(6aR,9R)-N9,N9-diethyl-N7-phenyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-7,9(4H)-dicarboxamide

ID: ALA584554

Chembl Id: CHEMBL584554

PubChem CID: 45482789

Max Phase: Preclinical

Molecular Formula: C26H28N4O2

Molecular Weight: 428.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(CC)C(=O)[C@@H]1C=C2c3cccc4[nH]cc(c34)C[C@H]2N(C(=O)Nc2ccccc2)C1

Standard InChI:  InChI=1S/C26H28N4O2/c1-3-29(4-2)25(31)18-13-21-20-11-8-12-22-24(20)17(15-27-22)14-23(21)30(16-18)26(32)28-19-9-6-5-7-10-19/h5-13,15,18,23,27H,3-4,14,16H2,1-2H3,(H,28,32)/t18-,23-/m1/s1

Standard InChI Key:  QIPWTYSOANVUKJ-WZONZLPQSA-N

Alternative Forms

1. Parent:

   

   ALA584554

   (6aR,9R)-N9,N9-diethyl-N7-phenyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-7,9(4H)-dicarboxamide

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: 428.54

Molecular Weight (Monoisotopic): 428.2212

AlogP: 4.51

#Rotatable Bonds: 4

Polar Surface Area: 68.44

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.36

CX Basic pKa: ┄

CX LogP: 3.42

CX LogD: 3.42

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.64

Np Likeness Score: -0.19

References

1. Thoma G, Baenteli R, Lewis I, Wagner T, Oberer L, Blum W, Glickman F, Streiff MB, Zerwes HG..  (2009)  Special ergolines are highly selective, potent antagonists of the chemokine receptor CXCR3: discovery, characterization and preliminary SAR of a promising lead.,  19  (21): [PMID:19783143] [10.1016/j.bmcl.2009.09.002]

2. Thoma G, Baenteli R, Lewis I, Jones D, Kovarik J, Streiff MB, Zerwes HG..  (2011)  Special ergolines efficiently inhibit the chemokine receptor CXCR3 in blood.,  21  (16): [PMID:21764306] [10.1016/j.bmcl.2011.06.070]

Source

Source(1):

• Scientific Literature