2-[2-Cyclopentyloxy]-12-(2-hydroxyethyl)-13,14-tetrahydronaphthol[2,1-a]pyrrolo[3,4-c]carbazole-5(6H)-one

ID: ALA517743

PubChem CID: 24971435

Max Phase: Preclinical

Molecular Formula: C29H28N2O3

Molecular Weight: 452.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1NCc2c1c1c(c3c2c2ccccc2n3CCO)CCc2cc(OC3CCCC3)ccc2-1

Standard InChI:  InChI=1S/C29H28N2O3/c32-14-13-31-24-8-4-3-7-21(24)26-23-16-30-29(33)27(23)25-20-12-10-19(34-18-5-1-2-6-18)15-17(20)9-11-22(25)28(26)31/h3-4,7-8,10,12,15,18,32H,1-2,5-6,9,11,13-14,16H2,(H,30,33)

Standard InChI Key:  FNZIPRHNOOCRHH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 40  0  0  0  0  0  0  0  0999 V2000
    2.6283  -16.7293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5379  -17.5493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2018  -18.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3784  -16.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0434  -16.8797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9541  -17.7035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7099  -18.0431    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8546  -16.7102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2633  -17.4301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5074  -16.7208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0879  -17.4357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4949  -18.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3231  -18.1606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3339  -16.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7387  -17.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5644  -17.4541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9863  -16.7424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5765  -16.0196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7521  -16.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8790  -18.8482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2691  -15.9988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0950  -16.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3553  -15.2203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6901  -14.7304    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0189  -15.2116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1392  -14.9711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8089  -16.7502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6608  -19.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8299  -19.9092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2270  -16.0418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0432  -15.9632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2219  -15.1602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5135  -14.7421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8970  -15.2867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
 17 27  1  0
  2  3  1  0
 20 28  1  0
 10 14  1  0
 28 29  1  0
 11 12  1  0
 27 30  1  0
 30 31  1  0
 12 13  1  0
 13 15  1  0
  3  6  2  0
  6  7  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA517743

   20-(Cyclopentyloxy)-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: 452.55

Molecular Weight (Monoisotopic): 452.2100

AlogP: 5.12

#Rotatable Bonds: 4

Polar Surface Area: 63.49

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.76

CX Basic pKa: ┄

CX LogP: 4.86

CX LogD: 4.86

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.45

Np Likeness Score: 0.38

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