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ID: ALA4217043
Max Phase: Preclinical
Molecular Formula: C17H23N9O2
Molecular Weight: 385.43
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: COc1ncc(-c2nc(C(=O)NC(=N)N)c(N)nc2N2CCCCCC2)cn1
Standard InChI: InChI=1S/C17H23N9O2/c1-28-17-21-8-10(9-22-17)11-14(26-6-4-2-3-5-7-26)24-13(18)12(23-11)15(27)25-16(19)20/h8-9H,2-7H2,1H3,(H2,18,24)(H4,19,20,25,27)
Standard InChI Key: WREBDSFOSWCPIS-UHFFFAOYSA-N
Associated Targets(Human)
Urokinase-type plasminogen activator 2016 Activities
HepG2 196354 Activities
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MDA-MB-231 73002 Activities
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Transmembrane protease serine 11D 59 Activities
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Lysosomal Pro-X carboxypeptidase 567 Activities
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Plasminogen 2339 Activities
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Complement C1s 188 Activities
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Trypsin 2137 Activities
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Plasma kallikrein 2047 Activities
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Vitamin K-dependent protein C 491 Activities
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Coagulation factor X 9693 Activities
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Coagulation factor XI 1733 Activities
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Thrombin 11687 Activities
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Tissue-type plasminogen activator 1057 Activities
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HEK293 82097 Activities
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HT-1080 3966 Activities
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ASPC1 1310 Activities
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HERG 29587 Activities
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Sodium channel protein type V alpha subunit 3462 Activities
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Associated Targets(non-human)
Urokinase-type plasminogen activator 56 Activities
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Rattus norvegicus 775804 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
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Properties
| Molecular Weight: 385.43 | Molecular Weight (Monoisotopic): 385.1975 | AlogP: 0.53 | #Rotatable Bonds: 4 |
| Polar Surface Area: 169.02 | Molecular Species: NEUTRAL | HBA: 9 | HBD: 4 |
| #RO5 Violations: 0 | HBA (Lipinski): 11 | HBD (Lipinski): 6 | #RO5 Violations (Lipinski): 2 |
| CX Acidic pKa: 11.80 | CX Basic pKa: 6.39 | CX LogP: 1.54 | CX LogD: 1.50 |
| Aromatic Rings: 2 | Heavy Atoms: 28 | QED Weighted: 0.43 | Np Likeness Score: -0.63 |
References
| 1. Buckley BJ, Aboelela A, Minaei E, Jiang LX, Xu Z, Ali U, Fildes K, Cheung CY, Cook SM, Johnson DC, Bachovchin DA, Cook GM, Apte M, Huang M, Ranson M, Kelso MJ.. (2018) 6-Substituted Hexamethylene Amiloride (HMA) Derivatives as Potent and Selective Inhibitors of the Human Urokinase Plasminogen Activator for Use in Cancer., 61 (18): [PMID:30130401] [10.1021/acs.jmedchem.8b00838] |
| 2. Buckley BJ,Aboelela A,Majed H,Bujaroski RS,White KL,Powell AK,Wang W,Katneni K,Saunders J,Shackleford DM,Charman SA,Cook GM,Kelso MJ,Ranson M. (2021) Systematic evaluation of structure-property relationships and pharmacokinetics in 6-(hetero)aryl-substituted matched pair analogs of amiloride and 5-(N,N-hexamethylene)amiloride., 37 [PMID:33799173] [10.1016/j.bmc.2021.116116] |
Source
Source(1):