(S)-6-Amino-2-[(R)-3-(3,5-dibromo-4-hydroxy-phenyl)-2-(4-phenyl-butyrylamino)-propionylamino]-hexanoic acid phenethyl-amide

ID: ALA196582

Chembl Id: CHEMBL196582

PubChem CID: 11578671

Max Phase: Preclinical

Molecular Formula: C33H40Br2N4O4

Molecular Weight: 716.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NCCCC[C@H](NC(=O)[C@@H](Cc1cc(Br)c(O)c(Br)c1)NC(=O)CCCc1ccccc1)C(=O)NCCc1ccccc1

Standard InChI:  InChI=1S/C33H40Br2N4O4/c34-26-20-25(21-27(35)31(26)41)22-29(38-30(40)16-9-14-23-10-3-1-4-11-23)33(43)39-28(15-7-8-18-36)32(42)37-19-17-24-12-5-2-6-13-24/h1-6,10-13,20-21,28-29,41H,7-9,14-19,22,36H2,(H,37,42)(H,38,40)(H,39,43)/t28-,29+/m0/s1

Standard InChI Key:  LBPLTZVLRLIUFZ-URLMMPGGSA-N

Alternative Forms

1. Parent:

   

   ALA196582

   deamino-hPhe-D-Tyr(3,5-diBr)-Lys-NHEtPh

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: 716.51

Molecular Weight (Monoisotopic): 714.1416

AlogP: 4.94

#Rotatable Bonds: 17

Polar Surface Area: 133.55

Molecular Species: BASE

HBA: 5

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 6.76

CX Basic pKa: 10.20

CX LogP: 4.74

CX LogD: 4.68

Aromatic Rings: 3

Heavy Atoms: 43

QED Weighted: 0.13

Np Likeness Score: 0.06

References

1. Rudolf K, Eberlein W, Engel W, Pieper H, Entzeroth M, Hallermayer G, Doods H..  (2005)  Development of human calcitonin gene-related peptide (CGRP) receptor antagonists. 1. Potent and selective small molecule CGRP antagonists. 1-[N2-[3,5-dibromo-N-[[4-(3,4-dihydro-2(1H)-oxoquinazolin-3-yl)-1-piperidinyl]carbonyl]-D-tyrosyl]-l-lysyl]-4-(4-pyridinyl)piperazine: the first CGRP antagonist for clinical trials in acute migraine.,  48  (19): [PMID:16161996] [10.1021/jm0490641]

2. Bell IM..  (2014)  Calcitonin gene-related peptide receptor antagonists: new therapeutic agents for migraine.,  57  (19): [PMID:24960305] [10.1021/jm500364u]

3. Dubowchik GM, Conway CM, Xin AW..  (2020)  Blocking the CGRP Pathway for Acute and Preventive Treatment of Migraine: The Evolution of Success.,  63  (13): [PMID:32058712] [10.1021/acs.jmedchem.9b01810]

Source

Source(1):

• Scientific Literature