1-Cyclopropyl-N-hydroxy-4-(4-(4-(trifluoromethoxy)phenoxy)-phenylsulfonyl)piperidine-4-carboxamide

ID: ALA1801430

Chembl Id: CHEMBL1801430

Cas Number: 308824-37-5

PubChem CID: 9871883

Max Phase: Preclinical

Molecular Formula: C22H23F3N2O6S

Molecular Weight: 500.50

Molecule Type: Small molecule

Names and Identifiers

Synonyms: SC-77964 | SC-77964|308824-37-5|CHEMBL1801430|1-cyclopropyl-N-hydroxy-4-[4-[4-(trifluoromethoxy)phenoxy]phenyl]sulfonylpiperidine-4-carboxamide|CID 9871883|SCHEMBL5919245|NBRBWZJMBITNBC-UHFFFAOYSA-N|BDBM50348651

Canonical SMILES:  O=C(NO)C1(S(=O)(=O)c2ccc(Oc3ccc(OC(F)(F)F)cc3)cc2)CCN(C2CC2)CC1

Standard InChI:  InChI=1S/C22H23F3N2O6S/c23-22(24,25)33-18-5-3-16(4-6-18)32-17-7-9-19(10-8-17)34(30,31)21(20(28)26-29)11-13-27(14-12-21)15-1-2-15/h3-10,15,29H,1-2,11-14H2,(H,26,28)

Standard InChI Key:  NBRBWZJMBITNBC-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA1801430

   CID 9871883

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: 500.50

Molecular Weight (Monoisotopic): 500.1229

AlogP: 3.65

#Rotatable Bonds: 7

Polar Surface Area: 105.17

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.66

CX Basic pKa: 6.28

CX LogP: 3.59

CX LogD: 3.54

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.44

Np Likeness Score: -0.76

References

1. Becker DP, Barta TE, Bedell LJ, Boehm TL, Bond BR, Carroll J, Carron CP, Decrescenzo GA, Easton AM, Freskos JN, Funckes-Shippy CL, Heron M, Hockerman S, Howard CP, Kiefer JR, Li MH, Mathis KJ, McDonald JJ, Mehta PP, Munie GE, Sunyer T, Swearingen CA, Villamil CI, Welsch D, Williams JM, Yu Y, Yao J..  (2010)  Orally active MMP-1 sparing α-tetrahydropyranyl and α-piperidinyl sulfone matrix metalloproteinase (MMP) inhibitors with efficacy in cancer, arthritis, and cardiovascular disease.,  53  (18): [PMID:20726512] [10.1021/jm100669j]

2. Freskos JN, Asmelash B, Gaston KR, Karwa A, Marzan TA, Nickols MA, Rogers TE, Schoenstein T, Sympson CJ, Vu B..  (2013)  Design and synthesis of MMP inhibitors with appended fluorescent tags for imaging and visualization of matrix metalloproteinase enzymes.,  23  (20): [PMID:23999043] [10.1016/j.bmcl.2013.08.050]

Source

Source(1):

• Scientific Literature