Details of the Drug

General Information of Drug (ID: DMI5XR1)

Drug Name
LPA
Synonyms
2-Hydroxy-3-(phosphonooxy)propyl oleate; lysophosphatidic acid; 1-Oleoyl-lyso-phosphatidic acid; Monooleylphosphatidic acid; Oleoyl lysophosphatidic acid; 1-Oleyllysophosphatidic acid; 22002-87-5; (2-hydroxy-3-phosphonooxypropyl) (Z)-octadec-9-enoate; 1-oleoyl-LPA; monooleylphosphatidate; [3H]1-oleoyl-LPA; [3H]lysophosphatidic acid; [3H]LPA; 1-oleoyl-lysophosphatidic acid; [3H]-LPA; AC1NUZKL; Lysophosphophatidic acid; Oleoyl lysophosphatidate; 1-Oleyllysophosphatidate; 1-Oleoyl-lysophosphatidate; lysophosphatidic acid
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): 2 Molecular Weight (mw) 436.5
Logarithm of the Partition Coefficient (xlogp) 5.2
Rotatable Bond Count (rotbonds) 21
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 7
Chemical Identifiers
Formula
C21H41O7P
IUPAC Name
(2-hydroxy-3-phosphonooxypropyl) (Z)-octadec-9-enoate
Canonical SMILES
CCCCCCCC/C=C\\CCCCCCCC(=O)OCC(COP(=O)(O)O)O
InChI
InChI=1S/C21H41O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)27-18-20(22)19-28-29(24,25)26/h9-10,20,22H,2-8,11-19H2,1H3,(H2,24,25,26)/b10-9-
InChIKey
WRGQSWVCFNIUNZ-KTKRTIGZSA-N
Cross-matching ID
PubChem CID
5497152
CAS Number
22002-87-5
TTD ID
D0X0UR

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
G protein coupled receptor 87 (GPR87) TTO897C GPR87_HUMAN Agonist [2]
Lysophosphatidate-3 receptor (LPAR3) TTE2YJR LPAR3_HUMAN Agonist [3]
Lysophosphatidic acid receptor 1 (LPAR1) TTQ6S1K LPAR1_HUMAN Agonist [4]
Lysophosphatidic acid receptor 2 (LPAR2) TTB7Y8I LPAR2_HUMAN Agonist [5]
Lysophosphatidic acid receptor 4 (LPAR4) TT7ZMY4 LPAR4_HUMAN Agonist [6]
Lysophosphatidic acid receptor 5 (LPAR5) TTABCJ6 LPAR5_HUMAN Agonist [7]
Lysophosphatidic acid receptor 6 (LPAR6) TTZDAGB LPAR6_HUMAN Agonist [8]
P2Y purinoceptor 10 (P2RY10) TTMFOU6 P2Y10_HUMAN Agonist [2]
Sphingosine-1-phosphate receptor 1 (S1PR1) TT9JZCK S1PR1_HUMAN Agonist [9]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
C-X-C chemokine receptor type 1 (CXCR1) OT5512B2 CXCR1_HUMAN Gene/Protein Processing [10]
Epidermal growth factor receptor (EGFR) OTAPLO1S EGFR_HUMAN Post-Translational Modifications [11]
Focal adhesion kinase 1 (PTK2) OT3Q1JDY FAK1_HUMAN Post-Translational Modifications [12]
Hypoxia-inducible factor 1-alpha (HIF1A) OTADSC03 HIF1A_HUMAN Gene/Protein Processing [13]
Laminin subunit alpha-3 (LAMA3) OTFME7HT LAMA3_HUMAN Gene/Protein Processing [14]
Laminin subunit beta-3 (LAMB3) OTFPU6W8 LAMB3_HUMAN Gene/Protein Processing [14]
Laminin subunit gamma-2 (LAMC2) OTJMTM72 LAMC2_HUMAN Gene/Protein Processing [14]
Lysophosphatidic acid receptor 1 (LPAR1) OTJNJQPF LPAR1_HUMAN Drug Response [15]
Matrix metalloproteinase-9 (MMP9) OTB2QDAV MMP9_HUMAN Gene/Protein Processing [11]
Mitogen-activated protein kinase 1 (MAPK1) OTH85PI5 MK01_HUMAN Post-Translational Modifications [13]
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: 5395).
2 Identification of the orphan GPCR, P2Y(10) receptor as the sphingosine-1-phosphate and lysophosphatidic acid receptor. Biochem Biophys Res Commun. 2008 Jul 11;371(4):707-12.
3 Molecular cloning and characterization of a novel human G-protein-coupled receptor, EDG7, for lysophosphatidic acid. J Biol Chem. 1999 Sep 24;274(39):27776-85.
4 Diversity of lysophosphatidic acid receptor-mediated intracellular calcium signaling in early cortical neurogenesis. J Neurosci. 2010 May 26;30(21):7300-9.
5 Synthesis and biological evaluation of phosphonic and thiophosphoric acid derivatives of lysophosphatidic acid. Bioorg Med Chem Lett. 2004 Jul 5;14(13):3473-6.
6 Identification of p2y9/GPR23 as a novel G protein-coupled receptor for lysophosphatidic acid, structurally distant from the Edg family. J Biol Chem. 2003 Jul 11;278(28):25600-6.
7 Screening beta-arrestin recruitment for the identification of natural ligands for orphan G-protein-coupled receptors. J Biomol Screen. 2013 Jun;18(5):599-609.
8 G protein-coupled receptor P2Y5 and its ligand LPA are involved in maintenance of human hair growth. Nat Genet. 2008 Mar;40(3):329-34.
9 Lysophosphatidic acid stimulates the G-protein-coupled receptor EDG-1 as a low affinity agonist. J Biol Chem. 1998 Aug 21;273(34):22105-12.
10 Neutrophil sphingosine 1-phosphate and lysophosphatidic acid receptors in pneumonia. Am J Respir Cell Mol Biol. 2006 Feb;34(2):233-41. doi: 10.1165/rcmb.2005-0126OC. Epub 2005 Oct 13.
11 EGFR mediates LPA-induced proteolytic enzyme expression and ovarian cancer invasion: inhibition by resveratrol. Mol Oncol. 2013 Feb;7(1):121-9. doi: 10.1016/j.molonc.2012.10.001. Epub 2012 Oct 23.
12 Attenuation of focal adhesion kinase signaling following depletion of agonist-sensitive pools of phosphatidylinositol 4,5-bisphosphate. J Neurochem. 1999 Nov;73(5):1933-44.
13 Hypoxia enhances LPA-induced HIF-1alpha and VEGF expression: their inhibition by resveratrol. Cancer Lett. 2007 Dec 8;258(1):63-9. doi: 10.1016/j.canlet.2007.08.011. Epub 2007 Oct 4.
14 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.
15 Expression and function of lysophosphatidic acid LPA1 receptor in prostate cancer cells. Endocrinology. 2006 Oct;147(10):4883-92. doi: 10.1210/en.2005-1635. Epub 2006 Jun 29.