A quinolinecarboxylic acid derivative with immunosuppressive and anti-neoplastic properties. Inhibits pyrimidine synthesis by blocking the activity of mammalian mitochondrial dihydroorotate dehydrogenase (DHODH; IC50 = 12 nM). Does not affect DHODH in non-mammalian species. Also reported to inhibit glycosylation of adhesion molecules. Potentiates the sensitivity of U1690 small cell lung cancer cells to TRAIL-induced apoptosis and synergistically enhances the anti-tumor effects of doxorubicin ( ~100 µM).

사양

동의어

BRQ, DuP 785, NSC 368390 | 6-Fluoro-2-(2'-fluoro[1,1'-biphenyl]-4-yl)-3-methyl-4-quinolinecarboxylic acid sodium

사양 및 순도

≥95%

생화학 및 생리적 메커니즘

Potent and selective dihydroorotate dehydrogenase (DHODH) inhibitor (IC50= ~20 nM). Causes depletion of pyrimidine nucleotides. Exhibits minimal inhibition against a panel of >400 kinases. Triggers differentiation of AML cell lines (ED50= ~ 1 μM. Note uri

보관 조건

Store at -20°C,Argon charged

배송

Ice chest + Ice pads

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순수함

≥95%

이름과 식별자

Pubchem Sid

528771629

정식 스마일

CC1=C(C2=C(C=CC(=C2)F)N=C1C3=CC=C(C=C3)C4=CC=CC=C4F)C(=O)[O-].[Na+]

IUPAC Name

sodium;6-fluoro-2-[4-(2-fluorophenyl)phenyl]-3-methylquinoline-4-carboxylate

InChIKey

PZOHOALJQOFNTB-UHFFFAOYSA-M

INCHI

1S/C23H15F2NO2.Na/c1-13-21(23(27)28)18-12-16(24)10-11-20(18)26-22(13)15-8-6-14(7-9-15)17-4-2-3-5-19(17)25;/h2-12H,1H3,(H,27,28);/q;+1/p-1

이성체 SMILES

CC1=C(C2=C(C=CC(=C2)F)N=C1C3=CC=C(C=C3)C4=CC=CC=C4F)C(=O)[O-].[Na+]

분자량

397.35

Reaxy-Rn

6466194

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=6466194&ln=

고급 데이터

Taxonomic Classification

Taxonomy Tree

Kingdom Organic compounds
- Superclass Organoheterocyclic compounds
  - 분류 Quinolines and derivatives
    - Subclass Phenylquinolines

Kingdom	Organic compounds
Superclass	Organoheterocyclic compounds
분류	Quinolines and derivatives
Subclass	Phenylquinolines
Intermediate Tree Nodes	Not available
Direct Parent	Phenylquinolines
Alternative Parents	Quinoline carboxylic acids Phenylpyridines Biphenyls and derivatives Haloquinolines Pyridinecarboxylic acids Fluorobenzenes Methylpyridines Aryl fluorides Heteroaromatic compounds Carboxylic acid salts Azacyclic compounds Carboxylic acids Organic metal halides Organic sodium salts Organic zwitterions Organooxygen compounds Organofluorides Organic oxides Hydrocarbon derivatives Organonitrogen compounds
Molecular Framework	Aromatic heteropolycyclic compounds
Substituents	Phenylquinoline - Quinoline-4-carboxylic acid - Biphenyl - 2-phenylpyridine - Haloquinoline - Pyridine carboxylic acid - Pyridine carboxylic acid or derivatives - Fluorobenzene - Halobenzene - Methylpyridine - Monocyclic benzene moiety - Benzenoid - Aryl fluoride - Aryl halide - Pyridine - Heteroaromatic compound - Carboxylic acid salt - Azacycle - Organic metal halide - Organic alkali metal salt - Carboxylic acid derivative - Carboxylic acid - Hydrocarbon derivative - Organofluoride - Organohalogen compound - Organic zwitterion - Organonitrogen compound - Organic sodium salt - Organooxygen compound - Organic nitrogen compound - Organic salt - Organic oxygen compound - Organic oxide - Aromatic heteropolycyclic compound
설명	This compound belongs to the class of organic compounds known as phenylquinolines. These are heterocyclic compounds containing a quinoline moiety substituted with a phenyl group.
External Descriptors	Not available
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

3D 구조

관련 대상(인간)

DHODH Tclin Dihydroorotate dehydrogenase (quinone), mitochondrial (6 Activities)

Discover Target: DHODH

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

DHODH Tclin Dihydroorotate dehydrogenase (2737 Activities)

Discover Target: DHODH

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

A-375 (9258 Activities)

용해성	Solvent:water, Max Conc. mg/mL: 39.73, Max Conc. mM: 100; Solvent:DMSO, Max Conc. mg/mL: 39.73, Max Conc. mM: 100
분자량	397.300 g/mol
XLogP3
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	3
Exact Mass	397.089 Da
Monoisotopic Mass	397.089 Da
Topological Polar Surface Area	53.000 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	557.000
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
The total count of all stereochemical bonds	0
Covalently-Bonded Unit Count	2

Brequinar sodium - ≥95% , CAS No.96201-88-6

개요

사양

고급 데이터

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