Human Metabolome Database Version 3.5

Showing metabocard for Acetylcholine (HMDB00895)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:29:34 -0600
HMDB ID HMDB00895
Secondary Accession Numbers None
Metabolite Identification
Common Name Acetylcholine
Description Acetylcholine (ACh) is a neurotransmitter. Acetylcholine in vertebrates is the major transmitter at neuromuscular junctions, autonomic ganglia, parasympathetic effector junctions, a subset of sympathetic effector junctions, and at many sites in the central nervous system. Its physiological and pharmacological effects, metabolism, release, and receptors have been well documented in several species. ACh has been considered an important excitatory neurotransmitter in the carotid body (CB). Various nicotinic and muscarinic ACh receptors are present in both afferent nerve endings and glomus cells. Therefore, ACh can depolarize or hyperpolarize the cell membrane depending on the available receptor type in the vicinity. Binding of ACh to its receptor can create a wide variety of cellular responses including opening cation channels (nicotinic ACh receptor activation), releasing Ca2+ from intracellular storage sites (via muscarinic ACh receptors), and modulating activities of K+ and Ca2+ channels. Interactions between ACh and other neurotransmitters (dopamine, adenosine, nitric oxide) have been known, and they may induce complicated responses. Cholinergic biology in the CB differs among species and even within the same species due to different genetic composition. Development and environment influence cholinergic biology. Pharmacological data clearly indicate that both muscarinic and nicotinic acetylcholine receptors have a role in the encoding of new memories. Localized lesions and antagonist infusions demonstrate the anatomical locus of these cholinergic effects, and computational modeling links the function of cholinergic modulation to specific cellular effects within these regions. Acetylcholine has been shown to increase the strength of afferent input relative to feedback, to contribute to theta rhythm oscillations, activate intrinsic mechanisms for persistent spiking, and increase the modification of synapses. These effects might enhance different types of encoding in different cortical structures. In particular, the effects in entorhinal and perirhinal cortex and hippocampus might be important for encoding new episodic memories. The role of ACh in attention has been repeatedly demonstrated in several tasks. Acetylcholine is linked to response accuracy in voluntary and reflexive attention and also to response speed in reflexive attention. It is well known that those with Attention-deficit/hyperactivity disorders tend to be inaccurate and slow to respond. (PMID: 17284361 Link_out, 17011181 Link_out, 15556286 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Acetyl choline ion
  2. Acetylcholine cation
  3. Acetylcholinium: acetyl-Choline
  4. ACh
  5. Choline acetate
  6. Choline acetate (ester)
  7. O-Acetylcholine
Chemical Formula C7H16NO2
Average Molecular Weight 146.2074
Monoisotopic Molecular Weight 146.118103761
IUPAC Name [2-(acetyloxy)ethyl]trimethylazanium
Traditional IUPAC Name acetylcholine
CAS Registry Number 51-84-3
SMILES CC(=O)OCC[N+](C)(C)C
InChI Identifier InChI=1S/C7H16NO2/c1-7(9)10-6-5-8(2,3)4/h5-6H2,1-4H3/q+1
InChI Key OIPILFWXSMYKGL-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aliphatic Acyclic Compounds
Class Alcohols and Polyols
Sub Class Cholines
Other Descriptors
  • Acetylcholine(KEGG)
  • a small molecule(Cyc)
  • acetate ester(ChEBI)
  • acylcholine(ChEBI)
Substituents
  • Carboxylic Acid Ester
  • Quaternary Ammonium Salt
Direct Parent Cholines
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Glycerophospholipid metabolism
Application Not Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Nucleus
