N-(2-acetamidoethyl)-8-chloro-N-(cyclohexylmethyl)-1-methyl-1,4-dihydrochromeno[4,3-c]pyrazole-3-carboxamide

ID: ALA4559492

PubChem CID: 155557882

Max Phase: Preclinical

Molecular Formula: C23H29ClN4O3

Molecular Weight: 444.96

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(=O)NCCN(CC1CCCCC1)C(=O)c1nn(C)c2c1COc1ccc(Cl)cc1-2

Standard InChI:  InChI=1S/C23H29ClN4O3/c1-15(29)25-10-11-28(13-16-6-4-3-5-7-16)23(30)21-19-14-31-20-9-8-17(24)12-18(20)22(19)27(2)26-21/h8-9,12,16H,3-7,10-11,13-14H2,1-2H3,(H,25,29)

Standard InChI Key:  BIPJSWDGVJGWPM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   14.9722   -3.0706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9710   -3.8902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6791   -4.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6773   -2.6618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3859   -3.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3847   -3.8877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0909   -4.2967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8028   -3.8897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0933   -2.6554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8022   -3.0649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4107   -2.5172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0778   -1.7691    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2636   -1.8547    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7169   -1.2473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2246   -2.5135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6364   -3.2193    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.6300   -1.8039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4536   -3.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8654   -3.9215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6826   -3.9178    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.0880   -3.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9051   -3.2046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6762   -2.5024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2310   -3.9289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6428   -4.6347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2644   -2.6622    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   19.2339   -5.3435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6422   -6.0473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4597   -6.0478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8673   -5.3384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4573   -4.6285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5  9  1  0
  6  7  1  0
  7  8  1  0
  8 10  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13  9  1  0
 13 14  1  0
 11 15  1  0
 15 16  1  0
 15 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 16 24  1  0
 24 25  1  0
  1 26  1  0
 25 27  1  0
 25 31  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4559492

   ---

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: 444.96

Molecular Weight (Monoisotopic): 444.1928

AlogP: 3.79

#Rotatable Bonds: 6

Polar Surface Area: 76.46

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.99

CX LogD: 2.99

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.73

Np Likeness Score: -1.25

References

1. Chianelli D, Rucker PV, Roland J, Tully DC, Nelson J, Liu X, Bursulaya B, Hernandez ED, Wu J, Prashad M, Schlama T, Liu Y, Chu A, Schmeits J, Huang DJ, Hill R, Bao D, Zoll J, Kim Y, Groessl T, McNamara P, Liu B, Richmond W, Sancho-Martinez I, Phimister A, Seidel HM, Badman MK, Joseph SB, Laffitte B, Molteni V..  (2020)  Nidufexor (LMB763), a Novel FXR Modulator for the Treatment of Nonalcoholic Steatohepatitis.,  63  (8): [PMID:31940200] [10.1021/acs.jmedchem.9b01621]

Source

Source(1):

• Scientific Literature