Lysophosphatidic acid

Lysophosphatidic acid
Names
	Systematic IUPAC name (2R)-2-hydroxy-3-{[(9Z)-octadec-9-enoyl]oxy}propyl dihydrogen phosphate
	Other names LPA; 1-acyl-sn-glycerol 3-phosphate
Identifiers
CAS Number	22002-87-5 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL117021 ;
ChemSpider	4593722;
ECHA InfoCard	100.040.631
EC Number	244-710-0;
IUPHAR/BPS	2906;
MeSH	lysophosphatidic+acid
PubChem CID	5497152;
UNII	PG6M3969SG ;
CompTox Dashboard (EPA)	DTXSID001015741 DTXSID5041061, DTXSID001015741 ;
	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- Key: WRGQSWVCFNIUNZ-KTKRTIGZSA-N;
	SMILES CCCCCCCC\C=C/CCCCCCCC(=O)OCC(COP(=O)(O)O)O;
Properties
Chemical formula	C21H41O7P
Molar mass	436.52 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

A lysophosphatidic acid (LPA) is a phospholipid derivative that can act as a signaling molecule.^[1]^[2]^[3]^[4]

^ van Corven, Emile J.; Groenink, Alida; Jalink, Kees; Eichholtz, Thomas; Moolenaar, Wouter H. (1989-10-06). "Lysophosphatidate-induced cell proliferation: Identification and dissection of signaling pathways mediated by G proteins". Cell. 59 (1): 45–54. doi:10.1016/0092-8674(89)90868-4. PMID 2551506. S2CID 25154850.
^ Tsukahara, Tamotsu; Tsukahara, Ryoko; Haniu, Hisao; Matsuda, Yoshikazu; Murakami-Murofushi, Kimiko (2015-09-05). "Cyclic phosphatidic acid inhibits the secretion of vascular endothelial growth factor from diabetic human coronary artery endothelial cells through peroxisome proliferator-activated receptor gamma". Molecular and Cellular Endocrinology. 412: 320–329. doi:10.1016/j.mce.2015.05.021. hdl:10069/35888. ISSN 0303-7207. PMID 26007326. S2CID 10454566.
^ Moolenaar, Wouter H. (1995-06-02). "Lysophosphatidic Acid, a Multifunctional Phospholipid Messenger ∗". Journal of Biological Chemistry. 270 (22): 12949–12952. doi:10.1074/jbc.270.22.12949. ISSN 0021-9258. PMID 7768880.
^ Tigyi, Gabor; Parrill, Abby L. (2003-11-01). "Molecular mechanisms of lysophosphatidic acid action". Progress in Lipid Research. 42 (6): 498–526. doi:10.1016/S0163-7827(03)00035-3. ISSN 0163-7827. PMID 14559069.

Names

Systematic IUPAC name (2R)-2-hydroxy-3-{[(9Z)-octadec-9-enoyl]oxy}propyl dihydrogen phosphate
Other names LPA 1-acyl-sn-glycerol 3-phosphate
Identifiers
CAS Number	22002-87-5^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL117021^N
ChemSpider	4593722
ECHA InfoCard	100.040.631
EC Number	244-710-0
IUPHAR/BPS	2906
MeSH	lysophosphatidic+acid
PubChem CID	5497152
UNII	PG6M3969SG^Y
CompTox Dashboard (EPA)	DTXSID001015741 DTXSID5041061, DTXSID001015741
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- Key: WRGQSWVCFNIUNZ-KTKRTIGZSA-N
SMILES CCCCCCCC\C=C/CCCCCCCC(=O)OCC(COP(=O)(O)O)O
Properties
Chemical formula	C₂₁H₄₁O₇P
Molar mass	436.52 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references