Isoquinoline-3-carboxylic acid ((R)-4-oxo-1-phenyl-3,4,6,7-tetrahydro-[1,4]diazepino[6,7,1-hi]indol-3-yl)-amide

ID: ALA125828

Chembl Id: CHEMBL125828

PubChem CID: 10812634

Max Phase: Preclinical

Molecular Formula: C27H20N4O2

Molecular Weight: 432.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@@H]1N=C(c2ccccc2)c2cccc3c2N(CC3)C1=O)c1cc2ccccc2cn1

Standard InChI:  InChI=1S/C27H20N4O2/c32-26(22-15-19-9-4-5-10-20(19)16-28-22)30-25-27(33)31-14-13-18-11-6-12-21(24(18)31)23(29-25)17-7-2-1-3-8-17/h1-12,15-16,25H,13-14H2,(H,30,32)/t25-/m0/s1

Standard InChI Key:  MHRHYMTVTFSTHJ-VWLOTQADSA-N

Alternative Forms

1. Parent:

   

   ALA125828

   N-[(11R)-12-oxo-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-11-yl]isoquinoline-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: 432.48

Molecular Weight (Monoisotopic): 432.1586

AlogP: 3.73

#Rotatable Bonds: 3

Polar Surface Area: 74.66

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.18

CX LogP: 3.95

CX LogD: 3.95

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.54

Np Likeness Score: -0.39

References

1. Pascal Y, Andrianjara CR, Auclair E, Avenel N, Bertin B, Calvet A, Féru F, Lardon S, Moodley I, Ouagued M, Payne A, Pruniaux MP, Szilagyi C..  (2000)  Synthesis and structure-activity relationships of 4-oxo-1-phenyl-3,4,6,7-tetrahydro-[1,4]diazepino[6,7,1-hi]indoles: novel PDE4 inhibitors.,  10  (1): [PMID:10636238] [10.1016/s0960-894x(99)00573-9]

2. Burnouf C, Auclair E, Avenel N, Bertin B, Bigot C, Calvet A, Chan K, Durand C, Fasquelle V, Féru F, Gilbertsen R, Jacobelli H, Kebsi A, Lallier E, Maignel J, Martin B, Milano S, Ouagued M, Pascal Y, Pruniaux MP, Puaud J, Rocher MN, Terrasse C, Wrigglesworth R, Doherty AM..  (2000)  Synthesis, structure-activity relationships, and pharmacological profile of 9-amino-4-oxo-1-phenyl-3,4,6,7-tetrahydro[1,4]diazepino[6, 7,1-hi]indoles: discovery of potent, selective phosphodiesterase type 4 inhibitors.,  43  (25): [PMID:11123995] [10.1021/jm000315p]

Source

Source(1):

• Scientific Literature