Information
Bedaquiline fumarate Bedaquiline fumarate (TMC-207), an oral diarylquinoline, is a bactericidal antimycobacterial drug. It is a proton-translocating ATP synthetase inhibitor.
| 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 |
Comprehensive hazard, handling, storage, and regulatory compliance document.
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View spec sheet →Taxonomy Tree
| 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 |
| Molecular Weight | 671.600 g/mol |
|---|---|
| XLogP3 | |
| 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 |
| 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] |
