(3S,7aR)-6-((2R,8aS)-1,4-Dioxo-hexahydro-pyrrolo[1,2-a]pyrazin-2-yl)-5-oxo-hexahydro-pyrrolo[2,1-b]thiazole-3-carboxylic acid amide

ID: ALA607228

Chembl Id: CHEMBL607228

PubChem CID: 10246513

Max Phase: Preclinical

Molecular Formula: C14H18N4O4S

Molecular Weight: 338.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)[C@H]1CS[C@@H]2C[C@@H](N3CC(=O)N4CCC[C@H]4C3=O)C(=O)N12

Standard InChI:  InChI=1S/C14H18N4O4S/c15-12(20)9-6-23-11-4-8(14(22)18(9)11)17-5-10(19)16-3-1-2-7(16)13(17)21/h7-9,11H,1-6H2,(H2,15,20)/t7-,8+,9+,11+/m0/s1

Standard InChI Key:  CKWXMNDKAZLYMW-YSSBGUOXSA-N

Alternative Forms

1. Parent:

   

   ALA607228

   (3S,6R,7aR)-6-[(8aS)-1,4-dioxo-6,7,8,8a-tetrahydro-3H-pyrrolo[1,2-a]pyrazin-2-yl]-5-oxo-3,6,7,7a-tetrahydro-2H-pyrrolo[2,1-b][1,3]thiazole-3-carboxamide

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: 338.39

Molecular Weight (Monoisotopic): 338.1049

AlogP: -1.65

#Rotatable Bonds: 2

Polar Surface Area: 104.02

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: -2.27

CX LogD: -2.27

Aromatic Rings: 0

Heavy Atoms: 23

QED Weighted: 0.65

Np Likeness Score: -0.03

References

1. Baures PW, Ojala WH, Costain WJ, Ott MC, Pradhan A, Gleason WB, Mishra RK, Johnson RL..  (1997)  Design, synthesis, and dopamine receptor modulating activity of diketopiperazine peptidomimetics of L-prolyl-L-leucylglycinamide.,  40  (22): [PMID:9357526] [10.1021/jm970328b]

2. Kumari S,Carmona AV,Tiwari AK,Trippier PC.  (2020)  Amide Bond Bioisosteres: Strategies, Synthesis, and Successes.,  63  (21.0): [PMID:32686940] [10.1021/acs.jmedchem.0c00530]

Source

Source(1):

• Scientific Literature