(S)-2-((S)-1,4-Dioxo-hexahydro-pyrrolo[1,2-a]pyrazin-2-yl)-4-methyl-pentanoic acid carbamoylmethyl-amide

ID: ALA332740

Chembl Id: CHEMBL332740

PubChem CID: 10663749

Max Phase: Preclinical

Molecular Formula: C15H24N4O4

Molecular Weight: 324.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C[C@@H](C(=O)NCC(N)=O)N1CC(=O)N2CCC[C@H]2C1=O

Standard InChI:  InChI=1S/C15H24N4O4/c1-9(2)6-11(14(22)17-7-12(16)20)19-8-13(21)18-5-3-4-10(18)15(19)23/h9-11H,3-8H2,1-2H3,(H2,16,20)(H,17,22)/t10-,11-/m0/s1

Standard InChI Key:  DNVVWPSQSKLWQF-QWRGUYRKSA-N

Alternative Forms

1. Parent:

   

   ALA332740

   (2S)-2-[(8aS)-1,4-dioxo-6,7,8,8a-tetrahydro-3H-pyrrolo[1,2-a]pyrazin-2-yl]-N-(2-amino-2-oxoethyl)-4-methylpentanamide

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: 324.38

Molecular Weight (Monoisotopic): 324.1798

AlogP: -1.16

#Rotatable Bonds: 6

Polar Surface Area: 112.81

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 12.68

CX Basic pKa:

CX LogP: -1.76

CX LogD: -1.76

Aromatic Rings: 0

Heavy Atoms: 23

QED Weighted: 0.64

Np Likeness Score: -0.44

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