ID: ALA4093294
PubChem CID: 137653026
Max Phase: Preclinical
Molecular Formula: C18H16ClNO3
Molecular Weight: 329.78
Molecule Type: Small molecule
Associated Items:
Canonical SMILES: O=C(/C=C/C#Cc1ccccc1Cl)NC1=C(C(=O)O)CCCC1
Standard InChI: InChI=1S/C18H16ClNO3/c19-15-10-4-1-7-13(15)8-2-6-12-17(21)20-16-11-5-3-9-14(16)18(22)23/h1,4,6-7,10,12H,3,5,9,11H2,(H,20,21)(H,22,23)/b12-6+
Standard InChI Key: GTBYYRMHGRYJPX-WUXMJOGZSA-N
Molfile:
RDKit 2D
23 24 0 0 0 0 0 0 0 0999 V2000
2.5368 -8.8776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.5357 -9.6972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.2437 -10.1061 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.9534 -9.6967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.9506 -8.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.2419 -8.4688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.6545 -8.4616 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.3607 -8.0503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.0668 -7.6391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.7761 -8.0450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
7.4822 -7.6337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
8.1915 -8.0397 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
7.4791 -6.8165 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
8.8976 -7.6284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
9.6036 -8.0391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
10.3077 -7.6313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
10.3088 -6.8138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
9.5997 -6.4057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
8.8895 -6.8151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
9.6028 -8.8563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
8.8948 -9.2642 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
10.3102 -9.2655 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4.6617 -10.1042 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0
1 2 2 0
2 3 1 0
3 4 2 0
4 5 1 0
5 6 2 0
6 1 1 0
7 8 3 0
5 7 1 0
8 9 1 0
9 10 2 0
10 11 1 0
11 12 1 0
11 13 2 0
12 14 1 0
14 15 2 0
14 19 1 0
15 16 1 0
16 17 1 0
17 18 1 0
18 19 1 0
15 20 1 0
20 21 2 0
20 22 1 0
4 23 1 0
M END| 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 |
| MESH ID | MESH Heading | EFO IDs | EFO Terms | Max Phase for Indication | References |
|---|
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
|---|
| Molecular Weight: 329.78 | Molecular Weight (Monoisotopic): 329.0819 | AlogP: 3.28 | #Rotatable Bonds: 3 |
| Polar Surface Area: 66.40 | Molecular Species: ACID | HBA: 2 | HBD: 2 |
| #RO5 Violations: ┄ | HBA (Lipinski): 4 | HBD (Lipinski): 2 | #RO5 Violations (Lipinski): ┄ |
| CX Acidic pKa: 2.94 | CX Basic pKa: ┄ | CX LogP: 3.45 | CX LogD: -0.03 |
| Aromatic Rings: 1 | Heavy Atoms: 23 | QED Weighted: 0.66 | Np Likeness Score: 0.02 |
| 1. Bobileva O, Ikaunieks M, Duburs G, Mandrika I, Petrovska R, Klovins J, Loza E.. (2017) Synthesis and evaluation of (E)-2-(5-phenylpent-2-en-4-ynamido)cyclohex-1-ene-1-carboxylate derivatives as HCA2 receptor agonists., 25 (16): [PMID:28668361] [10.1016/j.bmc.2017.06.028] |
| 2. Wise, Alan A and 16 more authors. 2003-03-14 Molecular identification of high and low affinity receptors for nicotinic acid. [PMID:12522134] |
| 3. Taggart, Andrew K P AK and 17 more authors. 2005-07-22 (D)-beta-Hydroxybutyrate inhibits adipocyte lipolysis via the nicotinic acid receptor PUMA-G. [PMID:15929991] |
| 4. Jung, Jae-Kyu JK and 11 more authors. 2007-04-05 Analogues of acifran: agonists of the high and low affinity niacin receptors, GPR109a and GPR109b. [PMID:17358052] |
| 5. Semple, Graeme G and 21 more authors. 2008-08-28 3-(1H-tetrazol-5-yl)-1,4,5,6-tetrahydro-cyclopentapyrazole (MK-0354): a partial agonist of the nicotinic acid receptor, G-protein coupled receptor 109a, with antilipolytic but no vasodilatory activity in mice. [PMID:18665582] |
| 6. Tang, Hua H, Lu, Jenny Ying-Lin JY, Zheng, Xiaomu X, Yang, Yuhua Y and Reagan, Jeff D JD. 2008-10-31 The psoriasis drug monomethylfumarate is a potent nicotinic acid receptor agonist. [PMID:18722346] |
| 7. Deng, Qiaolin Q and 13 more authors. 2008-09-15 Molecular modeling aided design of nicotinic acid receptor GPR109A agonists. [PMID:18760600] |
| 8. Boatman, P Douglas PD, Richman, Jeremy G JG and Semple, Graeme G. 2008-12-25 Nicotinic acid receptor agonists. [PMID:18983141] |
| 9. Ren, Ning N and 9 more authors. 2009-05 Phenolic acids suppress adipocyte lipolysis via activation of the nicotinic acid receptor GPR109A (HM74a/PUMA-G). [PMID:19136666] |
| 10. Shen, Hong C HC and 23 more authors. 2010-03-25 Discovery of a biaryl cyclohexene carboxylic acid (MK-6892): a potent and selective high affinity niacin receptor full agonist with reduced flushing profiles in animals as a preclinical candidate. [PMID:20184326] |
| 11. van Veldhoven, J P D JP and 8 more authors. 2011-05-01 Structure-activity relationships of trans-substituted-propenoic acid derivatives on the nicotinic acid receptor HCA2 (GPR109A). [PMID:21167710] |
| 12. Boatman, P Douglas PD and 26 more authors. 2012-04-26 (1aR,5aR)1a,3,5,5a-Tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic acid (MK-1903): a potent GPR109a agonist that lowers free fatty acids in humans. [PMID:22435740] |
| 13. Qin, Jun J and 22 more authors. 2011-02-10 Discovery of a potent nicotinic Acid receptor agonist for the treatment of dyslipidemia. [PMID:24900295] |
| 14. Palani, Anandan A and 29 more authors. 2012-01-12 Discovery of SCH 900271, a Potent Nicotinic Acid Receptor Agonist for the Treatment of Dyslipidemia. [PMID:24900372] |
| 15. Sprecher, Dennis D and 6 more authors. 2015-06-05 Discovery and characterization of GSK256073, a non-flushing hydroxy-carboxylic acid receptor 2 (HCA2) agonist. [PMID:25773497] |
| 16. Singh, L Ravithej LR and 8 more authors. 2018-05-25 Discovery of coumarin-dihydroquinazolinone analogs as niacin receptor 1 agonist with in-vivo anti-obesity efficacy. [PMID:29709786] |
Source(1):