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Aureothricin

CAT: 0804-HY-N6737-02Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N6737-02Size:5 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Aureothricin is a dithiolopyrrolone (DTP) antibiotic first isolated from Streptomyces and exhibits relatively broad-spectrum antibiotic activity. Aureothricin can inhibit adhesion of human umbilical vein endothelial cells (HUVECs) to vitronectin[1].
CAS Number
574-95-8
UNSPSC
12352005
Hazard Statement
H301+H311+H331
Target
Antibiotic; Bacterial
Type
Natural Products
Related Pathways
Anti-infection
Applications
COVID-19-immunoregulation
Field of Research
Infection
Assay Protocol
https://www.medchemexpress.com/aureothricin.html
Purity
99.72
Solubility
DMSO : 1 mg/mL (ultrasonic; warming)
Smiles
CN1C2=CSSC2=C(C1=O)NC(CC)=O
Molecular Formula
C9H10N2O2S2
Molecular Weight
242.32
Precautions
P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P361+P364-P403+P233-P405-P501
References & Citations
[1]Li B, et al. Dithiolopyrrolones: biosynthesis, synthesis, and activity of a unique class of disulfide-containing antibiotics. Nat Prod Rep. 2014 Jul;31 (7) :905-23.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

Aureothricin

Aureothricin is a dithiolopyrrolone antibiotic that is 4,5-dihydro[1,2]dithiolo[4,3-b]pyrrole in which the hydrogens at positions 4,5 and 6 have been replaced by methyl, oxo and propanoylamino groups, respectively. It is a moderate antimicrobial by-product of the thiolutin fermentation in various Streptomyces species. It has a role as an antibacterial agent, an EC 2.7.7.6 (RNA polymerase) inhibitor, an angiogenesis inhibitor and a bacterial metabolite. It is a secondary carboxamide and a dithiolopyrrolone antibiotic.

CAS Number574-95-8
PubChem CID68460
IUPAC NameN-(4-methyl-5-oxodithiolo[4,3-b]pyrrol-6-yl)propanamide
Molecular FormulaC9H10N2O2S2
Molecular Weight242.3
XLogP-0.1
Topological Polar Surface Area100
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count2
Heavy Atom Count15
Formal Charge0
Complexity401
SMILES
CCC(=O)NC1=C2C(=CSS2)N(C1=O)C
InChI
InChI=1S/C9H10N2O2S2/c1-3-6(12)10-7-8-5(4-14-15-8)11(2)9(7)13/h4H,3H2,1-2H3,(H,10,12)
InChIKey
UGZYFXMSMFMTSM-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Aureothricin
CAS: 574-95-8
CID: 68460
Formula: C9H10N2O2S2
MW: 242.3
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight242.3
XLogP3-0.1
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count2
Exact Mass242.01836991
Monoisotopic Mass242.01836991
Topological Polar Surface Area100 Ų
Heavy Atom Count15
Formal Charge0
Complexity401
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
573548Aureothricin
MBS651276-01Aureothricin (Propionylpyrrothione, Farcinin)
441921-01Aureothricin discontinued, see 207077
207077-01Aureothricin (Propionylpyrrothione, Farcinicin, N- (4-Methyl-5-oxo-4,5-dihydro-[1,2]dithiolo[4,3-b]pyrrol-6-yl) propionamide)

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