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ID: ALA563938
Max Phase: Preclinical
Molecular Formula: C12H18N6O3S
Molecular Weight: 326.38
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: NCCSC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O
Standard InChI: InChI=1S/C12H18N6O3S/c13-1-2-22-3-6-8(19)9(20)12(21-6)18-5-17-7-10(14)15-4-16-11(7)18/h4-6,8-9,12,19-20H,1-3,13H2,(H2,14,15,16)/t6-,8-,9-,12-/m1/s1
Standard InChI Key: APAPOJUCRZTCHD-WOUKDFQISA-N
Associated Targets(Human)
DNMT1 Tclin DNA (cytosine-5)-methyltransferase 1 (978 Activities)
DNMT3B Tchem DNA (cytosine-5)-methyltransferase 3B (150 Activities)
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DOT1L Tchem Histone-lysine N-methyltransferase, H3 lysine-79 specific (648 Activities)
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PNMT Tchem Phenylethanolamine N-methyltransferase (540 Activities)
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Associated Targets(non-human)
Trypanosoma brucei brucei (13300 Activities)
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Adra2a Alpha-2a adrenergic receptor (204 Activities)
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Molecule Features
| 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 |
Drug Indications
| MESH ID | MESH Heading | EFO IDs | EFO Terms | Max Phase for Indication | References |
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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: 326.38 | Molecular Weight (Monoisotopic): 326.1161 | AlogP: -1.28 | #Rotatable Bonds: 5 |
| Polar Surface Area: 145.33 | Molecular Species: BASE | HBA: 10 | HBD: 4 |
| #RO5 Violations: 0 | HBA (Lipinski): 9 | HBD (Lipinski): 6 | #RO5 Violations (Lipinski): 1 |
| CX Acidic pKa: 12.47 | CX Basic pKa: 9.71 | CX LogP: -1.67 | CX LogD: -3.90 |
| Aromatic Rings: 2 | Heavy Atoms: 22 | QED Weighted: 0.49 | Np Likeness Score: 0.69 |
References
| 1. Isakovic L, Saavedra OM, Llewellyn DB, Claridge S, Zhan L, Bernstein N, Vaisburg A, Elowe N, Petschner AJ, Rahil J, Beaulieu N, Gauthier F, MacLeod AR, Delorme D, Besterman JM, Wahhab A.. (2009) Constrained (l-)-S-adenosyl-l-homocysteine (SAH) analogues as DNA methyltransferase inhibitors., 19 (10): [PMID:19364644] [10.1016/j.bmcl.2009.03.132] |
| 2. Sufrin JR, Spiess AJ, Marasco CJ, Rattendi D, Bacchi CJ.. (2008) Novel trypanocidal analogs of 5'-(methylthio)-adenosine., 52 (1): [PMID:17954686] [10.1128/aac.00480-07] |
| 3. Anglin JL, Deng L, Yao Y, Cai G, Liu Z, Jiang H, Cheng G, Chen P, Dong S, Song Y.. (2012) Synthesis and structure-activity relationship investigation of adenosine-containing inhibitors of histone methyltransferase DOT1L., 55 (18): [PMID:22924785] [10.1021/jm300917h] |
| 4. Lu J,Bart AG,Wu Q,Criscione KR,McLeish MJ,Scott EE,Grunewald GL. (2020) Structure-Based Drug Design of Bisubstrate Inhibitors of Phenylethanolamine N-Methyltransferase Possessing Low Nanomolar Affinity at Both Substrate Binding Domains., 63 (22): [PMID:33147410] [10.1021/acs.jmedchem.0c01475] |
Source
Source(1):