4-[4-(1-isopropyl-7-oxo-spiro[4,6-dihydroindazole-5,4'-piperidine]-1'-carbonyl)-6-methoxy-2-pyridyl]benzoic acid

ID: ALA4567446

Cas Number: 1370448-25-1

PubChem CID: 57496611

Product Number: P413412, Order Now?

Max Phase: Phase

Molecular Formula: C28H30N4O5

Molecular Weight: 502.57

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Clesacostat | Pf-05221304 | PF-05221304 | PF05221304 | Clesacostat|PF-05221304|1370448-25-1|CHEMBL4567446|PF05221304|PF-05221304(Clesacostat)|Benzoic acid, 4-[6-methoxy-4-[[1,4,6,7-tetrahydro-1-(1-methylethyl)-7-oxospiro[5H-indazole-5,4'-piperidin]-1'-yl]carbonyl]-2-pyridinyl]-|Benzoic acid, 4-(6-methoxy-4-((1,4,6,7-tetrahydro-1-(1-methylethyl)-7-oxospiro(5H-indazole-5,4'-piperidin)-1'-yl)carbonyl)-2-pyridinyl)-|Clesacostat [USAN]|CLESACOSTAT [INN]|752DF9PPPI|SCHEMBL899298|GTPL12242|EX-A5142|BDBShow More⌵

Synonyms from Alternative Forms(2): PF-05221304 tromethamine | Clesacostat tromethamine

Canonical SMILES:  COc1cc(C(=O)N2CCC3(CC2)CC(=O)c2c(cnn2C(C)C)C3)cc(-c2ccc(C(=O)O)cc2)n1

Standard InChI:  InChI=1S/C28H30N4O5/c1-17(2)32-25-21(16-29-32)14-28(15-23(25)33)8-10-31(11-9-28)26(34)20-12-22(30-24(13-20)37-3)18-4-6-19(7-5-18)27(35)36/h4-7,12-13,16-17H,8-11,14-15H2,1-3H3,(H,35,36)

Standard InChI Key:  LXZMHBHEXAELHH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 37 41  0  0  0  0  0  0  0  0999 V2000
    2.6104   -1.6100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8959   -2.0226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3249   -2.8476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3249   -2.0226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8959   -0.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1815   -0.7850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1815   -1.6100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6104   -0.7850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4670    0.4525    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4670   -0.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2475    0.8650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9619    0.4525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9619   -0.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2475   -0.7850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3909    0.4525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3909   -0.3725    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6764   -0.7850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1053    0.8650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8198    0.4525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8198   -0.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1053   -0.7850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8198    1.2775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5343    1.6900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2488    1.2775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2488    0.4525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5343    0.0400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8618    1.8295    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5263    2.5832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7059    2.4970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6767    1.7004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9723    0.9302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1959    2.3416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9632    0.0400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6764   -1.6100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2907    1.6889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3768    2.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0393   -1.6101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  3  4  1  0
  1  4  1  0
  5  6  1  0
  6  7  2  0
  5  8  2  0
  1  8  1  0
  7  2  1  0
  9 10  2  0
 10  6  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 11  9  1  0
 14 10  1  0
 15 16  1  0
 16 17  1  0
 17 13  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 18 15  1  0
 21 16  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 19 22  1  0
 19 26  1  0
 27 28  1  0
 28 29  2  0
 23 29  1  0
 24 27  1  0
 27 30  1  0
 30 31  1  0
 30 32  1  0
 25 33  2  0
 17 34  2  0
 11 35  1  0
 35 36  1  0
  4 37  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4567446

   PF-05221304

2. Alternative Forms:

   

   ALA4567446

   CLESACOSTAT TROMETHAMINE

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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 502.57

Molecular Weight (Monoisotopic): 502.2216

AlogP: 4.28

#Rotatable Bonds: 5

Polar Surface Area: 114.62

Molecular Species: ACID

HBA: 7

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.93

CX Basic pKa: 1.66

CX LogP: 3.22

CX LogD: 0.02

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.55

Np Likeness Score: -0.95

References

1. Romero FA, Jones CT, Xu Y, Fenaux M, Halcomb RL..  (2020)  The Race to Bash NASH: Emerging Targets and Drug Development in a Complex Liver Disease.,  63  (10): [PMID:31930920] [10.1021/acs.jmedchem.9b01701]

2. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

3. Unpublished dataset, 

4. Huard K,Smith AC,Cappon G,Dow RL,Edmonds DJ,El-Kattan A,Esler WP,Fernando DP,Griffith DA,Kalgutkar AS,Ross TT,Bagley SW,Beebe D,Bi YA,Cabral S,Crowley C,Doran SD,Dowling MS,Liras S,Mascitti V,Niosi M,Pfefferkorn JA,Polivkova J,Préville C,Price DA,Shavnya A,Shirai N,Smith AH,Southers JR,Tess DA,Thuma BA,Varma MV,Yang X.  (2020)  Optimizing the Benefit/Risk of Acetyl-CoA Carboxylase Inhibitors through Liver Targeting.,  63  (19.0): [PMID:32809824] [10.1021/acs.jmedchem.0c00640]

Source

Source(3):

• Scientific Literature
• Clinical Candidates
• USP Dictionary of USAN and International Drug Names