2-(4-(2-bromo-5-fluorophenoxy)piperidin-1-yl)-5-(2H-tetrazol-5-yl)-1,3,4-thiadiazole

ID: ALA2153600

PubChem CID: 53388366

Max Phase: Preclinical

Molecular Formula: C14H13BrFN7OS

Molecular Weight: 426.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Fc1ccc(Br)c(OC2CCN(c3nnc(-c4nn[nH]n4)s3)CC2)c1

Standard InChI:  InChI=1S/C14H13BrFN7OS/c15-10-2-1-8(16)7-11(10)24-9-3-5-23(6-4-9)14-20-19-13(25-14)12-17-21-22-18-12/h1-2,7,9H,3-6H2,(H,17,18,21,22)

Standard InChI Key:  VJYMDTMHJYNRJZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   -0.3665   -8.9106    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0445   -9.6269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8657   -9.6291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2821   -8.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8711   -8.2005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0437   -8.1966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1069   -8.9200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5164   -9.6360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0983  -10.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5071  -11.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3328  -11.0665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7479  -10.3488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3367   -9.6363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7493   -8.9221    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.1915   -8.9105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6761   -8.2431    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4608   -8.4979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4608   -9.3226    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6764   -9.5778    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0979   -7.9701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493   -7.1467    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8174   -6.8460    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3406   -7.4836    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8961   -8.1783    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0915  -11.7751    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
 12 13  2  0
 13  8  1  0
 13 14  1  0
 18 19  1  0
  4  7  1  0
  1  2  1  0
 16 17  1  0
  7  8  1  0
  1  6  1  0
  8  9  2  0
 15 16  1  0
 17 18  2  0
 19 15  2  0
  1 15  1  0
 23 24  1  0
  2  3  1  0
  9 10  1  0
 21 22  2  0
  3  4  1  0
 10 11  2  0
  4  5  1  0
 20 21  1  0
 22 23  1  0
 24 20  2  0
 17 20  1  0
 11 12  1  0
 10 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2153600

   4-(2-Bromo-5-fluorophenoxy)-1-[5-(2H-tetrazol-5-yl)-1,3,4-thiadiazol-2-yl]piperidine

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: 426.28

Molecular Weight (Monoisotopic): 425.0070

AlogP: 2.67

#Rotatable Bonds: 4

Polar Surface Area: 92.71

Molecular Species: ACID

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.90

CX Basic pKa: ┄

CX LogP: 3.32

CX LogD: 1.81

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.69

Np Likeness Score: -1.78

References

1. Oballa RM, Belair L, Black WC, Bleasby K, Chan CC, Desroches C, Du X, Gordon R, Guay J, Guiral S, Hafey MJ, Hamelin E, Huang Z, Kennedy B, Lachance N, Landry F, Li CS, Mancini J, Normandin D, Pocai A, Powell DA, Ramtohul YK, Skorey K, Sørensen D, Sturkenboom W, Styhler A, Waddleton DM, Wang H, Wong S, Xu L, Zhang L..  (2011)  Development of a liver-targeted stearoyl-CoA desaturase (SCD) inhibitor (MK-8245) to establish a therapeutic window for the treatment of diabetes and dyslipidemia.,  54  (14): [PMID:21661758] [10.1021/jm200319u]

Source

Source(1):

• Scientific Literature