N-[1-((S)-(S)-4-Benzoyl-6-(S)-oxo-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl)-3-methyl-butyl]-4-dimethylamino-benzamide

ID: ALA607123

PubChem CID: 46878211

Max Phase: Preclinical

Molecular Formula: C28H34N4O4

Molecular Weight: 490.60

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[C@H](NC(=O)c1ccc(N(C)C)cc1)C(=O)N1CC[C@@H]2[C@H]1C(=O)CN2C(=O)c1ccccc1

Standard InChI: InChI=1S/C28H34N4O4/c1-18(2)16-22(29-26(34)19-10-12-21(13-11-19)30(3)4)28(36)31-15-14-23-25(31)24(33)17-32(23)27(35)20-8-6-5-7-9-20/h5-13,18,22-23,25H,14-17H2,1-4H3,(H,29,34)/t22-,23+,25-/m0/s1

Standard InChI Key: XVXGIBWJZKQFOS-ARNLJNQMSA-N

Molfile:

     RDKit          2D

 38 41  0  0  0  0  0  0  0  0999 V2000
   -3.7714   -0.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4859   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4859   -1.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7714   -2.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0569   -1.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0569   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2004   -2.3866    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3425   -0.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6280   -1.1491    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3425    0.0884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9135   -0.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1990   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9135    0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4969    0.6718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3219    0.6718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4969    1.4968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5154   -0.7366    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1990   -1.9741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2691   -1.0721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8211   -0.4590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4086    0.2554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6017    0.0839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6816   -1.7865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4886   -1.6150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5748   -0.7946    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2893   -0.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2893    0.4429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0037   -0.7946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0037   -1.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7182   -2.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4327   -1.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4327   -0.7946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7182   -0.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3460   -2.5402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2004   -3.2116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9149   -1.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4902    0.2841    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6000   -1.8153    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  2  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  3  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  2  0
 11  9  1  1
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 12 17  1  0
 12 18  2  0
 17 19  1  0
 17 22  1  0
 20 21  1  0
 21 22  1  0
 19 23  1  0
 20 19  1  0
 20 25  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
 28 33  2  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 23 34  2  0
  7 35  1  0
  7 36  1  0
 20 37  1  6
 19 38  1  6
M  END

Associated Targets(Human)

CTSK Tchem Cathepsin K (3011 Activities)

Discover Target: CTSK

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

CTSS Tchem Cathepsin S (3285 Activities)

Discover Target: CTSS

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: 490.60	Molecular Weight (Monoisotopic): 490.2580	AlogP: 2.59	#Rotatable Bonds: 7
Polar Surface Area: 90.03	Molecular Species: NEUTRAL	HBA: 5	HBD: 1
#RO5 Violations: ┄	HBA (Lipinski): 8	HBD (Lipinski): 1	#RO5 Violations (Lipinski): ┄
CX Acidic pKa: ┄	CX Basic pKa: 3.48	CX LogP: 2.87	CX LogD: 2.87
Aromatic Rings: 2	Heavy Atoms: 36	QED Weighted: 0.64	Np Likeness Score: -0.63

References

1. Wang Y, Benn A, Flinn N, Monk T, Ramjee M, Watts J, Quibell M.. (2005) cis-6-oxo-hexahydro-2-oxa-1,4-diazapentalene and cis-6-oxo-hexahydropyrrolo[3,2-c]pyrazole based scaffolds: design rationale, synthesis and cysteinyl proteinase inhibition., 15 (5): [PMID:15713380] [10.1016/j.bmcl.2005.01.022]
2. Marquis, R W RW and 18 more authors. 2001-03-01 Cyclic ketone inhibitors of the cysteine protease cathepsin K. [PMID:11262083]
3. Mendonca, Rohan V RV, Venkatraman, Shankar S and Palmer, James T JT. 2002-10-21 Novel route to the synthesis of peptides containing 2-amino-1'-hydroxymethyl ketones and their application as cathepsin K inhibitors. [PMID:12270170]
4. Robichaud, Joël J and 13 more authors. 2003-08-14 A novel class of nonpeptidic biaryl inhibitors of human cathepsin K. [PMID:12904076]
5. Tavares, Francis X FX and 12 more authors. 2004-01-29 Design of potent, selective, and orally bioavailable inhibitors of cysteine protease cathepsin k. [PMID:14736240]
6. Tavares, Francis X FX and 5 more authors. 2004-10-07 Potent and selective ketoamide-based inhibitors of cysteine protease, cathepsin K. [PMID:15456248]
7. Tavares, Francis X FX, Deaton, David N DN, Miller, Larry R LR and Wright, Lois L LL. 2004-10-07 Ketoamide-based inhibitors of cysteine protease, cathepsin K: P3 modifications. [PMID:15456249]
8. Barrett, David G DG and 8 more authors. 2005-05-02 A structural screening approach to ketoamide-based inhibitors of cathepsin K. [PMID:15837295]
9. Falgueyret, Jean-Pierre JP and 10 more authors. 2005-12-01 Lysosomotropism of basic cathepsin K inhibitors contributes to increased cellular potencies against off-target cathepsins and reduced functional selectivity. [PMID:16302795]
10. Palmer, James T JT and 6 more authors. 2006-06-01 Keto-1,3,4-oxadiazoles as cathepsin K inhibitors. [PMID:16546382]
11. Setti, Eduardo L EL and 7 more authors. 2006-08-15 Design and synthesis of tetracyclic nonpeptidic biaryl nitrile inhibitors of cathepsin K. [PMID:16750630]
12. Mott, Bryan T and 15 more authors. 2010-01-14 Identification and optimization of inhibitors of Trypanosomal cysteine proteases: cruzain, rhodesain, and TbCatB. [PMID:19908842]
13. Pan, Xulin X, Tan, Ninghua N, Zeng, Guangzhi G, Huang, Huoqiang H and Yan, He H. 2010-02 3D QSAR studies on ketoamides of human cathepsin K inhibitors based on two different alignment methods. [PMID:19962796]
14. Rankovic, Zoran Z and 30 more authors. 2010-03-01 Design and optimization of a series of novel 2-cyano-pyrimidines as cathepsin K inhibitors. [PMID:20149657]
15. Rankovic, Zoran Z and 14 more authors. 2010-03-01 Dioxo-triazines as a novel series of cathepsin K inhibitors. [PMID:20153187]
16. Dossetter, Alexander G AG and 24 more authors. 2012-07-26 (1R,2R)-N-(1-cyanocyclopropyl)-2-(6-methoxy-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carbonyl)cyclohexanecarboxamide (AZD4996): a potent and highly selective cathepsin K inhibitor for the treatment of osteoarthritis. [PMID:22742641]
17. Borišek, Jure J and 6 more authors. 2015-09-10 Development of N-(Functionalized benzoyl)-homocycloleucyl-glycinonitriles as Potent Cathepsin K Inhibitors. [PMID:26280490]
18. Galibert, Matthieu M and 10 more authors. 2018-01-20 Substrate-derived triazolo- and azapeptides as inhibitors of cathepsins K and S. [PMID:29272750]
19. Yuan, Xiao-Yu XY and 7 more authors. 2019-03-15 Design, synthesis and biological evaluation of inhibitors of cathepsin K on dedifferentiated chondrocytes. [PMID:30773420]

N-[1-((S)-(S)-4-Benzoyl-6-(S)-oxo-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl)-3-methyl-butyl]-4-dimethylamino-benzamide

Names and Identifiers

Alternative Forms

Associated Targets(Human)

Associated Targets(non-human)

Molecule Features

Drug Indications

Mechanisms of Action

Biocomponents

Calculated Properties

References

Source