ethyl (2S)-2-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-6-amino-2-{[(2S)-2,6-diaminohexyl]amino}hexanoyl]pyrrolidin-2-yl]formamido}-3-(1H-indol-3-yl)propanamido]-3,3-dimethylbutanamido]-4-methylpentanoate

• ChemBase ID: 176244
• Molecular Formular: C42H71N9O6
• Molecular Mass: 798.06984
• Monoisotopic Mass: 797.55273104
• SMILES: NCCCC[C@@H](CN[C@H](C(=O)N1[C@@H](CCC1)C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)OCC)CC(C)C)C(C)(C)C)Cc1c2c(cccc2)[nH]c1)CCCCN)N
• Canonical SMILES: NCCCC[C@@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)N[C@@H](C(C)(C)C)C(=O)N[C@H](C(=O)OCC)CC(C)C)Cc1c[nH]c2c1cccc2)NC[C@H](CCCCN)N
• InChI: InChI=1S/C42H71N9O6/c1-7-57-41(56)34(23-27(2)3)49-39(54)36(42(4,5)6)50-37(52)33(24-28-25-46-31-17-9-8-16-30(28)31)48-38(53)35-19-14-22-51(35)40(55)32(18-11-13-21-44)47-26-29(45)15-10-12-20-43/h8-9,16-17,25,27,29,32-36,46-47H,7,10-15,18-24,26,43-45H2,1-6H3,(H,48,53)(H,49,54)(H,50,52)/t29-,32-,33-,34-,35-,36+/m0/s1
• InChIKey: LVROVYGTQUFAMB-IDESOYSGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (2S)-2-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-6-amino-2-{[(2S)-2,6-diaminohexyl]amino}hexanoyl]pyrrolidin-2-yl]formamido}-3-(1H-indol-3-yl)propanamido]-3,3-dimethylbutanamido]-4-methylpentanoate
• IUPAC Traditional name: ethyl (2S)-2-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-6-amino-2-{[(2S)-2,6-diaminohexyl]amino}hexanoyl]pyrrolidin-2-yl]formamido}-3-(1H-indol-3-yl)propanamido]-3,3-dimethylbutanamido]-4-methylpentanoate
• Synonyms: N2-[(2S)-2,6-Diaminohexyl]-L-lysyl-L-prolyl-L-tryptophyl-3-methyl-L-valyl-L-leucine Ethyl Ester; PF-01472472; (S)-N-[N-[N-[1-[N2-(2,6-Diaminohexyl)-L-lysyl]-L-prolyl]-L-tryptophyl]-3-methyl-L-valyl]-L-leucine Ethyl Ester; PD-149163

Database IDs

• CAS Number: 169528-11-4
• PubChem SID: 164232154
• PubChem CID: 11693501

CALCULATED PROPERTIES

• Acid pKa: 11.955494
• H Acceptors: 9
• H Donor: 8
• LogD (pH = 5.5): -7.991918
• LogD (pH = 7.4): -5.1300044
• Log P: 2.113645
• Molar Refractivity: 221.4341 cm^3
• Polarizability: 89.12171 Å^3
• Polar Surface Area: 239.79 Å^2
• Rotatable Bonds: 26
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - P217480

PD 149163 is a selective, brain penetrating Neurotensin NTR1 receptor agonist. Neurotensin agonists such as PD 149163 block the prepulse inhibition deficits produced by a 5-HT2A and an α1 agonist. As a result, PD 149163 shows pro-cognitive, antipsychotic

REFERENCES

• Feifel, D. et al.: Neuropsychophamacology, 28, 651 (2003)
• Shilling, P.D. et al.: Psychopharmacolgy, 175, 353 (2003)