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2D Structure
Also known as: 37338-80-0, (2,2'-bipyridine)-3,3',4,4'-tetrol, 1,1'-dioxide, 2-(1,3-dihydroxy-4-oxopyridin-2-yl)-1,3-dihydroxypyridin-4-one, [2,2'-bipyridine]-3,3',4,4'-tetrol, 1,1'-dioxide, [2,2'-bipyridine]-3,3',4,4'-tetrol,1,1'-dioxide, Orellanine [hsdb]
Molecular Formula
C10H8N2O6
Molecular Weight
252.18  g/mol
InChI Key
JGRNMEQUBVRSQR-UHFFFAOYSA-N
FDA UNII
082U1GSX3D

orellanine is a natural product found in Cortinarius orellanus, Cortinarius speciosissimus, and Cortinarius rubellus with data available.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-(1,3-dihydroxy-4-oxopyridin-2-yl)-1,3-dihydroxypyridin-4-one
2.1.2 InChI
InChI=1S/C10H8N2O6/c13-5-1-3-11(17)7(9(5)15)8-10(16)6(14)2-4-12(8)18/h1-4,15-18H
2.1.3 InChI Key
JGRNMEQUBVRSQR-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CN(C(=C(C1=O)O)C2=C(C(=O)C=CN2O)O)O
2.2 Other Identifiers
2.2.1 UNII
082U1GSX3D
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. 37338-80-0

2. (2,2'-bipyridine)-3,3',4,4'-tetrol, 1,1'-dioxide

3. 2-(1,3-dihydroxy-4-oxopyridin-2-yl)-1,3-dihydroxypyridin-4-one

4. [2,2'-bipyridine]-3,3',4,4'-tetrol, 1,1'-dioxide

5. [2,2'-bipyridine]-3,3',4,4'-tetrol,1,1'-dioxide

6. Orellanine [hsdb]

7. Schembl388071

8. 082u1gsx3d

9. Chembl2152646

10. Chebi:190273

11. Zinc150339637

12. Q420527

13. 3,3',4,4'-tetrahydroxy-2,2'-bipyridyl-n,n'-dioxide

14. 3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide

15. 2-(3,4-dihydroxy-1-oxidopyridin-1-ium-2-yl)-3,4-dihydroxypyridin-1-ium-1-olate

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 252.18 g/mol
Molecular Formula C10H8N2O6
XLogP3-1
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count8
Rotatable Bond Count1
Exact Mass252.03823598 g/mol
Monoisotopic Mass252.03823598 g/mol
Topological Polar Surface Area122 Ų
Heavy Atom Count18
Formal Charge0
Complexity507
Isotope Atom Count0
Defined Atom Stereocenter Count0
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

A woman suffering from acute tubulo-interstitial nephritis was admitted to the hospital ten days after deliberate intoxication by ingestion of Cortinarius orellanus. Orellanine, the main toxin responsible for orellanine poisoning, was detected in biological fluids and renal biopsies. It was assayed by direct spectrofluorimetry on two-dimensional thin-layer chromatograms after specific photodecomposition into orelline. The orellanine concentration was 6.12 mg/L in the plasma (10 days after ingestion). Orellanine levels in renal biopsies were 7 ug per 25 cu mm of the first biopsy (13 days after ingestion) and 24 ug per 8 cu mm of the second biopsy (6 months later).

PMID:2615804 Rapior S et al; Mycopathologia 108 (3): 155-61 (1989).