ID: ALA571492

Max Phase: Preclinical

Molecular Formula: C21H24N2O4

Molecular Weight: 368.43

Molecule Type: Small molecule

Representations

Canonical SMILES:  Cc1cc(O)cc(C)c1C[C@H](N)C(=O)N1Cc2ccccc2C[C@H]1C(=O)O

Standard InChI:  InChI=1S/C21H24N2O4/c1-12-7-16(24)8-13(2)17(12)10-18(22)20(25)23-11-15-6-4-3-5-14(15)9-19(23)21(26)27/h3-8,18-19,24H,9-11,22H2,1-2H3,(H,26,27)/t18-,19-/m0/s1

Standard InChI Key:  QBLVXTMPLLWZDE-OALUTQOASA-N

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

Properties

Molecular Weight: 368.43

Molecular Weight (Monoisotopic): 368.1736

AlogP: 1.92

#Rotatable Bonds: 4

Polar Surface Area: 103.86

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 3.69

CX Basic pKa: 8.04

CX LogP: 0.63

CX LogD: 0.55

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.76

Np Likeness Score: 0.06

References

1. Pagé D, McClory A, Mischki T, Schmidt R, Butterworth J, St-Onge S, Labarre M, Payza K, Brown W..  (2000)  Novel Dmt-Tic dipeptide analogues as selective delta-opioid receptor antagonists.,  10  (2): [PMID:10673103] [10.1016/s0960-894x(99)00652-6]

2. Salvadori S, Balboni G, Guerrini R, Tomatis R, Bianchi C, Bryant SD, Cooper PS, Lazarus LH..  (1997)  Evolution of the Dmt-Tic pharmacophore: N-terminal methylated derivatives with extraordinary delta opioid antagonist activity.,  40  (19): [PMID:9301674] [10.1021/jm9607663]

3. Salvadori S, Balboni G, Guerrini R, Tomatis R, Bianchi C, Bryant SD, Cooper PS, Lazarus LH..  (1997)  Evolution of the Dmt-Tic pharmacophore: N-terminal methylated derivatives with extraordinary delta opioid antagonist activity.,  40  (19): [PMID:9301674] [10.1021/jm9607663]

4. Balboni G, Guerrini R, Salvadori S, Bianchi C, Rizzi D, Bryant SD, Lazarus LH..  (2002)  Evaluation of the Dmt-Tic pharmacophore: conversion of a potent delta-opioid receptor antagonist into a potent delta agonist and ligands with mixed properties.,  45  (3): [PMID:11806723] [10.1021/jm010449i]

5. Fujita Y, Tsuda Y, Motoyama T, Li T, Miyazaki A, Yokoi T, Sasaki Y, Ambo A, Niizuma H, Jinsmaa Y, Bryant SD, Lazarus LH, Okada Y..  (2005)  Studies on the structure-activity relationship of 2',6'-dimethyl-l-tyrosine (Dmt) derivatives: bioactivity profile of H-Dmt-NH-CH(3).,  15  (3): [PMID:15664820] [10.1016/j.bmcl.2004.11.040]

6. Li T, Fujita Y, Shiotani K, Miyazaki A, Tsuda Y, Ambo A, Sasaki Y, Jinsmaa Y, Marczak E, Bryant SD, Salvadori S, Lazarus LH, Okada Y..  (2005)  Potent Dmt-Tic pharmacophoric delta- and mu-opioid receptor antagonists.,  48  (25): [PMID:16335927] [10.1021/jm050377l]

7. Li T, Shiotani K, Miyazaki A, Fujita Y, Tsuda Y, Ambo A, Sasaki Y, Jinsmaa Y, Marczak E, Bryant SD, Lazarus LH, Okada Y..  (2005)  New series of potent delta-opioid antagonists containing the H-Dmt-Tic-NH-hexyl-NH-R motif.,  15  (24): [PMID:16183273] [10.1016/j.bmcl.2005.08.073]

8. Berezowska I, Chung NN, Lemieux C, Wilkes BC, Schiller PW..  (2009)  Agonist vs antagonist behavior of delta opioid peptides containing novel phenylalanine analogues in place of Tyr(1).,  52  (21): [PMID:19827750] [10.1021/jm9004913]

9. Ballet S, Marczak ED, Feytens D, Salvadori S, Sasaki Y, Abell AD, Lazarus LH, Balboni G, Tourwé D..  (2010)  Novel multiple opioid ligands based on 4-aminobenzazepinone (Aba), azepinoindole (Aia) and tetrahydroisoquinoline (Tic) scaffolds.,  20  (5): [PMID:20137938] [10.1016/j.bmcl.2010.01.055]

10. Weltrowska G, Nguyen TM, Chung NN, Wilkes BC, Schiller PW..  (2013)  N-terminal guanidinylation of TIPP (Tyr-Tic-Phe-Phe) peptides results in major changes of the opioid activity profile.,  23  (18): [PMID:23932788] [10.1016/j.bmcl.2013.07.036]

Source

Source(1):

• Scientific Literature