Tyr-Pro-Phe-Phe-OC(CH3)3

ID: ALA500195

Chembl Id: CHEMBL500195

PubChem CID: 44586192

Max Phase: Preclinical

Molecular Formula: C36H44N4O6

Molecular Weight: 628.77

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  CC(C)(C)OC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H]1CCCN1C(=O)[C@@H](N)Cc1ccc(O)cc1

Standard InChI:  InChI=1S/C36H44N4O6/c1-36(2,3)46-35(45)30(23-25-13-8-5-9-14-25)39-32(42)29(22-24-11-6-4-7-12-24)38-33(43)31-15-10-20-40(31)34(44)28(37)21-26-16-18-27(41)19-17-26/h4-9,11-14,16-19,28-31,41H,10,15,20-23,37H2,1-3H3,(H,38,43)(H,39,42)/t28-,29-,30-,31-/m0/s1

Standard InChI Key:  MUCJBMLSOAIPBH-ORYMTKCHSA-N

Alternative Forms

1. Parent:

   

   ALA500195

   Tyr-Pro-Phe-Phe-OC(CH3)3

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: 628.77

Molecular Weight (Monoisotopic): 628.3261

AlogP: 3.05

#Rotatable Bonds: 12

Polar Surface Area: 151.06

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.50

CX Basic pKa: 7.72

CX LogP: 3.81

CX LogD: 3.45

Aromatic Rings: 3

Heavy Atoms: 46

QED Weighted: 0.23

Np Likeness Score: -0.12

References

1. Wang CL, Yao JL, Yu Y, Shao X, Cui Y, Liu HM, Lai LH, Wang R..  (2008)  Structure-activity study of endomorphin-2 analogs with C-terminal modifications by NMR spectroscopy and molecular modeling.,  16  (12): [PMID:18490168] [10.1016/j.bmc.2008.05.001]

2. 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