(S)-1-[(S)-2-((S)-2-Mercaptomethyl-3-phenyl-propionylamino)-propionyl]-pyrrolidine-2-carboxylic acid

ID: ALA299181

Chembl Id: CHEMBL299181

PubChem CID: 14390729

Max Phase: Preclinical

Molecular Formula: C18H24N2O4S

Molecular Weight: 364.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](NC(=O)[C@@H](CS)Cc1ccccc1)C(=O)N1CCC[C@H]1C(=O)O

Standard InChI:  InChI=1S/C18H24N2O4S/c1-12(17(22)20-9-5-8-15(20)18(23)24)19-16(21)14(11-25)10-13-6-3-2-4-7-13/h2-4,6-7,12,14-15,25H,5,8-11H2,1H3,(H,19,21)(H,23,24)/t12-,14+,15-/m0/s1

Standard InChI Key:  AKSMLLXRBFIIDE-CFVMTHIKSA-N

Alternative Forms

1. Parent:

   

   ALA299181

   (S)-1-[(S)-2-((S)-2-Mercaptomethyl-3-phenyl-propionylamino)-propionyl]-pyrrolidine-2-carboxylic acid

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: 364.47

Molecular Weight (Monoisotopic): 364.1457

AlogP: 1.36

#Rotatable Bonds: 7

Polar Surface Area: 86.71

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.81

CX Basic pKa: ┄

CX LogP: 1.77

CX LogD: -1.49

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.64

Np Likeness Score: -0.41

References

1. Delaney NG, Barrish JC, Neubeck R, Natarajan S, Cohen M, Rovnyak GC, Huber G, Murugesan N, Girotra R, Sieber-McMaster E, Robl JA, Asaad MM, Cheung HS, Bird J, Waldron T, Petrillo EW.  (1994)  Mercaptoacyl dipeptides as dual inhibitors of angiotensin-converting enzyme and neutral endopeptidase. Preliminary structure-activity studies,  4  (15): [10.1016/S0960-894X(01)80371-1]

2. Robl JA, Simpkins LM, Stevenson J, Sun C, Murugesan N, Barrish JC, Asaad MM, Bird J, Schaeffer TR, Trippodo NC, Petrillo EW, Karanewsky DS.  (1994)  Dual metalloprotease inhibitors. I. constrained peptidomimetics of mercaptoacyl dipeptides,  4  (15): [10.1016/S0960-894X(01)80372-3]

3. Van der Poorten O, Knuhtsen A, Sejer Pedersen D, Ballet S, Tourwé D..  (2016)  Side Chain Cyclized Aromatic Amino Acids: Great Tools as Local Constraints in Peptide and Peptidomimetic Design.,  59  (24): [PMID:27690430] [10.1021/acs.jmedchem.6b01029]

Source

Source(1):

• Scientific Literature