N-{(S)-1-[3-(2-Bromo-ethoxy)-4-chloro-1-oxo-isochroman-7-ylcarbamoyl]-2-phenyl-ethyl}-nicotinamide

ID: ALA440537

PubChem CID: 44367845

Max Phase: Preclinical

Molecular Formula: C26H23BrClN3O5

Molecular Weight: 572.84

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@@H](Cc1ccccc1)C(=O)Nc1ccc2c(c1)C(=O)OC(OCCBr)C2Cl)c1cccnc1

Standard InChI:  InChI=1S/C26H23BrClN3O5/c27-10-12-35-26-22(28)19-9-8-18(14-20(19)25(34)36-26)30-24(33)21(13-16-5-2-1-3-6-16)31-23(32)17-7-4-11-29-15-17/h1-9,11,14-15,21-22,26H,10,12-13H2,(H,30,33)(H,31,32)/t21-,22?,26?/m0/s1

Standard InChI Key:  VTORLFVZJQHBDR-OKFDZGCWSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA440537

   N-[(2S)-1-[[3-(2-bromoethoxy)-4-chloro-1-oxo-3,4-dihydroisochromen-7-yl]amino]-1-oxo-3-phenylpropan-2-yl]pyridine-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: 572.84

Molecular Weight (Monoisotopic): 571.0510

AlogP: 4.25

#Rotatable Bonds: 9

Polar Surface Area: 106.62

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.87

CX Basic pKa: 3.62

CX LogP: 4.38

CX LogD: 4.38

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.29

Np Likeness Score: -0.30

References

1. Kerrigan JE, Oleksyszyn J, Kam CM, Selzler J, Powers JC..  (1995)  Mechanism-based isocoumarin inhibitors for human leukocyte elastase. Effect of the 7-amino substituent and 3-alkoxy group in 3-alkoxy-7-amino-4-chloroisocoumarins on inhibitory potency.,  38  (3): [PMID:7853347] [10.1021/jm00003a017]

Source

Source(1):

• Scientific Literature