[(S)-3-((S)-2-Mercapto-3-phenyl-propionylamino)-2-oxo-2,3,4,5-tetrahydro-benzo[b]azepin-1-yl]-acetic acid

ID: ALA299639

Chembl Id: CHEMBL299639

PubChem CID: 9801007

Max Phase: Preclinical

Molecular Formula: C21H22N2O4S

Molecular Weight: 398.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CN1C(=O)[C@@H](NC(=O)[C@@H](S)Cc2ccccc2)CCc2ccccc21

Standard InChI:  InChI=1S/C21H22N2O4S/c24-19(25)13-23-17-9-5-4-8-15(17)10-11-16(21(23)27)22-20(26)18(28)12-14-6-2-1-3-7-14/h1-9,16,18,28H,10-13H2,(H,22,26)(H,24,25)/t16-,18-/m0/s1

Standard InChI Key:  TYXFDFMUHPWCDX-WMZOPIPTSA-N

Alternative Forms

1. Parent:

   

   ALA299639

   [(S)-3-((S)-2-Mercapto-3-phenyl-propionylamino)-2-oxo-2,3,4,5-tetrahydro-benzo[b]azepin-1-yl]-acetic 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: 398.48

Molecular Weight (Monoisotopic): 398.1300

AlogP: 2.08

#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: 3.92

CX Basic pKa: ┄

CX LogP: 2.60

CX LogD: -0.61

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.65

Np Likeness Score: -0.43

References

1. 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]

2. Robl JA, Simpkins LM, Sulsky R, Sieber-McMaster E, Stevenson J, Kelly YF, Sun C, Misra RN, Ryono DE, Asaad MM, Bird J, Trippodo NC, Karanewsky DS.  (1994)  Dual metalloprotease inhibitors. II. Effect of substitution and stereochemistry on benzazepinone based mercaptoacetyls,  4  (15): [10.1016/S0960-894X(01)80373-5]

3. Robl JA, Sun C, Simpkins LM, Ryono DE, Barrish JC, Karanewsky DS, Asaad MM, Schaeffer TR, Trippodo NC.  (1994)  Dual metalloprotease inhibitors. III. utilization of bicyclic and monocyclic diazepinone based mercaptoacetyls,  4  (16): [10.1016/S0960-894X(01)80562-X]

4. 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]

5. 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