2-({4-[2-(trifluoromethyl)phenyl]piperidine-1-carbonyl}amino)benzoic acid

• ChemBase ID: 4638
• Molecular Formular: C20H19F3N2O3
• Molecular Mass: 392.3716696
• Monoisotopic Mass: 392.13477714
• SMILES: N1(CCC(CC1)c1c(cccc1)C(F)(F)F)C(=O)Nc1c(C(=O)O)cccc1
• Canonical SMILES: O=C(N1CCC(CC1)c1ccccc1C(F)(F)F)Nc1ccccc1C(=O)O
• InChI: InChI=1S/C20H19F3N2O3/c21-20(22,23)16-7-3-1-5-14(16)13-9-11-25(12-10-13)19(28)24-17-8-4-2-6-15(17)18(26)27/h1-8,13H,9-12H2,(H,24,28)(H,26,27)
• InChIKey: MEAQCLPMSVEOQF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-({4-[2-(trifluoromethyl)phenyl]piperidine-1-carbonyl}amino)benzoic acid
• IUPAC Traditional name: 2-{4-[2-(trifluoromethyl)phenyl]piperidine-1-carbonylamino}benzoic acid
• Synonyms: 2-[({4-[2-(trifluoromethyl)phenyl]piperidin-1-yl}carbonyl)amino]benzoic acid; 2-(4-(2-(trifluoromethyl)phenyl)piperidine-1-carboxamido)benzoic acid; A1120

Database IDs

• MDL Number: MFCD12912393
• PubChem SID: 99443456; 160968070
• PubChem CID: 25138295

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.5305867
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.8191328
• LogD (pH = 7.4): 1.4153595
• Log P: 4.7813835
• Molar Refractivity: 99.4066 cm^3
• Polarizability: 36.01992 Å^3
• Polar Surface Area: 69.64 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.68
• LOG S: -4.59
• Solubility (Water): 1.01e-02 g/l

PROPERTIES

Physical Property

• Solubility: DMSO: ≥10 mg/mL
• Apperance: off-white powder

Safety Information

• Storage Condition: desiccated
• European Hazard Symbols: Nature polluting (N); Harmful (Xn)
• UN Number: 3077
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 22-36-43-50/53
• Safety Statements: 26-36/37-60-61
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H317-H319-H400
• GHS Precautionary statements: P273-P280-P305 + P351 + P338
• RID/ADR: UN 3077 9/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C20H19F3N2O3

DETAILS

DrugBank - DB06985

Drug information: experimental

Sigma Aldrich - A3111

Biochem/physiol Actions
A1120 is a selective non-retinoid ligand for retinol-binding protein 4 (RBP4). RBP4 transports retinol from the liver to extrahepatic tissues and RBP4 lowering is reported to improve insulin sensitivity in mice. A1120 is a high affinity non-retinoid ligand for RBP4 which disrupts the interaction between RBP4 and its binding partner transthyretin (TTR). It binds to the same site as retinol and induces changes in the orientation (compared to the retinol bound form) of loops at the RBP4-TTR interaction interface.A1120 lowers RBP4 and retinol levels in a dose-dependent manner, to a similar extent as seen with fenretinide. However, unlike fenretinide (Sigma# H7779), A1120 does not have beneficial effects on insulin resistance.