ID: ALA5316208

Max Phase: Preclinical

Molecular Formula: C20H29NO

Molecular Weight: 299.46

This compound is available for customization.

Associated Items:

Bioactivity Summary Target Summary Assay Summary

Names and Identifiers

Canonical SMILES: C=CCCCCN1CC[C@]2(C)c3cc(O)ccc3C[C@@H]1[C@@H]2C

Standard InChI: InChI=1S/C20H29NO/c1-4-5-6-7-11-21-12-10-20(3)15(2)19(21)13-16-8-9-17(22)14-18(16)20/h4,8-9,14-15,19,22H,1,5-7,10-13H2,2-3H3/t15-,19+,20-/m0/s1

Standard InChI Key: MAYXDSGSHFBWRT-BEVDRBHNSA-N

Molfile:

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   -3.0750   -0.0697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4205   -0.5720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6583   -0.2563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5506    0.5617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2051    1.0639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9673    0.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1561   -0.9108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3381   -1.0185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3568    0.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8961    1.0639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3164   -0.5162    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1096    1.8608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0782    0.9562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4241    0.3017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6218    1.2504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6614    0.8737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0309   -0.9287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7453   -0.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4598   -0.9287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1743   -0.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8887   -0.9287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6032   -0.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1246   -1.8153    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  3  7  1  0
  8  7  1  0
  9  8  1  0
 10  9  1  0
  4 10  1  0
  8 11  1  0
 10 12  1  6
 10 13  1  0
 13 14  1  0
 11 14  1  0
  6 15  1  0
  9 16  1  1
 11 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
  8 23  1  1
M  END

Natural Product: No	Oral: No	Chemical Probe: No	Parenteral: No
Molecule Type:	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:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 299.46	Molecular Weight (Monoisotopic): 299.2249	AlogP: 4.27	#Rotatable Bonds: 5
Polar Surface Area: 23.47	Molecular Species: BASE	HBA: 2	HBD: 1
#RO5 Violations: ┄	HBA (Lipinski): 2	HBD (Lipinski): 1	#RO5 Violations (Lipinski): ┄
CX Acidic pKa: 9.93	CX Basic pKa: 10.78	CX LogP: 4.05	CX LogD: 1.94
Aromatic Rings: 1	Heavy Atoms: 22	QED Weighted: 0.65	Np Likeness Score: 1.56

