Introduction：Basic information about CAS 7229-50-7|Streptolydigin, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Streptolydigin |
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| CAS Number | 7229-50-7 | Molecular Weight | 600.70000 |
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| Density | 1.3 g/cm3 | Boiling Point | 826.6ºC at 760 mmHg |
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| Molecular Formula | C32H44N2O9 | Melting Point | / |
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| MSDS | / | Flash Point | 453.7ºC |
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Names
| Name | streptolydigin |
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| Synonym | More Synonyms |
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Streptolydigin BiologicalActivity
| Description | Streptolydigin (Portamycin) is a 3-acetyltetramic acid antibiotic and a potent bacterial RNA polymerase inhibitor with a Ki of 18 μM and a Kd of 15 μM. Streptolydigin inhibits RNA synthesis by binding to RNA polymerase and does not inhibit eukaryotic RNA polymerases[1][2][3]. Streptolydigin possess potent antibacterial activity, particularly against anaerobes and some Gram-positive aerobes[4]. |
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| Related Catalog | Research Areas >>InfectionSignaling Pathways >>Cell Cycle/DNA Damage >>DNA/RNA SynthesisSignaling Pathways >>Anti-infection >>Bacterial |
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| Target | Ki: 18 μM (Bacterial RNA polymerase)[3] Kd: 15 μM (Bacterial RNA polymerase)[3] |
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| In Vitro | The antibiotic Streptolydigin (Stl) is a derivative of 3-acetyltetramic acid. Binding of Streptolydigin to RNA polymerase strictly depends on a noncatalytic magnesium ion which is likely chelated by the aspartate of the bridge helix of the active center[1]. Streptolydigin inhibits T. thermophilus RNA polymerase with a Ki of 1.8 μM[3]. Streptolydigin (Stl) inhibits initiation, elongation, and pyrophosphorolysis by bacterial RNA polymerase. Streptolydigin interacts with three structural elements within RNAP: the Stl pocket, the bridge helix, and the trigger-loop region. The Streptolydigin streptolol moiety interacts with the Streptolydigin pocket and bridge helix, and the Streptolydigin tetramic-acid moiety interacts with the trigger-loop region[3]. |
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| References | [1]. Zorov S, et al. Antibiotic streptolydigin requires noncatalytic Mg2+ for binding to RNA polymerase. Antimicrob Agents Chemother. 2014;58(3):1420-4. [2]. Temiakov D, et al. Structural basis of transcription inhibition by antibiotic streptolydigin. Mol Cell. 2005 Sep 2;19(5):655-66. [3]. Tuske S, et al. Inhibition of bacterial RNA polymerase by streptolydigin: stabilization of a straight-bridge-helix active-center conformation. Cell. 2005 Aug 26;122(4):541-52. [4]. Rosen T, et al. Aromatic dienoyl tetramic acids. Novel antibacterial agents with activity against anaerobes and staphylococci. J Med Chem. 1989 May;32(5):1062-9. |
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Chemical & Physical Properties
| Density | 1.3 g/cm3 |
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| Boiling Point | 826.6ºC at 760 mmHg |
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| Molecular Formula | C32H44N2O9 |
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| Molecular Weight | 600.70000 |
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| Flash Point | 453.7ºC |
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| Exact Mass | 600.30500 |
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| PSA | 147.16000 |
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| LogP | 2.78890 |
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| Index of Refraction | 1.598 |
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| InChIKey | KVTPRMVXYZKLIG-UHFFFAOYSA-N |
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| SMILES | CNC(=O)C(C)C1C(=O)C(=C(O)C=CC(C)=CC(C)C2OC3(C)OC(C=CC34CO4)C2C)C(=O)N1C1CCC(O)C(C)O1 |
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Toxicological Information
CHEMICAL IDENTIFICATION - RTECS NUMBER :
- WK4250000
- CHEMICAL NAME :
- Streptolydigin
- CAS REGISTRY NUMBER :
- 7229-50-7
- LAST UPDATED :
- 199403
- DATA ITEMS CITED :
- 3
- MOLECULAR FORMULA :
- C32-H44-N2-O9
- MOLECULAR WEIGHT :
- 600.78
HEALTH HAZARD DATAACUTE TOXICITY DATA - TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 533 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LDLo - Lowest published lethal dose
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Bird - chicken
- DOSE/DURATION :
- 10 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
MUTATION DATA - TYPE OF TEST :
- Mutation test systems - not otherwise specified
- TEST SYSTEM :
- Bacteria - Bacillus subtilis
- DOSE/DURATION :
- 288 mg/L
- REFERENCE :
- FOMIAZ Folia Microbiologica (Prague). (Academia, Vodickova 40, 112 29 Prague 1, Czechoslavakia) V.4- 1959- Volume(issue)/page/year: 22,329,1977
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Safety Information
Synonyms
| Antibiotic D-45 |
| portamycin |
| Streptolydigin |
| 2-Pyrrolidineacetamide, 4-[6-(1,4-dimethylspiro[2,9-dioxabicyclo[3.3.1]non-6-ene-8,2'-oxiran-3-yl)-1-hydroxy-4-methyl-2,4-heptadienylidene]-N,.α.-dimethyl-3,5-dioxo-1-(tetrahydro-5-hydroxy-6-methyl-2H-pyran-2-yl)- |
