Piericidin A

Base Information

• Chemical Name: Piericidin A
• CAS No.: 2738-64-9
• Deprecated CAS: 24467-35-4,19855-42-6,5085-85-8,19855-42-6
• Molecular Formula: C25H37 N O4
• Molecular Weight: 415.573
• Hs Code.: 2933399990
• European Community (EC) Number: 634-776-2
• UNII: 8VT513UJ9R
• DSSTox Substance ID: DTXSID80880044
• Nikkaji Number: J2.761.376D,J2.797.186E
• Wikipedia: Piericidin_A
• Wikidata: Q7191888
• Metabolomics Workbench ID: 113911
• ChEMBL ID: CHEMBL272733
• Mol file: 2738-64-9.mol

Synonyms:2-(10-hydroxy-3,7,9,11-tetramethyl-2,4,7,11-tridecatetraenyl)-5,6-dimethoxy-3-methyl-4-pyridinol;AR 054;AR-054;piericidin A;piericidin A1

Chemical Property of Piericidin A

Chemical Property:

• Vapor Pressure: 1.83E-16mmHg at 25°C
• Boiling Point: 591.7oC at 760 mmHg。 产品描述 安全性：
• PKA: 5.21±0.33(Predicted)
• Flash Point: 85oC
• PSA: 71.81000
• Density: 1.05 g/cm3
• LogP: 5.45740
• Storage Temp.: 2-8°C
• Solubility.: Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 20 mg/ml).
• XLogP3: 6.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 415.27225866
• Heavy Atom Count: 30
• Complexity: 809

Purity/Quality:

97% ^*data from raw suppliers

Piericidin A ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T+,Xn
• Statements: 26/27/28-20/21/22
• Safety Statements: 28-36/37-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=C(C)C(C(C)C=C(C)C=CCC(=CCC1=C(C(=O)C(=C(N1)OC)OC)C)C)O
• Isomeric SMILES: C/C=C(\C)/[C@@H]([C@H](C)/C=C(\C)/C=C/C/C(=C/CC1=C(C(=O)C(=C(N1)OC)OC)C)/C)O
• Recent EU Clinical Trials: Randomised controlled single and chronic dosing crossover comparison of extra fine particle formoterol and coarse particle salmeterol in asthmatic patients with persistent small airways dysfunction
• Description: Piericidin A (2738-64-9) is a potent inhibitor of the mitochondrial and bacterial type I NADH-ubiquinone oxidoreductase (complex I).1?Piericidin A is a ubiquinone analog which binds to the ubiquinone binding site of the enzyme.2?It is an extremely useful tool for exploring the role of complex I in mitochondrial function in both normal and pathophysiology.3-5?Prevents upregulation of GRP78 and induces cell death in glucose-deprived, etoposide-resistant HT-29 cells (IC50=7.7 nM).6
• Uses: Piericidin A is the major analogue of a family of pyridyl antibiotics isolated from selected Streptomyces species. It is a specific, potent inhibitor of NADH-ubiquinone oxidoreductase (Complex I) that binds to ubiquinone binding site(s). Piericidin A inhibits both mitochondrial and bacterial NADH-ubiquinone oxidoreductases, binding close to NUOD-NUOB interface. Piericidin A is an antibiotic and a member of the Class I inhibitors that acts as an effective inhibitor of Complex I.

Technology Process of Piericidin A

There total 68 articles about Piericidin A which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

2-[(2E,5E,7E,11E)-(9R,10R)-10-(tert-Butyl-dimethyl-silanyloxy)-3,7,9,11-tetramethyl-trideca-2,5,7,11-tetraenyl]-5,6-dimethoxy-3-methyl-pyridin-4-ol (871316-26-6) → Piericidin A1 (2738-64-9,19855-42-6,5085-85-8)

Guidance literature:

With 4 A molecular sieve; tetrabutyl ammonium fluoride; In tetrahydrofuran; at 50 ℃; for 18h;

DOI:10.1021/ja055041f DOI:10.1021/ja0632862

Reference yield: 87.0%

C37H63NO6Si2 → Piericidin A1 (2738-64-9,19855-42-6,5085-85-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 50 ℃; for 15h; Molecular sieve; Inert atmosphere;

DOI:10.1021/jacs.8b08974

Reference yield: 69.0%

C31H51NO4Si → Piericidin A1 (2738-64-9,19855-42-6,5085-85-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 50 ℃; for 12h; Molecular sieve; Inert atmosphere;

DOI:10.1016/j.tetasy.2009.07.044

upstream raw materials:

2-[(2E,5E,7E,11E)-(9S,10S)-10-(tert-Butyl-dimethyl-silanyloxy)-3,7,9,11-tetramethyl-trideca-2,5,7,11-tetraenyl]-5,6-dimethoxy-3-methyl-pyridin-4-ol

2-[(Z)-Hydroxyimino]-3-methyl-but-3-enoic acid ethyl ester

(5,6-dimethoxy-3-methyl-pyridin-2-yl)-methanol

2-bromomethyl-5,6-dimethoxy-3-methyl-pyridin-4-ol

Downstream raw materials:

2-((2E,5E,7E,11E)-(9R,10S)-10-Hydroxy-3,7,9,11-tetramethyl-trideca-2,5,7,11-tetraenyl)-5,6-dimethoxy-3-methyl-pyridin-4-ol