(2E)-5-amino-N,5-dimethyl-N-[(1R)-1-{methyl[(1R)-1-(methylcarbamoyl)-2-phenylethyl]carbamoyl}-2-(naphthalen-2-yl)ethyl]hex-2-enamide

• ChemBase ID: 178039
• Molecular Formular: C32H40N4O3
• Molecular Mass: 528.685
• Monoisotopic Mass: 528.31004116
• SMILES: c1ccc2c(c1)cc(cc2)C[C@H](C(=O)N([C@@H](C(=O)NC)Cc1ccccc1)C)N(C(=O)/C=C/CC(N)(C)C)C
• Canonical SMILES: CNC(=O)[C@H](N(C(=O)[C@H](N(C(=O)/C=C/CC(N)(C)C)C)Cc1ccc2c(c1)cccc2)C)Cc1ccccc1
• InChI: InChI=1S/C32H40N4O3/c1-32(2,33)19-11-16-29(37)35(4)28(22-24-17-18-25-14-9-10-15-26(25)20-24)31(39)36(5)27(30(38)34-3)21-23-12-7-6-8-13-23/h6-18,20,27-28H,19,21-22,33H2,1-5H3,(H,34,38)/b16-11+/t27-,28-/m1/s1
• InChIKey: WURGZWOTGMLDJP-ZCYANPAGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-5-amino-N,5-dimethyl-N-[(1R)-1-{methyl[(1R)-1-(methylcarbamoyl)-2-phenylethyl]carbamoyl}-2-(naphthalen-2-yl)ethyl]hex-2-enamide
• IUPAC Traditional name: (2E)-5-amino-N,5-dimethyl-N-[(1R)-1-{methyl[(1R)-1-(methylcarbamoyl)-2-phenylethyl]carbamoyl}-2-(naphthalen-2-yl)ethyl]hex-2-enamide
• Synonyms: N-[(2E)-5-Amino-5-methyl-1-oxo-2-hexen-1-yl]-N-methyl-3-(2-naphthalenyl)-D-alanyl-N,Nα-Dimethyl-D-phenylalaninamide; NN 703; NNC 26-0703; Tabimorelin

Database IDs

• CAS Number: 193079-69-5
• PubChem SID: 164233949
• PubChem CID: 9810101

CALCULATED PROPERTIES

• Acid pKa: 15.645596
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.584644
• LogD (pH = 7.4): 0.93289703
• Log P: 3.6109192
• Molar Refractivity: 157.0044 cm^3
• Polarizability: 61.836735 Å^3
• Polar Surface Area: 95.74 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T003500

NN703 (Tabimorelin) is an orally active growth hormone (GH) secretagogue intended for use as an alternative to daily injections of GH. In vitro studies in human liver microsomes have indicated that NN703 is a mechanism-based inhibitor of CYP3A4.

REFERENCES

• Fabre, G., et al.: Biochem. Pharmacol., 37, 4389 (1988)
• Thummel, K., et al.: Clin. Pharmacol. Ther., 59, 491 (1988)
• Yu, D., et al.: J. Clin. Pharmacol., 39, 1203 (1988)