Piericidin A - ≥95% , CAS No.2738-64-9

CAS: 2738-64-9 Cat. No.: P329435 Fórmula: C₂₅H₃₇NO₄ Peso molecular: 415.57 Beilstein Registry Number: 1555726 Número CE: 634-776-2 PubChem CID: 6437838

GRADE & PURITY ≥95%

Synonyms

BRD-K73581776-001-01-6 | NCGC00180489-01 | Q7191888 | AKOS040746399 | Piericidine A | SCHEMBL18941698 | 2,6,9,11-Tridecatetraen-4-ol, 13-(4-hydroxy-5,6-dimethoxy-3-methyl-2-pyridyl)-3,5,7,11-tetramethyl-, (all-E)-(4R,5R)- | 2-[(2E,5E,7E,11E)-10R-hydroxy-3

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Visão geral

Piericidin A is an antibiotic and a member of the Class I inhibitors. Piericidin A acts as an effective inhibitor of the bacterial and mitochondrial type I NADH-ubiquinone oxidoreductases (Complex I). As an inhibitor of NADH dehydrogenase, Piericidin A inhibits electron transfer. Research indicates that Piericidin A prevents the translocation of the NADH-induced proton in the NADH-endogenous ubiquinone reductase reaction, and that Piericidin A binds near the NUOD-NUOB interface of Complex I. Piericidin A is also known as AR-054, Shaoguanmycin B, Antibiotic MT 1882-I, SN 198E, and 2-[(2E,5E,7E,9R,10R,11E)-10-Hydroxy-3,7,9,11-tetramethyl-2,5,7,11-tridecatetraen-1-yl]-5,6-dimethoxy-3-methyl-4(1H)-pyridinone.

Specifications

Sinónimos

BRD-K73581776-001-01-6 | NCGC00180489-01 | Q7191888 | AKOS040746399 | Piericidine A | SCHEMBL18941698 | 2,6,9,11-Tridecatetraen-4-ol, 13-(4-hydroxy-5,6-dimethoxy-3-methyl-2-pyridyl)-3,5,7,11-tetramethyl-, (all-E)-(4R,5R)- | 2-[(2E,5E,7E,11E)-10R-hydroxy-3

Especificações e pureza

≥95%

Fonte

Streptomycessp.

Condições de armazenamento de armazenamento

Store at -20°C

Enviado em

Ice chest + Ice pads

Este produto requer transporte de cadeia fria. Serviços terrestres e outros serviços econômicos não estão disponíveis.

Tipo de ação

INHIBITOR

Pureza

≥95%

Propriedades do produto

• pKa: pKa: 5.22 (Predicted), pKa: 10.17 (Predicted)

Nomes e identificadores

• Pubchem Sid: 528774490
• Sorrisos canónicos: CC=C(C)C(C(C)C=C(C)C=CCC(=CCC1=C(C(=O)C(=C(N1)OC)OC)C)C)O
• IUPAC Name: 2-[(2E,5E,7E,9R,10R,11E)-10-hydroxy-3,7,9,11-tetramethyltrideca-2,5,7,11-tetraenyl]-5,6-dimethoxy-3-methyl-1H-pyridin-4-one
• InChIKey: BBLGCDSLCDDALX-LKGBESRRSA-N
• INCHI: 1S/C25H37NO4/c1-9-18(4)22(27)19(5)15-17(3)12-10-11-16(2)13-14-21-20(6)23(28)24(29-7)25(26-21)30-8/h9-10,12-13,15,19,22,27H,11,14H2,1-8H3,(H,26,28)/b12-10+,16-13+,17-15+,18-9+/t19-,22+/m1/s1
• SMILES isoméricas: 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
• WGK Alemanha: 1
• RTECS: YD4588000
• PubChem CID: 6437838
• Peso molecular: 415.57
• Beilstein: 1555726

