Bedaquiline fumarate - ≥99% , ATP synthase inhibitor, CAS No.845533-86-0, ATP synthase inhibitor

CAS: 845533-86-0 Cat. No.: B413184 Molecular Weight: 671.58 EC Number: 805-637-5 PubChem CID: 24812732

GRADE & PURITY ≥99%

Synonyms

(1R,2S)-1-(6-BROMO-2-METHOXYQUINOLIN-3-YL)-4-(DIMETHYLAMINO)-2-(NAPHTHALEN-1-YL)-1-PHENYLBUTAN-2-OL (2E)-BUT-2-ENEDIOATE SALT (1:1) | AS-57710 | (1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(1-naphthyl)-1-phenylbutan-2-ol bis[(2Z)-but-2-

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Information

Bedaquiline fumarate Bedaquiline fumarate (TMC-207),  is a bactericidal antimycobacterial drug. It is a proton-translocating ATP synthetase inhibitor.

Specifications

Synonyms

(1R, 2S)-1-(6-BROMO-2-METHOXYQUINOLIN-3-YL)-4-(DIMETHYLAMINO)-2-(NAPHTHALEN-1-YL)-1-PHENYLBUTAN-2-OL (2E)-BUT-2-ENEDIOATE SALT (1:1) | AS-57710 | (1R, 2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(1-naphthyl)-1-phenylbutan-2-ol bis[(2Z)-but-2-

Specifications & Purity

≥99%

Biochemical and Physiological Mechanisms

Bedaquiline fumarate (TMC-207), is a bactericidal antimycobacterial drug. It is a proton-translocating ATP synthetase inhibitor.

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

Mechanism of action

ATP synthase inhibitor

Purity

≥99%

Names and Identifiers

• Pubchem Sid: 504769838
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504769838
• Canonical Smiles: CN(C)CCC(C1=CC=CC2=CC=CC=C21)(C(C3=CC=CC=C3)C4=C(N=C5C=CC(=CC5=C4)Br)OC)O.C(=CC(=O)O)C(=O)O
• IUPAC Name: (1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-naphthalen-1-yl-1-phenylbutan-2-ol;(E)-but-2-enedioic acid
• InChIKey: ZLVSPMRFRHMMOY-WWCCMVHESA-N
• INCHI: 1S/C32H31BrN2O2.C4H4O4/c1-35(2)19-18-32(36,28-15-9-13-22-10-7-8-14-26(22)28)30(23-11-5-4-6-12-23)27-21-24-20-25(33)16-17-29(24)34-31(27)37-3;5-3(6)1-2-4(7)8/h4-17,20-21,30,36H,18-19H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;2-1+/t30-,32-;/m1./s1
• Isomeric SMILES: CN(C)CC[C@@](C1=CC=CC2=CC=CC=C21)([C@H](C3=CC=CC=C3)C4=C(N=C5C=CC(=CC5=C4)Br)OC)O.C(=C/C(=O)O)\C(=O)O
• PubChem CID: 24812732
• Molecular Weight: 671.58

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Stilbenes

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Stilbenes
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Stilbenes
• Alternative Parents: Quinolones and derivatives Phenylbutylamines Haloquinolines Naphthalenes Alkyl aryl ethers Aralkylamines Unsaturated fatty acids Pyridines and derivatives Aryl bromides Dicarboxylic acids and derivatives Tertiary alcohols 1,3-aminoalcohols Heteroaromatic compounds Trialkylamines Azacyclic compounds Carboxylic acids Organopnictogen compounds Hydrocarbon derivatives Aromatic alcohols Organic oxides Carbonyl compounds Organobromides
• Molecular Framework: Not available
• Substituents: Stilbene - Phenylbutylamine - Haloquinoline - Quinolone - Naphthalene - Quinoline - Alkyl aryl ether - Aralkylamine - Fatty acyl - Fatty acid - Dicarboxylic acid or derivatives - Monocyclic benzene moiety - Benzenoid - Pyridine - Unsaturated fatty acid - Aryl halide - Aryl bromide - Heteroaromatic compound - 1,3-aminoalcohol - Tertiary alcohol - Tertiary aliphatic amine - Tertiary amine - Azacycle - Organoheterocyclic compound - Carboxylic acid derivative - Ether - Carboxylic acid - Alcohol - Organic nitrogen compound - Organohalogen compound - Organobromide - Organonitrogen compound - Organooxygen compound - Carbonyl group - Organic oxygen compound - Organopnictogen compound - Organic oxide - Amine - Hydrocarbon derivative - Aromatic alcohol - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
• External Descriptors: fumarate salt

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solubility (25°C) In vitro DMSO: 100 mg/mL (148.9 mM); Ethanol: 4 mg/mL (5.95 mM); Water: Insoluble
• Sensitivity: Moisture sensitive
• Molecular Weight: 671.600 g/mol
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 10
• Exact Mass: 670.168 Da
• Monoisotopic Mass: 670.168 Da
• Topological Polar Surface Area: 120.000 Ų
• Heavy Atom Count: 45
• Formal Charge: 0
• Complexity: 834.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 2

XLogP3

References

1. Ling Cheng, Ian Meliala, Yidi Kong, Jingyuan Chen, Christopher G Proud, Mikael Björklund.  (2025)  PEBP1 amplifies mitochondrial dysfunction-induced integrated stress response.  eLife,      [PMID:39878441] [10.7554/eLife.102852]