References

1. Turnaturi R, Montenegro L, Marrazzo A, Parenti R, Pasquinucci L, Parenti C.. (2018) Benzomorphan skeleton, a versatile scaffold for different targets: A comprehensive review., 155 [PMID:29908442] [10.1016/j.ejmech.2018.06.017]
2. Hu, L Y LY and 5 more authors. 1997-12-19 Synthesis and pharmacological evaluation of N-(2,5-disubstituted phenyl)-N'-(3-substituted phenyl)-N'-methylguanidines as N-methyl-D-aspartate receptor ion-channel blockers. [PMID:9435897]
3. Husbands, S M SM and 6 more authors. 1997-12-19 Isothiocyanate derivatives of 9-[3-(cis-3,5-dimethyl-1-piperazinyl)propyl]carbazole (rimcazole): irreversible ligands for the dopamine transporter. [PMID:9435903]
4. Ganapathy, M E ME and 5 more authors. 1999-04 Molecular and ligand-binding characterization of the sigma-receptor in the Jurkat human T lymphocyte cell line. [PMID:10087012]
5. Cao, Jianjing J and 8 more authors. 2003-06-19 Dual probes for the dopamine transporter and sigma1 receptors: novel piperazinyl alkyl-bis(4'-fluorophenyl)amine analogues as potential cocaine-abuse therapeutic agents. [PMID:12801223]
6. Becker, Oren M OM and 12 more authors. 2006-06-01 An integrated in silico 3D model-driven discovery of a novel, potent, and selective amidosulfonamide 5-HT1A agonist (PRX-00023) for the treatment of anxiety and depression. [PMID:16722631]
7. Hajipour, Abdol R AR, Fontanilla, Dominique D, Chu, Uyen B UB, Arbabian, Marty M and Ruoho, Arnold E AE. 2010-06-15 Synthesis and characterization of N,N-dialkyl and N-alkyl-N-aralkyl fenpropimorph-derived compounds as high affinity ligands for sigma receptors. [PMID:20493718]
8. Mésangeau, Christophe and 7 more authors. 2011-10 Synthesis and pharmacological evaluation of indole-based sigma receptor ligands. [PMID:21899931]
9. Tu, Zhude and 6 more authors. 2012-07-15 Synthesis and evaluation of in vitro bioactivity for vesicular acetylcholine transporter inhibitors containing two carbonyl groups. [PMID:22739089]
10. Riganas, Stefanos S and 17 more authors. 2012-11-26 New adamantane phenylalkylamines with σ-receptor binding affinity and anticancer activity, associated with putative antagonism of neuropathic pain. [PMID:23094992]
11. Germain, Andrew R AR and 14 more authors. 2013-03-15 Cinnamides as selective small-molecule inhibitors of a cellular model of breast cancer stem cells. [PMID:23403082]
12. Mach, Robert H; Zeng, Chenbo and Hawkins, William G. 2013-09-26 The σ2 receptor: a novel protein for the imaging and treatment of cancer. [PMID:23734634]
13. Majo, Vattoly J and 8 more authors. 2013-09-01 Synthesis and in vivo evaluation of [(18)F]2-(4-(4-(2-(2-fluoroethoxy)phenyl)piperazin-1-yl)butyl)-4-methyl-1,2,4-triazine-3,5(2H,4H)-dione ([(18)F]FECUMI-101) as an imaging probe for 5-HT1A receptor agonist in nonhuman primates. [PMID:23816046]
14. Di Fabio, Romano R and 15 more authors. 2013-11-01 Identification, biological characterization and pharmacophoric analysis of a new potent and selective NK1 receptor antagonist clinical candidate. [PMID:24075145]
15. Peddibhotla, Satyamaheshwar S and 27 more authors. 2013-07-20 Discovery of ML314, a Brain Penetrant Non-Peptidic β-Arrestin Biased Agonist of the Neurotensin NTR1 Receptor. [PMID:24611085]
16. Sampson, Dinithia and 9 more authors. 2014-06-15 Identification of a new selective dopamine D4 receptor ligand. [PMID:24800940]
17. Bai, Suping and 8 more authors. 2014-05-22 Synthesis and structure-activity relationship studies of conformationally flexible tetrahydroisoquinolinyl triazole carboxamide and triazole substituted benzamide analogues as σ2 receptor ligands. [PMID:24821398]
18. Mukherjee, Paramita and 7 more authors. 2015-02-12 Novel 2,4-disubstituted pyrimidines as potent, selective, and cell-permeable inhibitors of neuronal nitric oxide synthase. [PMID:25489882]
19. Gadhiya, Satishkumar and 7 more authors. 2016-05-01 Tetrahydroprotoberberine alkaloids with dopamine and σ receptor affinity. [PMID:27032890]
20. Rui, Marta M and 15 more authors. 2016-11-29 Synthesis and biological evaluation of new aryl-alkyl(alkenyl)-4-benzylpiperidines, novel Sigma Receptor (SR) modulators, as potential anticancer-agents. [PMID:27614411]
21. Salvino, Joseph M JM and 5 more authors. 2017-05-15 Novel small molecule guanidine Sigma1 inhibitors for advanced prostate cancer. [PMID:28385503]
22. Bautista-Aguilera, Óscar M ÓM and 9 more authors. 2018-08-09 Contilisant, a Tetratarget Small Molecule for Alzheimer's Disease Therapy Combining Cholinesterase, Monoamine Oxidase Inhibition, and H3R Antagonism with S1R Agonism Profile. [PMID:29969030]
23. Tosh, Dilip K and 16 more authors. 2019-02-14 Design and in Vivo Characterization of A1 Adenosine Receptor Agonists in the Native Ribose and Conformationally Constrained (N)-Methanocarba Series. [PMID:30605331]
24. García, Mónica and 11 more authors. 2020-03-12 4-Aryl-1-oxa-4,9-diazaspiro[5.5]undecane Derivatives as Dual μ-Opioid Receptor Agonists and σ1 Receptor Antagonists for the Treatment of Pain. [PMID:31743642]
25. Franchini, Silvia and 8 more authors. 2020-05-14 Novel Dithiolane-Based Ligands Combining Sigma and NMDA Receptor Interactions as Potential Neuroprotective Agents. [PMID:32435421]
26. Jung, Young-Hwan and 13 more authors. 2020-09-10 Exploration of Alternative Scaffolds for P2Y14 Receptor Antagonists Containing a Biaryl Core. [PMID:32787142]

Names and Identifiers

Alternative Forms

Associated Targets(Human)

Molecule Features

Drug Indications

Mechanisms of Action

Calculated Properties

References

Source