3-(2-hydroxyethyl)-3,13-diazahexacyclo[14.8.0.0^{2,10}.0^{4,9}.0^{11,15}.0^{17,22}]tetracosa-1(16),2(10),4,6,8,11(15),17(22),18,20-nonaen-14-one

ID: ALA510795

PubChem CID: 24971432

Max Phase: Preclinical

Molecular Formula: C24H20N2O2

Molecular Weight: 368.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1NCc2c1c1c(c3c2c2ccccc2n3CCO)CCc2ccccc2-1

Standard InChI:  InChI=1S/C24H20N2O2/c27-12-11-26-19-8-4-3-7-16(19)21-18-13-25-24(28)22(18)20-15-6-2-1-5-14(15)9-10-17(20)23(21)26/h1-8,27H,9-13H2,(H,25,28)

Standard InChI Key:  RKOKHRNEVZKOLO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 33  0  0  0  0  0  0  0  0999 V2000
    2.8000   -3.1113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7096   -3.9305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3729   -4.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5492   -2.7793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2136   -3.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1243   -4.0845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8794   -4.4237    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0239   -3.0923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4322   -3.8114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6750   -3.1029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2560   -3.8171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6625   -4.5329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4899   -4.5411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5007   -3.1048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9052   -3.8260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7299   -3.8354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1514   -3.1244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7420   -2.4024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9185   -2.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0483   -5.2280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4380   -2.3815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2630   -2.3868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5231   -1.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8587   -1.1144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1881   -1.5953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3063   -1.3550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8294   -5.4838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9983   -6.2880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0
 12 13  1  0
 13 15  1  0
  3  6  2  0
  6  7  1  0
 14 15  2  0
  7  9  1  0
 15 16  1  0
  8  5  1  0
 16 17  2  0
  1  2  2  0
 17 18  1  0
  5  4  2  0
 18 19  2  0
 19 14  1  0
  8  9  2  0
  7 20  1  0
 21 22  2  0
  9 11  1  0
 10 22  1  0
 21  8  1  0
 10 11  2  0
  4  1  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 21  1  0
  5  6  1  0
 23 26  2  0
  2  3  1  0
 20 27  1  0
 10 14  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA510795

   3-(2-Hydroxyethyl)-3,13-diazahexacyclo[14.8.0.0^{2,10}.0^{4,9}.0^{11,15}.0^{17,22}]tetracosa-1(16),2(10),4(9),5,7,11(15),17(22),18,20-nonaen-14-one

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: 368.44

Molecular Weight (Monoisotopic): 368.1525

AlogP: 3.80

#Rotatable Bonds: 2

Polar Surface Area: 54.26

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.75

CX Basic pKa: ┄

CX LogP: 3.66

CX LogD: 3.66

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.57

Np Likeness Score: 0.26

References

1. Hudkins RL, Diebold JL, Tao M, Josef KA, Park CH, Angeles TS, Aimone LD, Husten J, Ator MA, Meyer SL, Holskin BP, Durkin JT, Fedorov AA, Fedorov EV, Almo SC, Mathiasen JR, Bozyczko-Coyne D, Saporito MS, Scott RW, Mallamo JP..  (2008)  Mixed-lineage kinase 1 and mixed-lineage kinase 3 subtype-selective dihydronaphthyl[3,4-a]pyrrolo[3,4-c]carbazole-5-ones: optimization, mixed-lineage kinase 1 crystallography, and oral in vivo activity in 1-methyl-4-phenyltetrahydropyridine models.,  51  (18): [PMID:18714982] [10.1021/jm8005838]

Source

Source(1):

• Scientific Literature