Streptolydigin

Modify Date: 2026-07-16 19:57:11

Streptolydigin Structure
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].

Summary: streptolydigin (Chinese name: 链霉溶菌素), molecular formula: C32H44N2O9, molecular weight: 600.700. For research-use only, not for medical or clinical usage.


 Names

This table lists Chinese names, IUPAC names and various aliases of this chemical substance.

Name streptolydigin
Synonym More Synonyms

 Streptolydigin Biological Activity

This table contains bioactivity, target information and biological‑assay experimental data of this compound.

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
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.

 Chemical & Physical Properties

This table shows physicochemical parameters including melting point, boiling point, density, solubility and optical rotation. Missing data is marked as N/A.

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

 Toxicological Information

This table summarizes toxicological test data, acute & chronic toxicity and ecological hazard parameters for this chemical.

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

 Safety Information

This table covers safety warnings, protective measures, incompatible substances and disposal guidelines for this compound.

Hazard Codes Xi

 StreptolydiginBioassay

View more

This table contains target information, in‑vitro & in‑vivo assay data for this compound.

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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 Synonyms

This table collects all English aliases, systematic names and CAS‑related synonyms of the compound.

Antibiotic D-45
portamycin
Streptolydigin

 Streptolydigin | FAQ

This section contains frequently‑asked‑questions about this compound, including basic parameters, properties, storage conditions and corresponding answers.

Q: What is the InChIKey of streptolydigin?
A: InChIKey of streptolydigin is KVTPRMVXYZKLIG-UHFFFAOYSA-N.
Q: What is the English name of streptolydigin?
A: The English name of streptolydigin is streptolydigin.
Q: What is the LogP of streptolydigin?
A: LogP of streptolydigin is 2.78890.
Q: What is the molecular formula of streptolydigin?
A: Molecular formula of streptolydigin is C32H44N2O9.
Q: What English synonyms does streptolydigin have?
A: English synonyms of streptolydigin: Antibiotic D-45, portamycin, Streptolydigin.
Q: What is the SMILES notation of streptolydigin?
A: SMILES notation of streptolydigin is 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.
Q: What are the uses of streptolydigin?
A: Main uses 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].
Q: What is the polar surface area (PSA) of streptolydigin?
A: Polar surface area (PSA) of streptolydigin is 147.16000.
Q: What is the molecular weight of streptolydigin?
A: Molecular weight of streptolydigin is 600.70000.
Q: What is the boiling point of streptolydigin?
A: Boiling point of streptolydigin is 826.6ºC at 760 mmHg.

 Streptolydiginfactory

This table lists manufacturers and suppliers of this compound, including vendor names and product supply reference information.

Shanghai Nianxing Industrial Co., Ltd
Dayang Chem (Hangzhou) Co., Ltd.
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