Basic information
- CAS
2825-00-5- Standard SMILES
COc1oc([C@H]2C/C(=C/C(C)=C/c3ccc([N+](=O)[O-])cc3)CO2)c(C)c(=O)c1C- InChIKey
GQKXCBCSVYJUMI-WACKOAQBSA-N- Molecular formula
- C22H23NO6
- Average molar mass
- 397.4 g/mol
- Monoisotopic mass
- 397.15253745
Overview
Aureothin is a C-nitro compound that is (3Z)-3-[(2E)-2-methyl-3-(4-nitrophenyl)prop-2-en-1-ylidene]tetrahydrofuran which is substituted by a 6-methoxy-3,5-dimethyl-4-oxo-4H-pyran-2-yl group at position 5. It is isolated from the soil bacterium, Streptomyces thioluteus and exhibits antitumor, antifungal, and insecticidal activities. It has a role as an antibacterial agent, an antiparasitic agent, an antineoplastic agent, an antifungal agent, an EC 1.6.5.3 [NADH:ubiquinone reductase (H(+)-translocating)] inhibitor and a bacterial metabolite. It is a member of 4-pyranones, a ketene acetal, a member of oxolanes, a C-nitro compound and an olefinic compound. It is functionally related to a deoxyaureothin.
Names & identifiers
- Preferred name
- Aureothin
- IUPAC
- 2-methoxy-3,5-dimethyl-6-[(2R,4Z)-4-[(E)-2-methyl-3-(4-nitrophenyl)prop-2-enylidene]oxolan-2-yl]pyran-4-one
- English name
- Aureothin
- Molecular formula
- C22H23NO6
- Molecular weight
- 397.42
Names & synonyms
AureothinCHEBI:80024DTXSID2010437562-METHOXY-3,5-DIMETHYL-6-((2R,4Z)-TETRAHYDRO-4-((2E)-2-METHYL-3-(4-NITROPHENYL)-2-PROPEN-1-YLIDENE)-2-FURANYL)-4H-PYRAN-4-ONE2-methoxy-3,5-dimethyl-6-[(2R,4Z)-tetrahydro-4-[(2E)-2-methyl-3-(4-nitrophenyl)-2-propen-1-ylidene]-2-furanyl]-4H-pyran-4-oneRefChem:916501DTXCID6015261742-methoxy-3,5-dimethyl-6-((2R,4Z)-4-((E)-2-methyl-3-(4-nitrophenyl)prop-2-enylidene)oxolan-2-yl)pyran-4-one2-methoxy-3,5-dimethyl-6-(tetrahydro-4-(2-methyl-3-(4-nitrophenyl)-2-propenylidene)-2-fur anyl)-4H-pyran-4-one2-methoxy-3,5-dimethyl-6-((2R,5Z)-5-((E)-2-methyl-3-(4-nitrophenyl)prop-2-enylidene)oxolan-2-yl)pyran-4-one2825-00-5G359FGQ2RB
Show more names
(+)-(R)-Aureothin(+)-(R)-AureothinStrain 58 substanceAureothin, TrxR1 inhibitorDistacin, Mycolutein, 74A'', JA 2814K2-[(2R)-4-[(1Z,2E)-2-Methyl-3-(4-nitrophenyl)-2-propenylidene]tetrahydrofuran-2-yl]-3,5-dimethyl-6-methoxy-4H-pyran-4-one4H-Pyran-4-one, 2-methoxy-3,5-dimethyl-6-[(2R,4Z)-tetrahydro-4-[(2E)-2-methyl-3-(4-nitrophenyl)-2-propen-1-ylidene]-2-furanyl]-
Properties
Computed structural properties
- XLogP
- 3.6
- Topological polar surface area
- 90.6 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 4
- Heavy atoms
- 29
- Formal charge
- 0
- Complexity
- 806
Experimental & physicochemical properties
LipidsPolyketides [PK] -> Polyether antibiotics [PK09]
Physicochemical properties
- Melting point
- 157 · 157-158℃
- alpha
- 18 · D18 +51° (chloroform)
- Boiling point
- 520.87 °C · 520.87°C (rough estimate)
- Density
- 1.2976 · 1.2976 (rough estimate)
- refractive index
- 1.5614 · 1.5614 (estimate)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- DMF: soluble; DMSO: soluble; Ethanol: soluble
- form
- A solid
- color
- Yellow
- FDA UNII
- 359 FGQ2RB · G359FGQ2RB
- Symbol(GHS)
- 6 · GHS06,GHS07
- Signal word
- Danger
- Hazard statements
- 300 · H300+H310-H332-H319
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
- Signal word
- Danger
- Symbol(GHS)
- GHS06,GHS07
- Hazard statements
- H300+H310-H332-H319
- Precautionary statements
- P261-P262-P264-P270-P271-P280-P301+P310-P321-P330-P302+P352-P304+P340-P305+P351+P338-P312-P361+P364-P337+P313-P405-P501
Chemistry & industry
Applications
UsesAureothin, an unusual pyranone metabolite, has broad biological actions including antitumour, antimicrobial and insecticidal activities. Aureothin acts by inhibiting oxidoreductase. More recently, aureothin has been shown to be a potent inhibitor of Helicobacter pylori.
UsesAureothin, an unusual pyranone metabolite, has broad biological actions including antitumor, antimicrobial and insecticidal activities. Aureothin acts by inhibiting oxidoreductase. More recently, aureothin has been shown to be a potent inhibitor of Helicobacter pylori.
Suppliers20 total
陕西缔都医药有限责任公司029-81124775 17791530730 · [email protected]
上海赛可锐生物科技有限公司021-58000709 13120558703 · [email protected]
Aladdin Scientific[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]
上海一研生物科技有限公司021-69985186 13611928337 · [email protected]
安耐吉化学&3A（安徽泽升科技股份有限公司）400-0056266 · [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
0 records
No reaction records under the current filter.
Compound notes
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