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ID: ALA186014
Max Phase: Preclinical
Molecular Formula: C24H33NO6
Molecular Weight: 431.53
Molecule Type: Small molecule
Associated Items:
Representations
Synonyms (1): (+/-)-Myxopyronin B
Synonyms from Alternative Forms(1):
Canonical SMILES: CCCC/C(C)=C/C=C(\C)C(=O)c1c(O)cc(C(C)CC/C=C/NC(=O)OC)oc1=O
Standard InChI: InChI=1S/C24H33NO6/c1-6-7-10-16(2)12-13-18(4)22(27)21-19(26)15-20(31-23(21)28)17(3)11-8-9-14-25-24(29)30-5/h9,12-15,17,26H,6-8,10-11H2,1-5H3,(H,25,29)/b14-9+,16-12+,18-13+
Standard InChI Key: SPQDIDVJAZFBRL-NIXSKCKISA-N
Associated Targets(Human)
Plasma (7708 Activities)
Associated Targets(non-human)
rpoB DNA-directed RNA polymerase beta chain (70 Activities)
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Escherichia coli (133304 Activities)
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Staphylococcus aureus (210822 Activities)
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Bacillus spizizenii (1898 Activities)
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Haemophilus influenzae (8812 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: 431.53 | Molecular Weight (Monoisotopic): 431.2308 | AlogP: 5.36 | #Rotatable Bonds: 11 |
| Polar Surface Area: 105.84 | Molecular Species: NEUTRAL | HBA: 6 | HBD: 2 |
| #RO5 Violations: 1 | HBA (Lipinski): 7 | HBD (Lipinski): 2 | #RO5 Violations (Lipinski): 1 |
| CX Acidic pKa: 6.86 | CX Basic pKa: | CX LogP: 5.24 | CX LogD: 4.59 |
| Aromatic Rings: 1 | Heavy Atoms: 31 | QED Weighted: 0.28 | Np Likeness Score: 1.27 |
References
| 1. Doundoulakis T, Xiang AX, Lira R, Agrios KA, Webber SE, Sisson W, Aust RM, Shah AM, Showalter RE, Appleman JR, Simonsen KB.. (2004) Myxopyronin B analogs as inhibitors of RNA polymerase, synthesis and biological evaluation., 14 (22): [PMID:15482944] [10.1016/j.bmcl.2004.08.045] |
| 2. Yakushiji F, Miyamoto Y, Kunoh Y, Okamoto R, Nakaminami H, Yamazaki Y, Noguchi N, Hayashi Y.. (2013) Novel hybrid-type antimicrobial agents targeting the switch region of bacterial RNA polymerase., 4 (2): [PMID:24900654] [10.1021/ml300350p] |
| 3. Molodtsov V, Fleming PR, Eyermann CJ, Ferguson AD, Foulk MA, McKinney DC, Masse CE, Buurman ET, Murakami KS.. (2015) X-ray crystal structures of Escherichia coli RNA polymerase with switch region binding inhibitors enable rational design of squaramides with an improved fraction unbound to human plasma protein., 58 (7): [PMID:25798859] [10.1021/acs.jmedchem.5b00050] |
Source
Source(1):