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Aureothin

CAT: 0498-bs-75732C-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0498-bs-75732C-01Size:1 mg
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CAS Number
2825-00-5
Conjugation
Unconjugated
Purity
>96% (HPLC)
Buffer
Solid
Solubility
Soluble in 100% ethanol, methanol, DMSO, dimethylformamide, dicholormethane or acetone.
Smiles
COC1=C(C)C(=O)C(C)=C(O1)C1C\C(CO1)=C\C(\C)=C\C1=CC=C(C=C1)[N+]([O-])=O
Molecular Formula
C22H23NO6
Molecular Weight
397.4
Storage Conditions
Stable for 1 year after receipt when stored at -20°C. After reconstitution protect from light at -20°C.
Appearance
Yellow solid.

Chemical Information

Aureothin

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.

CAS Number2825-00-5
PubChem CID6569946
IUPAC Name2-methoxy-3,5-dimethyl-6-[(2R,4Z)-4-[(E)-2-methyl-3-(4-nitrophenyl)prop-2-enylidene]oxolan-2-yl]pyran-4-one
Molecular FormulaC22H23NO6
Molecular Weight397.4
XLogP3.6
Topological Polar Surface Area90.6
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count6
Rotatable Bond Count4
Heavy Atom Count29
Formal Charge0
Complexity806
SMILES
CC1=C(OC(=C(C1=O)C)OC)[C@H]2C/C(=C/C(=C/C3=CC=C(C=C3)[N+](=O)[O-])/C)/CO2
InChI
InChI=1S/C22H23NO6/c1-13(9-16-5-7-18(8-6-16)23(25)26)10-17-11-19(28-12-17)21-14(2)20(24)15(3)22(27-4)29-21/h5-10,19H,11-12H2,1-4H3/b13-9+,17-10-/t19-/m1/s1
InChIKey
GQKXCBCSVYJUMI-WACKOAQBSA-N
Chemical Structure
2D Structure
2D structure of Aureothin
CAS: 2825-00-5
CID: 6569946
Formula: C22H23NO6
MW: 397.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight397.4
XLogP33.6
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count6
Rotatable Bond Count4
Exact Mass397.15253745
Monoisotopic Mass397.15253745
Topological Polar Surface Area90.6 Ų
Heavy Atom Count29
Formal Charge0
Complexity806
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count2
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
A134-0.5MGAureothin
207076-01Aureothin (Mycolutein, Distacin, JA 2814K, Antibiotic 74A, BRN 0058476)
MBS651528-01Aureothin (Distacin, Distacyne, Mycolutein, Antibiotic 74A'', Antibiotic JA 2814K)

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