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ID: ALA5078078
Max Phase: Preclinical
Molecular Formula: C24H20F4N2O3
Molecular Weight: 460.43
Molecule Type: Unknown
Associated Items:
Representations
Canonical SMILES: CC(C)(O)c1ccc(N2Cc3c(ccnc3-c3ccc(F)cc3OCC(F)(F)F)C2=O)cc1
Standard InChI: InChI=1S/C24H20F4N2O3/c1-23(2,32)14-3-6-16(7-4-14)30-12-19-17(22(30)31)9-10-29-21(19)18-8-5-15(25)11-20(18)33-13-24(26,27)28/h3-11,32H,12-13H2,1-2H3
Standard InChI Key: OAZAPIKYVGRNCO-UHFFFAOYSA-N
Associated Targets(Human)
UGCG Tclin Ceramide glucosyltransferase (308 Activities)
KCNH2 Tclin HERG (29587 Activities)
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CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)
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CYP2C8 Tchem Cytochrome P450 2C8 (1492 Activities)
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CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)
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CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)
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CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)
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CACNA1C Tclin Voltage-gated L-type calcium channel alpha-1C subunit (766 Activities)
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SCN5A Tclin Sodium channel protein type V alpha subunit (3462 Activities)
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SLC6A4 Tclin Serotonin transporter (12625 Activities)
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ADORA2A Tclin Adenosine A2a receptor (16305 Activities)
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ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)
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ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)
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ADRB1 Tclin Beta-1 adrenergic receptor (6630 Activities)
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ADRB2 Tclin Beta-2 adrenergic receptor (11824 Activities)
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AVPR1A Tclin Vasopressin V1a receptor (5412 Activities)
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CCKAR Tclin Cholecystokinin A receptor (4460 Activities)
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CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)
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CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)
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CHRM3 Tclin Muscarinic acetylcholine receptor M3 (7750 Activities)
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CNR1 Tclin Cannabinoid CB1 receptor (20913 Activities)
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CNR2 Tchem Cannabinoid CB2 receptor (16942 Activities)
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DRD1 Tclin Dopamine D1 receptor (9720 Activities)
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DRD2 Tclin Dopamine D2 receptor (23596 Activities)
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EDNRA Tclin Endothelin receptor ET-A (5008 Activities)
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HRH1 Tclin Histamine H1 receptor (7573 Activities)
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HRH2 Tclin Histamine H2 receptor (5428 Activities)
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HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)
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HTR1B Tclin Serotonin 1b (5-HT1b) receptor (2801 Activities)
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HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)
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HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)
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OPRD1 Tclin Delta opioid receptor (15096 Activities)
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OPRK1 Tclin Kappa opioid receptor (16155 Activities)
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OPRM1 Tclin Mu opioid receptor (19785 Activities)
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HTR3A Tclin Serotonin 3a (5-HT3a) receptor (3366 Activities)
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KCNQ1 Tclin Voltage-gated potassium channel, IKs; KCNQ1(Kv7.1)/KCNE1(MinK) (185 Activities)
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CHRNB2 Tclin Neuronal acetylcholine receptor; alpha4/beta2 (3972 Activities)
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GRIN1 Tclin Glutamate NMDA receptor; GRIN1/GRIN2B (726 Activities)
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INSR Tclin Insulin receptor (5558 Activities)
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LCK Tclin Tyrosine-protein kinase LCK (9212 Activities)
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ROCK1 Tclin Rho-associated protein kinase 1 (4723 Activities)
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KDR Tclin Vascular endothelial growth factor receptor 2 (20924 Activities)
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AR Tclin Androgen Receptor (11781 Activities)
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NR3C1 Tclin Glucocorticoid receptor (14987 Activities)
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ACHE Tclin Acetylcholinesterase (18204 Activities)
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PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)
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PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)
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PDE3A Tclin Phosphodiesterase 3A (3309 Activities)
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PDE4D Tclin Phosphodiesterase 4D (3546 Activities)
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SLC6A3 Tclin Dopamine transporter (10535 Activities)
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SLC6A2 Tclin Norepinephrine transporter (10102 Activities)
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Associated Targets(non-human)
Ugcg Ceramide glucosyltransferase (150 Activities)
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Maoa Monoamine oxidase A (2058 Activities)
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Molecule Features
| Natural Product: No | Oral: No | Chemical Probe: No | Parenteral: No |
| Molecule Type: Unknown | Topical: No | First In Class: No | Black Box: No |
| Chirality: No | Availability: No | Prodrug: No |
Drug Indications
| MESH ID | MESH Heading | EFO IDs | EFO Terms | Max Phase for Indication | References |
|---|
Mechanisms of Action
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
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Properties
| Molecular Weight: 460.43 | Molecular Weight (Monoisotopic): 460.1410 | AlogP: 5.22 | #Rotatable Bonds: 5 |
| Polar Surface Area: 62.66 | Molecular Species: NEUTRAL | HBA: 4 | HBD: 1 |
| #RO5 Violations: 1 | HBA (Lipinski): 5 | HBD (Lipinski): 1 | #RO5 Violations (Lipinski): 1 |
| CX Acidic pKa: 11.80 | CX Basic pKa: 0.78 | CX LogP: 4.37 | CX LogD: 4.37 |
| Aromatic Rings: 3 | Heavy Atoms: 33 | QED Weighted: 0.53 | Np Likeness Score: -0.77 |
References
| 1. Tanaka Y, Seto M, Kakegawa K, Takami K, Kikuchi F, Yamamoto T, Nakamura M, Daini M, Murakami M, Ohashi T, Kasahara T, Wang J, Ikeda Z, Wada Y, Puenner F, Fujii T, Inazuka M, Sato S, Suzaki T, Oak JH, Takai Y, Kohara H, Kimoto K, Oki H, Mikami S, Sasaki M, Tanaka Y.. (2022) Discovery of Brain-Penetrant Glucosylceramide Synthase Inhibitors with a Novel Pharmacophore., 65 (5.0): [PMID:35188773] [10.1021/acs.jmedchem.1c02078] |
| 2. Wang J, Reynolds M, Ibáñez I, Sasaki Y, Tanaka Y, Kikuchi F, Ohashi T, Sato S, Miyabayashi M, Fujii T, Tanaka Y.. (2022) Photoredox-based late-stage functionalization in SAR study for in vivo potent glucosylceramide synthase inhibitor., 77 [PMID:36341811] [10.1016/j.bmcl.2022.129039] |
| 3. SGC Frankfurt. (2023) Data for DCP probe TP-060, [10.6019/CHEMBL5303768] |
Source
Source(2):