 3-phosphatedetails
General function:
Involved in damaged DNA binding
Specific function:
Acetyltransferase required for the establishment of sister chromatid cohesion and couple the processes of cohesion and DNA replication to ensure that only sister chromatids become paired together. In contrast to the structural cohesins, the deposition and establishment factors are required only during S phase. Acts by mediating the acetylation of cohesin component SMC3
Gene Name:
ESCO1
Uniprot ID:
Q5FWF5
Molecular weight:
94982.2
General function:
Not Available
Specific function:
Hydrolyzes ADP-ribose, IDP-ribose, CDP-glycerol, CDP-choline and CDP-ethanolamine, but not other non-reducing ADP-sugars or CDP-glucose. May be involved in immune cell signaling as suggested by the second-messenger role of ADP-ribose, which activates TRPM2 as a mediator of oxidative/nitrosative stress (By similarity).
Gene Name:
ADPRM
Uniprot ID:
Q3LIE5
Molecular weight:
39529.105
Reactions
CDP-glycerol + Water → Cytidine monophosphate + Glycerol 3-phosphatedetails
General function:
Not Available
Specific function:
May be involved in the negative regulation of skeletal muscle differentiation, independently of its glycerophosphocholine phosphodiesterase activity (By similarity).
Gene Name:
GPCPD1
Uniprot ID:
Q9NPB8
Molecular weight:
76034.185
Reactions
Glycerophosphocholine + Water → Choline + Glycerol 3-phosphatedetails