(2S)-2-({4-[(1H-imidazol-4-ylmethyl)amino]-2-(naphthalen-1-yl)phenyl}formamido)-4-methylpentanoic acid; trifluoroacetic acid

• ChemBase ID: 154242
• Molecular Formular: C29H29F3N4O5
• Molecular Mass: 570.5595696
• Monoisotopic Mass: 570.20900471
• SMILES: CC(C)C[C@@H](C(=O)O)NC(=O)c1ccc(cc1c1cccc2c1cccc2)NCc1c[nH]cn1.C(=O)(C(F)(F)F)O
• Canonical SMILES: OC(=O)C(F)(F)F.CC(C[C@@H](C(=O)O)NC(=O)c1ccc(cc1c1cccc2c1cccc2)NCc1c[nH]cn1)C
• InChI: InChI=1S/C27H28N4O3.C2HF3O2/c1-17(2)12-25(27(33)34)31-26(32)23-11-10-19(29-15-20-14-28-16-30-20)13-24(23)22-9-5-7-18-6-3-4-8-21(18)22;3-2(4,5)1(6)7/h3-11,13-14,16-17,25,29H,12,15H2,1-2H3,(H,28,30)(H,31,32)(H,33,34);(H,6,7)/t25-;/m0./s1
• InChIKey: FXXUNOYBYJFSRB-UQIIZPHYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-({4-[(1H-imidazol-4-ylmethyl)amino]-2-(naphthalen-1-yl)phenyl}formamido)-4-methylpentanoic acid; trifluoroacetic acid
• IUPAC Traditional name: (2S)-2-({4-[(1H-imidazol-4-ylmethyl)amino]-2-(naphthalen-1-yl)phenyl}formamido)-4-methylpentanoic acid; trifluoroacetic acid
• Synonyms: N-[[4-(Imidazol-4-yl)methylamino]-2-(1-naphthyl)benzoyl]leucine trifluoroacetate salt; GGTI-2133

Database IDs

• MDL Number: MFCD07776925
• PubChem SID: 24724491; 162248381
• PubChem CID: 16078972

CALCULATED PROPERTIES

• Acid pKa: 4.072431
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 2.849691
• LogD (pH = 7.4): 1.7675228
• Log P: 2.9108512
• Molar Refractivity: 133.1106 cm^3
• Polarizability: 52.585014 Å^3
• Polar Surface Area: 107.11 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: soluble25 mg/mL; H2O: insoluble
• Apperance: white solid
• Melting Point: 103-118.5 °C

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... FNTA(2339), PGGT1B(5229)

Product Information

• Purity: ≥98% (HPLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C27H28N4O3 · C2HF3O2

DETAILS

Sigma Aldrich - G5294

Biochem/physiol Actions
GGTI-2133 is a cell-permeable non-thiol peptidomimetic that acts as a potent and selective inhibitor of geranylgeranyltransferase I (GGTase I; IC50 = 38 nM) with a 140-fold selectivity over farnesyltransferase (FTase; IC50 = 5.4 μM).