Details of the Drug

General Information of Drug (ID: DM5D9YK)

Drug Name
Choline
Synonyms
choline; Choline ion; Bilineurine; Choline cation; Cholinum; 2-Hydroxy-N,N,N-trimethylethanaminium; 62-49-7; (2-Hydroxyethyl)trimethylammonium; trimethylethanolamine; N-trimethylethanolamine; Ethanaminium, 2-hydroxy-N,N,N-trimethyl-; CCRIS 5847; UNII-N91BDP6H0X; AI3-24208; BRN 1736748; N,N,N-trimethylethanol-ammonium; CHEBI:15354; (beta-hydroxyethyl)trimethylammonium; EINECS 200-535-1; CHEMBL920; N91BDP6H0X; 2-hydroxyethyl(trimethyl)ammonium
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 104.17
Topological Polar Surface Area (xlogp) -0.4
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 1
Chemical Identifiers
Formula
C5H14NO+
IUPAC Name
2-hydroxyethyl(trimethyl)azanium
Canonical SMILES
C[N+](C)(C)CCO
InChI
InChI=1S/C5H14NO/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3/q+1
InChIKey
OEYIOHPDSNJKLS-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
305
ChEBI ID
CHEBI:15354
CAS Number
62-49-7
DrugBank ID
DB00122
TTD ID
D08DAE
VARIDT ID
DR00121
INTEDE ID
DR0315

