(2S,4R,6R)-6-Benzyl-5-oxo-6-[((S)-pyrrolidine-2-carbonyl)-amino]-hexahydro-pyrrolo[2,1-b]thiazole-3-carboxylic acid amide

ID: ALA100977

Chembl Id: CHEMBL100977

PubChem CID: 10475388

Max Phase: Preclinical

Molecular Formula: C19H24N4O3S

Molecular Weight: 388.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)[C@H]1CS[C@@H]2C[C@@](Cc3ccccc3)(NC(=O)[C@@H]3CCCN3)C(=O)N12

Standard InChI:  InChI=1S/C19H24N4O3S/c20-16(24)14-11-27-15-10-19(18(26)23(14)15,9-12-5-2-1-3-6-12)22-17(25)13-7-4-8-21-13/h1-3,5-6,13-15,21H,4,7-11H2,(H2,20,24)(H,22,25)/t13-,14+,15+,19+/m0/s1

Standard InChI Key:  RXPLCTCCCYUBTM-NRTGNBEESA-N

Alternative Forms

1. Parent:

   

   ALA100977

   (3S,6R,7aR)-6-benzyl-5-oxo-6-[[(2S)-pyrrolidine-2-carbonyl]amino]-2,3,7,7a-tetrahydropyrrolo[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: 388.49

Molecular Weight (Monoisotopic): 388.1569

AlogP: 0.00

#Rotatable Bonds: 5

Polar Surface Area: 104.53

Molecular Species: BASE

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.19

CX Basic pKa: 9.50

CX LogP: 0.28

CX LogD: -1.80

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.66

Np Likeness Score: -0.15

References

1. Khalil EM, Pradhan A, Ojala WH, Gleason WB, Mishra RK, Johnson RL..  (1999)  Synthesis and dopamine receptor modulating activity of substituted bicyclic thiazolidine lactam peptidomimetics of L-prolyl-L-leucyl-glycinamide.,  42  (15): [PMID:10425107] [10.1021/jm990140n]

2. Dolbeare K, Pontoriero GF, Gupta SK, Mishra RK, Johnson RL..  (2003)  Synthesis and dopamine receptor modulating activity of 3-substituted gamma-lactam peptidomimetics of L-prolyl-L-leucyl-glycinamide.,  46  (5): [PMID:12593653] [10.1021/jm020441o]

Source

Source(1):

• Scientific Literature