Streptolydigin

Modify Date: 2025-09-16 18:24:55

Streptolydigin structure	Common Name	Streptolydigin
	CAS Number	7229-50-7	Molecular Weight	600.70000
	Density	1.3 g/cm3	Boiling Point	826.6ºC at 760 mmHg
	Molecular Formula	C₃₂H₄₄N₂O₉	Melting Point	N/A
	MSDS	N/A	Flash Point	453.7ºC

Use of Streptolydigin

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].

Name	streptolydigin
Synonym	More Synonyms

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].
Related Catalog	Research Areas >> Infection Signaling Pathways >> Cell Cycle/DNA Damage >> DNA/RNA Synthesis Signaling Pathways >> Anti-infection >> Bacterial
Target	Ki: 18 μM (Bacterial RNA polymerase)[3] Kd: 15 μM (Bacterial RNA polymerase)[3]
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].
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.

Density	1.3 g/cm3
Boiling Point	826.6ºC at 760 mmHg
Molecular Formula	C₃₂H₄₄N₂O₉
Molecular Weight	600.70000
Flash Point	453.7ºC
Exact Mass	600.30500
PSA	147.16000
LogP	2.78890
Index of Refraction	1.598
InChIKey	KVTPRMVXYZKLIG-UHFFFAOYSA-N
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

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 DATA

ACUTE 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

Hazard Codes	Xi

Name: Antimicrobial activity against transconjugant Streptomyces albus carrying pEM4T-Abeta...
Source: ChEMBL
Target: Streptomyces albus
External Id: CHEMBL1265482

Name: Antimicrobial activity against transconjugant Streptomyces albus carrying pEM4T-Abeta...
Source: ChEMBL
Target: Streptomyces albus
External Id: CHEMBL1265481

Name: Experimentally measured binding affinity data (Ki) for protein-ligand complexes deriv...
Source: Shanghai Institute of Organic Chemistry
Target: N/A
External Id: PDBbind-Ki for protein-ligand complexes

Name: Antimicrobial activity against transconjugant Streptomyces albus carrying pEM4T-Abeta...
Source: ChEMBL
Target: Streptomyces albus
External Id: CHEMBL1265480

Name: Antimicrobial activity against transconjugant Streptomyces albus carrying pEM4T-Lbeta...
Source: ChEMBL
Target: Streptomyces albus
External Id: CHEMBL1265479

Name: Antimicrobial activity against transconjugant Streptomyces albus carrying pEM4T-Lbeta...
Source: ChEMBL
Target: Streptomyces albus
External Id: CHEMBL1265478

Name: Inhibition of Staphylococcus epidermidis RNA polymerase mediated transcription
Source: ChEMBL
Target: N/A
External Id: CHEMBL986885

Name: Ratio of MBC for Staphylococcus epidermidis to MIC for Staphylococcus epidermidis
Source: ChEMBL
Target: Staphylococcus epidermidis
External Id: CHEMBL986884

Name: Antimicrobial activity against Staphylococcus epidermidis
Source: ChEMBL
Target: Staphylococcus epidermidis
External Id: CHEMBL986883

Name: Antimicrobial activity against transconjugant Streptomyces albus carrying pEM4T-Lbeta...
Source: ChEMBL
Target: Streptomyces albus
External Id: CHEMBL1265469

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Antibiotic D-45

portamycin

Streptolydigin

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Streptolydigin

Use of Streptolydigin

Names

Streptolydigin Biological Activity

Chemical & Physical Properties

Toxicological Information

CHEMICAL IDENTIFICATION

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

Safety Information

StreptolydiginBioassay

Synonyms

The content on this webpage is sourced from various professional data sources. If you have any questions or concerns regarding the content, please feel free to contact service1@chemsrc.com.