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 EC: 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

Descripción general

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

Especificaciones y pureza

≥95%

Fuente

Streptomycessp.

Condiciones de almacenamiento de almacenamiento

Store at -20°C

Enviado en

Ice chest + Ice pads

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Tipo de acción

INHIBITOR

Pureza

≥95%

Propiedades del producto

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

Nombres e identificadores

• Pubchem Sid: 528774490
• Sonrisas canónicas: 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
• Isómeros 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 Alemania: 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
    • Clase Prenol lipids
      • Subclass Sesquiterpenoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Clase: 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
• Descripción: 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

Objetivos asociados (humanos)

NR1H3 Tchem LXR-alpha (2891 Activities)

Discover Target: NR1H3

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

ACHN (49357 Activities)

Explore this target

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

HL-60 (67320 Activities)

Explore this target

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

SW480 (6023 Activities)

Explore this target

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

U2OS (164939 Activities)

Explore this target

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

786-0 (47912 Activities)

Explore this target

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

HepG2 (196354 Activities)

Explore this target

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

HeLa (62764 Activities)

Explore this target

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

MDA-MB-231 (73002 Activities)

Explore this target

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

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

Discover Target: IDO1

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

PRDX1 Tchem Peroxiredoxin-1 (29 Activities)

Discover Target: PRDX1

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

OS-RC-2 (487 Activities)

Explore this target

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

Objetivos asociados (no humanos)

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

Discover Target: MT-ND1

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

Mus musculus (284745 Activities)

Explore this target

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

L929 (3802 Activities)

Explore this target

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

NDUFV1 Mitochondrial complex I; NADH oxidoreductase (130 Activities)

Discover Target: NDUFV1

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

Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: Soluble in 100% ethanol, DMF, DMSO, and water (poorly).
• Índice de refracción: n20D1.53 (Predicted)
• Punto de inflamación (°F): 185 °F
• Punto de inflamación (°C): 85 °C
• Punto de ebullición (°C): ~591.7° C at 760 mmHg (Predicted) (tautomer)
• Punto de fusión (°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

Referencias

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]