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Identification
YMDB IDYMDB00073
NameGlycerol 3-phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionGlycerol 3-phosphate is produced from glycerol, the triose sugar backbone of triglycerides and glycerophospholipids, by the enzyme glycerol kinase. Glycerol 3-phosphate 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. [Wikipedia]
Structure
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Synonyms
  • (R)-glycerol 1-phosphate
  • 1-(dihydrogen phosphate) Glycerol
  • 1-Glycerophosphate
  • 1-Glycerophosphorate
  • 1-Glycerophosphoric acid
  • 1-phosphoglycerol
  • 1,2,3-propanetriol, 1-(dihydrogen phosphate)
  • 2,3-dihydroxypropyl dihydrogen phosphate
  • 2,3-hydroxy-1-propyl dihydrogen phosphate
  • 3-Glycerophosphate
  • a-Glycerophosphate
  • a-Glycerophosphorate
  • a-Glycerophosphoric acid
  • a-Phosphoglycerol
  • alpha-Glycerophosphate
  • alpha-Glycerophosphorate
  • alpha-Glycerophosphoric acid
  • alpha-Phosphoglycerol
  • D-(glycerol 1-phosphate)
  • D-Glycerol 1-phosphate
  • dihydrogen a-glycerophosphate
  • DL-a-Glycerol phosphate
  • DL-a-Glycerophosphate
  • DL-a-Glycerophosphorate
  • DL-a-Glycerophosphoric acid
  • DL-a-Glyceryl phosphate
  • DL-alpha-Glycerol phosphate
  • DL-alpha-Glycerophosphate
  • DL-alpha-Glycerophosphorate
  • DL-alpha-Glycerophosphoric acid
  • DL-alpha-Glyceryl phosphate
  • DL-Glycerol 1-phosphate
  • DL-Glycerol 3-phosphate
  • Glycerol 1-phosphate
  • Glycerol a-phosphate
  • glycerol alpha-phosphate
  • Glycerol monophosphate
  • Glycerol-3-phosphate
  • Glycerophosphate
  • Glycerophosphorate
  • Glycerophosphoric acid
  • Glycerophosphoric acid I
  • Glyceryl phosphate
  • Glyceryl phosphic acid
  • L-(glycerol 3-phosphate)
  • PG
  • phosphatidyl glycerol
  • phosphoric acid mono-((R)-2,3-dihydroxy-propyl) ester
  • Phosphorsaeure-mono-((R)-2,3-dihydroxy-propylester)
  • sn-glycerol 3-phosphate
  • SN-GLYCEROL-3-PHOSPHATE
  • sn-Gro-1-P
  • (R)-Glycerol 1-phosphoric acid
  • D-(Glycerol 1-phosphoric acid)
  • D-Glycerol 1-phosphoric acid
  • Glycerol-3-phosphoric acid
  • L-(Glycerol 3-phosphoric acid)
  • Phosphate mono-((R)-2,3-dihydroxy-propyl) ester
  • sn-GLYCEROL-3-phosphoric acid
  • Glycerol 3-phosphoric acid
  • alpha-Glycerophosphoric acid, (DL)-isomer
  • alpha-Glycerophosphoric acid, (R)-isomer
  • alpha-Glycerophosphoric acid, (S)-isomer
  • alpha-Glycerophosphoric acid, 1,2,3-propanetriol-1-(18)O,3-(dihydrogen phosphate)-labeled
  • alpha-Glycerophosphoric acid, 1,2,3-propanetriol-2-(18)O,3-(dihydrogen phosphate)-labeled
  • alpha-Glycerophosphoric acid, fe salt
  • alpha-Glycerophosphoric acid, fe(+3) salt (3:2)
  • alpha-Glycerophosphoric acid, calcium salt
  • alpha-Glycerophosphoric acid, disodium salt
  • alpha-Glycerophosphoric acid, disodium salt (+-)-isomer
  • alpha-Glycerophosphoric acid, disodium salt hexahydrate(+-)-isomer
  • alpha-Glycerophosphoric acid, monocalcium salt
  • alpha-Glycerophosphoric acid, monocalcium salt (S)-isomer
  • alpha-Glycerophosphoric acid, monomagnesium salt
  • alpha-Glycerophosphoric acid, sodium salt
