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3-(2-Carboxyethyl)-5-hydroxy-6-methyl-2-((4-sulfophenyl)diazenyl)isonicotinic acid

ID: ALA2376129

PubChem CID: 136088913

Max Phase: Preclinical

Molecular Formula: C16H15N3O8S

Molecular Weight: 409.38

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  Cc1nc(/N=N/c2ccc(S(=O)(=O)O)cc2)c(CCC(=O)O)c(C(=O)O)c1O

Standard InChI:  InChI=1S/C16H15N3O8S/c1-8-14(22)13(16(23)24)11(6-7-12(20)21)15(17-8)19-18-9-2-4-10(5-3-9)28(25,26)27/h2-5,22H,6-7H2,1H3,(H,20,21)(H,23,24)(H,25,26,27)/b19-18+

Standard InChI Key:  NOCWIMPGLDJXJH-VHEBQXMUSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
   22.1790  -20.6957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7707  -21.4123    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   22.5955  -21.4077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7693  -17.7082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7681  -18.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4830  -18.9484    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1994  -18.5350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1965  -17.7046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4812  -17.2954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0534  -18.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0548  -17.2959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4786  -16.4704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1919  -16.0558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9095  -17.2893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6254  -17.6992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9145  -18.9464    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9158  -19.7714    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.6309  -20.1828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6276  -21.0051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3418  -21.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0567  -21.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0526  -20.1735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3379  -19.7660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3384  -17.2840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0550  -17.6938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3359  -16.4589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7747  -22.2382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7630  -16.0601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  5 10  1  0
  4 11  1  0
  9 12  1  0
 12 13  2  0
  8 14  1  0
 14 15  1  0
  7 16  1  0
 16 17  2  0
 17 18  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 24  1  0
 24 25  1  0
 24 26  2  0
 21  2  1  0
  2 27  1  0
 12 28  1  0
M  END

Alternative Forms

  1. Parent:

    ALA2376129

    ---

Associated Targets(Human)

P2RX7 Tchem P2X purinoceptor 7 (5534 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
P2RX3 Tclin P2X purinoceptor 3 (1991 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

P2rx1 P2X purinoceptor 1 (68 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

Biocomponents

Calculated Properties

Molecular Weight: 409.38Molecular Weight (Monoisotopic): 409.0580AlogP: 2.47#Rotatable Bonds: 7
Polar Surface Area: 186.81Molecular Species: ACIDHBA: 8HBD: 4
#RO5 Violations: HBA (Lipinski): 11HBD (Lipinski): 4#RO5 Violations (Lipinski): 1
CX Acidic pKa: -3.97CX Basic pKa: CX LogP: 0.88CX LogD: -5.83
Aromatic Rings: 2Heavy Atoms: 28QED Weighted: 0.39Np Likeness Score: -0.23

References

1. Jung KY, Cho JH, Lee JS, Kim HJ, Kim YC..  (2013)  Synthesis and structure-activity relationships of carboxylic acid derivatives of pyridoxal as P2X receptor antagonists.,  21  (9): [PMID:23510563] [10.1016/j.bmc.2013.01.073]
2. Alcaraz, L L and 14 more authors.  2003-11-17  Novel P2X7 receptor antagonists.  [PMID:14592504]
3. Honore, Prisca P and 16 more authors.  2006-12  A-740003 [N-(1-{[(cyanoimino)(5-quinolinylamino) methyl]amino}-2,2-dimethylpropyl)-2-(3,4-dimethoxyphenyl)acetamide], a novel and selective P2X7 receptor antagonist, dose-dependently reduces neuropathic pain in the rat.  [PMID:16982702]
4. Furber, Mark M and 25 more authors.  2007-11-29  Discovery of potent and selective adamantane-based small-molecule P2X(7) receptor antagonists/interleukin-1beta inhibitors.  [PMID:17963373]
5. Michel, A D AD, Chambers, L J LJ and Walter, D S DS.  2008-02  Negative and positive allosteric modulators of the P2X(7) receptor.  [PMID:18071294]
6. Nelson, Derek W DW and 10 more authors.  2008-05-22  Structure-activity relationship studies on N'-aryl carbohydrazide P2X7 antagonists.  [PMID:18438986]
7. Duplantier, Allen J AJ and 16 more authors.  2011-06-15  Optimization of the physicochemical and pharmacokinetic attributes in a 6-azauracil series of P2X7 receptor antagonists leading to the discovery of the clinical candidate CE-224,535.  [PMID:21565499]
8. Hernandez-Olmos, Victor V and 5 more authors.  2012-11-26  N-substituted phenoxazine and acridone derivatives: structure-activity relationships of potent P2X4 receptor antagonists.  [PMID:23075067]
9. Bhattacharya, Anindya A and 13 more authors.  2013-10  Pharmacological characterization of a novel centrally permeable P2X7 receptor antagonist: JNJ-47965567.  [PMID:23889535]
10. Park, Jin-Hee JH and 11 more authors.  2015-03-12  Discovery of novel 2,5-dioxoimidazolidine-based P2X(7) receptor antagonists as constrained analogues of KN62.  [PMID:25597334]
11. Rudolph, Dale A DA and 14 more authors.  2015-08-15  Novel methyl substituted 1-(5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)methanones are P2X7 antagonists.  [PMID:26099534]
12. Caseley, Emily A EA and 5 more authors.  2015-08-15  Docking of competitive inhibitors to the P2X7 receptor family reveals key differences responsible for changes in response between rat and human.  [PMID:26099538]
13. Lopez-Tapia, Francisco F and 23 more authors.  2015-11-12  Novel Series of Dihydropyridinone P2X7 Receptor Antagonists.  [PMID:26460788]
14. Rech, Jason C JC, Bhattacharya, Anindya A, Letavic, Michael A MA and Savall, Brad M BM.  2016-08-15  The evolution of P2X7 antagonists with a focus on CNS indications.  [PMID:27426304]
15. Gonzaga, Daniel Tadeu Gomes DTG and 16 more authors.  2017-10-20  1-Aryl-1H- and 2-aryl-2H-1,2,3-triazole derivatives blockade P2X7 receptor in vitro and inflammatory response in vivo.  [PMID:28858765]
16. Chrovian, Christa C CC and 17 more authors.  2018-01-11  A Dipolar Cycloaddition Reaction To Access 6-Methyl-4,5,6,7-tetrahydro-1H-[1,2,3]triazolo[4,5-c]pyridines Enables the Discovery Synthesis and Preclinical Profiling of a P2X7 Antagonist Clinical Candidate.  [PMID:29211470]
17. Homerin, Germain and 21 more authors.  2020-03-12  Pyroglutamide-Based P2X7 Receptor Antagonists Targeting Inflammatory Bowel Disease.  [PMID:31525963]
18. Bibic, Lucka; Herzig, Volker; King, Glenn F and Stokes, Leanne.  2019-09-27  Development of High-Throughput Fluorescent-Based Screens to Accelerate Discovery of P2X Inhibitors from Animal Venoms.  [PMID:31532206]
19. Calzaferri, Francesco and 7 more authors.  2021-02-25  Synthesis and Pharmacological Evaluation of Novel Non-nucleotide Purine Derivatives as P2X7 Antagonists for the Treatment of Neuroinflammation.  [PMID:33560845]

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