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Aflatoxin G2
Also known as: 7241-98-7, Dihydroaflatoxin g1, 2ms0d8wa29, (7ar-cis)-3,4,7a,9,10,10a-hexahydro-5-methoxy-1h,12h-furo[3',2':4,5]furo[2,3-h]pyrano[3,4-c][1]benzopyran-1,12-dione, Aflatoxin g2 0.5 microg/ml in acetonitrile, 1h,12h-furo[3',2':4,5]furo[2,3-h]pyrano[3,4-c][1]benzopyran-1,12-dione, 3,4,7a,9,10,10a-hexahydro-5-methoxy-, (7ar,10as)-
Molecular Formula
C17H14O7
Molecular Weight
330.29  g/mol
InChI Key
WPCVRWVBBXIRMA-WNWIJWBNSA-N
FDA UNII
2MS0D8WA29

aflatoxin g2 is a natural product found in Aspergillus nomiae, Aspergillus flavus, and Aspergillus parasiticus with data available.
1 2D Structure

Aflatoxin G2

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(3S,7R)-11-methoxy-6,8,16,20-tetraoxapentacyclo[10.8.0.02,9.03,7.013,18]icosa-1,9,11,13(18)-tetraene-17,19-dione
2.1.2 InChI
InChI=1S/C17H14O7/c1-20-9-6-10-12(8-3-5-22-17(8)23-10)14-11(9)7-2-4-21-15(18)13(7)16(19)24-14/h6,8,17H,2-5H2,1H3/t8-,17+/m0/s1
2.1.3 InChI Key
WPCVRWVBBXIRMA-WNWIJWBNSA-N
2.1.4 Canonical SMILES
COC1=C2C3=C(C(=O)OCC3)C(=O)OC2=C4C5CCOC5OC4=C1
2.1.5 Isomeric SMILES
COC1=C2C3=C(C(=O)OCC3)C(=O)OC2=C4[C@@H]5CCO[C@@H]5OC4=C1
2.2 Other Identifiers
2.2.1 UNII
2MS0D8WA29
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. 7241-98-7

2. Dihydroaflatoxin G1

3. 2ms0d8wa29

4. (7ar-cis)-3,4,7a,9,10,10a-hexahydro-5-methoxy-1h,12h-furo[3',2':4,5]furo[2,3-h]pyrano[3,4-c][1]benzopyran-1,12-dione

5. Aflatoxin G2 0.5 Microg/ml In Acetonitrile

6. 1h,12h-furo[3',2':4,5]furo[2,3-h]pyrano[3,4-c][1]benzopyran-1,12-dione, 3,4,7a,9,10,10a-hexahydro-5-methoxy-, (7ar,10as)-

7. Aflatoxing2

8. Unii-2ms0d8wa29

9. Ccris 4936

10. Hsdb 3456

11. 1h,12h-furo(3',2':4,5)furo(2,3-h)pyrano(3,4-c)(1)benzopyran-1,12-dione, 3,4,7a,9,10,10a-hexahydro-5-methoxy-, (7ar,10as)-

12. Einecs 230-643-4

13. Aflatoxin G2 [mi]

14. Aflatoxin G2 [hsdb]

15. Aflatoxin G2 In Acetonitrile

16. Chebi:80705

17. Aflatoxin G2, Reference Material

18. Dtxsid80891796

19. Ex-a4123

20. Hy-n6698

21. Zinc2029390

22. Mfcd00078141

23. 1h,12h-furo(3',2':4,5)furo(2,3-h)pyrano(3,4-c)(1)benzopyran-1,12-dione,3,4,7aalpha,9,10,10aalpha-hexahydro-5-methoxy-

24. 1h,12h-furo[3',2':4,5]furo[2,3-h]pyrano[3,4-c][1]benzopyran-1,12-dione, 3,4,7a,9,10,10a-hexahydro-5-

25. 3,4,7aalpha,9,10,10aalpha-hexahydro-5-methoxy-1h,12h-furo(3',2':4,5)furo(2,3-h)pyrano(3,4-c)(1)-benzopyran-1,12-dione