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Neuronal acetylcholine receptor alpha-2 (CHRNA2) TTF4E0J ACHA2_HUMAN Inhibitor [2]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Choline transporter-like protein 5 (SLC44A5) DTU8NCX CTL5_HUMAN Substrate [3]
Choline transporter-like protein 2 (SLC44A2) DTSF91X CTL2_HUMAN Substrate [4]
Choline transporter-like protein 4 (SLC44A4) DT8KXR9 CTL4_HUMAN Substrate [5]
Na(+)/Cl(-) betaine/GABA transporter (SLC6A12) DTBPTJF S6A12_HUMAN Substrate [6]
Choline transporter-like protein 1 (SLC44A1) DT3I2SU CTL1_HUMAN Substrate [7]
Organic cation transporter 1 (SLC22A1) DTT79CX S22A1_HUMAN Substrate [8]
Organic cation transporter 2 (SLC22A2) DT9IDPW S22A2_HUMAN Substrate [9]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Choline O-acetyltransferase (CHAT) DE5NGOW CLAT_HUMAN Substrate [10]
Choline/ethanolaminephosphotransferase 1 (CEPT1) DEL87ZT CEPT1_HUMAN Substrate [11]
Choline kinase alpha (CHKA) DEMRAYN CHKA_HUMAN Substrate [12]
Choline dehydrogenase (CHDH) DEAHED0 CHDH_HUMAN Substrate [13]
Choline/ethanolamine kinase (CHKB) DEHWR6V CHKB_HUMAN Substrate [12]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4551).
2 Pharmacology of the agonist binding sites of rat neuronal nicotinic receptor subtypes expressed in HEK 293 cells. Bioorg Med Chem Lett. 2004 Apr 19;14(8):1845-8.
3 The molecular effects of a polymorphism in the 5'UTR of solute carrier family 44, member 5 that is associated with birth weight in Holsteins. PLoS One. 2012;7(7):e41267.
4 The choline transporter-like family SLC44: properties and roles in human diseases. Mol Aspects Med. 2013 Apr-Jun;34(2-3):646-54.
5 SLC44A4 mutation causes autosomal dominant hereditary postlingual non-syndromic mid-frequency hearing loss. Hum Mol Genet. 2017 Jan 15;26(2):383-394.
6 Interpreting metabolomic profiles using unbiased pathway models. PLoS Comput Biol. 2010 Feb 26;6(2):e1000692.
7 Decreased biosynthesis of lung surfactant constituent phosphatidylcholine due to inhibition of choline transporter by gefitinib in lung alveolar cells. Pharm Res. 2008 Feb;25(2):417-27.
8 Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007.
9 Ventricular choline transport: a role for organic cation transporter 2 expressed in choroid plexus. J Biol Chem. 2001 Nov 9;276(45):41611-9.
10 The effect of trichlorfon and methylazoxymethanol on the development of guinea pig cerebellum. Toxicol Appl Pharmacol. 2007 Mar;219(2-3):128-35.
11 PC and PE synthesis: mixed micellar analysis of the cholinephosphotransferase and ethanolaminephosphotransferase activities of human choline/ethanolamine phosphotransferase 1 (CEPT1). Lipids. 2002 Jul;37(7):663-72.
12 Crystal structures of human choline kinase isoforms in complex with hemicholinium-3: single amino acid near the active site influences inhibitor sensitivity. J Biol Chem. 2010 May 21;285(21):16330-40.
13 Usual choline and betaine dietary intake and incident coronary heart disease: the atherosclerosis risk in communities (ARIC) study. BMC Cardiovasc Disord. 2007 Jul 13;7:20.
14 Are organic cation transporters capable of transporting prostaglandins? Naunyn Schmiedebergs Arch Pharmacol. 2005 Aug;372(2):125-30.
15 Cisplatin nephrotoxicity is critically mediated via the human organic cation transporter 2. Am J Pathol. 2005 Dec;167(6):1477-84.
16 Relevance of copper transporter 1 and organic cation transporters 1-3 for oxaliplatin uptake and drug resistance in colorectal cancer cells. Metallomics. 2018 Mar 1;10(3):414-425.
17 Cloning and characterization of two human polyspecific organic cation transporters. DNA Cell Biol. 1997 Jul;16(7):871-81.
18 Differential pharmacological in vitro properties of organic cation transporters and regional distribution in rat brain. Neuropharmacology. 2006 Jun;50(8):941-52.
19 Influx Transport of Cationic Drug at the Blood-Retinal Barrier: Impact on the Retinal Delivery of Neuroprotectants. Biol Pharm Bull. 2017;40(8):1139-1145.
20 The organic cation transporters (OCT1, OCT2, EMT) and the plasma membrane monoamine transporter (PMAT) show differential distribution and cyclic expression pattern in human endometrium and early pregnancy decidua. Mol Reprod Dev. 2007 Oct;74(10):1303-11.
21 Metformin is a superior substrate for renal organic cation transporter OCT2 rather than hepatic OCT1. Drug Metab Pharmacokinet. 2005 Oct;20(5):379-86.
22 A species difference in the transport activities of H2 receptor antagonists by rat and human renal organic anion and cation transporters. J Pharmacol Exp Ther. 2005 Oct;315(1):337-45.
23 Cisplatin and oxaliplatin, but not carboplatin and nedaplatin, are substrates for human organic cation transporters (SLC22A1-3 and multidrug and toxin extrusion family). J Pharmacol Exp Ther. 2006 Nov;319(2):879-86.
24 Pharmacologic markers and predictors of responses to imatinib therapy in patients with chronic myeloid leukemia. Leuk Lymphoma. 2008 Apr;49(4):639-42.
25 Organic cation transporters are determinants of oxaliplatin cytotoxicity. Cancer Res. 2006 Sep 1;66(17):8847-57.
26 Implications of genetic polymorphisms in drug transporters for pharmacotherapy. Cancer Lett. 2006 Mar 8;234(1):4-33.
27 Upregulation of histone acetylation reverses organic anion transporter 2 repression and enhances 5-fluorouracil sensitivity in hepatocellular carcinoma
28 Comparison of type I and type II organic cation transport by organic cation transporters and organic anion-transporting polypeptides. J Pharmacol Exp Ther. 2001 Jul;298(1):110-5.
29 Organic cation transporters and their pharmacokinetic and pharmacodynamic consequences. Drug Metab Pharmacokinet. 2008;23(4):243-53.
30 Choline transporter-like protein 4 (CTL4) links to non-neuronal acetylcholine synthesis. J Neurochem. 2013 Aug;126(4):451-61.
31 Molecular identification and functional characterization of the human colonic thiamine pyrophosphate transporter. J Biol Chem. 2017 Oct 6;292(40):16526.
32 The Transporter Classification Database (TCDB): recent advances. Nucleic Acids Res. 2016 Jan 4;44(D1):D372-9. (ID: 2.A.22.3.1)
33 Deletion of the betaine-GABA transporter (BGT1; slc6a12) gene does not affect seizure thresholds of adult mice. Epilepsy Res. 2011 Jun;95(1-2):70-81.
34 Pharmacological characteristics of the inhibition of nondepolarizing neuromuscular blocking agents at human adult muscle nicotinic acetylcholine receptor. Anesthesiology. 2009 Jun;110(6):1244-52.
35 Synergy between pairs of competitive antagonists at adult human muscle acetylcholine receptors. Anesth Analg. 2008 Aug;107(2):525-33.
36 Synthesis and pharmacological evaluation of novel 9- and 10-substituted cytisine derivatives. Nicotinic ligands of enhanced subtype selectivity. J Med Chem. 2006 May 4;49(9):2673-6.
37 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 463).