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Orellanine

Orellanine

Synopsis, Chemistry

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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

Orellanine

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 Formula	C₁₀H₈N₂O₆
Molecular Weight	252.18 g/mol
XLogP3	-1
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	1
Exact Mass	252.03823598 g/mol
Monoisotopic Mass	252.03823598 g/mol
Topological Polar Surface Area	122 Å²
Heavy Atom Count	18
Formal Charge	0
Complexity	507
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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).