1-Oleoyl lysophosphatidic acid - ≥95%，10mg/ml in ethanol , CAS No.65528-98-5

CAS: 65528-98-5 Cat. No.: O353308 Molecular Weight: 436.52 PubChem CID: 5311263

GRADE & PURITY ≥95%，10mg/ml in ethanol

Synonyms

CHEBI:62837 | 1-Oleoyl-sn-glycerol 3-phosphate | 1-Oleoyl-sn-glycero-3-phosphate | LysoPA(18:1) | lysophosphatidic acid | 1-oleylglycerol 3-phosphate | 1-(9Z-octadecenoyl)-sn-glycero-3-phosphate | PA(18:1/0:0)

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

1-Oleoyl lysophosphatidic acid is a species of lysophosphatidic acid (LPA) containing oleic acid at the sn-1 position. Phosphatidic acid is made either through a two step process involving liberation of diacylglycerol (DAG) by phospholipase C (PLC) follow by phosphorylation of DAG by diglycerol kinase or directly through the action of phospholipase D (PLD). Hydrolysis of the fatty acid at the sn-2 position by phospholipase A2 (PLA2) yields bioactive LPA, which binds to one of five different G protein linked receptors to mediate a variety of biological responses including platelet aggregation, cell proliferation, smooth muscle contraction, cell motility and neurite retraction. 1-Oleoyl lysophosphatidic acid is the most potent of the LPA analogs for calcium mobilization in A431 cells and for growth stimulation of a variety of cell lines.

Specifications

Synonyms

CHEBI:62837 | 1-Oleoyl-sn-glycerol 3-phosphate | 1-Oleoyl-sn-glycero-3-phosphate | LysoPA(18:1) | lysophosphatidic acid | 1-oleylglycerol 3-phosphate | 1-(9Z-octadecenoyl)-sn-glycero-3-phosphate | PA(18:1/0:0)

Specifications & Purity

≥95%，10mg/ml in ethanol

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

ACTIVATOR

Product Properties

• pKa: pKₐ: 1.82 (Predicted)
• Ki Data: Autotaxin: Ki= 100 nM (human)

Names and Identifiers

• Canonical Smiles: CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@@H](O)COP(=O)(O)O
• IUPAC Name: [(2R)-2-hydroxy-3-phosphonooxypropyl] (Z)-octadec-9-enoate
• InChIKey: WRGQSWVCFNIUNZ-GDCKJWNLSA-N
• 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
• Isomeric SMILES: CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)O)O
• PubChem CID: 5311263
• UN Number: 1170
• Packing Group: II
• Molecular Weight: 436.52

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Glycerophospholipids
      • Subclass Glycerophosphates
        • Level5 Monoacylglycerophosphates
          • Level6 Lysophosphatidic acids
            • Level7 1-acylglycerol-3-phosphates

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Glycerophospholipids
• Subclass: Glycerophosphates
• Intermediate Tree Nodes: Monoacylglycerophosphates - Lysophosphatidic acids
• Direct Parent: 1-acylglycerol-3-phosphates
• Alternative Parents: Monoalkyl phosphates Fatty acid esters Secondary alcohols Carboxylic acid esters Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: 1-acylglycerol-3-phosphate - Fatty acid ester - Monoalkyl phosphate - Fatty acyl - Alkyl phosphate - Phosphoric acid ester - Organic phosphoric acid derivative - Carboxylic acid ester - Secondary alcohol - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Carbonyl group - Alcohol - Organooxygen compound - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as 1-acylglycerol-3-phosphates. These are lysophosphatidic acids where the glycerol is esterified with a fatty acid at O-1 position.
• External Descriptors: Monoacylglycerophosphates

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

ENPP2 Tchem Ectonucleotide pyrophosphatase/phosphodiesterase family member 2 (3 Activities)

Discover Target: ENPP2

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

TRPV1 Tclin Transient receptor potential cation channel subfamily V member 1 (1 Activities)

Discover Target: TRPV1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

LPAR4 Tchem Lysophosphatidic acid receptor 4 (2 Activities)

Discover Target: LPAR4

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

LPAR3 Tchem Lysophosphatidic acid receptor 3 (2 Activities)

Discover Target: LPAR3

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

LPAR1 Tchem Lysophosphatidic acid receptor 1 (5 Activities)

Discover Target: LPAR1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

LPAR5 Tchem Lysophosphatidic acid receptor 5 (3 Activities)

Discover Target: LPAR5

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

LPAR2 Tchem Lysophosphatidic acid receptor 2 (4 Activities)

Discover Target: LPAR2

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

TRPV1 Tclin Vanilloid receptor (8273 Activities)

Discover Target: TRPV1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

LPAR1 Tchem Lysophosphatidic acid receptor Edg-2 (779 Activities)

Discover Target: LPAR1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

LPAR2 Tchem Lysophosphatidic acid receptor Edg-4 (418 Activities)

Discover Target: LPAR2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

LPAR3 Tchem Lysophosphatidic acid receptor Edg-7 (471 Activities)

Discover Target: LPAR3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PC-3 (62116 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ENPP2 Tchem Autotaxin (2645 Activities)

Discover Target: ENPP2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

LPAR4 Tchem Lysophosphatidic acid receptor 4 (71 Activities)

Discover Target: LPAR4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

LPAR5 Tchem Lysophosphatidic acid receptor 5 (213 Activities)

Discover Target: LPAR5

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

CHO (4503 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MEF (1005 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

B103 cell line (42 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in DMSO (~2 mg/ml), DMF (~2 mg/ml), PBS (pH 7.2) (~3 mg/ml), and ethanol.
• Refractive Index: n20D1.49 (Predicted)
• Boil Point(°C): 78° C
• Molecular Weight: 436.500 g/mol
• XLogP3: 5.200
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 21
• Exact Mass: 436.259 Da
• Monoisotopic Mass: 436.259 Da
• Topological Polar Surface Area: 113.000 Ų
• Heavy Atom Count: 29
• Formal Charge: 0
• Complexity: 462.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

References

1. Xiaoyang Sun, Lifen Zhang, Shaojun Tian, Kaizhou Yang, Jianchun Xie.  (2019)  Phospholipid composition and emulsifying properties of rice bran lecithin from enzymatic degumming.  LWT-FOOD SCIENCE AND TECHNOLOGY,      [PMID:] [10.1016/j.lwt.2019.108588]

2. Zhang Sitong, Sun Zhongquan, Chen Zhenhua, Bi Yanli, Wei Shenyu, Mao Zhengwei, Jin Jin, Ding Yuan, Wang Weilin.  (2024)  Endothelial YAP/TEAD1-CXCL17 signaling recruits myeloid-derived suppressor cells against liver ischemia-reperfusion injury.  HEPATOLOGY,      [PMID:38407233] [10.1097/HEP.0000000000000773]

3. Na Zhang, Suhui Ji, Zhiqi He, Di Wu.  (2026)  Lpar3-mediated macrophage polarization promotes inflammatory tooth extraction socket healing and alveolar bone regeneration.  Regenerative Therapy,      [PMID:42059006] [10.1016/j.reth.2026.101116]