(2S)-1-[(3S)-4-(1H-imidazol-4-yl)-3-{[(3R,6R)-6-methyl-5-oxothiomorpholin-3-yl]formamido}butanoyl]pyrrolidine-2-carboxylic acid; trifluoroacetic acid

• ChemBase ID: 154716
• Molecular Formular: C20H26F3N5O7S
• Molecular Mass: 537.5099496
• Monoisotopic Mass: 537.15050386
• SMILES: C[C@@H]1C(=O)N[C@@H](CS1)C(=O)N[C@@H](Cc1c[nH]cn1)CC(=O)N1CCC[C@H]1C(=O)O.C(=O)(C(F)(F)F)O
• Canonical SMILES: OC(=O)C(F)(F)F.O=C([C@@H]1CS[C@@H](C(=O)N1)C)N[C@@H](Cc1c[nH]cn1)CC(=O)N1CCC[C@H]1C(=O)O
• InChI: InChI=1S/C18H25N5O5S.C2HF3O2/c1-10-16(25)22-13(8-29-10)17(26)21-11(5-12-7-19-9-20-12)6-15(24)23-4-2-3-14(23)18(27)28;3-2(4,5)1(6)7/h7,9-11,13-14H,2-6,8H2,1H3,(H,19,20)(H,21,26)(H,22,25)(H,27,28);(H,6,7)/t10-,11+,13+,14+;/m1./s1
• InChIKey: YUARRBAFDZBNIK-JSQNCYBOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-[(3S)-4-(1H-imidazol-4-yl)-3-{[(3R,6R)-6-methyl-5-oxothiomorpholin-3-yl]formamido}butanoyl]pyrrolidine-2-carboxylic acid; trifluoroacetic acid
• IUPAC Traditional name: (2S)-1-[(3S)-4-(1H-imidazol-4-yl)-3-{[(3R,6R)-6-methyl-5-oxothiomorpholin-3-yl]formamido}butanoyl]pyrrolidine-2-carboxylic acid; trifluoroacetic acid
• Synonyms: CG-3703; (2R)-2-Mercaptopropanoyl-L-cysteinyl-L-histidyl-prolinamide; (3R,6R)-6-methyl-5-oxo-3-thiomorpholinecarbonyl-L-histidyl-L-Prolinamide; CNK-602A; NS-3; cyclic (1>2)-sulfide; Montirelin trifluoroacetate salt

Database IDs

• MDL Number: MFCD16879006
• PubChem SID: 162248854
• PubChem CID: 71311951

CALCULATED PROPERTIES

• Acid pKa: 3.4571226
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -2.826934
• LogD (pH = 7.4): -3.687783
• Log P: -2.7963185
• Molar Refractivity: 104.305 cm^3
• Polarizability: 40.689903 Å^3
• Polar Surface Area: 144.49 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: ≥1 mg/mL
• Apperance: white to off-white powder

Safety Information

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

Product Information

• Purity: ≥95% (HPLC)
• Empirical Formula (Hill Notation): C17H24N6O4S · xC2HF3O2

DETAILS

Sigma Aldrich - M1699

Biochem/physiol Actions
Montirelin is a potent, biologically stable TRH analog with Ki = 35.2 nM for brain receptor binding.