8-Ethyl-2,5,6,12-tetrahydro-3,10,10-trimethyl-9-oxopyrazolo[4,3:6,7]cyclohepta[1,2-b]pyrrolo[2,3-f]indole

ID: ALA223147

PubChem CID: 135564980

Max Phase: Preclinical

Molecular Formula: C21H24N4O

Molecular Weight: 348.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN1C(=O)C(C)(C)c2cc3[nH]c4c(c3cc21)CCCc1c(C)n[nH]c1-4

Standard InChI:  InChI=1S/C21H24N4O/c1-5-25-17-9-14-13-8-6-7-12-11(2)23-24-19(12)18(13)22-16(14)10-15(17)21(3,4)20(25)26/h9-10,22H,5-8H2,1-4H3,(H,23,24)

Standard InChI Key:  AOMMPEGZDRAGRC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 30  0  0  0  0  0  0  0  0999 V2000
   -0.0881    0.6444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1053   -0.1805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8282   -0.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8767   -1.2514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1726    0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6738   -0.4517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9973    0.2253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5270   -0.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3628   -1.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2923   -0.0988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6194    0.3054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7946    0.2882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3237   -0.3892    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5950   -1.1683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0558   -1.7928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2959    0.9454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0016    1.3727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9447    1.6919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5167    0.6742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7938    1.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5339   -0.1507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7017    0.8829    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6283   -1.5914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9915   -0.5367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2355    0.7242    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4351    0.9245    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
 20  1  1  0
  1 22  1  0
  2  3  1  0
  2  6  1  0
 21  3  2  0
  4  6  1  0
 23  4  1  0
  5  6  2  0
  7  5  1  0
  5 22  1  0
  7  8  2  0
  7 26  1  0
  8  9  1  0
  8 10  1  0
  9 23  1  0
 10 24  1  0
 10 25  2  0
 12 11  2  0
 12 13  1  0
 16 12  1  0
 14 13  1  0
 21 13  1  0
 14 15  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 20  2  0
 21 19  1  0
 26 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA223147

   ---

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: 348.45

Molecular Weight (Monoisotopic): 348.1950

AlogP: 4.00

#Rotatable Bonds: 1

Polar Surface Area: 64.78

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.37

CX LogP: 3.42

CX LogD: 3.42

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.70

Np Likeness Score: -0.37

References

1. Rawson TE, Rüth M, Blackwood E, Burdick D, Corson L, Dotson J, Drummond J, Fields C, Georges GJ, Goller B, Halladay J, Hunsaker T, Kleinheinz T, Krell HW, Li J, Liang J, Limberg A, McNutt A, Moffat J, Phillips G, Ran Y, Safina B, Ultsch M, Walker L, Wiesmann C, Zhang B, Zhou A, Zhu BY, Rüger P, Cochran AG..  (2008)  A pentacyclic aurora kinase inhibitor (AKI-001) with high in vivo potency and oral bioavailability.,  51  (15): [PMID:18630890] [10.1021/jm800052b]

2. Mark Wenlock and Nicholas Tomkinson. Experimental in vitro DMPK and physicochemical data on a set of publicly disclosed compounds,  [10.6019/CHEMBL3301361]

Source

Source(2):

• Scientific Literature
• AstraZeneca Deposited Data