26. Cs-0099736

27. C16754

28. Q26841280

29. Aflatoxin G2, From Aspergillus Flavus, >=98.0% (hplc/tlc)

30. Aflatoxin G2 Solution, 0.5 Mug/ml In Acetonitrile, Analytical Standard

31. Aflatoxin G2 Solution, 3.80 Mug/g In Acetonitrile, Erm(r) Certified Reference Material

32. (3s,7r)-11-methoxy-6,8,16,20-tetraoxapentacyclo[10.8.0.02,9.03,7.013,18]icosa-1,9,11,13(18)-tetraene-17,19-dione

33. (7ar,cis)3,4,7a,9,10,10a-hexahydro-5-methoxy-1h,12h- Furo(3',2':4,5)furo(2,3-h)pyrano(3,4-c)chromene-1,12-dione

34. (7ar,cis)3,4,7a,9,10,10a-hexahydro-5-methoxy-1h,12h-furo(3',2':4,5)furo(2,3-h)pyrano(3,4-c)chromene-1,12-dione

35. 1h,12h-furo(3',2':4,5)furo(2,3-h)pyrano(3,4-c)(1)benzopyran- 1,12-dione, 3,4,7a,9,10,10a-hexahydro-5-methoxy-, (7ar,10as)-

36. 1h,12h-furo(3',2':4,5)furo(2,3-h)pyrano(3,4-c)(1)benzopyran-1,12-dione, 3,4,7a-alpha,9,10,10a-alpha-hexahydro-5-methoxy-

37. Aflatoxin G2 Solution, Certified Reference Material, 3 Mug/ml In Benzene:acetonitrile (98:2), Ampule Of 1 Ml

2.4 Create Date
2005-07-19
3 Chemical and Physical Properties
Molecular Weight 330.29 g/mol
Molecular Formula C17H14O7
XLogP31.5
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count7
Rotatable Bond Count1
Exact Mass330.07395278 g/mol
Monoisotopic Mass330.07395278 g/mol
Topological Polar Surface Area80.3 Ų
Heavy Atom Count24
Formal Charge0
Complexity626
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 Absorption, Distribution and Excretion

To evaluate the rate at which the four main aflatoxins (aflatoxins B1, B2, G1 and G2) are able to cross the luminal membrane of the rat small intestine, a study about intestinal absorption kinetics of these mycotoxins has been made. In situ results obtained showed that the absorption of aflatoxins in rat small intestine is a very fast process that follows first-order kinetics, with an absorption rate constant (ka) of 5.84 +/- 0.05 (aflatoxin B1), 4.06 +/- 0.09 (aflatoxin B2), 2.09 +/- 0.03 (aflatoxin G1) and 1.58 +/- 0.04 (aflatoxin G2) h-1, respectively.

Ramos A et al; Mycopathologia 134(1): p.27-30 (1996)


4.2 Metabolism/Metabolites

Aflatoxin G2 ... /is/ the 9,10-dihydro derivative of aflatoxin G1.

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 35


4.3 Mechanism of Action

With the 4 principal Aflatoxins tested, the order of inhibitory effect on RNA polymerase II was: B1 greater than G1 greater than B1, G2.

Yu FL et al; Carcinogenesis (London) 3 (9): 1005 (1982)


Phagocytosis, intracellular killing of Candida albicans, and superoxide production by rat peritoneal macrophages exposed to aflatoxins B1, B2, G1, G2, B2a, and M1 at several times and concentration were analyzed to evaluate the intensity of a depressive effect for each mycotoxin. All aflatoxins used at very low concn had a depressive effect on the functions of macrophages. The biggest impairment of phagocytosis, intracellular killing, and spontaneous superoxide production was observed in macrophages exposed to aflatoxins B1 and M1.

PMID:2176448 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC184993 Cusumano V et al; Appl Environ Microbiol 56 (11): 3482-4 (1990)


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