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Classe Prenol lipids
      • Subclass Sesquiterpenoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Classe: Prenol lipids
• Subclass: Sesquiterpenoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Sesquiterpenoids
• Alternative Parents: Methylpyridines Dihydropyridines Alkyl aryl ethers Vinylogous esters Vinylogous amides Heteroaromatic compounds Secondary alcohols Cyclic ketones Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Farsesane sesquiterpenoid - Sesquiterpenoid - Alkyl aryl ether - Dihydropyridine - Methylpyridine - Hydropyridine - Pyridine - Heteroaromatic compound - Vinylogous ester - Vinylogous amide - Cyclic ketone - Secondary alcohol - Ether - Azacycle - Organoheterocyclic compound - Alcohol - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Aromatic heteromonocyclic compound
• Descrição: This compound belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
• External Descriptors: Not available

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

Alvos associados (humanos)

NR1H3 Tchem LXR-alpha (2891 Activities)

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ACHN (49357 Activities)

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HL-60 (67320 Activities)

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SW480 (6023 Activities)

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U2OS (164939 Activities)

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786-0 (47912 Activities)

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HepG2 (196354 Activities)

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HeLa (62764 Activities)

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MDA-MB-231 (73002 Activities)

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IDO1 Tchem Indoleamine 2,3-dioxygenase (6650 Activities)

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PRDX1 Tchem Peroxiredoxin-1 (29 Activities)

Discover Target: PRDX1

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OS-RC-2 (487 Activities)

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Alvos associados (não humanos)

MT-ND1 NADH-ubiquinone oxidoreductase chain 1 (124 Activities)

Discover Target: MT-ND1

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Mus musculus (284745 Activities)

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L929 (3802 Activities)

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NDUFV1 Mitochondrial complex I; NADH oxidoreductase (130 Activities)

Discover Target: NDUFV1

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Mecanismos de ação

Propriedades químicas e físicas

• Solubilidade: Soluble in 100% ethanol, DMF, DMSO, and water (poorly).
• Índice de refração: n20D1.53 (Predicted)
• Ponto de inflamação (°F): 185 °F
• Ponto de inflamação (°C): 85 °C
• Ponto de ebulição (°C): ~591.7° C at 760 mmHg (Predicted) (tautomer)
• Ponto de fusão (°C): 220.48° C (Predicted) (tautomer)
• Peso molecular: 415.600 g/mol
• XLogP3: 6.100
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 415.272 Da
• Monoisotopic Mass: 415.272 Da
• Topological Polar Surface Area: 67.800 Ų
• Heavy Atom Count: 30
• Formal Charge: 0
• Complexity: 809.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 4
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 4
• Covalently-Bonded Unit Count: 1

Referências

1. Rui Miao, Cong Jiang, Winston Y. Chang, Haiwei Zhang, Jinsu An, Felicia Ho, Pengcheng Chen, Han Zhang, Caroline Junqueira, Dulguun Amgalan, Felix G. Liang, Junbing Zhang, Charles L. Evavold, Iva Hafner-Bratkovič, Zhibin Zhang, Pietro Fontana, Shiyu Xia, Markus Waldeck-Weiermair, Youdong Pan, Thomas Michel, Liron Bar-Peled, Hao Wu, Jonathan C. Kagan, Richard N. Kitsis, Peng Zhang, Xing Liu, Judy Lieberman.  (2023)  Gasdermin D permeabilization of mitochondrial inner and outer membranes accelerates and enhances pyroptosis.  IMMUNITY,      [PMID:37924812] [10.1016/j.immuni.2023.10.004]

2. He Ya-Wen, Law Jodi Woan-Fei, Azad Sepideh Mazhari, Hu Wen-Da, Song Kai, Chua Kah-Ooi, Jiang Lian, Jin Yu, Lee Learn-Han, Zhou Lian.  (2025)  Identification and genomic analyses of a novel actinobacterium Streptomyces shaowuensis sp. nov. with biocontrol potential for rice bacterial blight.  Phytopathology Research,  7  (1): (1-16).  [PMID:] [10.1186/s42483-025-00313-9]