  • Disodium glycerophosphate
  • Sodium glycerophosphate
CAS number17989-41-2
WeightAverage: 172.0737
Monoisotopic: 172.013674532
InChI KeyAWUCVROLDVIAJX-GSVOUGTGSA-N
InChIInChI=1S/C3H9O6P/c4-1-3(5)2-9-10(6,7)8/h3-5H,1-2H2,(H2,6,7,8)/t3-/m1/s1
IUPAC Name[(2R)-2,3-dihydroxypropoxy]phosphonic acid
Traditional IUPAC Name3-phosphoglycerol
Chemical FormulaC3H9O6P
SMILES[H]OC([H])([H])[C@@]([H])(O[H])C([H])([H])OP(=O)(O[H])O[H]
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
Physical Properties
StateSolid
Charge0
Melting point102-104 °C
Experimental Properties
PropertyValueReference
Water Solubility1000 mg/mL [MERCK INDEX (1996); readily soluble]PhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility30.6 g/LALOGPS
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
Biological Properties
Cellular Locations
  • mitochondrion
  • lipid particle
  • endoplasmic reticulum
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Triacylglycerol metabolism TG(16:0/18:0/20:0)PW007842 ThumbThumb?image type=greyscaleThumb?image type=simple
Triacylglycerol metabolism TG(16:0/18:0/22:0)PW007878 ThumbThumb?image type=greyscaleThumb?image type=simple
Triacylglycerol metabolism TG(16:0/20:0/20:0)PW007879 ThumbThumb?image type=greyscaleThumb?image type=simple
Triacylglycerol metabolism TG(18:0/18:0/18:0)PW007843 ThumbThumb?image type=greyscaleThumb?image type=simple
Triacylglycerol metabolism TG(18:0/18:0/20:0)PW007880 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Glycerolipid metabolismec00561 Map00561
Glycerophospholipid metabolismec00564 Map00564
SMPDB Reactions
Glycerol + Adenosine triphosphateADP + Glycerol 3-phosphate
water + Glycerol 3-phosphate Glycerol + phosphate
Glycerol 3-phosphate + oleoyl-CoACoenzyme A + 1-oleyl-2-lyso-phosphatidate
Glycerol 3-phosphate + hexadec-2-enoyl-CoACoenzyme A + PA(16:0/0:0)
Glycerol 3-phosphate + hexadec-2-enoyl-CoA Coenzyme A + PA(16:0/0:0)
KEGG Reactions
Adenosine triphosphate + GlycerolGlycerol 3-phosphate + hydron + ADP
Glycerol 3-phosphate + waterGlycerol + phosphate
Glycerol 3-phosphate + FADFADH2 + Dihydroxyacetone phosphate
NADH + Dihydroxyacetone phosphate + hydronNAD + Glycerol 3-phosphate
acyl-CoA + Glycerol 3-phosphatePA(18:1(9Z)/0:0) + Coenzyme A + hydron
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
0.0 ± 0.0 µM Minimal medium supplemented with ammonia salts and glucoseaerobic;resting cellsBaker's yeastPMID: 4578278
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Norbeck, J., Pahlman, A. K., Akhtar, N., Blomberg, A., Adler, L. (1996). "Purification and characterization of two isoenzymes of DL-glycerol-3-phosphatase from Saccharomyces cerevisiae. Identification of the corresponding GPP1 and GPP2 genes and evidence for osmotic regulation of Gpp2p expression by the osmosensing mitogen-activated protein kinase signal transduction pathway." J Biol Chem 271:13875-13881.8662716
  • Andre, L., Hemming, A., Adler, L. (1991). "Osmoregulation in Saccharomyces cerevisiae. Studies on the osmotic induction of glycerol production and glycerol-3-phosphate dehydrogenase (NAD+)" FEBS Lett 286:13-17.1864360
