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Escherichia coli K-12 substr. MG1655 Compound: glycerol

Synonyms: 1,2,3-trihydroxypropane, glycerin, 1,2,3-trihydroxypropanol

Superclasses: all carbohydratesa carbohydratea glycana sugara sugar alcohol
an alcohola sugar alcohol


Component of: GlpR-glycerol

Chemical Formula: C3H8O3

Molecular Weight: 92.094 Daltons

Monoisotopic Molecular Weight: 92.0473441231 Daltons

glycerol compound structure

SMILES: C(C(O)CO)O

InChI: InChI=1S/C3H8O3/c4-1-3(6)2-5/h3-6H,1-2H2

InChIKey: InChIKey=PEDCQBHIVMGVHV-UHFFFAOYSA-N

Unification Links: CAS:56-81-5, ChEBI:17754, ChemSpider:733, DrugBank:DB04077, HMDB:HMDB00131, IAF1260:33915, KEGG:C00116, MetaboLights:MTBLC17754, PubChem:753

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -118.9

Reactions known to consume the compound:

glycerol degradation I :
glycerol + ATP → sn-glycerol 3-phosphate + ADP + H+

Reactions known to produce the compound:

cardiolipin biosynthesis I :
2 an L-1-phosphatidyl-glycerol → a cardiolipin + glycerol

Not in pathways:
glycerol 2-phosphate + H2O → glycerol + phosphate
glycerol 1-phosphate + H2O → glycerol + phosphate
glycerophosphoglycerol + H2O → glycerol + sn-glycerol 3-phosphate + H+

Not in pathways:
a sugar phosphate + H2O → a sugar + phosphate

β-D-glucuronide and D-glucuronate degradation :
a β-D-glucuronoside + H2O → D-glucopyranuronate + an alcohol

glycerophosphodiester degradation :
a glycerophosphodiester + H2O → an alcohol + sn-glycerol 3-phosphate + H+

Not in pathways:
an organic hydroperoxide + NADH + H+an alcohol + NAD+ + H2O
an N-acetyl-β-D-hexosaminide + H2O → an N-acetyl-β-D-hexosamine + an alcohol
a carboxylic ester + H2O → an alcohol + a carboxylate + H+
an acetic ester + H2O → an alcohol + acetate + H+
an organic hydroperoxide + a reduced thioredoxin → an alcohol + an oxidized thioredoxin + H2O
a phosphate monoester[periplasm] + H2O[periplasm]an alcohol[periplasm] + phosphate[periplasm]
a phosphate monoester[periplasm] + H2O[periplasm]an alcohol[periplasm] + phosphate[periplasm]

Reactions known to both consume and produce the compound:

glycerol degradation V :
glycerol + NAD+ ↔ dihydroxyacetone + NADH + H+

In Reactions of unknown directionality:

Not in pathways:
GlpR + glycerol = GlpR-glycerol

Not in pathways:
an alcohol + NADP+ = an aldehyde + NADPH + H+

In Transport reactions:
glycerol[periplasm]glycerol[cytosol],
a sugar alcohol[periplasm]a sugar alcohol[extracellular space],
a [PTS enzyme I]-Nπ-phospho-L-histidine + a sugar[periplasm] → a [PTS enzyme I]-L-histidine + a sugar phosphate[cytosol]

Enzymes inhibited by glycerol, sorted by the type of inhibition, are:

Inhibitor (Uncompetitive) of: fructose 6-phosphate aldolase [Schurmann01] Inhibitor (Mechanism unknown) of: glycerol kinase [Pettigrew90, Comment 1]

This compound has been characterized as an alternative substrate of the following enzymes: L-1,2-propanediol oxidoreductase, D-aminopropanol dehydrogenase

In Growth Media: MOPS medium with 2% glycerol, M63 medium with 2% glycerol, M9 medium with 2% glycerol, M9 medium with 1% glycerol, ATCC medium 57, PMA carbon source test + glycerol


References

Pettigrew90: Pettigrew DW, Yu GJ, Liu Y (1990). "Nucleotide regulation of Escherichia coli glycerol kinase: initial-velocity and substrate binding studies." Biochemistry 1990;29(37);8620-7. PMID: 2148683

Schurmann01: Schurmann M, Sprenger GA (2001). "Fructose-6-phosphate aldolase is a novel class I aldolase from Escherichia coli and is related to a novel group of bacterial transaldolases." J Biol Chem 2001;276(14);11055-61. PMID: 11120740


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Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
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