Details of the Drug

General Information of Drug (ID: DMOGFVH)

Drug Name
lysophosphatidylcholine
Synonyms
Lysophosphatidylcholine; 1-acetyl-sn-glycero-3-phosphocholine; AC1NSKBT; GTPL2508; SCHEMBL19821626; CHEBI:138424; LMGP01050043; [(2R)-3-acetyloxy-2-hydroxypropyl] 2-trimethylazaniumylethyl phosphate; [(2R)-3-acetyloxy-2-hydroxypropyl] 2-(trimethylazaniumyl)ethyl phosphate; 3,5,9-Trioxa-4-phosphaundecan-1-aminium, 4,7-dihydroxy-N,N,N-trimethyl-10-oxo-, inner salt, 4-oxide, (R)-
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL is unavailable 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 299.26
Logarithm of the Partition Coefficient (xlogp) -1.8
Rotatable Bond Count (rotbonds) 10
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 7
Chemical Identifiers
Formula
C10H22NO7P
IUPAC Name
[(2R)-3-acetyloxy-2-hydroxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
Canonical SMILES
CC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O
InChI
InChI=1S/C10H22NO7P/c1-9(12)16-7-10(13)8-18-19(14,15)17-6-5-11(2,3)4/h10,13H,5-8H2,1-4H3/t10-/m1/s1
InChIKey
RYCNUMLMNKHWPZ-SNVBAGLBSA-N
Cross-matching ID
PubChem CID
5311264
ChEBI ID
CHEMBL138424
CAS Number
9008-30-4
TTD ID
D0KT5E
VARIDT ID
DR00231
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Short transient receptor potential channel 5 (TRPC5) TT32NQ1 TRPC5_HUMAN Activator [2]
Short transient receptor potential channel 6 (TRPC6) TTRBT3W TRPC6_HUMAN Activator [3]
Transient receptor potential cation channel V2 (TRPV2) TTBECWA TRPV2_HUMAN Activator [4]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Major facilitator superfamily domain-containing protein 2A (SLC59A1) DT5G94L NLS1_HUMAN Substrate [5]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Ectonucleotide pyrophosphatase/phosphodiesterase family member 7 (ENPP7) OTWOBMQ9 ENPP7_HUMAN Biotransformations [6]
G-protein coupled receptor 4 (GPR4) OTIBF32I GPR4_HUMAN Gene/Protein Processing [7]
Laminin subunit alpha-3 (LAMA3) OTFME7HT LAMA3_HUMAN Gene/Protein Processing [8]
Laminin subunit beta-3 (LAMB3) OTFPU6W8 LAMB3_HUMAN Gene/Protein Processing [8]
Laminin subunit gamma-2 (LAMC2) OTJMTM72 LAMC2_HUMAN Gene/Protein Processing [8]
NACHT, LRR and PYD domains-containing protein 3 (NLRP3) OTZM6MHU NLRP3_HUMAN Gene/Protein Processing [7]
Patatin-like phospholipase domain-containing protein 6 (PNPLA6) OTT5T45Q PLPL6_HUMAN Regulation of Drug Effects [9]
Sodium-dependent lysophosphatidylcholine symporter 1 (MFSD2A) OTVG1VG0 NLS1_HUMAN Regulation of Drug Effects [10]
Vascular cell adhesion protein 1 OTP74K37 VCAM1_HUMAN Gene/Protein Processing [11]
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: 2508).
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. (Target id: 490).
3 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: 491).
4 Lysophospholipids stimulate prostate cancer cell migration via TRPV2 channel activation. Biochim Biophys Acta. 2009 Mar;1793(3):528-39.
5 Mfsd2a is a transporter for the essential omega-3 fatty acid docosahexaenoic acid. Nature. 2014 May 22;509(7501):503-6.
6 Identification of human intestinal alkaline sphingomyelinase as a novel ecto-enzyme related to the nucleotide phosphodiesterase family. J Biol Chem. 2003 Oct 3;278(40):38528-36. doi: 10.1074/jbc.M305437200. Epub 2003 Jul 28.
7 Lysophosphatidylcholine induces apoptosis and inflammatory damage in brain microvascular endothelial cells via GPR4-mediated NLRP3 inflammasome activation. Toxicol In Vitro. 2021 Dec;77:105227. doi: 10.1016/j.tiv.2021.105227. Epub 2021 Jul 20.
8 Increase of laminin 5 synthesis in human keratinocytes by acute wound fluid, inflammatory cytokines and growth factors, and lysophospholipids. Br J Dermatol. 2004 Nov;151(5):961-70. doi: 10.1111/j.1365-2133.2004.06175.x.
9 The alteration of the expression level of neuropathy target esterase in human neuroblastoma SK-N-SH cells disrupts cellular phospholipids homeostasis. Toxicol In Vitro. 2023 Feb;86:105509. doi: 10.1016/j.tiv.2022.105509. Epub 2022 Nov 4.
10 A partially inactivating mutation in the sodium-dependent lysophosphatidylcholine transporter MFSD2A causes a non-lethal microcephaly syndrome. Nat Genet. 2015 Jul;47(7):814-7. doi: 10.1038/ng.3313. Epub 2015 May 25.
11 Effect of quercetin and its metabolite on caveolin-1 expression induced by oxidized LDL and lysophosphatidylcholine in endothelial cells. J Clin Biochem Nutr. 2016 May;58(3):193-201. doi: 10.3164/jcbn.16-2. Epub 2016 Apr 16.