N-(2-acetamidoethyl)-N-benzyl-8-bromo-1,4,4-trimethyl-1,4-dihydrochromeno[4,3-c]pyrazole-3-carboxamide

ID: ALA4483715

PubChem CID: 155540812

Max Phase: Preclinical

Molecular Formula: C25H27BrN4O3

Molecular Weight: 511.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(=O)NCCN(Cc1ccccc1)C(=O)c1nn(C)c2c1C(C)(C)Oc1ccc(Br)cc1-2

Standard InChI:  InChI=1S/C25H27BrN4O3/c1-16(31)27-12-13-30(15-17-8-6-5-7-9-17)24(32)22-21-23(29(4)28-22)19-14-18(26)10-11-20(19)33-25(21,2)3/h5-11,14H,12-13,15H2,1-4H3,(H,27,31)

Standard InChI Key:  CFUGYMRDZZPXBR-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   32.3203   -4.2015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5031   -4.2015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9117   -4.9092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6746   -3.3843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6734   -4.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3815   -4.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3797   -2.9754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0883   -3.3807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0871   -4.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7933   -4.6104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.7957   -2.9691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5046   -3.3785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1131   -2.8308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7802   -2.0828    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.9660   -2.1683    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.9270   -2.8272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3388   -3.5330    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.3324   -2.1176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.1560   -3.5293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5678   -4.2352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3850   -4.2315    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.7904   -3.5219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6075   -3.5183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.3786   -2.8161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9334   -4.2426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3452   -4.9484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9668   -2.9759    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   32.9377   -5.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3488   -6.3588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1669   -6.3555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5721   -5.6410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1587   -4.9386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4193   -1.5610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  8 11  1  0
  9 10  1  0
 10  2  1  0
  2 12  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 11  1  0
 13 16  1  0
 16 17  1  0
 16 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 17 25  1  0
 25 26  1  0
  4 27  1  0
 26 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 26  1  0
 15 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4483715

   ---

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: 511.42

Molecular Weight (Monoisotopic): 510.1267

AlogP: 4.26

#Rotatable Bonds: 6

Polar Surface Area: 76.46

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.46

CX LogD: 3.46

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.54

Np Likeness Score: -0.96

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