You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.
Identification
YMDB IDYMDB00227
NameCholine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionCholine, also known as bilineurine or choline ion, belongs to the class of organic compounds known as cholines. These are organic compounds containing a N,N,N-trimethylethanolammonium cation. Choline is an extremely weak basic (essentially neutral) compound (based on its pKa). Choline exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
  • (2-Hydroxyethyl)trimethyl ammonium
  • (2-Hydroxyethyl)trimethylammonium
  • (beta-hydroxyethyl)trimethylammonium
  • 2-hydroxy-N,N,N-trimethyl-ethanaminium
  • 2-hydroxy-N,N,N-trimethylethanaminium
  • Bilineurine
  • Biocolina
  • Biocoline
  • Choline
  • Choline cation
  • Choline ion
  • Cholinum
  • Hepacholine
  • Hormocline
  • Lipotril
  • N,N,N-trimethylethanol-ammonium
  • N,N,N-trimethylethanolammonium
  • Neocolina
  • Paresan
  • N-Trimethylethanolamine
  • Trimethylethanolamine
  • Choline O-sulfate
  • Citrate, choline
  • Fagine
  • Hydroxide, choline
  • Vidine
  • Bursine
  • Chloride, choline
  • Choline chloride
  • Choline citrate
  • Bitartrate, choline
  • Choline bitartrate
  • Choline hydroxide
  • Choline O sulfate
  • O-Sulfate, choline
CAS number62-49-7
WeightAverage: 104.1708
Monoisotopic: 104.107539075
InChI KeyOEYIOHPDSNJKLS-UHFFFAOYSA-N
InChIInChI=1S/C5H14NO/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3/q+1
IUPAC Name(2-hydroxyethyl)trimethylazanium
Traditional IUPAC Namecholine
Chemical FormulaC5H14NO
SMILES[H]OC([H])([H])C([H])([H])[N+](C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as cholines. These are organic compounds containing a N,N,N-trimethylethanolammonium cation.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassQuaternary ammonium salts
Direct ParentCholines
Alternative Parents
Substituents
  • Choline
  • Tetraalkylammonium salt
  • 1,2-aminoalcohol
  • Alkanolamine
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic salt
  • Primary alcohol
  • Organooxygen compound
  • Amine
  • Alcohol
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge1
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility3.61 g/LALOGPS
logP-3.6ALOGPS
logP-4.7ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)13.97ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity42.19 m³·mol⁻¹ChemAxon
Polarizability12.57 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • cell envelope
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Choline metabolismPW002494 ThumbThumb?image type=greyscaleThumb?image type=simple
Glycerophospholipid metabolismPW002493 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into ERPW002532 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into ER PC(10:0/10:0)PW002780 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into ER PC(14:0/14:0)PW002783 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Glycerophospholipid metabolismec00564 Map00564
Glycine, serine and threonine metabolismec00260 Map00260
SMPDB Reactions
PC(16:0/16:0) + waterCholine + hydron + PA(16:0/16:0)
Glycerophosphocholine + waterhydron + Glycerol 3-phosphate + Choline
Glycerophosphocholine + waterEthanol + Choline
Choline + Adenosine triphosphateADP + hydron + Phosphorylcholine
KEGG Reactions
Adenosine triphosphate + CholinePhosphorylcholine + hydron + ADP
water + GlycerophosphocholineGlycerol 3-phosphate + Choline + hydron
phosphatidylcholine + waterLPA(16:0/0:0) + Choline
Concentrations
Intracellular ConcentrationsNot Available
Extracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
970 ± 0 µM hops, malted barleyanaerobicBaker's yeastAlcoholic beverage, beer, regular, all - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page
547 ± 0 µM grape juiceanaerobicBaker's yeastAlcoholic beverage, wine, table, red - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page
Conversion Details Here
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
  • McMaster, C. R., Bell, R. M. (1994). "Phosphatidylcholine biosynthesis in Saccharomyces cerevisiae. Regulatory insights from studies employing null and chimeric sn-1,2-diacylglycerol choline- and ethanolaminephosphotransferases." J Biol Chem 269:28010-28016.7961735
  • Alcoholic beverage, beer, regular, all - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page
  • Alcoholic beverage, wine, table, red - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page
  • Rose, K., Rudge, S. A., Frohman, M. A., Morris, A. J., Engebrecht, J. (1995). "Phospholipase D signaling is essential for meiosis." Proc Natl Acad Sci U S A 92:12151-12155.8618862
  • 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
  • Kim, K., Kim, K. H., Storey, M. K., Voelker, D. R., Carman, G. M. (1999). "Isolation and characterization of the Saccharomyces cerevisiae EKI1 gene encoding ethanolamine kinase." J Biol Chem 274:14857-14866.10329685
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.
External Links:
ResourceLink
CHEBI ID15354
HMDB IDHMDB00097
Pubchem Compound ID305
Kegg IDC00114
ChemSpider ID73580
FOODB IDFDB000710
WikipediaCholine
BioCyc IDCPD-563

Enzymes

General function:
Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:
Responsible for phosphatidylcholine synthesis via the CDP-choline pathway. Also exhibits ethanolamine kinase activity but at 14% efficiency compared with choline
Gene Name:
CKI1
Uniprot ID:
P20485
Molecular weight:
66316.0
Reactions
ATP + choline → ADP + O-phosphocholine.
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 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 protein binding
Specific function:
Required for meiosis and spore formation. Seems to be involved in the coordinate induction of late meiotic events. PLD activity is induced under sporulation conditions and seems to be necessary to complete the meiotic cycle, but not for vegetative cell growth
Gene Name:
SPO14
Uniprot ID:
P36126
Molecular weight:
195202.0
Reactions
A phosphatidylcholine + H(2)O → choline + a phosphatidate.

Transporters

General function:
Involved in transport
Specific function:
Sole choline transporter in yeast
Gene Name:
HNM1
Uniprot ID:
P19807
Molecular weight:
62055.39844