Basic information
- CAS
574-95-8- Standard SMILES
CCC(=O)Nc1c2sscc-2n(C)c1=O- InChIKey
UGZYFXMSMFMTSM-UHFFFAOYSA-N- Molecular formula
- C9H10N2O2S2
- Average molar mass
- 242.3 g/mol
- Monoisotopic mass
- 242.01836991
Overview
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antibiotic that is 4,5-dihydro[1,2]dithiolo[4,3-b]pyrrole in which the hydrogens at positions 4,5 and 6 have been replaced by methyl, oxo and propanoylamino groups, respectively.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.
Names & identifiers
- Preferred name
- Aureothricin
- IUPAC
- N-(4-methyl-5-oxodithiolo[4,3-b]pyrrol-6-yl)propanamide
- English name
- aureothricin
- Molecular formula
- C9H10N2O2S2
- Molecular weight
- 242.32
Names & synonyms
Aureothricin574-95-8propionopyrrothinepropanoyl-pyrrothineN-(4-methyl-5-oxodithiolo[4,3-b]pyrrol-6-yl)propanamideCHEBI:1564520KX00L19Q2DTXSID60205993N-(4-methyl-5-oxo-4,5-dihydro[1,2]dithiolo[4,3-b]pyrrol-6-yl)propanamide4-methyl-6-propionamido-1,2-dithiolo[4,3-b]pyrrol-5(4H)-one4-METHYL-6-PROPIONAMIDO-1,2-DITHIOLO(4,3-B)PYRROL-5(4H)-ONEN-(4-methyl-5-oxodithiolo(4,3-b)pyrrol-6-yl)propanamide
Show more names
Propionylpyrrothione, Farcinin5-Methyl-3-propionamidopyrrolin-4-one-[4,3-d]-1,2-dithioleN-(4,5-Dihydro-4-methyl-5-oxo-1,2-dithiolo[4,3-b]pyrrol-6-yl)propanamidePropanamide, N-(4,5-dihydro-4-methyl-5-oxo-1,2-dithiolo[4,3-b]pyrrol-6-yl)-Propionopyrrothine, 5-Methyl-3-propionamidopyrrolin-4-one[4,3-d]-1,2-dithiole
N-(4-methyl-5-oxo-4,5-dihydro(1,2)dithiolo(4,3-b)pyrrol-6-yl)propanamideRefChem:115636DTXCID90128484N-(4,5-dihydro-4-methyl-5-oxo-1,2-dithiolo[4,3-b]pyrrol-6-yl)propionamideN-(4-Methyl-5-oxo-4,5-dihydro-dithiolopyrrol-6-yl)propionamideN-(4-Methyl-5-oxo-4,5-dihydro-[1,2]dithiolo[4,3-b]pyrrol-6-yl)propionamideN-{4-methyl-5-oxo-4H,5H-[1,2]dithiolo[4,3-b]pyrrol-6- yl}propanamideUNII-0KX00L19Q2
Properties
Computed structural properties
- XLogP
- -0.1
- Topological polar surface area
- 100 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 401
Experimental & physicochemical properties
DrugsPharmaceuticals -> Antibiotics
Physicochemical properties
- Melting point
- 260 · 260-270℃ (decomposition)
- Boiling point
- 479.1 · 479.1±45.0 °C(Predicted)
- Density
- 1.48 · 1.48±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- DMF: soluble; DMSO: soluble; Ethanol: partially soluble; Methanol: partially soluble
- pka
- 10.54 · 10.54±0.20(Predicted)
- form
- Yellow to orange solid.
- color
- Yellow
- FDA UNII
- 0 KX00L19Q2 · 0KX00L19Q2
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 301 · H301+H311+H331
- Precautionary statements
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- hs_code
- 29419090
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- Hazard statements
- H301+H311+H331
- Precautionary statements
- P280
Chemistry & industry
Applications
UsesAureothricin is an antibiotic first described by Umezawa and co-workers in Japan in 1949. Resurgent interest in this class of microbial metabolites was stimulated by the discovery of their selective antitumour activity. Aureothricin is a more hydrophobic analogue of thiolutin, but has received only limited attention. Members of this class, notably thiolutin, are potent inhibitors of bacterial and yeast RNA polymerases, inhibitors of mannan and glucan formation in fungi, and inhibitors of tumour-cell induced angiogenesis in vivo.
Suppliers25 total
上海赛可锐生物科技有限公司021-58000709 13120558703 · [email protected]
安耐吉化学&3A（安徽泽升科技有限公司）021-58432009 400-005-6266 · [email protected]
孟成科技（上海）有限公司400-820-6829 · [email protected]
MedBio脉铂医药021-69568360 18916172912 · [email protected]
上海维亦特生物科技有限公司15317051735 · [email protected]
四川省维克奇生物科技有限公司028-81700200 18116577057 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
BOC Sciences16314854226; +8616314854226 · [email protected]
浙江珲达生物科技有限公司0571-89903022 18679456698 · [email protected]
上海一飞生物科技有限公司021-65675885 18964387627 · [email protected]
Related reactions
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Compound notes
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