N-(5-(2-aminoethylcarbamoyl)-2-(4-o-tolylpiperazin-1-yl)phenyl)furan-2-carboxamide

ID: ALA3263684

PubChem CID: 71234072

Max Phase: Preclinical

Molecular Formula: C25H29N5O3

Molecular Weight: 447.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccccc1N1CCN(c2ccc(C(=O)NCCN)cc2NC(=O)c2ccco2)CC1

Standard InChI:  InChI=1S/C25H29N5O3/c1-18-5-2-3-6-21(18)29-12-14-30(15-13-29)22-9-8-19(24(31)27-11-10-26)17-20(22)28-25(32)23-7-4-16-33-23/h2-9,16-17H,10-15,26H2,1H3,(H,27,31)(H,28,32)

Standard InChI Key:  GBKGEVJVIPUJIV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   30.3887  -23.0231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2041  -23.0243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6111  -22.3198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2037  -21.6137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3851  -21.6165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9819  -22.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4282  -22.3200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8367  -23.0278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.8370  -21.6124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.9739  -20.9103    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.3798  -20.2011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9686  -19.4991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1970  -20.1980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.1624  -22.3251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.7529  -21.6168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9392  -21.6173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5289  -22.3244    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.9384  -23.0327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7582  -23.0339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7115  -22.3282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3041  -21.6185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4877  -21.6175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0777  -22.3255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4901  -23.0358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3052  -23.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7152  -23.7403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2922  -18.7537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6842  -18.2132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9822  -18.6245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1565  -19.4191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.6528  -21.6154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0640  -20.9092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8812  -20.9122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  3  7  1  0
  7  8  2  0
  7  9  1  0
  5 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 14 15  1  0
 14 19  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
  6 14  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 17 20  1  0
 25 26  1  0
 12 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 12  1  0
  9 31  1  0
 31 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3263684

   N-[5-(2-aminoethylcarbamoyl)-2-[4-(2-methylphenyl)piperazin-1-yl]phenyl]furan-2-carboxamide

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: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 447.54

Molecular Weight (Monoisotopic): 447.2270

AlogP: 2.86

#Rotatable Bonds: 7

Polar Surface Area: 103.84

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.52

CX Basic pKa: 9.16

CX LogP: 2.76

CX LogD: 1.01

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.51

Np Likeness Score: -1.61

References

1. Yu HN, Richardson TE, Nataraja S, Fischer DJ, Sriraman V, Jiang X, Bharathi P, Foglesong RJ, Haxell TF, Heasley BH, Jenks M, Li J, Dugas MS, Collis R, Tian H, Palmer S, Goutopoulos A..  (2014)  Discovery of substituted benzamides as follicle stimulating hormone receptor allosteric modulators.,  24  (9): [PMID:24685543] [10.1016/j.bmcl.2014.03.018]

Source

Source(1):

• Scientific Literature