3-[[(2S)-2-[[(2R)-5-guanidino-2-[[(2S)-2-guanidino-3-(4-hydroxyphenyl)propanoyl]amino]pentanoyl]amino]-3-phenyl-propanoyl]amino]propanoic acid

ID: ALA5169797

Chembl Id: CHEMBL5169797

PubChem CID: 11082558

Max Phase: Preclinical

Molecular Formula: C28H39N9O6

Molecular Weight: 597.68

Names and Identifiers

Canonical SMILES:  N=C(N)NCCC[C@@H](NC(=O)[C@H](Cc1ccc(O)cc1)NC(=N)N)C(=O)N[C@@H](Cc1ccccc1)C(=O)NCCC(=O)O

Standard InChI:  InChI=1S/C28H39N9O6/c29-27(30)34-13-4-7-20(35-26(43)22(37-28(31)32)16-18-8-10-19(38)11-9-18)25(42)36-21(15-17-5-2-1-3-6-17)24(41)33-14-12-23(39)40/h1-3,5-6,8-11,20-22,38H,4,7,12-16H2,(H,33,41)(H,35,43)(H,36,42)(H,39,40)(H4,29,30,34)(H4,31,32,37)/t20-,21+,22+/m1/s1

Standard InChI Key:  MXGJDILSMMVXLA-FSSWDIPSSA-N

Alternative Forms

1. Parent:

   

   ALA5169797

   Nalpha-amidino-Tyr-D-Arg-Phe-betaAla-OH

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 597.68

Molecular Weight (Monoisotopic): 597.3023

AlogP: -1.15

#Rotatable Bonds: 17

Polar Surface Area: 268.63

Molecular Species: ZWITTERION

HBA: 7

HBD: 11

#RO5 Violations: 2

HBA (Lipinski): 15

HBD (Lipinski): 13

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 4.07

CX Basic pKa: 11.85

CX LogP: -4.18

CX LogD: -4.80

Aromatic Rings: 2

Heavy Atoms: 43

QED Weighted: 0.06

Np Likeness Score: 0.14

References

1. 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