SB 204990 - ≥98%(HPLC) , CAS No.154566-12-8

CAS: 154566-12-8 Cat. No.: S286623 Molecular Weight: 389.27 PubChem CID: 10340264

GRADE & PURITY ≥98%(HPLC)

Synonyms

(3R,5S)-rel-5-[6-(2,4-Dichlorophenyl)hexyl]tetrahydro-3-hydroxy-2-oxo-3-furanacetic acid | SB-204990 | 2-[(3S,5R)-5-[6-(2,4-dichlorophenyl)hexyl]-3-hydroxy-2-oxooxolan-3-yl]acetic acid | EX-A6876 | 3-Furanacetic acid, 5-(6-(2,4-dichlorophenyl)hexyl)tetrah

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Specifications

Synonyms

(3R, 5S)-rel-5-[6-(2, 4-Dichlorophenyl)hexyl]tetrahydro-3-hydroxy-2-oxo-3-furanacetic acid | SB-204990 | 2-[(3S, 5R)-5-[6-(2, 4-dichlorophenyl)hexyl]-3-hydroxy-2-oxooxolan-3-yl]acetic acid | EX-A6876 | 3-Furanacetic acid, 5-(6-(2, 4-dichlorophenyl)hexyl)tetrah

Specifications & Purity

≥98%(HPLC)

Biochemical and Physiological Mechanisms

SB-204990 is a cell-permeable and orally available γ-lactone prodrug of the non-cell-permeable SB-201076 that inhibits human and rat ATP citrate-lyase (Ki =1 μM against human and rat ACL) in a predominantly competitive manner with a small but significant

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

≥98%(HPLC)

Names and Identifiers

• Canonical Smiles: C1C(OC(=O)C1(CC(=O)O)O)CCCCCCC2=C(C=C(C=C2)Cl)Cl
• IUPAC Name: 2-[(3S,5R)-5-[6-(2,4-dichlorophenyl)hexyl]-3-hydroxy-2-oxooxolan-3-yl]acetic acid
• InChIKey: YTRNLFYTHYWDAU-KDOFPFPSSA-N
• INCHI: 1S/C18H22Cl2O5/c19-13-8-7-12(15(20)9-13)5-3-1-2-4-6-14-10-18(24,11-16(21)22)17(23)25-14/h7-9,14,24H,1-6,10-11H2,(H,21,22)/t14-,18+/m1/s1
• Isomeric SMILES: C1[C@H](OC(=O)[C@]1(CC(=O)O)O)CCCCCCC2=C(C=C(C=C2)Cl)Cl
• PubChem CID: 10340264
• Molecular Weight: 389.27

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Halobenzenes
        • Level5 Chlorobenzenes
          • Level6 Dichlorobenzenes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Halobenzenes
• Intermediate Tree Nodes: Chlorobenzenes
• Direct Parent: Dichlorobenzenes
• Alternative Parents: Gamma butyrolactones Dicarboxylic acids and derivatives Aryl chlorides Tertiary alcohols Oxolanes Carboxylic acid esters Oxacyclic compounds Carboxylic acids Organochlorides Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: 1,3-dichlorobenzene - Aryl chloride - Aryl halide - Dicarboxylic acid or derivatives - Gamma butyrolactone - Tertiary alcohol - Oxolane - Carboxylic acid ester - Lactone - Organoheterocyclic compound - Oxacycle - Carboxylic acid - Carboxylic acid derivative - Organohalogen compound - Hydrocarbon derivative - Alcohol - Carbonyl group - Organic oxide - Organic oxygen compound - Organochloride - Organooxygen compound - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as dichlorobenzenes. These are compounds containing a benzene with exactly two chlorine atoms attached to it.
• 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)

ACLY Tclin ATP-citrate synthase (168 Activities)

Discover Target: ACLY

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

PC-3 (62116 Activities)

Explore this target

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

SK-OV-3 (52876 Activities)

Explore this target

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

A549 (127892 Activities)

Explore this target

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

Associated Targets(non-human)

Rattus norvegicus (775804 Activities)

Explore this target

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solvent:DMSO, Max Conc. mg/mL: 38.93, Max Conc. mM: 100; Solvent:ethanol, Max Conc. mg/mL: 38.93, Max Conc. mM: 100
• Molecular Weight: 389.300 g/mol
• XLogP3: 5.100
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 388.084 Da
• Monoisotopic Mass: 388.084 Da
• Topological Polar Surface Area: 83.800 Ų
• Heavy Atom Count: 25
• Formal Charge: 0
• Complexity: 472.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• 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: 1

References

1. Jun Li, Xiaomin Wang, Min Tan, Jianxiong Zheng, Jing Mao, Jiayao Hao, Haili Shen.  (2024)  Neutrophil extracellular traps in rheumatoid arthritis: Activating fibroblast-like synoviocytes via ATP citrate lyase.  INTERNATIONAL IMMUNOPHARMACOLOGY,      [PMID:39522314] [10.1016/j.intimp.2024.113518]