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 148 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
LogP -2.91 ALOGPS
LogP -4.2 ChemAxon
LogS -3.13 ALOGPS
pKa (strongest basic) -7 ChemAxon
Hydrogen Acceptor Count 1 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 26.3 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 51.35 ChemAxon
Polarizability 16.83 ChemAxon
Formal Charge 1 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters)
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Nucleus
Biofluid Locations
  • Cerebrospinal Fluid (CSF)
Tissue Location
  • Muscle
  • Skeletal Muscle
  • Bladder
  • Fibroblasts
  • Intestine
  • Neuron
  • Pancreas
  • Placenta
  • Testes
  • Kidney
  • Brain
  • Myelin
  • Prostate
  • Skin
  • Adipose Tissue
  • Adrenal Medulla
  • Lung
  • Nerve Cells
  • Platelet
  • Spleen
Pathways
Name SMPDB Link KEGG Link
Phospholipid Biosynthesis SMP00025 map00564 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Cerebrospinal Fluid (CSF) Detected and Quantified
0.034 +/- 0.009 uM Adult (>18 years old) Not Specified Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Cerebrospinal Fluid (CSF) Detected and Quantified 0.01 +/- 0.005 uM Adult (>18 years old) Not Specified Alzheimer's disease
Cerebrospinal Fluid (CSF) Detected and Quantified 0.016 +/- 0.007 uM Adult (>18 years old) Not Specified Vascular dementia
Associated Disorders and Diseases
Disease References
Alzheimer's disease
  • Jia JP, Jia JM, Zhou WD, Xu M, Chu CB, Yan X, Sun YX: Differential acetylcholine and choline concentrations in the cerebrospinal fluid of patients with Alzheimer's disease and vascular dementia. Chin Med J (Engl). 2004 Aug;117(8):1161-4. Pubmed: 15361288 Link_out
      Multi-infarct dementia
      • Jia JP, Jia JM, Zhou WD, Xu M, Chu CB, Yan X, Sun YX: Differential acetylcholine and choline concentrations in the cerebrospinal fluid of patients with Alzheimer's disease and vascular dementia. Chin Med J (Engl). 2004 Aug;117(8):1161-4. Pubmed: 15361288 Link_out
          Associated OMIM IDs
          DrugBank ID Not Available
          DrugBank Metabolite ID Not Available
          Phenol Explorer Compound ID Not Available
          Phenol Explorer Metabolite ID Not Available
          FoodDB ID FDB012191
          KNApSAcK ID Not Available
          Chemspider ID 182 Link_out
          KEGG Compound ID C01996 Link_out
          BioCyc ID ACETYLCHOLINE Link_out
          BiGG ID 38868 Link_out
          Wikipedia Link Acetylcholine Link_out
          NuGOwiki Link HMDB00895 Link_out
          Metagene Link HMDB00895 Link_out
          METLIN ID 57 Link_out
          PubChem Compound 187 Link_out
          PDB ID ACH Link_out
          ChEBI ID 15355 Link_out
          References
          Synthesis Reference Szutowicz, Andrzej. Acetylcholine synthesis in synaptosomes. Postepy Biochemii (1979), 25(1), 59-84.
          Material Safety Data Sheet (MSDS) Download (PDF)
          General References
          1. Nguyen VT, Ndoye A, Hall LL, Zia S, Arredondo J, Chernyavsky AI, Kist DA, Zelickson BD, Lawry MA, Grando SA: Programmed cell death of keratinocytes culminates in apoptotic secretion of a humectant upon secretagogue action of acetylcholine. J Cell Sci. 2001 Mar;114(Pt 6):1189-204. Pubmed: 11228162 Link_out
          2. Chia S, Megson IL, Ludlam CA, Fox KA, Newby DE: Preserved endothelial vasomotion and fibrinolytic function in patients with acute stent thrombosis or in-stent restenosis. Thromb Res. 2003;111(6):343-9. Pubmed: 14698651 Link_out
          3. Grando SA, Kist DA, Qi M, Dahl MV: Human keratinocytes synthesize, secrete, and degrade acetylcholine. J Invest Dermatol. 1993 Jul;101(1):32-6. Pubmed: 8331294 Link_out
          4. Beilin B, Bessler H, Papismedov L, Weinstock M, Shavit Y: Continuous physostigmine combined with morphine-based patient-controlled analgesia in the postoperative period. Acta Anaesthesiol Scand. 2005 Jan;49(1):78-84. Pubmed: 15675987 Link_out
