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Orellanine

HCID 89579
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
37338-80-0
Standard SMILES
O=c1ccn(O)c(-c2c(O)c(=O)ccn2O)c1O
InChIKey
JEWWXPOUSBVQKG-UHFFFAOYSA-N
Molecular formula
C10H8N2O6
Average molar mass
252.18 g/mol
Monoisotopic mass
252.03823598

Overview

Orellanine is a member of bipyridines.

Names & identifiers

Preferred name
Orellanine
IUPAC
2-(1,3-dihydroxy-4-oxo-2-pyridinyl)-1,3-dihydroxypyridin-4-one
English name
orellanine
Molecular formula
C10H8N2O6
Molecular weight
252.18

Names & synonyms

Orellanine37338-80-02-(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'-dioxideORELLANINE [HSDB]SCHEMBL388071082U1GSX3DCHEMBL2152646SCHEMBL31022844CHEBI:190273MBA33880
Show more names
Orellanine, 10 mM in DMSOJEWWXPOUSBVQKG-UHFFFAOYSA-N2,2'-Bi[pyridine-3,4-diol]1,1'-dioxide[2,2'-Bipyridine]-3,3',4,4'-tetrol,1,1'-dioxide2-(3,4-Dihydroxy-1-oxidopyridin-1-ium-2-yl)-3,4-dihydroxypyridin-1-ium-1-olate
HY-W661499DA-76453CS-0745189NS00121449Q4205273,3',4,4'-tetrahydroxy-2,2'-bipyridyl-N,N'-dioxide3,3',4,4'-tetrahydroxy-[2,2'-bipyridine] 1,1'-dioxide3,3',4,4'-TETRAHYDROXY-2,2'-BIPYRIDINE-1,1'-DIOXIDE

Database identifiers

CAS
37338-80-0
PubChem CID
89579
ChEMBL

Properties

Computed structural properties

XLogP
-1
Topological polar surface area
122 Ų
Hydrogen bond donors
4
Hydrogen bond acceptors
8
Rotatable bonds
1
Heavy atoms
18
Formal charge
0
Complexity
507

Physicochemical properties

Boiling point
834.6 · 834.6±65.0 °C(Predicted)
Density
1.77 · 1.77±0.1 g/cm3(Predicted)
pka
4.5 · 4.50±0.45(Predicted)
form
Solid
color
Light yellow to yellow
FDA UNII
82 U1GSX3D · 082U1GSX3D
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
315 · H315-H319-H335
Precautionary statements
261 · P261-P271-P280
HS Code
2933399990 · 2933399990
Hazardous Substances Data
37338 · 37338-80-0(Hazardous Substances Data)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Toxicology

Treatment · 1 item

Although there is no known antidote against orellanine poisoning, early hospitalization can sometimes prevent serious injury and usually prevent death. Research is ongoing. Some treatments make use of anti-oxidant therapy and corticosteroids to help victims recover from their renal failure. (L998)

Health Effects · 1 item

The symptoms are followed by early stages of renal failure (immense thirst, frequent urination, pain on and around the kidneys) and eventually decreased or nonexistent urine output and other symptoms of renal failure occur. If left untreated death will follow. (L998)

Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity Summary · 1 item

Bipyridines with charged nitrogen atoms confound important redox reactions in organisms, ‘stealing’ one or two electrons and sometimes bypass the electrons into other and often undesirable redox reactions. The terminal product can be peroxide or superoxide ions, the latter of which is harmful to the cells, especially kidney cells. (L998)

Signs and Symptoms · 1 item

In humans, a characteristic of poisoning by the nephrotoxin orellanine is the long latency; the first symptoms usually do not appear until 2–3 days after ingestion and can in some cases take as long as 3 weeks. The first symptoms of orellanine poisoning are similar to the common flu (nausea, vomiting, stomach pains, headaches, myalgia, etc) (L998)

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Safety data

hs_code
2933399990
Signal word
Warning

Chemistry & industry

Uses & manufacturing

UsesOrellanine or Orellanin is a pyridine N-oxide and a crystalline alkaloid that is found naturally in some lifeforms, specifically certain fungi. It has been found in at least 34 types of mushrooms in the Cortinariaceae family. (L998)

Applications

UsesOrellanine is a nephrotoxin found in various Cortinaceae mushroom species. Orellanine at high concentration is toxic, but at low concentration it is being evaluated as a potential cure of metastatic renal cancer.

Suppliers18 total

武汉敬康恩生物医药科技有限公司13720134139 086-15871494362 13720134139 · [email protected]
杭州摩库生物医药科技有限公司+86-057181025280; +8617767106207 · [email protected]
安耐吉化学&3A(安徽泽升科技有限公司)021-58432009 400-005-6266 · [email protected]
欧利希(湖北)医药科技有限公司17316404525 17316404525 · [email protected]
成都思天德生物科技有限公司028-83243028 19136088901 · [email protected]
Wuhan Jingkang en Biomedical Technology Co., Ltd+86-0086-13720134139 · [email protected]
池州凯隆进出口贸易有限公司[email protected]
深圳振强药物研发有限公司+86-0755-66853366 +86-13670046396 · [email protected]
上海陶术生物科技股份有限公司

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
CHEMBL2152646
ChEBI
CHEBI:190273
UNII
082U1GSX3D
Nikkaji
J18.373C
Symbol(GHS)
GHS07
Hazard statements
H315-H319-H335
Precautionary statements
P261-P271-P280
Hazardous Substances Data
37338-80-0(Hazardous Substances Data)
+1-781-999-5354; +1-00000000000 · [email protected]
成都标样生物科技有限公司028-81700200 13308200041 · [email protected]
长沙福臻生物科技有限公司15111215862 18229892877 · [email protected]
TargetMol中国(陶术生物)4008200310 15002144251 · [email protected]
陕西缔都医药有限责任公司81148925 17391631969 · [email protected]
上海一飞生物科技有限公司021-65675885 18964387627 · [email protected]
烟台盛凯伦化学科技有限公司开发区第一分公司13356901049 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354 · [email protected]
天门恒昌化工有限公司027-59322316 15172518801 · [email protected]
上海阿摩尔生物科技有限公司13370042665 18916960931 · [email protected]

Additional notes

DefinitionChEBI: Orellanine is a member of bipyridines.