(2S,5S,8S,16R)-16-((S)-2-amino-3-(4-hydroxyphenyl)propanamido)-2,5-dibenzyl-3,6,10,17-tetraoxo-1,4,7,11-tetraazacycloheptadecane-8-carboxamide

ID: ALA1927270

Chembl Id: CHEMBL1927270

PubChem CID: 57401062

Max Phase: Preclinical

Molecular Formula: C37H45N7O7

Molecular Weight: 699.81

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  NC(=O)[C@@H]1CC(=O)NCCCC[C@@H](NC(=O)[C@@H](N)Cc2ccc(O)cc2)C(=O)N[C@@H](Cc2ccccc2)C(=O)N[C@@H](Cc2ccccc2)C(=O)N1

Standard InChI:  InChI=1S/C37H45N7O7/c38-27(19-25-14-16-26(45)17-15-25)34(48)41-28-13-7-8-18-40-32(46)22-29(33(39)47)42-36(50)30(20-23-9-3-1-4-10-23)44-37(51)31(43-35(28)49)21-24-11-5-2-6-12-24/h1-6,9-12,14-17,27-31,45H,7-8,13,18-22,38H2,(H2,39,47)(H,40,46)(H,41,48)(H,42,50)(H,43,49)(H,44,51)/t27-,28+,29-,30-,31-/m0/s1

Standard InChI Key:  XGFIVOHFTMYGLC-JZVHMONDSA-N

Alternative Forms

1. Parent:

   

   ALA1927270

   H-Tyr-D-Lys(1)-Phe-Phe-Asp(1)-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: 699.81

Molecular Weight (Monoisotopic): 699.3380

AlogP: -0.14

#Rotatable Bonds: 9

Polar Surface Area: 234.84

Molecular Species: NEUTRAL

HBA: 8

HBD: 8

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 10

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 9.48

CX Basic pKa: 7.73

CX LogP: 0.25

CX LogD: -0.10

Aromatic Rings: 3

Heavy Atoms: 51

QED Weighted: 0.15

Np Likeness Score: 0.44

References

1. Fichna J, Perlikowska R, Wyrębska A, Gach K, Piekielna J, do-Rego JC, Toth G, Kluczyk A, Janecki T, Janecka A..  (2011)  Effect of 2',6'-dimethyl-L-tyrosine (Dmt) on pharmacological activity of cyclic endomorphin-2 and morphiceptin analogs.,  19  (23): [PMID:22047797] [10.1016/j.bmc.2011.10.040]

2. Piekielna J, Gentilucci L, De Marco R, Perlikowska R, Adamska A, Olczak J, Mazur M, Artali R, Modranka J, Janecki T, Tömböly C, Janecka A..  (2014)  Cyclic side-chain-linked opioid analogs utilizing cis- and trans-4-aminocyclohexyl-D-alanine.,  22  (23): [PMID:25456075] [10.1016/j.bmc.2014.10.022]

3. Perlikowska R, Piekielna J, Gentilucci L, De Marco R, Cerlesi MC, Calo G, Artali R, Tömböly C, Kluczyk A, Janecka A..  (2016)  Synthesis of mixed MOR/KOR efficacy cyclic opioid peptide analogs with antinociceptive activity after systemic administration.,  109  [PMID:26785295] [10.1016/j.ejmech.2015.12.012]

4. Adamska-Bartłomiejczyk A, De Marco R, Gentilucci L, Kluczyk A, Janecka A..  (2017)  Design and characterization of opioid ligands based on cycle-in-macrocycle scaffold.,  25  (8): [PMID:28318893] [10.1016/j.bmc.2017.02.057]

5. Smith MT, Kong D, Kuo A, Imam MZ, Williams CM..  (2022)  Analgesic Opioid Ligand Discovery Based on Nonmorphinan Scaffolds Derived from Natural Sources.,  65  (3.0): [PMID:34995453] [10.1021/acs.jmedchem.0c01915]

Source

Source(1):

• Scientific Literature