(+/-)-trans-4-((1-((2,4-Dichlorophenyl)sulfonyl)-4-hydroxy-4-(hydroxymethyl)pyrrolidin-3-yl)oxy)-2-fluorobenzonitrile

ID: ALA4164465

Chembl Id: CHEMBL4164465

PubChem CID: 139300630

Max Phase: Preclinical

Molecular Formula: C18H15Cl2FN2O5S

Molecular Weight: 461.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1ccc(O[C@H]2CN(S(=O)(=O)c3ccc(Cl)cc3Cl)C[C@@]2(O)CO)cc1F

Standard InChI:  InChI=1S/C18H15Cl2FN2O5S/c19-12-2-4-16(14(20)5-12)29(26,27)23-8-17(18(25,9-23)10-24)28-13-3-1-11(7-22)15(21)6-13/h1-6,17,24-25H,8-10H2/t17-,18+/m0/s1

Standard InChI Key:  VEKPUFJACSQBMV-ZWKOTPCHSA-N

Alternative Forms

1. Parent:

   

   ALA4164465

   ---

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: 461.30

Molecular Weight (Monoisotopic): 460.0063

AlogP: 2.18

#Rotatable Bonds: 5

Polar Surface Area: 110.86

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.60

CX Basic pKa: ┄

CX LogP: 2.37

CX LogD: 2.37

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.71

Np Likeness Score: -1.15

References

1. Brnardic EJ, Ye G, Brooks C, Donatelli C, Barton L, McAtee J, Sanchez RM, Shu A, Erhard K, Terrell L, Graczyk-Millbrandt G, He Y, Costell MH, Behm DJ, Roethke T, Stoy P, Holt DA, Lawhorn BG..  (2018)  Discovery of Pyrrolidine Sulfonamides as Selective and Orally Bioavailable Antagonists of Transient Receptor Potential Vanilloid-4 (TRPV4).,  61  (21): [PMID:30335378] [10.1021/acs.jmedchem.8b01317]

2. Brnardic EJ, Ye G, Brooks C, Donatelli C, Barton L, McAtee J, Sanchez RM, Shu A, Erhard K, Terrell L, Graczyk-Millbrandt G, He Y, Costell MH, Behm DJ, Roethke T, Stoy P, Holt DA, Lawhorn BG..  (2018)  Discovery of Pyrrolidine Sulfonamides as Selective and Orally Bioavailable Antagonists of Transient Receptor Potential Vanilloid-4 (TRPV4).,  61  (21): [PMID:30335378] [10.1021/acs.jmedchem.8b01317]

3. Brooks CA, Barton LS, Behm DJ, Brnardic EJ, Costell MH, Holt DA, Jolivette LJ, Matthews JM, McAtee JJ, McCleland BW, Patterson JR, Pero JE, Rivero RA, Roethke TJ, Sanchez RM, Shenje R, Terrell LR, Lawhorn BG..  (2019)  Discovery of GSK3527497: A Candidate for the Inhibition of Transient Receptor Potential Vanilloid-4 (TRPV4).,  62  (20): [PMID:31532662] [10.1021/acs.jmedchem.9b01247]

Source

Source(1):

• Scientific Literature