Glycerol (PAMDB000050)
Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Version | 1.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 1/22/2018 12:54:54 PM | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Metabolite ID | PAMDB000050 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | Glycerol | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description: | Glycerol is an organic compound, also called glycerin or glycerine. It is a colorless, odorless, viscous liquid that is widely used in pharmaceutical formulations. Glycerol has three hydrophilic hydroxyl groups that are responsible for its solubility in water and its hygroscopic nature. Metabolism of glycerol in Pseudomonas aeruginosa, generally requires the presence of external electron acceptors. The respiratory pathways mediating this metabolic process involve a glycerol transporter (encoded by glpF), a glycerol kinase (encoded by glpK), and two respiratory glycerol-3-phosphate dehydrogenases (G3PDHs). Glycerol may also be metabolized fermentatively leading to the production of ethanol. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Chemical Formula: | C3H8O3 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Average Molecular Weight: | 92.0938 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Monoisotopic Molecular Weight: | 92.047344122 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | PEDCQBHIVMGVHV-UHFFFAOYSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C3H8O3/c4-1-3(6)2-5/h3-6H,1-2H2 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 56-81-5 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | propane-1,2,3-triol | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | glycerol | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | OCC(O)CO | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Taxonomy Description | This compound belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Organooxygen compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Carbohydrates and carbohydrate conjugates | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Sugar alcohols | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Sugar alcohols | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Alternative Parents | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Substituents |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Molecular Framework | Aliphatic acyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Liquid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | 20 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Predicted Properties |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | D-Glyceraldehyde + Hydrogen ion + NADH <> Glycerol + NAD Glycerol 3-phosphate + Water > Glycerol + Phosphate Glycerophosphoglycerol + Water > Glycerol + Glycerol 3-phosphate + Hydrogen ion Glycerol 2-phosphate + Water > Glycerol + Phosphate Adenosine triphosphate + Glycerol <> ADP + Glycerol 3-phosphate + Hydrogen ion Glycerol + NAD <> Dihydroxyacetone + Hydrogen ion + NADH Adenosine triphosphate + Glycerol <> ADP + Glycerol 3-phosphate 2 Phosphatidylglycerol <> Cardiolipin + Glycerol an L-1-phosphatidyl-glycerol <> a cardiolipin + Glycerol glycerol 1-phosphate + Water Glycerol + Phosphate 2 Phosphatidylglycerol > diphosphatidylglycerol + Glycerol Glycerol + NAD > Dihydroxyacetone + NADH More...PS(14:0/18:1(11Z)) > Glycerol + a cardiolipin