1-Oleoyl Lysophosphatidic Acid

Details

• Internal ID: cc552753-b1bf-4b3e-b4fa-a40e48354d2f
• Taxonomy: Lipids and lipid-like molecules > Glycerophospholipids > Glycerophosphates > Lysophosphatidic acids > 1-acylglycerol-3-phosphates
• IUPAC Name: [(2R)-2-hydroxy-3-phosphonooxypropyl] (Z)-octadec-9-enoate
• SMILES (Canonical): CCCCCCCCC=CCCCCCCCC(=O)OCC(COP(=O)(O)O)O
• SMILES (Isomeric): CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@H](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-/t20-/m1/s1
• InChI Key: WRGQSWVCFNIUNZ-GDCKJWNLSA-N
• Popularity: 1,972 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₄₁O₇P
• Molecular Weight: 436.50 g/mol
• Exact Mass: 436.25899064 g/mol
• Topological Polar Surface Area (TPSA): 113.00 Ų
• XlogP: 5.20
• Atomic LogP (AlogP): 5.04
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 20

Synonyms

• 1-Oleoyl-sn-glycerol 3-phosphate
• 65528-98-5
• lysophosphatidic acid
• 1-Oleoyl-sn-glycero-3-phosphate
• CHEBI:62837
• 1-(9Z-octadecenoyl)-sn-glycero-3-phosphate
• PA(18:1/0:0)
• LysoPA(18:1)
• 1-oleylglycerol 3-phosphate
• 1-oleoylglycerol 3-phosphate
• Lysophosphatidic acid(18:1)
• CHEMBL117021
• 1-oleyl-sn-glycerol 3-phosphate
• LysoPA(18:1w9/0:0)
• 1-O-oleyl-sn-glycerol 3-phosphate
• 18:1 LPA
• 1-O-9Z-Octadecenoyl-sn-glyceryl-3-phosphoric acid
• 1-O-oleoyl-sn-glycerol 3-phosphate
• Lysophosphatidic acid(18:1/0:0)
• LPA(18:1n9/0:0)
• LPA(18:1w9/0:0)
• LysoPA(18:1(9Z)/0:0)
• Lysophosphatidic acid(18:1n9/0:0)
• Lysophosphatidic acid(18:1w9/0:0)
• LPA(18:1/0:0)
• Monooleylphosphatidic acid
• LPA(18:1(9Z)/0:0)
• PA(18:1(9Z)/0:0)
• 1-oleyl-2-lyso-sn-glycerol 3-phosphatidic acid
• 1-oleoyl-2-lyso-sn-glycerol 3-phosphatidic acid
• 9-Octadecenoic acid (Z)-, 2-hydroxy-3-(phosphonooxy)propyl ester, (R)-
• LPA 18:1
• Epitope ID:158640
• BSPBio_001406
• 9-Octadecenoic acid (9Z)-, 2-hydroxy-3-(phosphonooxy)propyl ester
• SCHEMBL1560791
• DTXSID10425008
• WRGQSWVCFNIUNZ-GDCKJWNLSA-N
• HMS1791G08
• HMS1989G08
• HMS3650F05
• BDBM50148348
• LMGP10050008
• AKOS040755516
• IDI1_033876
• NCGC00161386-01
• NCGC00161386-02
• NCGC00161386-03
• 1-Oleoyl-L-.alpha.-lysophosphatidic acid
• HY-137862
• CS-0142436
• F82782
• SR-01000946335
• SR-01000946335-1
• Q27132220
• (2R)-2-hydroxy-3-(phosphonooxy)propyl (9Z)-octadec-9-enoate
• (R)-Octadec-9-enoic acid 2-hydroxy-3-phosphonooxy-propyl ester
• [(2R)-2-Hydroxy-3-[(9Z)-octadec-9-enoyloxy]propoxy]phosphonicacid
• [(2R)-2-Hydroxy-3-[(9Z)-octadec-9-enoyloxy]propoxy]phosphonic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6721	67.21%
Caco-2	-	0.7384	73.84%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7379	73.79%
OATP2B1 inhibitior	-	0.8536	85.36%
OATP1B1 inhibitior	+	0.8435	84.35%
OATP1B3 inhibitior	+	0.9408	94.08%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6427	64.27%
P-glycoprotein inhibitior	-	0.5963	59.63%
P-glycoprotein substrate	-	0.8447	84.47%
CYP3A4 substrate	+	0.5347	53.47%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8588	85.88%
CYP3A4 inhibition	-	0.9108	91.08%
CYP2C9 inhibition	-	0.8698	86.98%
CYP2C19 inhibition	-	0.8100	81.00%
CYP2D6 inhibition	-	0.8933	89.33%
CYP1A2 inhibition	-	0.8351	83.51%
CYP2C8 inhibition	-	0.8410	84.10%
CYP inhibitory promiscuity	-	0.9640	96.40%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7100	71.00%
