[(1R,5S,6R)-3-{5-Cyano-6-[(2S,3R)-3-hydroxy-2-methylazetidin-1-yl]-4-(trifluoromethyl)pyridin-2-yl}-3-azabicyclo[3.1.0]hex-6-yl]-acetic Acid

ID: ALA4754053

PubChem CID: 129278497

Max Phase: Preclinical

Molecular Formula: C18H19F3N4O3

Molecular Weight: 396.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@H]1[C@H](O)CN1c1nc(N2C[C@@H]3[C@@H](CC(=O)O)[C@@H]3C2)cc(C(F)(F)F)c1C#N

Standard InChI:  InChI=1S/C18H19F3N4O3/c1-8-14(26)7-25(8)17-10(4-22)13(18(19,20)21)3-15(23-17)24-5-11-9(2-16(27)28)12(11)6-24/h3,8-9,11-12,14,26H,2,5-7H2,1H3,(H,27,28)/t8-,9-,11-,12+,14+/m0/s1

Standard InChI Key:  BMYWDILFDVCFJX-GMEDAVPMSA-N

Molfile:  

 
     RDKit          2D

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   13.6998   -8.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4120   -8.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1258   -8.2604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1230   -7.4336    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4102   -7.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4078   -6.2071    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9880   -5.6293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4043   -5.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8240   -5.6328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8093   -5.6290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4019   -4.2278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8383   -8.6720    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9255   -9.4863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5889   -8.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9877   -8.6731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2762   -8.2598    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.9870   -9.4944    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.2703   -9.0758    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.9896   -7.0293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2777   -6.6167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1368   -8.9424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7314   -9.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5510   -9.6514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2643  -10.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7235  -10.4749    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.1321   -8.1183    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.9706   -9.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6838  -10.0527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9678   -8.8253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  9 10  1  0
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  8 11  1  6
  9 12  1  1
  4 13  1  0
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  2 16  1  0
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 20 21  3  0
  1 20  1  0
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 24 25  1  1
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 28 29  1  0
 28 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4754053

   ---

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: 396.37

Molecular Weight (Monoisotopic): 396.1409

AlogP: 1.70

#Rotatable Bonds: 4

Polar Surface Area: 100.69

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.54

CX Basic pKa: 4.73

CX LogP: 0.93

CX LogD: -1.19

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.80

Np Likeness Score: -0.40

References

1. Futatsugi K,Smith AC,Tu M,Raymer B,Ahn K,Coffey SB,Dowling MS,Fernando DP,Gutierrez JA,Huard K,Jasti J,Kalgutkar AS,Knafels JD,Pandit J,Parris KD,Perez S,Pfefferkorn JA,Price DA,Ryder T,Shavnya A,Stock IA,Tsai AS,Tesz GJ,Thuma BA,Weng Y,Wisniewska HM,Xing G,Zhou J,Magee TV.  (2020)  Discovery of PF-06835919: A Potent Inhibitor of Ketohexokinase (KHK) for the Treatment of Metabolic Disorders Driven by the Overconsumption of Fructose.,  63  (22): [PMID:32910646] [10.1021/acs.jmedchem.0c00944]

Source

Source(1):

• Scientific Literature