3-[(3aR,9bS)-6,8-difluoro-3H,3aH,4H,5H,9bH-cyclopenta[c]quinolin-4-yl]pyridine

• ChemBase ID: 155512
• Molecular Formular: C17H14F2N2
• Molecular Mass: 284.3032664
• Monoisotopic Mass: 284.1125049
• SMILES: c1cc(cnc1)C1[C@@H]2CC=C[C@@H]2c2cc(cc(c2N1)F)F
• Canonical SMILES: Fc1cc(F)c2c(c1)[C@H]1C=CC[C@H]1C(N2)c1cccnc1
• InChI: InChI=1S/C17H14F2N2/c18-11-7-14-12-4-1-5-13(12)16(10-3-2-6-20-9-10)21-17(14)15(19)8-11/h1-4,6-9,12-13,16,21H,5H2/t12-,13+,16?/m0/s1
• InChIKey: NJZHEQOUHLZCOX-FTLRAWMYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(3aR,9bS)-6,8-difluoro-3H,3aH,4H,5H,9bH-cyclopenta[c]quinolin-4-yl]pyridine
• IUPAC Traditional name: 3-[(3aR,9bS)-6,8-difluoro-3H,3aH,4H,5H,9bH-cyclopenta[c]quinolin-4-yl]pyridine
• Synonyms: 6,8-Difluoro-4-pyridin-3-yl-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline; CID 25113626; GCA; Golgicide A; (3aR,9bS)-rel-6,8-Difluoro-3a,4,5,9b-tetrahydro-4-(3-pyridinyl)-3H-cyclopenta[c]quinoline; Golgicide A

Database IDs

• CAS Number: 1005036-73-6; 1139889-93-2
• PubChem SID: 162249650
• PubChem CID: 25113626

CALCULATED PROPERTIES

• Acid pKa: 14.197743
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.9847121
• LogD (pH = 7.4): 3.052412
• Log P: 3.0533657
• Molar Refractivity: 79.6567 cm^3
• Polarizability: 28.831083 Å^3
• Polar Surface Area: 24.92 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: solid

Safety Information

• German water hazard class: 3
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H319
• GHS Precautionary statements: P305 + P351 + P338
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C17H14F2N2

DETAILS

Sigma Aldrich - G0923

Biochem/physiol Actions
Golgicide A is a potent, highly specific, reversible inhibitor of the cis-Golgi ArfGEF GBF1. Arf proteins are members of the Ras superfamily of small guanosine triphosphatases (GTPases) that mediate vesicular transport. Golgicide A binds within an interfacial cleft formed between Arf1 and the GBF1 Sec7 domain. Golgicide A is a unique and powerful tool for further elucidating the mechanisms underlying assembly and transport within the Golgi, comparable to the use of dynasore for studying the dynamics of dynamin-mediated clathrin coat formation.

Toronto Research Chemicals - G766500

Golgicide A, a potent, highly specific, reversible inhibitor of the cis-Golgi ArfGEF GBF1.

REFERENCES

• Shmuel, M., et al.: J. Biol. Chem., 281, 13300 (2006)
• Cohen, L., et al.: Mol. Biol. Cell., 18, 2244 (2006)