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Choline (ECMDB00097) (M2MDB000036)
Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 09:57:14 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-09-13 12:56:06 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | Choline | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | Choline is a trimethylammonium compound. Choine can be used as a substrate by bacteria to generate osmoprotectants. Choline dehydrogenase (CHD) catalyzes the first step in the biosynthesis of the osmoprotectant glycine betaine from choline. CHD is associated with the membrane, is electron transfer-linked and oxygen dependent. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C5H14NO | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 104.1708 Monoisotopic: 104.107539075 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | OEYIOHPDSNJKLS-UHFFFAOYSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C5H14NO/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3/q+1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 62-49-7 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | (2-hydroxyethyl)trimethylazanium | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | choline | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | C[N+](C)(C)CCO | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | belongs to the class of organic compounds known as cholines. These are organic compounds containing a N,N,N-trimethylethanolammonium cation. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Organic nitrogen compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Organonitrogen compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Quaternary ammonium salts | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Cholines | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Alternative Parents | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Substituents |
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Molecular Framework | Aliphatic acyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors |
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Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | 1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | 302-303 °C (Chloride salt) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | Adenosine triphosphate + Water + Choline > ADP + Choline + Hydrogen ion + Phosphate Adenosine triphosphate + Water + Choline > ADP + Choline + Hydrogen ion + Phosphate Choline + NAD > Betaine aldehyde + Hydrogen ion + NADH Glycerophosphocholine + Water > Choline + Glycerol 3-phosphate + Hydrogen ion Choline + Acceptor + Acceptor <> Betaine aldehyde + Reduced acceptor + Reduced acceptor Glycerophosphocholine + Water <> Choline + Glycerol 3-phosphate Choline + an oxidized electron acceptor > Betaine aldehyde + a reduced electron acceptor Choline + acceptor > Betaine aldehyde + reduced acceptor Glycerophosphocholine + Water > Choline + Glycerol 3-phosphate + Hydrogen ion Choline + Acceptor <> Betaine aldehyde + Reduced acceptor Glycerophosphocholine + Water > Choline + Glycerol 3-phosphate + Hydrogen ion Choline + Acceptor <> Betaine aldehyde + Reduced acceptor | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
KEGG Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
EcoCyc Pathways: |
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Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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Synthesis Reference: | Hasegawa, Yoichi; Hyoda, Shunji; Sawada, Hirotoshi; Baba, Masakatsu. Preparation of high-purity organic carboxylic acid choline salts and choline. Jpn. Kokai Tokkyo Koho (1999), 9 pp. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Links: |
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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
- Uniprot ID:
- P09394
- Molecular weight:
- 40843
Reactions
A glycerophosphodiester + H(2)O = an alcohol + sn-glycerol 3-phosphate. |
- General function:
- Involved in glycerophosphodiester phosphodiesterase activity
- Specific function:
- Glycerophosphoryl diester phosphodiesterase hydrolyzes deacylated phospholipids to G3P and the corresponding alcohols
- Gene Name:
- ugpQ
- Uniprot ID:
- P10908
- Molecular weight:
- 27409
Reactions
A glycerophosphodiester + H(2)O = an alcohol + sn-glycerol 3-phosphate. |
- General function:
- Involved in choline dehydrogenase activity
- Specific function:
- Can catalyze the oxidation of choline to betaine aldehyde and betaine aldehyde to glycine betaine at the same rate
- Gene Name:
- betA
- Uniprot ID:
- P17444
- Molecular weight:
- 61877
Reactions
Choline + acceptor = betaine aldehyde + reduced acceptor. |
- General function:
- Involved in transporter activity
- Specific function:
- May be part of an ABC transporter complex involved in uptake of osmoprotectant molecules. Probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- yehW
- Uniprot ID:
- P33359
- Molecular weight:
- 25514
- General function:
- Involved in transporter activity
- Specific function:
- May be part of an ABC transporter complex involved in uptake of osmoprotectant molecules. Probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- yehY
- Uniprot ID:
- P33361
- Molecular weight:
- 41138
- General function:
- Involved in nucleotide binding
- Specific function:
- May be part of an ABC transporter complex involved in uptake of osmoprotectant molecules. Probably responsible for energy coupling to the transport system
- Gene Name:
- yehX
- Uniprot ID:
- P33360
- Molecular weight:
- 34424
- General function:
- Involved in transporter activity
- Specific function:
- May be part of an ABC transporter complex involved in uptake of osmoprotectant molecules
- Gene Name:
- osmF
- Uniprot ID:
- P33362
- Molecular weight:
- 32609
Transporters
- General function:
- Involved in transporter activity
- Specific function:
- Probable transporter whose substrate is unknown. Is not involved in aerobic D-malate transport
- Gene Name:
- yeaV
- Uniprot ID:
- P0ABD1
- Molecular weight:
- 52881
- General function:
- Involved in transporter activity
- Specific function:
- May be part of an ABC transporter complex involved in uptake of osmoprotectant molecules. Probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- yehW
- Uniprot ID:
- P33359
- Molecular weight:
- 25514
- General function:
- Involved in transporter activity
- Specific function:
- May be part of an ABC transporter complex involved in uptake of osmoprotectant molecules. Probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- yehY
- Uniprot ID:
- P33361
- Molecular weight:
- 41138
- General function:
- Involved in transporter activity
- Specific function:
- Non-specific porin
- Gene Name:
- ompN
- Uniprot ID:
- P77747
- Molecular weight:
- 41220
- General function:
- Involved in transporter activity
- Specific function:
- High-affinity uptake of choline driven by a proton- motive force
- Gene Name:
- betT
- Uniprot ID:
- P0ABC9
- Molecular weight:
- 75842
- General function:
- Involved in nucleotide binding
- Specific function:
- May be part of an ABC transporter complex involved in uptake of osmoprotectant molecules. Probably responsible for energy coupling to the transport system
- Gene Name:
- yehX
- Uniprot ID:
- P33360
- Molecular weight:
- 34424
- General function:
- Involved in transporter activity
- Specific function:
- Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
- Gene Name:
- phoE
- Uniprot ID:
- P02932
- Molecular weight:
- 38922
- General function:
- Involved in transporter activity
- Specific function:
- OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
- Gene Name:
- ompF
- Uniprot ID:
- P02931
- Molecular weight:
- 39333
- General function:
- Involved in transporter activity
- Specific function:
- May be part of an ABC transporter complex involved in uptake of osmoprotectant molecules
- Gene Name:
- osmF
- Uniprot ID:
- P33362
- Molecular weight:
- 32609
- General function:
- Involved in transporter activity
- Specific function:
- Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
- Gene Name:
- ompC
- Uniprot ID:
- P06996
- Molecular weight:
- 40368