ID: ALA4093990
PubChem CID: 137652577
Max Phase: Preclinical
Molecular Formula: C18H16FNO4
Molecular Weight: 329.33
Molecule Type: Small molecule
Associated Items:
Canonical SMILES: O=C(/C=C/C#Cc1ccc(O)cc1F)NC1=C(C(=O)O)CCCC1
Standard InChI: InChI=1S/C18H16FNO4/c19-15-11-13(21)10-9-12(15)5-1-4-8-17(22)20-16-7-3-2-6-14(16)18(23)24/h4,8-11,21H,2-3,6-7H2,(H,20,22)(H,23,24)/b8-4+
Standard InChI Key: RSIXRSXTZVORGJ-XBXARRHUSA-N
Molfile:
RDKit 2D
24 25 0 0 0 0 0 0 0 0999 V2000
31.7865 -3.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
31.7854 -4.7486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
32.4934 -5.1576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
33.2031 -4.7481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
33.2002 -3.9255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
32.4916 -3.5202 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
33.9042 -3.5130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
34.6103 -3.1018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
35.3165 -2.6905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
36.0257 -3.0964 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
36.7319 -2.6852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
37.4411 -3.0911 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
36.7288 -1.8680 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
38.1473 -2.6799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
38.8533 -3.0905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
39.5574 -2.6828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
39.5585 -1.8652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
38.8494 -1.4571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
38.1392 -1.8666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
38.8525 -3.9077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
38.1444 -4.3157 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
39.5598 -4.3170 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
31.0773 -5.1567 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
33.9114 -5.1556 0.0000 F 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
2 23 1 0
4 24 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: 329.33 | Molecular Weight (Monoisotopic): 329.1063 | AlogP: 2.47 | #Rotatable Bonds: 3 |
| Polar Surface Area: 86.63 | Molecular Species: ACID | HBA: 3 | HBD: 3 |
| #RO5 Violations: ┄ | HBA (Lipinski): 5 | HBD (Lipinski): 3 | #RO5 Violations (Lipinski): ┄ |
| CX Acidic pKa: 2.92 | CX Basic pKa: ┄ | CX LogP: 2.69 | CX LogD: -0.81 |
| Aromatic Rings: 1 | Heavy Atoms: 24 | QED Weighted: 0.59 | Np Likeness Score: 0.18 |
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| 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] |
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| 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] |
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