2-fluoro-4-(2-(4-(2-(1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)piperazin-1-yl)ethyl)benzonitrile

ID: ALA2146873

Chembl Id: CHEMBL2146873

PubChem CID: 53354783

Max Phase: Preclinical

Molecular Formula: C23H24FN3O2

Molecular Weight: 393.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1ccc(CCN2CCN(CCc3ccc4c(c3)COC4=O)CC2)cc1F

Standard InChI:  InChI=1S/C23H24FN3O2/c24-22-14-18(1-3-19(22)15-25)6-8-27-11-9-26(10-12-27)7-5-17-2-4-21-20(13-17)16-29-23(21)28/h1-4,13-14H,5-12,16H2

Standard InChI Key:  XPHJICKYBJRKLW-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA2146873

   2-fluoro-4-[2-[4-[2-(1-oxo-3H-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]benzonitrile

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: 393.46

Molecular Weight (Monoisotopic): 393.1853

AlogP: 2.77

#Rotatable Bonds: 6

Polar Surface Area: 56.57

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.69

CX LogP: 3.62

CX LogD: 3.15

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.71

Np Likeness Score: -0.89

References

1. Tang H, Walsh SP, Yan Y, de Jesus RK, Shahripour A, Teumelsan N, Zhu Y, Ha S, Owens KA, Thomas-Fowlkes BS, Felix JP, Liu J, Kohler M, Priest BT, Bailey T, Brochu R, Alonso-Galicia M, Kaczorowski GJ, Roy S, Yang L, Mills SG, Garcia ML, Pasternak A..  (2012)  Discovery of Selective Small Molecule ROMK Inhibitors as Potential New Mechanism Diuretics.,  3  (5): [PMID:24900480] [10.1021/ml3000066]

2.  (2015)  Inhibitors of the renal outer medullary potassium channel, 

3. Chobanian HR, Guo Y, Pio B, Tang H, Teumelsan N, Clements M, Frie J, Ferguson R, Guo Z, Thomas-Fowlkes BS, Felix JP, Liu J, Kohler M, Priest B, Hampton C, Pai LY, Corona A, Metzger J, Tong V, Joshi EM, Xu L, Owens K, Maloney K, Sullivan K, Pasternak A..  (2017)  The design and synthesis of novel spirocyclic heterocyclic sulfone ROMK inhibitors as diuretics.,  27  (4): [PMID:28111141] [10.1016/j.bmcl.2016.10.032]

Source

Source(2):

• Scientific Literature
• BindingDB Database