  • Fernandez-Murray, J. P., McMaster, C. R. (2005). "Glycerophosphocholine catabolism as a new route for choline formation for phosphatidylcholine synthesis by the Kennedy pathway." J Biol Chem 280:38290-38296.16172116
  • Athenstaedt, K., Weys, S., Paltauf, F., Daum, G. (1999). "Redundant systems of phosphatidic acid biosynthesis via acylation of glycerol-3-phosphate or dihydroxyacetone phosphate in the yeast Saccharomyces cerevisiae." J Bacteriol 181:1458-1463.10049376
  • Fisher, E., Almaguer, C., Holic, R., Griac, P., Patton-Vogt, J. (2005). "Glycerophosphocholine-dependent growth requires Gde1p (YPL110c) and Git1p in Saccharomyces cerevisiae." J Biol Chem 280:36110-36117.16141200
  • Huh, W. K., Falvo, J. V., Gerke, L. C., Carroll, A. S., Howson, R. W., Weissman, J. S., O'Shea, E. K. (2003). "Global analysis of protein localization in budding yeast." Nature 425:686-691.14562095
  • Zheng, Z., Zou, J. (2001). "The initial step of the glycerolipid pathway: identification of glycerol 3-phosphate/dihydroxyacetone phosphate dual substrate acyltransferases in Saccharomyces cerevisiae." J Biol Chem 276:41710-41716.11544256
  • Albertyn, J., Hohmann, S., Thevelein, J. M., Prior, B. A. (1994). "GPD1, which encodes glycerol-3-phosphate dehydrogenase, is essential for growth under osmotic stress in Saccharomyces cerevisiae, and its expression is regulated by the high-osmolarity glycerol response pathway." Mol Cell Biol 14:4135-4144.8196651
  • Gancedo, J. M., Gancedo, C. (1973). "Concentrations of intermediary metabolites in yeast." Biochimie 55:205-211.4578278
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.
External Links:
ResourceLink
CHEBI ID15978
HMDB IDHMDB00126
Pubchem Compound ID439162
Kegg IDC00093
ChemSpider ID388308
FOODB IDFDB021800
WikipediaGlycerol_3-phosphate
BioCyc IDGLYCEROL-3P

Enzymes

General function:
Involved in catalytic activity
Specific function:
Bifunctional enzyme that catalyzes the enolization of 2,3-diketo-5-methylthiopentyl-1-phosphate (DK-MTP-1-P) into the intermediate 2-hydroxy-3-keto-5-methylthiopentenyl-1-phosphate (HK-MTPenyl-1-P), which is then dephosphorylated to form the acireductone 1,2-dihydroxy-3-keto-5-methylthiopentene (DHK-MTPene)
Gene Name:
UTR4
Uniprot ID:
P32626
Molecular weight:
25187.19922
Reactions
5-(methylthio)-2,3-dioxopentyl phosphate + H(2)O → 1,2-dihydroxy-5-(methylthio)pent-1-en-3-one + phosphate.
2-Phosphoglycolate + H2O → glycolate + phosphate
General function:
Involved in acyltransferase activity
Specific function:
G-3-P/dihydroxyacetone phosphate dual substrate-specific sn-1 acyltransferase
Gene Name:
GPT1
Uniprot ID:
P32784
Molecular weight:
85693.5
Reactions
Acyl-CoA + sn-glycerol 3-phosphate → CoA + 1-acyl-sn-glycerol 3-phosphate.
Acyl-CoA + glycerone phosphate → CoA + acylglycerone phosphate.
General function:
Involved in acyltransferase activity
Specific function:
G-3-P/dihydroxyacetone phosphate dual substrate-specific sn-1 acyltransferase
Gene Name:
GPT2
Uniprot ID:
P36148
Molecular weight:
83644.0
Reactions
Acyl-CoA + sn-glycerol 3-phosphate → CoA + 1-acyl-sn-glycerol 3-phosphate.
