(4S)-N-[(2S)-1-[(2S)-2-carbamoylpyrrolidin-1-yl]-3-(1H-imidazol-4-yl)-1-oxopropan-2-yl]-1-methyl-2,6-dioxo-1,3-diazinane-4-carboxamide

• ChemBase ID: 70497
• Molecular Formular: C17H23N7O5
• Molecular Mass: 405.40842
• Monoisotopic Mass: 405.17606687
• SMILES: C1(=O)N[C@@H](CC(=O)N1C)C(=O)N[C@H](C(=O)N1[C@@H](CCC1)C(=O)N)Cc1nc[nH]c1
• Canonical SMILES: CN1C(=O)C[C@H](NC1=O)C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N)Cc1nc[nH]c1
• InChI: InChI=1S/C17H23N7O5/c1-23-13(25)6-10(22-17(23)29)15(27)21-11(5-9-7-19-8-20-9)16(28)24-4-2-3-12(24)14(18)26/h7-8,10-12H,2-6H2,1H3,(H2,18,26)(H,19,20)(H,21,27)(H,22,29)/t10-,11-,12-/m0/s1
• InChIKey: LQZAIAZUDWIVPM-SRVKXCTJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-N-[(2S)-1-[(2S)-2-carbamoylpyrrolidin-1-yl]-3-(1H-imidazol-4-yl)-1-oxopropan-2-yl]-1-methyl-2,6-dioxo-1,3-diazinane-4-carboxamide; (4S)-N-[(2S)-1-[(2S)-2-carbamoylpyrrolidin-1-yl]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]-1-methyl-2,6-dioxo-1,3-diazinane-4-carboxamide
• IUPAC Traditional name: (4S)-N-[(2S)-1-[(2S)-2-carbamoylpyrrolidin-1-yl]-3-(1H-imidazol-4-yl)-1-oxopropan-2-yl]-1-methyl-2,6-dioxo-1,3-diazinane-4-carboxamide; taltirelin
• Synonyms: Taltirelin; (4S)-Hexahydro-1-methyl-2,6-dioxo-4-pyrimidinecarbonyl-L-histidyl-L-prolinamide; (S)-N-(1Methyl-4,5-dihydroorotyl)-L-histidyl-L-prolinamide; TA 0910

Database IDs

• CAS Number: 103300-74-9
• MDL Number: MFCD00894697
• PubChem SID: 162036212
• PubChem CID: 114750

CALCULATED PROPERTIES

• Acid pKa: 11.318714
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -4.204918
• LogD (pH = 7.4): -3.7403688
• Log P: -3.677751
• Molar Refractivity: 98.1399 cm^3
• Polarizability: 37.763596 Å^3
• Polar Surface Area: 170.59 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Warning: IRRITANT
• TSCA Listed: false

Product Information

• Purity: 95+%

DETAILS

Toronto Research Chemicals - T005650

Analog of thyrotropin releasing hormone TRH, with pronounced CNS activity. Used in the treatment of spinocerebellar degeneration.

REFERENCES

• Yamamura, M., et al.: Jpn. J. Pharmacol., 53, 451 (1990)
• Iwasaki, Y., et al.: Neurol. Res., 19, 613 (1990)
• Kinoshita, K., et al.: CNS Drug Rev., 4, 25 (1990)
• Morikawa, S., et al.: J. Pharm. Biomed. Anal., 16, 1267 (1990)