N-({(2R)-1-[4-(3-Buten-1-ylamino)-6-({[2-(2-thienyl)-1,3-thiazol-4-yl]methyl}amino)-1,3,5-triazin-2-yl]-2-pyrrolidinyl}-methyl)-4-(trifluoromethyl)benzenesulfonamide

ID: ALA2164120

PubChem CID: 66559934

Max Phase: Preclinical

Molecular Formula: C27H29F3N8O2S3

Molecular Weight: 650.78

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CCCNc1nc(NCc2csc(-c3cccs3)n2)nc(N2CCC[C@@H]2CNS(=O)(=O)c2ccc(C(F)(F)F)cc2)n1

Standard InChI:  InChI=1S/C27H29F3N8O2S3/c1-2-3-12-31-24-35-25(32-15-19-17-42-23(34-19)22-7-5-14-41-22)37-26(36-24)38-13-4-6-20(38)16-33-43(39,40)21-10-8-18(9-11-21)27(28,29)30/h2,5,7-11,14,17,20,33H,1,3-4,6,12-13,15-16H2,(H2,31,32,35,36,37)/t20-/m1/s1

Standard InChI Key:  ZDDSIQGYVHATQX-HXUWFJFHSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA2164120

   CID 66559934

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: 650.78

Molecular Weight (Monoisotopic): 650.1528

AlogP: 5.62

#Rotatable Bonds: 13

Polar Surface Area: 125.03

Molecular Species: BASE

HBA: 11

HBD: 3

#RO5 Violations: 3

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.14

CX Basic pKa: 8.76

CX LogP: 5.98

CX LogD: 4.91

Aromatic Rings: 4

Heavy Atoms: 43

QED Weighted: 0.12

Np Likeness Score: -1.74

References

1. Deng H, O'Keefe H, Davie CP, Lind KE, Acharya RA, Franklin GJ, Larkin J, Matico R, Neeb M, Thompson MM, Lohr T, Gross JW, Centrella PA, O'Donovan GK, Bedard KL, van Vloten K, Mataruse S, Skinner SR, Belyanskaya SL, Carpenter TY, Shearer TW, Clark MA, Cuozzo JW, Arico-Muendel CC, Morgan BA..  (2012)  Discovery of highly potent and selective small molecule ADAMTS-5 inhibitors that inhibit human cartilage degradation via encoded library technology (ELT).,  55  (16): [PMID:22891645] [10.1021/jm300449x]

Source

Source(1):

• Scientific Literature