PG(18:0/18:0) + PG(18:0/18:0) > Glycerol + CL(16:0/16:0/16:0/16:1(9Z)) PG(18:2(9Z,12Z)/18:2(9Z,12Z)) > CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) + Glycerol 2 PG(18:1(9Z)/18:1(9Z)) > Glycerol + CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/18:1(9Z)) PG(14:0(3-OH)/15:0) > Glycerol + CL(15:0cyclo/15:0cyclo/14:0/16:0) PG(14:0/14:0) > Glycerol + cardiolipin (tetratetradecanoyl, n-C14:0) PG(14:0/16:0) > CL(14:0/16:0/14:0/16:0) + Glycerol 2 PG(16:1(9Z)/16:1(9Z)) > Glycerol + cardiolipin (tetrahexadec-9-enoyl, n-C16:1) PG(19:0cycv8c/19:iso) > Glycerol + CL(19:0cycv8c/19:0cycv8c/19:0cycv8c/19:0cycv8c) PG(15:0/16:1) > Glycerol + CL(15:0cyclo/15:0cyclo/15:0cyclo/15:0cyclo) 2 PG(10:0/19:iso) > Glycerol + CL(19:0cycv8c/14:0/14:0/17:0cycw7c) 2 PG(10:0/19:iso) > Glycerol + CL(19:0cycv8c/14:0/17:0cycw7c/14:0) 2 PG(16:0/14:0) > Glycerol + CL(19:0cycv8c/14:0/14:0/19:0cycv8c) 2 PG(16:0/14:0) > CL(19:0cycv8c/14:0/19:0cycv8c/14:0) + Glycerol 2 PG(16:0/14:0) > Glycerol + CL(19:0cycv8c/15:0cyclo/15:0cyclo/17:0cycw7c) 2 PG(16:0/14:0) > Glycerol + CL(19:0cycv8c/15:0cyclo/17:0cycw7c/15:0cyclo) 2 PG(10:0/19:iso) > Glycerol + CL(19:0cycv8c/17:0cycw7c/14:0/14:0) 2 PG(16:0/14:0) > Glycerol + CL(19:0cycv8c/19:0cycv8c/14:0/14:0) 2 PG(16:0/14:0) > Glycerol + CL(17:0cycw7c/18:1(9Z)/17:0cycw7c/14:0) 2 PG(10:0/19:iso) > Glycerol + CL(17:0cycw7c/19:0cycv8c/14:0/14:0) 2 PG(10:0/19:iso) > Glycerol + CL(18:1(9Z)/14:0/14:0/18:1(9Z)) 2 PG(16:0/14:0) > Glycerol + CL(18:1(9Z)/14:0/17:0cycw7c/17:0cycw7c) 2 PG(10:0/19:iso) > Glycerol + CL(18:1(9Z)/14:0/18:1(9Z)/14:0) 2 PG(14:0/14:0) > Glycerol + CL(18:1(9Z)/15:0cyclo/14:0/15:0cyclo) 2 PG(14:0/14:0) > Glycerol + CL(18:1(9Z)/15:0cyclo/15:0cyclo/14:0) 2 PG(16:0/14:0) > Glycerol + CL(18:1(9Z)/15:0cyclo/18:1(9Z)/15:0cyclo) 2 PG(14:0/14:0) > Glycerol + CL(18:1(9Z)/16:0/14:0/14:0) 2 PG(10:0/19:iso) > Glycerol + CL(18:1(9Z)/16:0/14:0/16:0) 2 PG(16:0/14:0) > Glycerol + CL(18:1(9Z)/16:0/14:0/18:1(9Z)) 2 PG(16:0/14:0) > Glycerol + CL(18:1(9Z)/16:0/18:1(9Z)/14:0) 2 PG(14:0/14:0) > Glycerol + CL(18:1(9Z)/16:1(9Z)/14:0/14:0) 2 PG(10:0/19:iso) > Glycerol + CL(18:1(9Z)/16:1(9Z)/14:0/16:1(9Z)) 2 PG(16:0/14:0) > Glycerol + CL(18:1(9Z)/16:1(9Z)/14:0/18:1(9Z)) 2 PG(10:0/19:iso) > Glycerol + CL(18:1(9Z)/16:1(9Z)/16:1(9Z)/14:0) 2 PG(16:0/14:0) > Glycerol + CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/14:0) 2 PG(16:0/14:0) > Glycerol + CL(18:1(9Z)/17:0cycw7c/14:0/17:0cycw7c) 2 PG(16:0/14:0) > Glycerol + CL(18:1(9Z)/17:0cycw7c/17:0cycw7c/14:0) 2 PG(10:0/19:iso) > Glycerol + CL(18:1(9Z)/18:1(9Z)/14:0/14:0) 2 PG(16:0/14:0) > Glycerol + CL(18:1(9Z)/18:1(9Z)/14:0/16:0) 2 PG(16:0/14:0) > Glycerol + CL(18:1(9Z)/18:1(9Z)/14:0/16:1(9Z)) 2 PG(10:0/19:iso) > Glycerol + CL(17:0cycw7c/16:1(9Z)/14:0/17:0cycw7c) 2 PG(10:0/19:iso) > Glycerol + CL(17:0cycw7c/16:1(9Z)/17:0cycw7c/14:0) 2 PG(16:0/14:0) > Glycerol + CL(17:0cycw7c/16:1(9Z)/17:0cycw7c/16:1(9Z)) 2 PG(10:0/19:iso) > Glycerol + CL(17:0cycw7c/17:0cycw7c/14:0/16:0) 2 PG(10:0/19:iso) > Glycerol + CL(17:0cycw7c/17:0cycw7c/14:0/16:1(9Z)) 2 PG(16:0/14:0) > Glycerol + CL(17:0cycw7c/18:1(9Z)/14:0/17:0cycw7c) 2 PG(16:1(9Z)/12:0(3-OH)) > Glycerol + CL(18:1(9Z)/15:0cyclo/14:0/15:0cyclo) 2 PG(14:0(3-OH)/14:0) > Glycerol + CL(18:1(9Z)/15:0cyclo/14:0/15:0cyclo) 2 PG(18:1(9Z)/16:0) > Glycerol + CL(18:1(9Z)/16:0/18:1(9Z)/16:0) 2 PG(18:1(9Z)/16:1(9Z)) > Glycerol + CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/16:1(9Z)) Glycerol + Adenosine triphosphate > Hydrogen ion + Adenosine diphosphate + Glycerol 3-phosphate + ADP 2 PG(10:0(3-OH)/10:0) > Glycerol + CL(10:0(3-OH)/10:0/10:0(3-OH)/10:0) 2 PG(10:0(3-OH)/12:0(3-OH)) > Glycerol + CL(10:0(3-OH)/12:0(3-OH)/10:0(3-OH)/12:0(3-OH)) 2 PG(10:0(3-OH)/12:0) > Glycerol + CL(10:0(3-OH)/12:0/10:0(3-OH)/12:0) 2 PG(10:0(3-OH)/15:0cyclo) > CL(10:0(3-OH)/15:0cyclo/10:0(3-OH)/15:0cyclo) + Glycerol 2 PG(10:0(3-OH)/16:0) > CL(10:0(3-OH)/16:0/10:0(3-OH)/16:0) + Glycerol 2 PG(10:0(3-OH)/16:1(9Z)) > Glycerol + CL(10:0(3-OH)/16:1(9Z)/10:0(3-OH)/16:1(9Z)) 2 PG(10:0(3-OH)/17:0cycw7c) > Glycerol + CL(10:0(3-OH)/17:0cycw7c/10:0(3-OH)/17:0cycw7c) 2 PG(10:0(3-OH)/19:0cycv8c) > Glycerol + CL(10:0(3-OH)/19:0cycv8c/10:0(3-OH)/19:0cycv8c) 2 PG(10:0(3-OH)/19:iso) > Glycerol + CL(10:0(3-OH)/19:iso/10:0(3-OH)/19:iso) 2 PG(10:0/10:0(3-OH)) > Glycerol + CL(10:0/10:0(3-OH)/10:0/10:0(3-OH)) 2 PG(10:0/12:0(3-OH)) > Glycerol + CL(10:0/12:0(3-OH)/10:0/12:0(3-OH)) 2 PG(12:0(3-OH)/10:0(3-OH)) > Glycerol + CL(12:0(3-OH)/10:0(3-OH)/12:0(3-OH)/10:0(3-OH)) 2 PG(12:0(3-OH)/10:0) > Glycerol + CL(12:0(3-OH)/10:0/12:0(3-OH)/10:0) 2 PG(12:0(3-OH)/14:0(3-OH)) > CL(12:0(3-OH)/14:0(3-OH)/12:0(3-OH)/14:0(3-OH)) + Glycerol 2 PG(12:0(3-OH)/14:0) > Glycerol + CL(12:0(3-OH)/14:0/12:0(3-OH)/14:0) 2 PG(12:0(3-OH)/15:0) > CL(12:0(3-OH)/15:0/12:0(3-OH)/15:0) + Glycerol 2 PG(12:0(3-OH)/15:0cyclo) > Glycerol + CL(12:0(3-OH)/15:0cyclo/12:0(3-OH)/15:0cyclo) 2 PG(12:0(3-OH)/17:0cycw7c) > Glycerol + CL(12:0(3-OH)/17:0cycw7c/12:0(3-OH)/17:0cycw7c) 2 PG(12:0(3-OH)/18:1(9Z)) > Glycerol + CL(12:0(3-OH)/18:1(9Z)/12:0(3-OH)/18:1(9Z)) 2 PG(12:0(3-OH)/19:0cycv8c) > Glycerol + CL(12:0(3-OH)/19:0cycv8c/12:0(3-OH)/19:0cycv8c) 2 PG(12:0(3-OH)/19:iso) > Glycerol + CL(12:0(3-OH)/19:iso/12:0(3-OH)/19:iso) 2 PG(12:0/10:0(3-OH)) > CL(12:0/10:0(3-OH)/12:0/10:0(3-OH)) + Glycerol 2 PG(12:0/12:0) > Glycerol + cardiolipin (tetradodecanoyl, n-C12:0) 2 PG(12:0/14:0(3-OH)) > Glycerol + CL(12:0/14:0(3-OH)/12:0/14:0(3-OH)) 2 PG(12:0/19:iso) > Glycerol + CL(12:0/19:iso/12:0/19:iso) 2 PG(14:0(3-OH)/12:0(3-OH)) > CL(14:0(3-OH)/12:0(3-OH)/14:0(3-OH)/12:0(3-OH)) + Glycerol 2 PG(14:0(3-OH)/12:0) > Glycerol + CL(14:0(3-OH)/12:0/14:0(3-OH)/12:0) 2 PG(14:0(3-OH)/16:1(9Z)) > Glycerol + CL(14:0(3-OH)/16:1(9Z)/14:0(3-OH)/16:1(9Z)) 2 PG(14:0(3-OH)/17:0cycw7c) > Glycerol + CL(14:0(3-OH)/17:0cycw7c/14:0(3-OH)/17:0cycw7c) 2 PG(14:0/12:0(3-OH)) > Glycerol + CL(14:0/12:0(3-OH)/14:0/12:0(3-OH)) 2 PG(15:0/10:0(3-OH)) > Glycerol + CL(15:0/10:0(3-OH)/15:0/10:0(3-OH)) 2 PG(15:0/12:0(3-OH)) > Glycerol + CL(15:0/12:0(3-OH)/15:0/12:0(3-OH)) 2 PG(15:0cyclo/10:0(3-OH)) > Glycerol + CL(15:0cyclo/10:0(3-OH)/15:0cyclo/10:0(3-OH)) 2 PG(16:0/10:0(3-OH)) > Glycerol + CL(16:0/10:0(3-OH)/16:0/10:0(3-OH)) 2 PG(16:0/14:0(3-OH)) > Glycerol + CL(16:0/14:0(3-OH)/16:0/14:0(3-OH)) 2 PG(16:1(9Z)/14:0(3-OH)) > Glycerol + CL(16:1(9Z)/14:0(3-OH)/16:1(9Z)/14:0(3-OH)) 2 PG(17:0cycw7c/10:0(3-OH)) > Glycerol + CL(17:0cycw7c/10:0(3-OH)/17:0cycw7c/10:0(3-OH)) 2 PG(17:0cycw7c/12:0(3-OH)) > Glycerol + CL(17:0cycw7c/12:0(3-OH)/17:0cycw7c/12:0(3-OH)) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synthesis Reference: | Yang, Yifang. Purification of glycerol. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 3pp. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Links: |
|
Enzymes
- General function:
- Involved in glycerophosphodiester phosphodiesterase activity
