3-chloro-4-[(3R,4S)-4-(4-chlorophenyl)sulfonyl-3-hydroxy-3-(hydroxymethyl)pyrrolidin-1-yl]sulfonyl-benzonitrile

ID: ALA4439190

Chembl Id: CHEMBL4439190

PubChem CID: 134374895

Max Phase: Preclinical

Molecular Formula: C18H16Cl2N2O6S2

Molecular Weight: 491.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N#Cc1ccc(S(=O)(=O)N2C[C@H](S(=O)(=O)c3ccc(Cl)cc3)[C@](O)(CO)C2)c(Cl)c1

Standard InChI:  InChI=1S/C18H16Cl2N2O6S2/c19-13-2-4-14(5-3-13)29(25,26)17-9-22(10-18(17,24)11-23)30(27,28)16-6-1-12(8-21)7-15(16)20/h1-7,17,23-24H,9-11H2/t17-,18+/m0/s1

Standard InChI Key:  TUADROHZTJLERW-ZWKOTPCHSA-N

Alternative Forms

1. Parent:

   

   ALA4439190

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 491.37

Molecular Weight (Monoisotopic): 489.9827

AlogP: 1.44

#Rotatable Bonds: 5

Polar Surface Area: 135.77

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.55

CX Basic pKa: ┄

CX LogP: 1.53

CX LogD: 1.53

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.65

Np Likeness Score: -1.17

References

1. 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]

2. Pero JE, Matthews JM, Behm DJ, Brnardic EJ, Brooks C, Budzik BW, Costell MH, Donatelli CA, Eisennagel SH, Erhard K, Fischer MC, Holt DA, Jolivette LJ, Li H, Li P, McAtee JJ, McCleland BW, Pendrak I, Posobiec LM, Rivera KLK, Rivero RA, Roethke TJ, Sender MR, Shu A, Terrell LR, Vaidya K, Xu X, Lawhorn BG..  (2018)  Design and Optimization of Sulfone Pyrrolidine Sulfonamide Antagonists of Transient Receptor Potential Vanilloid-4 with in Vivo Activity in a Pulmonary Edema Model.,  61  (24): [PMID:30500190] [10.1021/acs.jmedchem.8b01344]

Source

Source(1):

• Scientific Literature