ID: ALA2441437

Max Phase: Preclinical

Molecular Formula: C23H24N6O3

Molecular Weight: 432.48

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=C1OCc2cc(CCN3CCN(C(=O)Cc4ccc(-n5cnnn5)cc4)CC3)ccc21

Standard InChI:  InChI=1S/C23H24N6O3/c30-22(14-17-1-4-20(5-2-17)29-16-24-25-26-29)28-11-9-27(10-12-28)8-7-18-3-6-21-19(13-18)15-32-23(21)31/h1-6,13,16H,7-12,14-15H2

Standard InChI Key:  LKLRNYYBQWYHND-UHFFFAOYSA-N

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

Properties

Molecular Weight: 432.48

Molecular Weight (Monoisotopic): 432.1910

AlogP: 1.26

#Rotatable Bonds: 6

Polar Surface Area: 93.45

Molecular Species: NEUTRAL

HBA: 8

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 6.92

CX LogP: 1.70

CX LogD: 1.58

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.54

Np Likeness Score: -1.57

References

1. Tang H, de Jesus RK, Walsh SP, Zhu Y, Yan Y, Priest BT, Swensen AM, Alonso-Galicia M, Felix JP, Brochu RM, Bailey T, Thomas-Fowlkes B, Zhou X, Pai LY, Hampton C, Hernandez M, Owens K, Roy S, Kaczorowski GJ, Yang L, Garcia ML, Pasternak A..  (2013)  Discovery of a novel sub-class of ROMK channel inhibitors typified by 5-(2-(4-(2-(4-(1H-Tetrazol-1-yl)phenyl)acetyl)piperazin-1-yl)ethyl)isobenzofuran-1(3H)-one.,  23  (21): [PMID:24075732] [10.1016/j.bmcl.2013.08.104]

2. Walsh SP, Shahripour A, Tang H, Teumelsan N, Frie J, Zhu Y, Priest BT, Swensen AM, Liu J, Margulis M, Visconti R, Weinglass A, Felix JP, Brochu RM, Bailey T, Thomas-Fowlkes B, Alonso-Galicia M, Zhou X, Pai LY, Corona A, Hampton C, Hernandez M, Bentley R, Chen J, Shah K, Metzger J, Forrest M, Owens K, Tong V, Ha S, Roy S, Kaczorowski GJ, Yang L, Parmee E, Garcia ML, Sullivan K, Pasternak A..  (2015)  Discovery of a Potent and Selective ROMK Inhibitor with Pharmacokinetic Properties Suitable for Preclinical Evaluation.,  6  (7): [PMID:26191360] [10.1021/ml500440u]

3.  (2015)  Inhibitors of the renal outer medullary potassium channel, 

4. Walsh SP, Shahripour A, Tang H, de Jesus RK, Teumelsan N, Zhu Y, Frie J, Priest BT, Swensen AM, Alonso-Galicia M, Felix JP, Brochu RM, Bailey T, Thomas-Fowlkes B, Zhou X, Pai LY, Hampton C, Hernandez M, Owens K, Ehrhart J, Roy S, Kaczorowski GJ, Yang L, Garcia ML, Pasternak A..  (2016)  Differentiation of ROMK potency from hERG potency in the phenacetyl piperazine series through heterocycle incorporation.,  26  (9): [PMID:27017115] [10.1016/j.bmcl.2016.03.035]

5. 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