(R)-3-methyl-2-(4'-(3-(trifluoromethyl)benzyloxy)biphenyl-4-ylsulfonamido)butanoic acid

ID: ALA1910472

PubChem CID: 56928417

Max Phase: Preclinical

Molecular Formula: C25H24F3NO5S

Molecular Weight: 507.53

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Bioactivity Summary Target Summary Assay Summary

Names and Identifiers

Canonical SMILES: CC(C)[C@@H](NS(=O)(=O)c1ccc(-c2ccc(OCc3cccc(C(F)(F)F)c3)cc2)cc1)C(=O)O

Standard InChI: InChI=1S/C25H24F3NO5S/c1-16(2)23(24(30)31)29-35(32,33)22-12-8-19(9-13-22)18-6-10-21(11-7-18)34-15-17-4-3-5-20(14-17)25(26,27)28/h3-14,16,23,29H,15H2,1-2H3,(H,30,31)/t23-/m1/s1

Standard InChI Key: ODOUKZOJMQSYME-HSZRJFAPSA-N

Molfile:

     RDKit          2D

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   -3.3037  -22.6983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1764  -23.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4646  -23.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3943  -25.8862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6058  -22.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0347  -22.1756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1099  -26.2966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5389  -26.2925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2457  -25.8776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9611  -26.2842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9641  -27.1107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2563  -27.5267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.3875  -26.2757    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.6644  -25.0432    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.3792  -25.4500    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0
  9  4  1  0
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  2  1  2  0
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  7  8  1  0
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 32 35  1  0
M  END

Associated Targets(Human)

ADAMTS4 Tchem ADAMTS4 (425 Activities)

Discover Target: ADAMTS4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADAMTS5 Tchem ADAMTS5 (711 Activities)

Discover Target: ADAMTS5

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MMP13 Tchem Matrix metalloproteinase 13 (4133 Activities)

Discover Target: MMP13

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

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: 507.53	Molecular Weight (Monoisotopic): 507.1327	AlogP: 5.34	#Rotatable Bonds: 9
Polar Surface Area: 92.70	Molecular Species: ACID	HBA: 4	HBD: 2
#RO5 Violations: 2	HBA (Lipinski): 6	HBD (Lipinski): 2	#RO5 Violations (Lipinski): 2
CX Acidic pKa: 3.33	CX Basic pKa: ┄	CX LogP: 5.83	CX LogD: 2.41
Aromatic Rings: 3	Heavy Atoms: 35	QED Weighted: 0.41	Np Likeness Score: -1.07

References

1. Hu Y, Xing L, Thomason JR, Xiang J, Ipek M, Guler S, Li H, Sabatini J, Chockalingam P, Reifenberg E, Sheldon R, Morris EA, Georgiadis KE, Tam S.. (2011) Continued exploration of biphenylsulfonamide scaffold as a platform for aggrecanase-1 inhibition., 21 (22): [PMID:21982494] [10.1016/j.bmcl.2011.09.036]
2. Xiang, Jason S JS and 12 more authors. 2006-01-15 Synthesis and biological evaluation of biphenylsulfonamide carboxylate aggrecanase-1 inhibitors. [PMID:16275085]
3. Hopper, Darrin W DW and 17 more authors. 2009-05-01 Synthesis and biological evaluation of ((4-keto)-phenoxy)methyl biphenyl-4-sulfonamides: a class of potent aggrecanase-1 inhibitors. [PMID:19329309]
4. De Savi, Chris C and 13 more authors. 2011-03-01 The design and synthesis of novel N-hydroxyformamide inhibitors of ADAM-TS4 for the treatment of osteoarthritis. [PMID:21300546]
5. Shiozaki, Makoto M and 24 more authors. 2011-04-28 Discovery of (1S,2R,3R)-2,3-dimethyl-2-phenyl-1-sulfamidocyclopropanecarboxylates: novel and highly selective aggrecanase inhibitors. [PMID:21417219]
6. De Savi, Chris C and 11 more authors. 2011-06-01 Orally active achiral N-hydroxyformamide inhibitors of ADAM-TS4 (aggrecanase-1) and ADAM-TS5 (aggrecanase-2) for the treatment of osteoarthritis. [PMID:21536437]
7. Deng, Hongfeng H and 24 more authors. 2012-08-23 Discovery of highly potent and selective small molecule ADAMTS-5 inhibitors that inhibit human cartilage degradation via encoded library technology (ELT). [PMID:22891645]
8. Nuti, Elisa E and 14 more authors. 2013-04 Arylsulfonamide inhibitors of aggrecanases as potential therapeutic agents for osteoarthritis: synthesis and biological evaluation. [PMID:23376997]
9. Maingot, Lucie L and 12 more authors. 2013-11 Aggrecanase-2 inhibitors based on the acylthiosemicarbazide zinc-binding group. [PMID:24044937]
10. Durham, Timothy B TB and 13 more authors. 2014-12-26 Identification of potent and selective hydantoin inhibitors of aggrecanase-1 and aggrecanase-2 that are efficacious in both chemical and surgical models of osteoarthritis. [PMID:25415648]
11. Ding, Yun Y and 13 more authors. 2015-08-13 Discovery of Potent and Selective Inhibitors for ADAMTS-4 through DNA-Encoded Library Technology (ELT). [PMID:26288689]
12. Durham, Timothy B TB and 10 more authors. 2017-07-13 A Highly Selective Hydantoin Inhibitor of Aggrecanase-1 and Aggrecanase-2 with a Low Projected Human Dose. [PMID:28613895]

(R)-3-methyl-2-(4'-(3-(trifluoromethyl)benzyloxy)biphenyl-4-ylsulfonamido)butanoic acid

Names and Identifiers

Alternative Forms

Associated Targets(Human)

Associated Targets(non-human)

Molecule Features

Drug Indications

Mechanisms of Action

Biocomponents

Calculated Properties

References

Source