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

ID: ALA287896

Chembl Id: CHEMBL287896

PubChem CID: 9998020

Max Phase: Preclinical

Molecular Formula: C17H22N2O4S

Molecular Weight: 350.44

Molecule Type: Small molecule

Names and Identifiers

Synonyms: SQ-26332 | SQ-26332|CHEMBL287896|SCHEMBL9068759|BDBM50048514|(S)-1-[(S)-2-((S)-2-Mercapto-3-phenyl-propionylamino)-propionyl]-pyrrolidine-2-carboxylic acid

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

Standard InChI:  InChI=1S/C17H22N2O4S/c1-11(16(21)19-9-5-8-13(19)17(22)23)18-15(20)14(24)10-12-6-3-2-4-7-12/h2-4,6-7,11,13-14,24H,5,8-10H2,1H3,(H,18,20)(H,22,23)/t11-,13-,14-/m0/s1

Standard InChI Key:  YSFYVNRABGRTNY-UBHSHLNASA-N

Alternative Forms

1. Parent:

   

   ALA287896

   (S)-1-[(S)-2-((S)-2-Mercapto-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: 350.44

Molecular Weight (Monoisotopic): 350.1300

AlogP: 1.11

#Rotatable Bonds: 6

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: 3.80

CX Basic pKa: ┄

CX LogP: 1.43

CX LogD: -1.84

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.67

Np Likeness Score: -0.48

References

1. Coric P, Turcaud S, Meudal H, Roques BP, Fournie-Zaluski MC..  (1996)  Optimal recognition of neutral endopeptidase and angiotensin-converting enzyme active sites by mercaptoacyldipeptides as a means to design potent dual inhibitors.,  39  (6): [PMID:8632427] [10.1021/jm950590p]

2. Robl JA, Sun CQ, Stevenson J, Ryono DE, Simpkins LM, Cimarusti MP, Dejneka T, Slusarchyk WA, Chao S, Stratton L, Misra RN, Bednarz MS, Asaad MM, Cheung HS, Abboa-Offei BE, Smith PL, Mathers PD, Fox M, Schaeffer TR, Seymour AA, Trippodo NC..  (1997)  Dual metalloprotease inhibitors: mercaptoacetyl-based fused heterocyclic dipeptide mimetics as inhibitors of angiotensin-converting enzyme and neutral endopeptidase.,  40  (11): [PMID:9171867] [10.1021/jm970041e]

3. 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]

4. 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]

5. Robl JA, Cimarusti MP, Simpkins LM, Brown B, Ryono DE, Bird JE, Asaad MM, Schaeffer TR, Trippodo NC..  (1996)  Dual metalloprotease inhibitors. 6. Incorporation of bicyclic and substituted monocyclic azepinones as dipeptide surrogates in angiotensin-converting enzyme/neutral endopeptidase inhibitors.,  39  (2): [PMID:8558518] [10.1021/jm950677a]

6. Morphy R, Rankovic Z..  (2005)  Designed multiple ligands. An emerging drug discovery paradigm.,  48  (21): [PMID:16220969] [10.1021/jm058225d]

7. 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