(S)-2-[(S)-2-((S)-2-Mercaptomethyl-3-phenyl-propionylamino)-propionyl]-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid

ID: ALA49920

Chembl Id: CHEMBL49920

PubChem CID: 44295650

Max Phase: Preclinical

Molecular Formula: C23H26N2O4S

Molecular Weight: 426.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](NC(=O)[C@@H](CS)Cc1ccccc1)C(=O)N1Cc2ccccc2C[C@H]1C(=O)O

Standard InChI:  InChI=1S/C23H26N2O4S/c1-15(24-21(26)19(14-30)11-16-7-3-2-4-8-16)22(27)25-13-18-10-6-5-9-17(18)12-20(25)23(28)29/h2-10,15,19-20,30H,11-14H2,1H3,(H,24,26)(H,28,29)/t15-,19+,20-/m0/s1

Standard InChI Key:  UACOVYDVQRXMCG-BEVDRBHNSA-N

Alternative Forms

1. Parent:

   

   ALA49920

   (S)-2-[(S)-2-((S)-2-Mercaptomethyl-3-phenyl-propionylamino)-propionyl]-1,2,3,4-tetrahydro-isoquinoline-3-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: 426.54

Molecular Weight (Monoisotopic): 426.1613

AlogP: 2.32

#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: 3.82

CX Basic pKa: ┄

CX LogP: 3.13

CX LogD: -0.13

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.59

Np Likeness Score: -0.42

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. 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