Tyr-Pro-Phe-Phe-OMe

ID: ALA361922

Chembl Id: CHEMBL361922

PubChem CID: 44390652

Max Phase: Preclinical

Molecular Formula: C33H38N4O6

Molecular Weight: 586.69

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  COC(=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/C33H38N4O6/c1-43-33(42)28(21-23-11-6-3-7-12-23)36-30(39)27(20-22-9-4-2-5-10-22)35-31(40)29-13-8-18-37(29)32(41)26(34)19-24-14-16-25(38)17-15-24/h2-7,9-12,14-17,26-29,38H,8,13,18-21,34H2,1H3,(H,35,40)(H,36,39)/t26-,27-,28-,29-/m0/s1

Standard InChI Key:  YYNCXEIEPLRPCR-DZUOILHNSA-N

Alternative Forms

1. Parent:

   

   ALA361922

   Tyr-Pro-Phe-Phe-OCH3

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: 586.69

Molecular Weight (Monoisotopic): 586.2791

AlogP: 1.88

#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: 2.76

CX LogD: 2.40

Aromatic Rings: 3

Heavy Atoms: 43

QED Weighted: 0.24

Np Likeness Score: -0.08

References

1. Gao Y, Liu X, Wei J, Zhu B, Chen Q, Wang R..  (2005)  Structure-activity relationship of the novel bivalent and C-terminal modified analogues of endomorphin-2.,  15  (7): [PMID:15780619] [10.1016/j.bmcl.2005.02.021]

2. 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]

3. 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