Prostaglandin E₂ - γ-irradiated, BioReagent, for cell culture, powder , CAS No.363-24-6

CAS: 363-24-6 Cat. No.: P755675 Molecular Weight: 352.47 EC Number: 206-656-6

GRADE & PURITY BioReagent, for Cell culture, γ-irradiated, powder

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

For use in cell culture applications for the study of prostaglandin regulated cell signaling and gene regulation.

Prostaglandin E2 has been used to determine its effects on collagen gel contraction mediated by alveolar cell carcinoma cell line A549.

Specifications

Specifications & Purity

γ-irradiated, BioReagent, for cell culture, powder

Biochemical and Physiological Mechanisms

Most biologically active prostaglandin. PGE2 induces cervical ripening and parturition; mediates bradykinin-induced vasodilation; regulates adenylyl cyclase. Tumor cells that over-express cyclooxygenase 2 display increased invasiveness, angiogenesis, and

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.

Grade

BioReagent, for Cell culture, γ-irradiated

Product Properties

• ALogP: 2.8

Names and Identifiers

• Canonical Smiles: CCCCCC(C=CC1C(CC(=O)C1CC=CCCCC(=O)O)O)O
• IUPAC Name: (Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]hept-5-enoic acid
• InChIKey: XEYBRNLFEZDVAW-ARSRFYASSA-N
• INCHI: 1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,19+/m0/s1
• Isomeric SMILES: CCCCC[C@@H](/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1C/C=C\CCCC(=O)O)O)O
• RTECS: UK8000000
• Molecular Weight: 352.47
• Reaxy-Rn: 2705862
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2705862&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Fatty Acyls
      • Subclass Eicosanoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Fatty Acyls
• Subclass: Eicosanoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Prostaglandins and related compounds
• Alternative Parents: Long-chain fatty acids Hydroxy fatty acids Unsaturated fatty acids Cyclopentanols Cyclic ketones Cyclic alcohols and derivatives Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic homomonocyclic compounds
• Substituents: Prostaglandin skeleton - Long-chain fatty acid - Hydroxy fatty acid - Cyclopentanol - Fatty acid - Unsaturated fatty acid - Cyclic alcohol - Ketone - Cyclic ketone - Secondary alcohol - Carboxylic acid - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Alcohol - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Organooxygen compound - Carbonyl group - Aliphatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.
• External Descriptors: Prostaglandins

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

Chemical and Physical Properties

• Solubility: ethanol: 1 mg/mL
• Melt Point(°C): 66°C(lit.)
• Molecular Weight: 352.500 g/mol
• XLogP3: 2.800
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 12
• Exact Mass: 352.225 Da
• Monoisotopic Mass: 352.225 Da
• Topological Polar Surface Area: 94.800 Ų
• Heavy Atom Count: 25
• Formal Charge: 0
• Complexity: 469.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 2
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 2
• Covalently-Bonded Unit Count: 1

References

1. Jian Xiao, Shuqing Cao, Jiawei Wang, Pengyu Li, Quan Cheng, Xinyi Zhou, Jiacheng Dong, Yuan Li, Xinyu Zhao, Zekuan Xu, Li Yang.  (2024)  Leptin-mediated suppression of lipoprotein lipase cleavage enhances lipid uptake and facilitates lymph node metastasis in gastric cancer.  Cancer Communications,      [PMID:38958445] [10.1002/cac2.12583]

2. Qi-Rui Hu, Qing-Xin Huang, Huan Hong, Yao Pan, Ting Luo, Jing Li, Ze-Yuan Deng, Fang Chen.  (2023)  Ginsenoside Rh2 and its octyl ester derivative inhibited invasion and metastasis of hepatocellular carcinoma via the c-Jun/COX2/PGE2 pathway.  PHYTOMEDICINE,      [PMID:37806155] [10.1016/j.phymed.2023.155131]

3. Mingrui Xiong, Hong Chen, Yu Fan, Muchuan Jin, Dong Yang, Yuchen Chen, Yu Zhang, Robert B. Petersen, Hua Su, Anlin Peng, Congyi Wang, Ling Zheng, Kun Huang.  (2023)  Tubular Elabela-APJ axis attenuates ischemia-reperfusion induced acute kidney injury and the following AKI-CKD transition by protecting renal microcirculation.  Theranostics,      [PMID:37351176] [10.7150/thno.84308]

4. Yongzhi Cui, Yuanyuan Guo, Li Kong, Jingyu Shi, Ping Liu, Rui Li, Yongtao Geng, Weihang Gao, Zhiping Zhang, Dehao Fu.  (2021)  A bone-targeted engineered exosome platform delivering siRNA to treat osteoporosis.  Bioactive Materials,      [PMID:34901540] [10.1016/j.bioactmat.2021.09.015]

5. Guobin Li, Lan Zhang, Kaiting Ning, Baoqiang Yang, Francisca M. Acosta, Peng Shang, Jean X. Jiang, Huiyun Xu.  (2021)  Osteocytic Connexin43 Channels Regulate Bone–Muscle Crosstalk.  Cells,  10  (2): (237).  [PMID:33530465] [10.3390/cells10020237]

6. Lei Yu, Bai Yaowei, Bai Xiatong, Sun Bo, Zhu Licheng, Wu Wenlong, Su Yang, Zhang Hongsen, Wang Yingliang, Zheng Chuansheng.  (2025)  COX-2/PGE2 axis blockade with celecoxib enhances anti-PD-1 efficacy by activating natural killer cells for residual hepatocellular carcinoma after radiofrequency ablation.  JOURNAL OF EXPERIMENTAL & CLINICAL CANCER RESEARCH,  44  (1): (321).  [PMID:41408296] [10.1186/s13046-025-03582-6]