Acyl-CoA + glycerone phosphate → CoA + acylglycerone phosphate.
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the production and accumulation of glycerol during hyperosmotic stress conditions. Glycerol acts as a osmoregulator that prevents loss of water and turgor of the cells
Gene Name:
GPD1
Uniprot ID:
Q00055
Molecular weight:
42868.5
Reactions
sn-glycerol 3-phosphate + NAD(+) → glycerone phosphate + NADH.
General function:
Involved in protein binding
Specific function:
Glycerophosphocholine glycerophosphodiesterase responsible for the hydrolysis of intracellular glycerophosphocholine into glycerol-phosphate and choline. The choline is used for phosphatidyl-choline synthesis. Required for utilization of glycerophosphocholine as phosphate source
Gene Name:
GDE1
Uniprot ID:
Q02979
Molecular weight:
138013.0
Reactions
A glycerophosphodiester + H(2)O → an alcohol + sn-glycerol 3-phosphate.
General function:
Involved in catalytic activity
Specific function:
Glycerol 3-phosphate + H(2)O = glycerol + phosphate
Gene Name:
HOR2
Uniprot ID:
P40106
Molecular weight:
27813.5
Reactions
Glycerol 3-phosphate + H(2)O → glycerol + phosphate.
glycerol 1-phosphate + H2O → glycerol + phosphate
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the production of glycerol under anaerobic growth conditions. Glycerol production serves as a redox sink by consuming the excess cytosolic NADH during anaerobic metabolism
Gene Name:
GPD2
Uniprot ID:
P41911
Molecular weight:
49421.30078
Reactions
sn-glycerol 3-phosphate + NAD(+) → glycerone phosphate + NADH.
General function:
Involved in glycerophosphodiester phosphodiesterase activity
Specific function:
Probable glycerophosphocholine glycerophosphodiesterase which may be responsible for the hydrolysis of intracellular glycerophosphocholine into glycerol-phosphate and choline. The choline is used for phosphatidyl-choline synthesis
Gene Name:
Not Available
Uniprot ID:
Q08959
Molecular weight:
37069.39844
Reactions
A glycerophosphodiester + H(2)O → an alcohol + sn-glycerol 3-phosphate.
General function:
Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:
ATP + glycerol = ADP + sn-glycerol 3- phosphate
Gene Name:
GUT1
Uniprot ID:
P32190
Molecular weight:
79823.60156
Reactions
ATP + glycerol → ADP + sn-glycerol 3-phosphate.
General function:
Involved in oxidoreductase activity
Specific function:
sn-glycerol 3-phosphate + a quinone = glycerone phosphate + a quinol
Gene Name:
GUT2
Uniprot ID:
P32191
Molecular weight:
72388.29688
Reactions
sn-glycerol 3-phosphate + a quinone → glycerone phosphate + a quinol.
General function:
Involved in catalytic activity
Specific function:
Glycerol 3-phosphate + H(2)O = glycerol + phosphate
Gene Name:
RHR2
Uniprot ID:
P41277
Molecular weight:
27946.59961
Reactions
Glycerol 3-phosphate + H(2)O → glycerol + phosphate.
glycerol 1-phosphate + H2O → glycerol + phosphate
General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
Essential for the viability of mitochondrial petite mutant. Catalyzes the committed step to the synthesis of the acidic phospholipids
Gene Name:
PGS1
Uniprot ID:
P25578
Molecular weight:
59369.69922
Reactions
CDP-diacylglycerol + sn-glycerol 3-phosphate → CMP + 3(3-sn-phosphatidyl)-sn-glycerol 1-phosphate.
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q12486
Molecular weight:
24839.80078
Reactions
2-Phosphoglycolate + H2O → glycolate + phosphate
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q04223
Molecular weight:
35278.10156
Reactions
2-Phosphoglycolate + H2O → glycolate + phosphate