Carcinogenicity (trinary)	Non-required	0.6139	61.39%
Eye corrosion	-	0.5967	59.67%
Eye irritation	-	0.7138	71.38%
Skin irritation	-	0.6995	69.95%
Skin corrosion	+	0.5878	58.78%
Ames mutagenesis	-	0.8900	89.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3708	37.08%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.5341	53.41%
skin sensitisation	-	0.8349	83.49%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	-	0.8889	88.89%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.6972	69.72%
Acute Oral Toxicity (c)	III	0.5863	58.63%
Estrogen receptor binding	+	0.7762	77.62%
Androgen receptor binding	-	0.6848	68.48%
Thyroid receptor binding	-	0.5286	52.86%
Glucocorticoid receptor binding	-	0.6321	63.21%
Aromatase binding	-	0.7583	75.83%
PPAR gamma	+	0.6272	62.72%
Honey bee toxicity	-	0.8593	85.93%
Biodegradation	+	0.7000	70.00%
Crustacea aquatic toxicity	+	0.7078	70.78%
Fish aquatic toxicity	+	0.9747	97.47%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3691	Q13822	Autotaxin	100 nM	Ki	via Super-PRED
CHEMBL5968	Q99677	Lysophosphatidic acid receptor 4	8.1 nM	EC50	via Super-PRED
CHEMBL5700	Q9H1C0	Lysophosphatidic acid receptor 5	54.95 nM	EC50	via Super-PRED
CHEMBL3819	Q92633	Lysophosphatidic acid receptor Edg-2	80 nM; 450 nM; 5.6 nM	EC50; EC50; Kd	via Super-PRED; via Super-PRED; via Super-PRED
CHEMBL3724	Q9HBW0	Lysophosphatidic acid receptor Edg-4	2 nM	EC50	via Super-PRED
CHEMBL3250	Q9UBY5	Lysophosphatidic acid receptor Edg-7	290 nM; 77 nM	EC50; EC50	via Super-PRED; via Super-PRED
CHEMBL4794	Q8NER1	Vanilloid receptor	754 nM	Kd	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	99.51%	97.29%
CHEMBL3060	Q9Y345	Glycine transporter 2	98.37%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.96%	96.09%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	96.50%	92.86%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	96.49%	85.94%
CHEMBL230	P35354	Cyclooxygenase-2	96.39%	89.63%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	94.03%	100.00%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	93.19%	95.17%
CHEMBL2581	P07339	Cathepsin D	92.62%	98.95%
CHEMBL4333	P21453	Sphingosine 1-phosphate receptor Edg-1	90.26%	96.99%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	89.67%	92.08%
CHEMBL3230	O95977	Sphingosine 1-phosphate receptor Edg-6	89.30%	94.01%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	89.18%	91.71%
CHEMBL5255	O00206	Toll-like receptor 4	86.45%	92.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.16%	94.33%
CHEMBL1781	P11387	DNA topoisomerase I	84.52%	97.00%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	84.36%	91.81%
CHEMBL1907	P15144	Aminopeptidase N	84.31%	93.31%
CHEMBL3401	O75469	Pregnane X receptor	84.11%	94.73%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.32%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.09%	93.56%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	82.41%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.34%	91.19%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.23%	96.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	82.06%	89.34%

Plants that contains it

• Amaranthus blitum subsp. oleraceus

Cross-Links

• PubChem: 5311263
• LOTUS: LTS0240355
• wikiData: Q27132220