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

CAS: 2738-64-9 Cat. No.: P329435 Formula: C₂₅H₃₇NO₄ Molecular Weight: 415.57 Beilstein Registry Number: 1555726 EC Number: 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

Overview

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

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

Specifications & Purity

≥95%

Source

Streptomycessp.

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

INHIBITOR

Purity

≥95%

Product Properties

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

Names and Identifiers

• Pubchem Sid: 528774490
• 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
• 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
• 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
• WGK Germany: 1
• RTECS: YD4588000
• PubChem CID: 6437838
• Molecular Weight: 415.57
• Beilstein: 1555726

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: 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
• Description: 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

Associated Targets(Human)

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)

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OS-RC-2 (487 Activities)

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Associated Targets(non-human)

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

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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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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in 100% ethanol, DMF, DMSO, and water (poorly).
• Refractive Index: n20D1.53 (Predicted)
• Flash Point(°F): 185 °F
• Flash Point(°C): 85 °C
• Boil Point(°C): ~591.7° C at 760 mmHg (Predicted) (tautomer)
• Melt Point(°C): 220.48° C (Predicted) (tautomer)
• Molecular Weight: 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