4-chloro-N-((R)-1-((1R,3S,5S,6r)-3-(5,6-difluoro-1H-benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide

ID: ALA4861332

PubChem CID: 148916634

Max Phase: Preclinical

Molecular Formula: C23H22ClF2N3O

Molecular Weight: 429.90

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC[C@@H](NC(=O)c1ccc(Cl)cc1)[C@H]1[C@@H]2C[C@@H](n3cnc4cc(F)c(F)cc43)C[C@@H]21

Standard InChI:  InChI=1S/C23H22ClF2N3O/c1-2-19(28-23(30)12-3-5-13(24)6-4-12)22-15-7-14(8-16(15)22)29-11-27-20-9-17(25)18(26)10-21(20)29/h3-6,9-11,14-16,19,22H,2,7-8H2,1H3,(H,28,30)/t14-,15-,16+,19-,22+/m1/s1

Standard InChI Key:  PJRNKUWABSYXJP-PZJWQNMWSA-N

Molfile:  

 
     RDKit          2D

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   29.3868   -6.4107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4259   -7.1795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8572   -6.4755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6835   -6.4999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1147   -5.7967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   31.8910   -5.0512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6034   -7.1581    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.2108   -6.4351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8185   -7.9025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.6546   -6.8003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6854   -5.9754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9104   -5.6911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4005   -6.3405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8605   -7.0259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5970   -5.6095    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   28.4378   -7.5914    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   28.6787   -5.1524    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   26.5763   -6.3324    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.3001   -6.7349    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.0816   -6.9972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3082   -5.9106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0936   -5.6669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2738   -4.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6696   -4.3090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8824   -4.5575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7058   -5.3574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6418   -5.7344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4642   -5.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2505   -5.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8489   -3.5060    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   33.1495   -4.3680    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   24.2754   -4.0021    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0
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  4  5  1  0
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 29  3  1  0
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  9  1  1  0
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 11 15  1  0
  1 16  1  1
 11 17  1  6
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 19 23  1  0
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 20 21  2  0
 21 19  1  0
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 23 24  1  0
 24 25  2  0
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 26 27  2  0
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  9 28  1  1
 28 30  1  0
 25 31  1  0
  6 32  1  0
 26 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4861332

   ---

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: 429.90

Molecular Weight (Monoisotopic): 429.1419

AlogP: 5.37

#Rotatable Bonds: 5

Polar Surface Area: 46.92

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 5.55

CX LogP: 4.83

CX LogD: 4.82

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.59

Np Likeness Score: -0.85

References

1. Hamilton MM, Mseeh F, McAfoos TJ, Leonard PG, Reyna NJ, Harris AL, Xu A, Han M, Soth MJ, Czako B, Theroff JP, Mandal PK, Burke JP, Virgin-Downey B, Petrocchi A, Pfaffinger D, Rogers NE, Parker CA, Yu SS, Jiang Y, Krapp S, Lammens A, Trevitt G, Tremblay MR, Mikule K, Wilcoxen K, Cross JB, Jones P, Marszalek JR, Lewis RT..  (2021)  Discovery of IACS-9779 and IACS-70465 as Potent Inhibitors Targeting Indoleamine 2,3-Dioxygenase 1 (IDO1) Apoenzyme.,  64  (15.0): [PMID:34292726] [10.1021/acs.jmedchem.1c00679]

Source

Source(1):

• Scientific Literature