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ID: ALA1830118
Max Phase: Preclinical
Molecular Formula: C11H14F2NO5P
Molecular Weight: 309.20
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: CN(O)C(=O)CCC(c1ccc(F)c(F)c1)P(=O)(O)O
Standard InChI: InChI=1S/C11H14F2NO5P/c1-14(16)11(15)5-4-10(20(17,18)19)7-2-3-8(12)9(13)6-7/h2-3,6,10,16H,4-5H2,1H3,(H2,17,18,19)
Standard InChI Key: IZWIBRNXHRUNKD-UHFFFAOYSA-N
Associated Targets(Human)
MRC5 9203 Activities
HeLa 62764 Activities
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Associated Targets(non-human)
Plasmodium falciparum 966862 Activities
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Plasmodium berghei 192651 Activities
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1-deoxy-D-xylulose 5-phosphate reductoisomerase 191 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: 309.20 | Molecular Weight (Monoisotopic): 309.0578 | AlogP: 1.81 | #Rotatable Bonds: 5 |
| Polar Surface Area: 98.07 | Molecular Species: ACID | HBA: 3 | HBD: 3 |
| #RO5 Violations: 0 | HBA (Lipinski): 6 | HBD (Lipinski): 3 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 1.68 | CX Basic pKa: | CX LogP: 0.23 | CX LogD: -2.17 |
| Aromatic Rings: 1 | Heavy Atoms: 20 | QED Weighted: 0.44 | Np Likeness Score: -0.76 |
References
| 1. Behrendt CT, Kunfermann A, Illarionova V, Matheeussen A, Pein MK, Gräwert T, Kaiser J, Bacher A, Eisenreich W, Illarionov B, Fischer M, Maes L, Groll M, Kurz T.. (2011) Reverse fosmidomycin derivatives against the antimalarial drug target IspC (Dxr)., 54 (19): [PMID:21866890] [10.1021/jm200694q] |
| 2. Brücher K, Illarionov B, Held J, Tschan S, Kunfermann A, Pein MK, Bacher A, Gräwert T, Maes L, Mordmüller B, Fischer M, Kurz T.. (2012) α-Substituted β-oxa isosteres of fosmidomycin: synthesis and biological evaluation., 55 (14): [PMID:22731758] [10.1021/jm300652f] |
| 3. Kunfermann A, Lienau C, Illarionov B, Held J, Gräwert T, Behrendt CT, Werner P, Hähn S, Eisenreich W, Riederer U, Mordmüller B, Bacher A, Fischer M, Groll M, Kurz T.. (2013) IspC as target for antiinfective drug discovery: synthesis, enantiomeric separation, and structural biology of fosmidomycin thia isosters., 56 (20): [PMID:24032981] [10.1021/jm4012559] |
| 4. Brücher K, Gräwert T, Konzuch S, Held J, Lienau C, Behrendt C, Illarionov B, Maes L, Bacher A, Wittlin S, Mordmüller B, Fischer M, Kurz T.. (2015) Prodrugs of reverse fosmidomycin analogues., 58 (4): [PMID:25633870] [10.1021/jm5019719] |
Source
Source(1):