(R)-N-Hydroxy-2-methyl-2-(methylsulfonyl)-4-(6-((1-(oxetan-3-yl)azetidin-3-yl)buta-1,3-diyn-1-yl)-3-oxo-1H-pyrrolo[1,2-c]imidazol-2(3H)-yl)butanamide

ID: ALA4548003

Chembl Id: CHEMBL4548003

PubChem CID: 118368757

Max Phase: Preclinical

Molecular Formula: C22H26N4O6S

Molecular Weight: 474.54

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@@](CCN1Cc2cc(C#CC#CC3CN(C4COC4)C3)cn2C1=O)(C(=O)NO)S(C)(=O)=O

Standard InChI:  InChI=1S/C22H26N4O6S/c1-22(20(27)23-29,33(2,30)31)7-8-24-13-18-9-16(12-26(18)21(24)28)5-3-4-6-17-10-25(11-17)19-14-32-15-19/h9,12,17,19,29H,7-8,10-11,13-15H2,1-2H3,(H,23,27)/t22-/m1/s1

Standard InChI Key:  IPQXVVDWTSLWOF-JOCHJYFZSA-N

Alternative Forms

1. Parent:

   

   ALA4548003

   (2R)-N-hydroxy-2-methyl-2-methylsulfonyl-4-[6-[4-[1-(oxetan-3-yl)azetidin-3-yl]buta-1,3-diynyl]-3-oxo-1H-pyrrolo[1,2-c]imidazol-2-yl]butanamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 474.54

Molecular Weight (Monoisotopic): 474.1573

AlogP: -0.34

#Rotatable Bonds: 6

Polar Surface Area: 121.18

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.67

CX Basic pKa: 5.49

CX LogP: -0.98

CX LogD: -1.01

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.33

Np Likeness Score: 0.01

References

1. Panchaud P, Surivet JP, Diethelm S, Blumstein AC, Gauvin JC, Jacob L, Masse F, Mathieu G, Mirre A, Schmitt C, Enderlin-Paput M, Lange R, Gnerre C, Seeland S, Herrmann C, Locher HH, Seiler P, Ritz D, Rueedi G..  (2020)  Optimization of LpxC Inhibitor Lead Compounds Focusing on Efficacy and Formulation for High Dose Intravenous Administration.,  63  (1): [PMID:31804829] [10.1021/acs.jmedchem.9b01605]

Source

Source(1):

• Scientific Literature