but-2-enedioic acid; {6-[4-(4-bromobenzoyl)-3-fluorophenoxy]hexyl}(methyl)(prop-2-en-1-yl)amine

• ChemBase ID: 154206
• Molecular Formular: C27H31BrFNO6
• Molecular Mass: 564.4405432
• Monoisotopic Mass: 563.13187794
• SMILES: CN(CCCCCCOc1ccc(c(c1)F)C(=O)c1ccc(cc1)Br)CC=C.C(=C\C(=O)O)/C(=O)O
• Canonical SMILES: OC(=O)/C=C/C(=O)O.C=CCN(CCCCCCOc1ccc(c(c1)F)C(=O)c1ccc(cc1)Br)C
• InChI: InChI=1S/C23H27BrFNO2.C4H4O4/c1-3-14-26(2)15-6-4-5-7-16-28-20-12-13-21(22(25)17-20)23(27)18-8-10-19(24)11-9-18;5-3(6)1-2-4(7)8/h3,8-13,17H,1,4-7,14-16H2,2H3;1-2H,(H,5,6)(H,7,8)
• InChIKey: XCYAYLWZCRGKDS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: but-2-enedioic acid; {6-[4-(4-bromobenzoyl)-3-fluorophenoxy]hexyl}(methyl)(prop-2-en-1-yl)amine
• IUPAC Traditional name: C23H27BrFNO2; butenedioic acid
• Synonyms: [4′-[6-(Allylmethylamino)hexyloxy]-4-bromo-2′-fluorobenzophenone fumarate (1:1); Ro 48-8071 fumarate

Database IDs

• CAS Number: 189197-69-1
• MDL Number: MFCD05865242
• PubChem SID: 162248345
• PubChem CID: 9959583

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.0422175
• LogD (pH = 7.4): 4.3948054
• Log P: 6.402736
• Molar Refractivity: 116.8297 cm^3
• Polarizability: 44.703552 Å^3
• Polar Surface Area: 29.54 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: >5 mg/mL at ~60 °C
• Apperance: white solid
• Melting Point: 90-92.7 °C

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C23H27NO2BrF · C4H4O4

DETAILS

Sigma Aldrich - R2278

Biochem/physiol Actions
Orally active 2,3-oxidosqualene:lanosterol cyclase (OSC) inhibitor. OSC (EC 5.4.99.7) represents a unique target for a cholesterol-lowering drug. Partial inhibition of OSC should reduce synthesis of lanosterol and subsequent sterols, and also stimulate the production of epoxysterols that repress HMG-CoA reductase expression, generating a synergistic, self-limited negative regulatory loop.