1N-[1-[4-amino(imino)methylamino-1-carbamoyl-(1S)-butylcarbamoyl]-3-methyl-(1S)-butyl]-2-[1-[1-amino-2-hydroxy-(1S)-ethylcarboxamido]-2-phenyl-(1S)-ethylcarboxamido]-4-methyl-(2S)-pentanamide

ID: ALA115543

Chembl Id: CHEMBL115543

Cas Number: 141923-41-3

PubChem CID: 9809471

Max Phase: Preclinical

Molecular Formula: C30H51N9O6

Molecular Weight: 633.80

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H](N)CO)C(=O)N[C@@H](CCCN=C(N)N)C(N)=O

Standard InChI:  InChI=1S/C30H51N9O6/c1-17(2)13-22(27(43)36-21(25(32)41)11-8-12-35-30(33)34)38-28(44)23(14-18(3)4)39-29(45)24(37-26(42)20(31)16-40)15-19-9-6-5-7-10-19/h5-7,9-10,17-18,20-24,40H,8,11-16,31H2,1-4H3,(H2,32,41)(H,36,43)(H,37,42)(H,38,44)(H,39,45)(H4,33,34,35)/t20-,21-,22-,23-,24-/m0/s1

Standard InChI Key:  CDBPTZOOUNAWQA-LSBAASHUSA-N

Alternative Forms

1. Parent:

   

   ALA115543

   H-Ser-phe-leu-leu-arg-NH2

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Protein

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 633.80

Molecular Weight (Monoisotopic): 633.3962

AlogP: -1.88

#Rotatable Bonds: 20

Polar Surface Area: 270.14

Molecular Species: BASE

HBA: 8

HBD: 9

#RO5 Violations: 2

HBA (Lipinski): 15

HBD (Lipinski): 13

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.89

CX Basic pKa: 15.12

CX LogP: -1.69

CX LogD: -4.15

Aromatic Rings: 1

Heavy Atoms: 45

QED Weighted: 0.04

Np Likeness Score: 0.37

References

1. Alexopoulos K, Panagiotopoulos D, Mavromoustakos T, Fatseas P, Paredes-Carbajal MC, Mascher D, Mihailescu S, Matsoukas J..  (2001)  Design, synthesis, and modeling of novel cyclic thrombin receptor-derived peptide analogues of the Ser42-Phe-Leu-Leu-Arg46 motif sequence with fixed conformations of pharmacophoric groups: importance of a Phe/Arg/NH2 cluster for receptor activation and implications in the design of nonpeptide thrombin receptor mimetics.,  44  (3): [PMID:11462974] [10.1021/jm0001525]

2. Matsoukas JM, Panagiotopoulos D, Keramida M, Mavromoustakos T, Yamdagni R, Wu Q, Moore GJ, Saifeddine M, Hollenberg MD..  (1996)  Synthesis and contractile activities of cyclic thrombin receptor-derived peptide analogues with a Phe-Leu-Leu-Arg motif: importance of the Phe/Arg relative conformation and the primary amino group for activity.,  39  (18): [PMID:8784457] [10.1021/jm950690v]

3. Feng DM, Veber DF, Connolly TM, Condra C, Tang MJ, Nutt RF..  (1995)  Development of a potent thrombin receptor ligand.,  38  (20): [PMID:7562949] [10.1021/jm00020a029]

4. Bernatowicz MS, Klimas CE, Hartl KS, Peluso M, Allegretto NJ, Seiler SM..  (1996)  Development of potent thrombin receptor antagonist peptides.,  39  (25): [PMID:8960546] [10.1021/jm960455s]

5. Wang Y, Qu C, Liu T, Wang C..  (2020)  PFKFB3 inhibitors as potential anticancer agents: Mechanisms of action, current developments, and structure-activity relationships.,  203  [PMID:32679452] [10.1016/j.ejmech.2020.112612]

Source

Source(1):

• Scientific Literature