2-Phenyl-2-(3,4,5-Trihydroxy-6-((3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl)Oxymethyl)Oxan-2-Yl)Oxyacetonitrile

識別子と物理属性

CAS No.	1173199-73-9
分子式	C20H27NO11
平均分子量	457.4 g/mol
単同位体質量	457.15841068 g/mol
SMILES	N#CC(OC1OC(COC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O)c1ccccc1
InChIKey	XUCIJNAGGSZNQT-UHFFFAOYSA-N
PubChem CID	2180
ChEMBL	CHEMBL1967951
DTXSID	DTXSID20872004

化学・物理的性質

XLogP	-2.7
極性表面積	202
水素結合供与体数	7
水素結合受容体数	12
回転可能結合数	7
重原子数	32
形式電荷	0
複雑度	638
融点	214 °C
Physical Description	Solid

安全性と法規制

毒性の概要	Amygdalin can be metabolized into hydrogen cyanide in the stomach causing discomfort or illness. (L402) Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97)
Carcinogen Classification	No indication of carcinogenicity to humans (not listed by IARC).

毒性の概要

Amygdalin can be metabolized into hydrogen cyanide in the stomach causing discomfort or illness. (L402) Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97)

Carcinogen Classification

No indication of carcinogenicity to humans (not listed by IARC).