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
Insomnia 7A00-7A0Z Approved [1]
Leukemia N.A. Approved [1]
Discovery agent N.A. Investigative [2]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 104.17
Logarithm of the Partition Coefficient (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
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

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 [3]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Choline transporter-like protein 5 (SLC44A5) DTU8NCX CTL5_HUMAN Substrate [4]
Choline transporter-like protein 2 (SLC44A2) DTSF91X CTL2_HUMAN Substrate [5]
Choline transporter-like protein 4 (SLC44A4) DT8KXR9 CTL4_HUMAN Substrate [6]
Na(+)/Cl(-) betaine/GABA transporter (SLC6A12) DTBPTJF S6A12_HUMAN Substrate [7]
Choline transporter-like protein 1 (SLC44A1) DT3I2SU CTL1_HUMAN Substrate [8]
Organic cation transporter 1 (SLC22A1) DTT79CX S22A1_HUMAN Substrate [9]
Organic cation transporter 2 (SLC22A2) DT9IDPW S22A2_HUMAN Substrate [10]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Choline O-acetyltransferase (CHAT) DE5NGOW CLAT_HUMAN Substrate [11]
Choline/ethanolaminephosphotransferase 1 (CEPT1) DEL87ZT CEPT1_HUMAN Substrate [12]
Choline kinase alpha (CHKA) DEMRAYN CHKA_HUMAN Substrate [13]
Choline dehydrogenase (CHDH) DEAHED0 CHDH_HUMAN Substrate [14]
Choline/ethanolamine kinase (CHKB) DEHWR6V CHKB_HUMAN Substrate [13]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
1,4-alpha-glucan-branching enzyme (GBE1) OTK2N05B GLGB_HUMAN Gene/Protein Processing [15]
28 kDa heat- and acid-stable phosphoprotein (PDAP1) OTJSWMOD HAP28_HUMAN Gene/Protein Processing [15]
72 kDa type IV collagenase (MMP2) OT5NIWA2 MMP2_HUMAN Gene/Protein Processing [15]
Acetylcholinesterase (ACHE) OT2H8HG6 ACES_HUMAN Gene/Protein Processing [16]
Aminopeptidase RNPEPL1 (RNPEPL1) OT58DCKC RNPL1_HUMAN Gene/Protein Processing [15]
Borealin (CDCA8) OT17D55D BOREA_HUMAN Gene/Protein Processing [15]
C-1-tetrahydrofolate synthase, cytoplasmic (MTHFD1) OTMKHVWC C1TC_HUMAN Drug Response [15]
C-C motif chemokine 2 (CCL2) OTAD2HEL CCL2_HUMAN Gene/Protein Processing [17]
Choline dehydrogenase, mitochondrial (CHDH) OTO2DPGL CHDH_HUMAN Drug Response [15]
Cholinesterase (BCHE) OTOH3WQ9 CHLE_HUMAN Gene/Protein Processing [16]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Choline FDA Label
2 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).
3 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.
4 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.
5 The choline transporter-like family SLC44: properties and roles in human diseases. Mol Aspects Med. 2013 Apr-Jun;34(2-3):646-54.
6 SLC44A4 mutation causes autosomal dominant hereditary postlingual non-syndromic mid-frequency hearing loss. Hum Mol Genet. 2017 Jan 15;26(2):383-394.
7 Interpreting metabolomic profiles using unbiased pathway models. PLoS Comput Biol. 2010 Feb 26;6(2):e1000692.
8 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.
9 Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007.
10 Ventricular choline transport: a role for organic cation transporter 2 expressed in choroid plexus. J Biol Chem. 2001 Nov 9;276(45):41611-9.
11 The effect of trichlorfon and methylazoxymethanol on the development of guinea pig cerebellum. Toxicol Appl Pharmacol. 2007 Mar;219(2-3):128-35.
12 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.
13 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.
14 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.
15 Lymphocyte gene expression in subjects fed a low-choline diet differs between those who develop organ dysfunction and those who do not. Am J Clin Nutr. 2007 Jul;86(1):230-9. doi: 10.1093/ajcn/86.1.230.
16 alpha,beta-Dehydrophenylalanine choline esters, a new class of reversible inhibitors of human acetylcholinesterase and butyrylcholinesterase. Chem Biol Interact. 2008 Jan 10;171(1):108-16.
17 Folic Acid Improves the Inflammatory Response in LPS-Activated THP-1 Macrophages. Mediators Inflamm. 2018 Jul 4;2018:1312626. doi: 10.1155/2018/1312626. eCollection 2018.