(trans)-4-(2-(6-Fluoro-5H-imidazo[5,1-a]isoindol-5-yl)-1-hydroxyethyl)cyclohexanol

ID: ALA4476312

Max Phase: Preclinical

Molecular Formula: C18H21FN2O2

Molecular Weight: 316.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  OC(CC1c2c(F)cccc2-c2cncn21)[C@H]1CC[C@H](O)CC1

Standard InChI:  InChI=1S/C18H21FN2O2/c19-14-3-1-2-13-16-9-20-10-21(16)15(18(13)14)8-17(23)11-4-6-12(22)7-5-11/h1-3,9-12,15,17,22-23H,4-8H2/t11-,12-,15?,17?

Standard InChI Key:  YGACXVRLDHEXKY-DMMRXEJWSA-N

Molfile:  

 
     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   12.6389   -7.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6875  -10.6916    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0204  -10.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3624  -10.2137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8917   -6.9912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7151   -8.1516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1152   -9.4236    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2897   -9.4142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2156   -7.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2994   -8.2822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3790   -8.6413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0392   -8.6262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2028   -8.6378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6205   -9.3512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4457   -9.3478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2088  -10.0682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8546  -10.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6763  -10.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0918   -9.3472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6753   -8.6319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8475   -8.6318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3132   -6.8603    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   17.9128   -9.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0280   -8.6336    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  2  0
  7 11  1  0
  5  9  1  0
  2  4  2  0
  4  7  1  0
 11  6  1  0
 12  6  2  0
  6  1  1  0
 12  8  1  0
  3  2  1  0
 10 12  1  0
  8  7  1  0
  8  3  2  0
  1  5  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 15 17  1  0
 15 21  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
  1 22  1  0
 19 23  1  1
 15 24  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4476312

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 316.38

Molecular Weight (Monoisotopic): 316.1587

AlogP: 2.89

#Rotatable Bonds: 3

Polar Surface Area: 58.28

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.76

CX Basic pKa: 6.01

CX LogP: 1.76

CX LogD: 1.74

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.92

Np Likeness Score: 0.05

References

1. Kumar S, Waldo JP, Jaipuri FA, Marcinowicz A, Van Allen C, Adams J, Kesharwani T, Zhang X, Metz R, Oh AJ, Harris SF, Mautino MR..  (2019)  Discovery of Clinical Candidate (1R,4r)-4-((R)-2-((S)-6-Fluoro-5H-imidazo[5,1-a]isoindol-5-yl)-1-hydroxyethyl)cyclohexan-1-ol (Navoximod), a Potent and Selective Inhibitor of Indoleamine 2,3-Dioxygenase 1.,  62  (14): [PMID:31264862] [10.1021/acs.jmedchem.9b00662]

Source

Source(1):

• Scientific Literature