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N-(2-(2-methyl-1H-indol-1-yl)ethyl)-4-(1H-tetrazol-5-yl)benzamide

ID: ALA3286660

PubChem CID: 90680555

Max Phase: Preclinical

Molecular Formula: C19H18N6O

Molecular Weight: 346.39

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  Cc1cc2ccccc2n1CCNC(=O)c1ccc(-c2nnn[nH]2)cc1

Standard InChI:  InChI=1S/C19H18N6O/c1-13-12-16-4-2-3-5-17(16)25(13)11-10-20-19(26)15-8-6-14(7-9-15)18-21-23-24-22-18/h2-9,12H,10-11H2,1H3,(H,20,26)(H,21,22,23,24)

Standard InChI Key:  NSBLUZNHTPDUIL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   17.9793   -9.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6938   -8.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4082   -9.2000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1227   -8.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8372   -9.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1227   -7.9625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2648   -8.7875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5110   -9.1210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9589   -8.5080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8348  -10.0262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5485  -10.4386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2640  -10.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2612   -9.1967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5471   -8.7880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3384   -9.9277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3743   -7.7944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1820   -7.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7337   -7.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4788   -6.5720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6673   -6.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1115   -7.0119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9789  -10.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0709  -11.2577    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.8781  -11.4282    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.2897  -10.7132    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.7367  -10.1009    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  1  7  1  0
  7 17  1  0
  9  8  2  0
  8  7  1  0
  9 16  1  0
  5 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  5  1  0
  8 15  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 12 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 22  1  0
M  END

Associated Targets(Human)

PTGER2 Tclin Prostanoid EP2 receptor (1730 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PTGER4 Tclin Prostanoid EP4 receptor (2181 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PTGDR Tclin Prostanoid DP receptor (1356 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PTGIR Tclin Prostanoid IP receptor (1280 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Liver microsome (8277 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

C6 (2371 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Liver (8163 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mus musculus (284745 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: 346.39Molecular Weight (Monoisotopic): 346.1542AlogP: 2.56#Rotatable Bonds: 5
Polar Surface Area: 88.49Molecular Species: ACIDHBA: 5HBD: 2
#RO5 Violations: HBA (Lipinski): 7HBD (Lipinski): 2#RO5 Violations (Lipinski):
CX Acidic pKa: 4.25CX Basic pKa: CX LogP: 2.65CX LogD: 1.05
Aromatic Rings: 4Heavy Atoms: 26QED Weighted: 0.58Np Likeness Score: -2.09

References

1. Ganesh T, Jiang J, Dingledine R..  (2014)  Development of second generation EP2 antagonists with high selectivity.,  82  [PMID:24937185] [10.1016/j.ejmech.2014.05.076]
2. Das B, Baidya ATK, Mathew AT, Yadav AK, Kumar R..  (2022)  Structural modification aimed for improving solubility of lead compounds in early phase drug discovery.,  56  [PMID:35033884] [10.1016/j.bmc.2022.116614]
3. Sluter MN, Hou R, Li L, Yasmen N, Yu Y, Liu J, Jiang J..  (2021)  EP2 Antagonists (2011-2021): A Decade's Journey from Discovery to Therapeutics.,  64  (16.0): [PMID:34352171] [10.1021/acs.jmedchem.1c00816]
4. Regan, J W JW and 9 more authors.  1994-08  Cloning of a novel human prostaglandin receptor with characteristics of the pharmacologically defined EP2 subtype.  [PMID:8078484]
5. Bastien, L L, Sawyer, N N, Grygorczyk, R R, Metters, K M KM and Adam, M M.  1994-04-22  Cloning, functional expression, and characterization of the human prostaglandin E2 receptor EP2 subtype.  [PMID:8163486]
6. Stillman, B A BA, Breyer, M D MD and Breyer, R M RM.  1999-09  Importance of the extracellular domain for prostaglandin EP(2) receptor function.  [PMID:10462542]
7. Yoshida, Keiji K and 17 more authors.  2002-04-02  Stimulation of bone formation and prevention of bone loss by prostaglandin E EP4 receptor activation.  [PMID:11917107]
8. Sugimoto, Yukihiko Y and 7 more authors.  2004-03-19  A cluster of aromatic amino acids in the i2 loop plays a key role for Gs coupling in prostaglandin EP2 and EP3 receptors.  [PMID:14699136]
9. Jiang, Jianxiong J and 9 more authors.  2012-02-21  Small molecule antagonist reveals seizure-induced mediation of neuronal injury by prostaglandin E2 receptor subtype EP2.  [PMID:22323596]
10. Cappelli, Andrea A and 16 more authors.  2013-05  Synthesis and structure-activity relationship studies in serotonin 5-HT(1A) receptor agonists based on fused pyrrolidone scaffolds.  [PMID:23466604]
11. Ganesh, Thota T, Jiang, Jianxiong J, Shashidharamurthy, Rangaiah R and Dingledine, Ray R.  2013-07-11  Discovery and characterization of carbamothioylacrylamides as EP2 selective antagonists.  [PMID:23914286]
12. and Ganesh, Thota.  2014-06-12  Prostanoid receptor EP2 as a therapeutic target.  [PMID:24279689]
13. Ganesh, Thota; Jiang, Jianxiong and Dingledine, Ray.  2014-07-23  Development of second generation EP2 antagonists with high selectivity.  [PMID:24937185]
14. Waszkielewicz, A M AM and 9 more authors.  2016-04-15  Design, physico-chemical properties and biological evaluation of some new N-[(phenoxy)alkyl]- and N-{2-[2-(phenoxy)ethoxy]ethyl}aminoalkanols as anticonvulsant agents.  [PMID:26988801]
15. Iwamura, Ryo R and 6 more authors.  2018-08-09  Identification of a Selective, Non-Prostanoid EP2 Receptor Agonist for the Treatment of Glaucoma: Omidenepag and its Prodrug Omidenepag Isopropyl.  [PMID:29995405]
16. Coleman, R A RA and 6 more authors.  2019-03  The affinity, intrinsic activity and selectivity of a structurally novel EP2 receptor agonist at human prostanoid receptors.  [PMID:30341781]

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