5-(3,5-dibromo-4-(3-(dimethylamino)propoxy)phenyl)-3-isopropylpyrazin-2(1H)-one

ID: ALA2417880

PubChem CID: 72163728

Max Phase: Preclinical

Molecular Formula: C18H23Br2N3O2

Molecular Weight: 473.21

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)c1nc(-c2cc(Br)c(OCCCN(C)C)c(Br)c2)c[nH]c1=O

Standard InChI:  InChI=1S/C18H23Br2N3O2/c1-11(2)16-18(24)21-10-15(22-16)12-8-13(19)17(14(20)9-12)25-7-5-6-23(3)4/h8-11H,5-7H2,1-4H3,(H,21,24)

Standard InChI Key:  FWYBFLRVURSQCH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   33.1747  -12.6293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1747  -13.4465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8799  -13.8510    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.5852  -13.4465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5852  -12.6293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8799  -12.2166    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.2905  -12.2249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9973  -12.6372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7057  -12.2314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7085  -11.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9971  -11.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2915  -11.4110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4658  -12.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4634  -11.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4675  -13.8561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.9966  -10.1856    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   37.4120  -12.6424    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   37.4169  -11.0059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.1239  -11.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8323  -11.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5394  -11.4179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2477  -11.0104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.9548  -11.4201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2490  -10.1932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7593  -12.6335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  5  7  1  0
  1 13  1  0
 13 14  1  0
  2 15  2  0
 11 16  1  0
  9 17  1  0
 10 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 13 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2417880

   5-[3,5-dibromo-4-[3-(dimethylamino)propoxy]phenyl]-3-propan-2-yl-1H-pyrazin-2-one

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: 473.21

Molecular Weight (Monoisotopic): 471.0157

AlogP: 4.42

#Rotatable Bonds: 7

Polar Surface Area: 58.22

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.83

CX Basic pKa: 9.24

CX LogP: 3.55

CX LogD: 1.82

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.61

Np Likeness Score: -0.52

References

1. Saha S, Reddy ChV, Xu S, Sankar S, Neamati N, Patro B..  (2013)  Synthesis and SAR studies of marine natural products ma'edamines A, B and their analogues.,  23  (18): [PMID:23927972] [10.1016/j.bmcl.2013.07.017]

Source

Source(1):

• Scientific Literature