- Specific function:
- Glycerophosphoryl diester phosphodiesterase hydrolyzes deacylated phospholipids to G3P and the corresponding alcohols
- Gene Name:
- glpQ
- Locus Tag:
- PA0347
- Molecular weight:
- 42 kDa
Reactions
A glycerophosphodiester + H(2)O = an alcohol + sn-glycerol 3-phosphate. |
- General function:
- Involved in phosphotransferase activity, alcohol group as acceptor
- Specific function:
- Key enzyme in the regulation of glycerol uptake and metabolism
- Gene Name:
- glpK
- Locus Tag:
- PA3582
- Molecular weight:
- 56 kDa
Reactions
ATP + glycerol = ADP + sn-glycerol 3-phosphate. |
- General function:
- Involved in phosphatidylinositol phosphorylation
- Specific function:
- Myo-inositol phosphate + H(2)O = myo-inositol + phosphate
- Gene Name:
- suhB
- Locus Tag:
- PA3818
- Molecular weight:
- 29.5 kDa
Reactions
Myo-inositol phosphate + H(2)O = myo-inositol + phosphate. |
- General function:
- Involved in acid phosphatase activity
- Specific function:
- Dephosphorylates several organic phosphomonoesters and catalyzes the transfer of low-energy phosphate groups from phosphomonoesters to hydroxyl groups of various organic compounds. Preferentially acts on aryl phosphoesters. Might function as a broad-spectrum dephosphorylating enzyme able to scavenge both 3'- and 5'-nucleotides and also additional organic phosphomonoesters
- Gene Name:
- aphA
- Locus Tag:
- PA1409
- Molecular weight:
- 38 kDa
Reactions
A phosphate monoester + H(2)O = an alcohol + phosphate. |
- General function:
- Involved in zinc ion binding
- Specific function:
- Has high formaldehyde dehydrogenase activity in the presence of glutathione and catalyzes the oxidation of normal alcohols in a reaction that is not GSH-dependent. In addition, hemithiolacetals other than those formed from GSH, including omega-thiol fatty acids, also are substrates
- Gene Name:
- frmA
- Locus Tag:
- PA3629
- Molecular weight:
- 39.2 kDa
Reactions
S-(hydroxymethyl)glutathione + NAD(P)(+) = S-formylglutathione + NAD(P)H. |
An alcohol + NAD(+) = an aldehyde or ketone + NADH. |
- General function:
- Involved in phosphotransferase activity, for other substituted phosphate groups
- Specific function:
- Catalyzes the reversible phosphatidyl group transfer from one phosphatidylglycerol molecule to another to form cardiolipin (CL) (diphosphatidylglycerol) and glycerol. Affects resistance to the gyrase inhibitor novobiocin
- Gene Name:
- cls
- Locus Tag:
- PA5394
- Molecular weight:
- 54.6 kDa
Reactions
2 Phosphatidylglycerol = diphosphatidylglycerol + glycerol. |
- General function:
- Involved in catalytic activity
- Specific function:
- Catalyzes, in vitro, the phosphatidyl group transfer from one phosphatidylglycerol molecule to another to form cardiolipin (CL) (diphosphatidylglycerol) and glycerol. Can also catalyze phosphatidyl group transfer to water to form phosphatidate. Catalyzes little, if any, cardiolipin synthesis in vivo, even when the expression level is very high
- Gene Name:
- ybhO
- Locus Tag:
- PA2155
- Molecular weight:
- 46.5 kDa
Reactions
2 Phosphatidylglycerol = diphosphatidylglycerol + glycerol. |
Transporters
- General function:
- Involved in transporter activity
- Specific function:
- Transporter of glycerol across the cytoplasmic membrane, with limited permeability to water and small uncharged compounds such as polyols
- Gene Name:
- glpF
- Locus Tag:
- PA3581
- Molecular weight:
- 28.9 kDa