          5. Tao J, Jin YF, Yang Z, Wang LC, Gao XR, Lui L, Ma H: Reduced arterial elasticity is associated with endothelial dysfunction in persons of advancing age: comparative study of noninvasive pulse wave analysis and laser Doppler blood flow measurement. Am J Hypertens. 2004 Aug;17(8):654-9. Pubmed: 15288882 Link_out
          6. Jiang JL, Jiang DJ, Tang YH, Li NS, Deng HW, Li YJ: Effect of simvastatin on endothelium-dependent vaso-relaxation and endogenous nitric oxide synthase inhibitor. Acta Pharmacol Sin. 2004 Jul;25(7):893-901. Pubmed: 15210062 Link_out
          7. Haug KH, Bogen IL, Osmundsen H, Walaas I, Fonnum F: Effects on cholinergic markers in rat brain and blood after short and prolonged administration of donepezil. Neurochem Res. 2005 Dec;30(12):1511-20. Pubmed: 16362770 Link_out
          8. Katoh H, Shimada T, Inoue S, Takahashi N, Shimizu H, Ohta Y, Nakamura K, Murakami Y, Ishibashi Y, Matsumori A: Reduced high serum hepatocyte growth factor levels after successful cardioversion in patients with atrial fibrillation. Clin Exp Pharmacol Physiol. 2004 Mar;31(3):145-51. Pubmed: 15008956 Link_out
          9. Main C, Blennerhassett P, Collins SM: Human recombinant interleukin 1 beta suppresses acetylcholine release from rat myenteric plexus. Gastroenterology. 1993 Jun;104(6):1648-54. Pubmed: 8500722 Link_out
          10. Ikarashi Y, Harigaya Y, Tomidokoro Y, Kanai M, Ikeda M, Matsubara E, Kawarabayashi T, Kuribara H, Younkin SG, Maruyama Y, Shoji M: Decreased level of brain acetylcholine and memory disturbance in APPsw mice. Neurobiol Aging. 2004 Apr;25(4):483-90. Pubmed: 15013569 Link_out
          11. Katz SD, Krum H: Acetylcholine-mediated vasodilation in the forearm circulation of patients with heart failure: indirect evidence for the role of endothelium-derived hyperpolarizing factor. Am J Cardiol. 2001 May 1;87(9):1089-92. Pubmed: 11348607 Link_out
          12. Hanna ST, Cao K, Wang R: Interaction of acetylcholine with Kir6.1 channels heterologously expressed in human embryonic kidney cells. Eur J Pharmacol. 2005 May 16;515(1-3):34-42. Pubmed: 15894309 Link_out
          13. Greig NH, Utsuki T, Ingram DK, Wang Y, Pepeu G, Scali C, Yu QS, Mamczarz J, Holloway HW, Giordano T, Chen D, Furukawa K, Sambamurti K, Brossi A, Lahiri DK: Selective butyrylcholinesterase inhibition elevates brain acetylcholine, augments learning and lowers Alzheimer beta-amyloid peptide in rodent. Proc Natl Acad Sci U S A. 2005 Nov 22;102(47):17213-8. Epub 2005 Nov 7. Pubmed: 16275899 Link_out
          14. Shirahata M, Balbir A, Otsubo T, Fitzgerald RS: Role of acetylcholine in neurotransmission of the carotid body. Respir Physiol Neurobiol. 2007 Jul 1;157(1):93-105. Epub 2007 Jan 11. Pubmed: 17284361 Link_out
          15. Hasselmo ME: The role of acetylcholine in learning and memory. Curr Opin Neurobiol. 2006 Dec;16(6):710-5. Epub 2006 Sep 29. Pubmed: 17011181 Link_out
          16. Beane M, Marrocco RT: Norepinephrine and acetylcholine mediation of the components of reflexive attention: implications for attention deficit disorders. Prog Neurobiol. 2004 Oct;74(3):167-81. Pubmed: 15556286 Link_out

          Enzymes
          Name: Choline O-acetyltransferase
          Reactions:
          Acetyl-CoA + Choline unknown Coenzyme A + Acetylcholine details
          Gene Name: CHAT
          Uniprot ID: P28329 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Acetylcholinesterase
          Reactions:
          Acetylcholine + Water unknown Choline + Acetic acid details
          Gene Name: ACHE
          Uniprot ID: P22303 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Cholinesterase
          Reactions: Not Available
          Gene Name: BCHE
          Uniprot ID: P06276 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA