trifluoroacetic acid methyl (2S)-2-[(4-{[(2R)-2-amino-3-sulfanylpropyl]amino}-2-(naphthalen-1-yl)phenyl)formamido]-4-methylpentanoate

• ChemBase ID: 154248
• Molecular Formular: C29H34F3N3O5S
• Molecular Mass: 593.6575696
• Monoisotopic Mass: 593.21712686
• SMILES: CC(C)C[C@@H](C(=O)OC)NC(=O)c1ccc(cc1c1cccc2c1cccc2)NC[C@H](CS)N.C(=O)(C(F)(F)F)O
• Canonical SMILES: OC(=O)C(F)(F)F.SC[C@@H](CNc1ccc(c(c1)c1cccc2c1cccc2)C(=O)N[C@H](C(=O)OC)CC(C)C)N
• InChI: InChI=1S/C27H33N3O3S.C2HF3O2/c1-17(2)13-25(27(32)33-3)30-26(31)23-12-11-20(29-15-19(28)16-34)14-24(23)22-10-6-8-18-7-4-5-9-21(18)22;3-2(4,5)1(6)7/h4-12,14,17,19,25,29,34H,13,15-16,28H2,1-3H3,(H,30,31);(H,6,7)/t19-,25+;/m1./s1
• InChIKey: WALKWJPZELDSKT-UFABNHQSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: trifluoroacetic acid methyl (2S)-2-[(4-{[(2R)-2-amino-3-sulfanylpropyl]amino}-2-(naphthalen-1-yl)phenyl)formamido]-4-methylpentanoate
• IUPAC Traditional name: trifluoroacetic acid methyl (2S)-2-[(4-{[(2R)-2-amino-3-sulfanylpropyl]amino}-2-(naphthalen-1-yl)phenyl)formamido]-4-methylpentanoate
• Synonyms: N-[[4-(2-(R)-Amino-3-mercaptopropyl)amino]-2-naphthylbenzoyl]leucine methyl ester trifluoroacetate salt hydrate; GGTI 298 trifluoroacetate salt hydrate

Database IDs

• CAS Number: 1217457-86-7(anhydrous)
• MDL Number: MFCD06409252
• PubChem SID: 162248387; 24724490
• PubChem CID: 16078971

CALCULATED PROPERTIES

• Acid pKa: 10.253076
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): 1.3153441
• LogD (pH = 7.4): 2.445939
• Log P: 4.057935
• Molar Refractivity: 140.9294 cm^3
• Polarizability: 56.57051 Å^3
• Polar Surface Area: 93.45 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL
• Apperance: colorless film; lyophilized
• Melting Point: 99.5-100 °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 ... PGGT1B(5229)

Product Information

• Purity: ≥90% (HPLC)
• Impurities: <10% dimer
• Empirical Formula (Hill Notation): C27H33N3O3S · C2HF3O2 · xH2O

DETAILS

Sigma Aldrich - G5169

Biochem/physiol Actions
GGTI 298 is a cell-permeable, prodrug form of the geranylgeranyltransferase I (GGTase I) inhibitor GGTI-297. It inhibits the processing of Rap 1A without effecting the processing of H-Ras.