(S)-Benzyl-(1-(4-(1-Naphthoyl)piperazin-1-yl)-6-acrylamido-1-oxohexan-2-yl)carbamate

ID: ALA4093689

Chembl Id: CHEMBL4093689

PubChem CID: 132024475

Max Phase: Preclinical

Molecular Formula: C32H36N4O5

Molecular Weight: 556.66

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CC(=O)NCCCC[C@H](NC(=O)OCc1ccccc1)C(=O)N1CCN(C(=O)c2cccc3ccccc23)CC1

Standard InChI:  InChI=1S/C32H36N4O5/c1-2-29(37)33-18-9-8-17-28(34-32(40)41-23-24-11-4-3-5-12-24)31(39)36-21-19-35(20-22-36)30(38)27-16-10-14-25-13-6-7-15-26(25)27/h2-7,10-16,28H,1,8-9,17-23H2,(H,33,37)(H,34,40)/t28-/m0/s1

Standard InChI Key:  IQDAHYYYLIDXSI-NDEPHWFRSA-N

Alternative Forms

1. Parent:

   

   ALA4093689

   ---

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

Calculated Properties

Molecular Weight: 556.66

Molecular Weight (Monoisotopic): 556.2686

AlogP: 3.89

#Rotatable Bonds: 11

Polar Surface Area: 108.05

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.49

CX Basic pKa: ┄

CX LogP: 3.59

CX LogD: 3.59

Aromatic Rings: 3

Heavy Atoms: 41

QED Weighted: 0.28

Np Likeness Score: -0.70

References

1. Akbar A, McNeil NMR, Albert MR, Ta V, Adhikary G, Bourgeois K, Eckert RL, Keillor JW..  (2017)  Structure-Activity Relationships of Potent, Targeted Covalent Inhibitors That Abolish Both the Transamidation and GTP Binding Activities of Human Tissue Transglutaminase.,  60  (18): [PMID:28858494] [10.1021/acs.jmedchem.7b01070]

2. McNeil NMR, Gates EWJ, Firoozi N, Cundy NJ, Leccese J, Eisinga S, Tyndall JDA, Adhikary G, Eckert RL, Keillor JW..  (2022)  Structure-activity relationships of N-terminal variants of peptidomimetic tissue transglutaminase inhibitors.,  232  [PMID:35158154] [10.1016/j.ejmech.2022.114172]

3. Cundy NJ, Arciszewski J, Gates EWJ, Acton SL, Passley KD, Awoonor-Williams E, Boyd EK, Xu N, Pierson É, Fernandez-Ansieta C, Albert MR, McNeil NMR, Adhikary G, Eckert RL, Keillor JW..  (2023)  Novel irreversible peptidic inhibitors of transglutaminase 2.,  14  (2.0): [PMID:36846375] [10.1039/d2md00417h]

Source

Source(1):

• Scientific Literature