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1-(4'-((2,4-dioxo-3-phenylimidazolidin-1-yl)methyl)-[1,1'-biphenyl]-4-yl)cyclopropane-1-carboxylic acid

ID: ALA3741261

PubChem CID: 127038372

Max Phase: Preclinical

Molecular Formula: C26H22N2O4

Molecular Weight: 426.47

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  O=C1CN(Cc2ccc(-c3ccc(C4(C(=O)O)CC4)cc3)cc2)C(=O)N1c1ccccc1

Standard InChI:  InChI=1S/C26H22N2O4/c29-23-17-27(25(32)28(23)22-4-2-1-3-5-22)16-18-6-8-19(9-7-18)20-10-12-21(13-11-20)26(14-15-26)24(30)31/h1-13H,14-17H2,(H,30,31)

Standard InChI Key:  WPFDIDGDNBZAAH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
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   -6.5020    3.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2558    4.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3786   -3.8595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8056   -3.8679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3372   -5.2929    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8372   -5.2877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1285   -6.2561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9460   -3.4943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5987    1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6012    3.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9015    3.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1993    2.9963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1969    1.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8967    0.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2151   -6.5101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7096   -6.4704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4930   -7.7496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7769   -9.0676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2774   -9.1065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4940   -7.8274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7994    2.9880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7953    1.7880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8408    3.5841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  1  3  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  4  1  0
  8  9  2  0
  6 10  2  0
  5 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 15 18  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
  7 24  1  0
 21  2  1  0
  2 30  1  0
 30 31  1  0
 30 32  2  0
M  END

Alternative Forms

  1. Parent:

    ALA3741261

    ---

Associated Targets(Human)

ENPP2 Tchem Autotaxin (2645 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Biocomponents

Calculated Properties

Molecular Weight: 426.47Molecular Weight (Monoisotopic): 426.1580AlogP: 4.44#Rotatable Bonds: 6
Polar Surface Area: 77.92Molecular Species: ACIDHBA: 3HBD: 1
#RO5 Violations: HBA (Lipinski): 6HBD (Lipinski): 1#RO5 Violations (Lipinski):
CX Acidic pKa: 4.51CX Basic pKa: CX LogP: 4.30CX LogD: 1.50
Aromatic Rings: 3Heavy Atoms: 32QED Weighted: 0.59Np Likeness Score: -0.61

References

1. Castagna D, Duffy EL, Semaan D, Young LC, Pritchard JM, Macdonald SJF, Budd DC, Jamieson C, Watson AJB.  (2015)  Identification of a novel class of autotaxin inhibitors through cross-screening,  (6): [10.1039/C5MD00081E]
2. North, E Jeffrey EJ and 5 more authors.  2010-04-22  Pharmacophore development and application toward the identification of novel, small-molecule autotaxin inhibitors.  [PMID:20349977]
3. Albers, Harald M H G HM and 5 more authors.  2010-07-08  Discovery and optimization of boronic acid based inhibitors of autotaxin.  [PMID:20536182]
4. Gupte, Renuka and 14 more authors.  2010-12-15  Synthesis and pharmacological evaluation of the stereoisomers of 3-carba cyclic-phosphatidic acid.  [PMID:21051230]
5. Castagna, Diana D, Budd, David C DC, Macdonald, Simon J F SJ, Jamieson, Craig C and Watson, Allan J B AJ.  2016-06-23  Development of Autotaxin Inhibitors: An Overview of the Patent and Primary Literature.  [PMID:26745766]
6. Ragle, Lauren E LE and 7 more authors.  2016-10-01  Discovery and synthetic optimization of a novel scaffold for hydrophobic tunnel-targeted autotaxin inhibition.  [PMID:27544588]
7. Jones, Spencer B SB and 19 more authors.  2016-09-08  Novel Autotaxin Inhibitors for the Treatment of Osteoarthritis Pain: Lead Optimization via Structure-Based Drug Design.  [PMID:27660691]
8. Shah, Pritom P and 23 more authors.  2016-11-15  Discovery of potent inhibitors of the lysophospholipase autotaxin.  [PMID:27780639]
9. Banerjee, Souvik S and 7 more authors.  2017-02-23  Highly Potent Non-Carboxylic Acid Autotaxin Inhibitors Reduce Melanoma Metastasis and Chemotherapeutic Resistance of Breast Cancer Stem Cells.  [PMID:28112925]
10. Desroy, Nicolas N and 29 more authors.  2017-05-11  Discovery of 2-[[2-Ethyl-6-[4-[2-(3-hydroxyazetidin-1-yl)-2-oxoethyl]piperazin-1-yl]-8-methylimidazo[1,2-a]pyridin-3-yl]methylamino]-4-(4-fluorophenyl)thiazole-5-carbonitrile (GLPG1690), a First-in-Class Autotaxin Inhibitor Undergoing Clinical Evaluation for the Treatment of Idiopathic Pulmonary Fibrosis.  [PMID:28414242]
11. Lanier, Marion M and 7 more authors.  2017-06-22  Repurposing Suzuki Coupling Reagents as a Directed Fragment Library Targeting Serine Hydrolases and Related Enzymes.  [PMID:28564542]
12. Balupuri, Anand A and 7 more authors.  2017-09-01  Design, synthesis, docking and biological evaluation of 4-phenyl-thiazole derivatives as autotaxin (ATX) inhibitors.  [PMID:28743508]
13. Baader, Manuel M and 6 more authors.  2018-02  Characterization of the properties of a selective, orally bioavailable autotaxin inhibitor in preclinical models of advanced stages of liver fibrosis.  [PMID:29197066]
14. Kuttruff, Christian A CA and 8 more authors.  2017-12-14  Discovery of BI-2545: A Novel Autotaxin Inhibitor That Significantly Reduces LPA Levels in Vivo.  [PMID:29259743]
15. Balupuri, Anand A and 15 more authors.  2018-03-25  Discovery and optimization of ATX inhibitors via modeling, synthesis and biological evaluation.  [PMID:29477073]
16. Nikolaou, Aikaterini A and 6 more authors.  2018-04-26  Hydroxamic Acids Constitute a Novel Class of Autotaxin Inhibitors that Exhibit in Vivo Efficacy in a Pulmonary Fibrosis Model.  [PMID:29620892]
17. Kawaguchi, Mitsuyasu and 11 more authors.  2020-03-26  Identification of Potent In Vivo Autotaxin Inhibitors that Bind to Both Hydrophobic Pockets and Channels in the Catalytic Domain.  [PMID:32134652]
18. Lei, Hongrui and 9 more authors.  2020-07-09  Discovery of Novel Indole-Based Allosteric Highly Potent ATX Inhibitors with Great In Vivo Efficacy in a Mouse Lung Fibrosis Model.  [PMID:32479084]
19. Iwaki, Yuzo and 20 more authors.  2020-06-11  ONO-8430506: A Novel Autotaxin Inhibitor That Enhances the Antitumor Effect of Paclitaxel in a Breast Cancer Model.  [PMID:32551021]
20. Cuozzo, John W and 13 more authors.  2020-07-23  Novel Autotaxin Inhibitor for the Treatment of Idiopathic Pulmonary Fibrosis: A Clinical Candidate Discovered Using DNA-Encoded Chemistry.  [PMID:32584034]
21. and Abdel-Magid, Ahmed F.  2020-11-12  Therapeutic Potential of Autotaxin Inhibitors in Treatment of Interstitial Lung Diseases.  [PMID:33214812]

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