(R)-ethyl 2-(3-((5-(4-hydroxybenzylamino)-4-(2,2-diphenylacetamido)-5-oxopentylamino)(amino)methylene)ureido)acetate

ID: ALA508974

Chembl Id: CHEMBL508974

PubChem CID: 10008757

Max Phase: Preclinical

Molecular Formula: C32H38N6O6

Molecular Weight: 602.69

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)CNC(=O)/N=C(/N)NCCC[C@@H](NC(=O)C(c1ccccc1)c1ccccc1)C(=O)NCc1ccc(O)cc1

Standard InChI:  InChI=1S/C32H38N6O6/c1-2-44-27(40)21-36-32(43)38-31(33)34-19-9-14-26(29(41)35-20-22-15-17-25(39)18-16-22)37-30(42)28(23-10-5-3-6-11-23)24-12-7-4-8-13-24/h3-8,10-13,15-18,26,28,39H,2,9,14,19-21H2,1H3,(H,35,41)(H,37,42)(H4,33,34,36,38,43)/t26-/m1/s1

Standard InChI Key:  DLLWIQHESQBDLY-AREMUKBSSA-N

Alternative Forms

1. Parent:

   

   ALA508974

   (R)-ethyl 2-(3-((5-(4-hydroxybenzylamino)-4-(2,2-diphenylacetamido)-5-oxopentylamino)(amino)methylene)ureido)acetate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 602.69

Molecular Weight (Monoisotopic): 602.2853

AlogP: 2.28

#Rotatable Bonds: 14

Polar Surface Area: 184.24

Molecular Species: BASE

HBA: 6

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 9.49

CX Basic pKa: 13.33

CX LogP: 1.76

CX LogD: 0.62

Aromatic Rings: 3

Heavy Atoms: 44

QED Weighted: 0.07

Np Likeness Score: -0.39

References

1. Keller M, Pop N, Hutzler C, Beck-Sickinger AG, Bernhardt G, Buschauer A..  (2008)  Guanidine-acylguanidine bioisosteric approach in the design of radioligands: synthesis of a tritium-labeled N(G)-propionylargininamide ([3H]-UR-MK114) as a highly potent and selective neuropeptide Y Y1 receptor antagonist.,  51  (24): [PMID:19053784] [10.1021/jm801018u]

2. Keller M, Weiss S, Hutzler C, Kuhn KK, Mollereau C, Dukorn S, Schindler L, Bernhardt G, König B, Buschauer A..  (2015)  N(ω)-Carbamoylation of the Argininamide Moiety: An Avenue to Insurmountable NPY Y1 Receptor Antagonists and a Radiolabeled Selective High-Affinity Molecular Tool ([(3)H]UR-MK299) with Extended Residence Time.,  58  (22): [PMID:26466164] [10.1021/acs.jmedchem.5b00925]

Source

Source(1):

• Scientific Literature