(R)-N-((R)-1-amino-1-oxo-3-phenylpropan-2-yl)-2-(3,3-diphenylacrylamido)-5-guanidinopentanamide

ID: ALA5074999

PubChem CID: 166626813

Max Phase: Preclinical

Molecular Formula: C30H34N6O3

Molecular Weight: 526.64

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N=C(N)NCCC[C@@H](NC(=O)C=C(c1ccccc1)c1ccccc1)C(=O)N[C@H](Cc1ccccc1)C(N)=O

Standard InChI:  InChI=1S/C30H34N6O3/c31-28(38)26(19-21-11-4-1-5-12-21)36-29(39)25(17-10-18-34-30(32)33)35-27(37)20-24(22-13-6-2-7-14-22)23-15-8-3-9-16-23/h1-9,11-16,20,25-26H,10,17-19H2,(H2,31,38)(H,35,37)(H,36,39)(H4,32,33,34)/t25-,26-/m1/s1

Standard InChI Key:  DHTFKWGWZOSSLT-CLJLJLNGSA-N

Molfile:  

 
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M  END

Alternative Forms

1. Parent:

   

   ALA5074999

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 526.64

Molecular Weight (Monoisotopic): 526.2692

AlogP: 2.08

#Rotatable Bonds: 13

Polar Surface Area: 163.19

Molecular Species: BASE

HBA: 4

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.42

CX Basic pKa: 11.82

CX LogP: 2.11

CX LogD: 0.02

Aromatic Rings: 3

Heavy Atoms: 39

QED Weighted: 0.09

Np Likeness Score: 0.04

References

1. Quillet R, Schneider S, Utard V, Drieu la Rochelle A, Elhabazi K, Henningsen JB, Gizzi P, Schmitt M, Kugler V, Simonneaux V, Ilien B, Simonin F, Bihel F..  (2021)  Identification of an N-acylated-^DArg-Leu-NH₂ Dipeptide as a Highly Selective Neuropeptide FF1 Receptor Antagonist That Potently Prevents Opioid-Induced Hyperalgesia.,  64  (11.0): [PMID:34008968] [10.1021/acs.jmedchem.1c00256]

2. Gaubert, Gilles G and 8 more authors.  2009-11-12  Discovery of selective nonpeptidergic neuropeptide FF2 receptor agonists.  [PMID:19803524]

3. Findeisen, Maria and 6 more authors.  2012-07-12  Selective mode of action of guanidine-containing non-peptides at human NPFF receptors.  [PMID:22708927]

4. Journigan, V Blair VB and 7 more authors.  2014-11-13  Nonpeptide small molecule agonist and antagonist original leads for neuropeptide FF1 and FF2 receptors.  [PMID:25268943]

5. Wang, Zi-Long ZL and 12 more authors.  2016-11-23  Structure-Based Optimization of Multifunctional Agonists for Opioid and Neuropeptide FF Receptors with Potent Nontolerance Forming Analgesic Activities.  [PMID:27798836]

6. Zhang, Mengna and 14 more authors.  2020-12-24  Synthesis and Biological Characterization of Cyclic Disulfide-Containing Peptide Analogs of the Multifunctional Opioid/Neuropeptide FF Receptor Agonists That Produce Long-Lasting and Nontolerant Antinociception.  [PMID:33271020]

Source

Source(1):

• Scientific Literature