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5-Methoxysterigmatocystin

CAT: 0804-HY-126841Size: 1 EachDry Ice: NoHazardous: No
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Description
5-Methoxysterigmatocystin is a mycotoxin with cytotoxic and genotoxic properties. 5-Methoxysterigmatocystin exhibits cytotoxicity against cancer cells A549 and HepG2 (IC50 of 5.5 and 0.7 μM), and induces DNA damage. 5-Methoxysterigmatocystin is a photosensitizer, which utilizes the visible to generate singlet oxygen (1O2) [1][2].
CAS Number
22897-08-1
UNSPSC
12352005
Target
Photosensitizer
Type
Natural Products
Related Pathways
Apoptosis
Applications
Cancer-programmed cell death
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/5-methoxysterigmatocystin.html
Smiles
O=C1C2=C(OC3=C1C(O)=CC=C3OC)C4=C(O[C@]5([H])[C@@]4([H])C=CO5)C=C2OC
Molecular Formula
C19H14O7
Molecular Weight
354.31
References & Citations
[1]Dabelić S, et al., Sterigmatocystin, 5-Methoxysterigmatocistin, and Their Combinations Are Cytotoxic and Genotoxic to A549 and Hepg2 Cells and Provoke Phosphorylation of Chk2, but Not Fancd2 Checkpoint Proteins. Toxins (Basel) . 2021 Jun 30;13 (7) :464. |[2]Espinoza C, et al., Photosensitizer ability of 5-methoxysterigmatocystin isolated from aquatic fungus Acremonium persicinum[J]. Electronic Journal of Biotechnology, 2023, 62: 21-26.
Shipping Conditions
Room temperature
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

5-Methoxysterigmatocystin

5-methoxysterigmatocystin is a member of sterigmatocystins.

CAS Number22897-08-1
PubChem CID5351257
IUPAC Name(3S,7R)-15-hydroxy-11,18-dimethoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,4,9,11,14,16,18-heptaen-13-one
Molecular FormulaC19H14O7
Molecular Weight354.3
XLogP3.3
Topological Polar Surface Area83.5
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count7
Rotatable Bond Count2
Heavy Atom Count26
Formal Charge0
Complexity607
SMILES
COC1=C2C(=C(C=C1)O)C(=O)C3=C(C=C4C(=C3O2)[C@@H]5C=CO[C@@H]5O4)OC
InChI
InChI=1S/C19H14O7/c1-22-10-4-3-9(20)14-16(21)15-11(23-2)7-12-13(18(15)26-17(10)14)8-5-6-24-19(8)25-12/h3-8,19-20H,1-2H3/t8-,19+/m0/s1
InChIKey
VVRUNWFPOWIBDY-WPCRTTGESA-N
Chemical Structure
2D Structure
2D structure of 5-Methoxysterigmatocystin
CAS: 22897-08-1
CID: 5351257
Formula: C19H14O7
MW: 354.3
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight354.3
XLogP33.3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count7
Rotatable Bond Count2
Exact Mass354.07395278
Monoisotopic Mass354.07395278
Topological Polar Surface Area83.5 Ų
Heavy Atom Count26
Formal Charge0
Complexity607
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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