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

Identifikatoren & physikalische Daten

CAS No.	1173199-73-9
Summenformel	C20H27NO11
Durchschnittliche Molmasse	457,4 g/mol
Monoisotopische Masse	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

Chemische & physikalische Eigenschaften

XLogP	-2,7
Polarare Oberfläche (TPSA)	202
H-Brücken-Donoren	7
H-Brücken-Akzeptoren	12
Frei drehbare Bindungen	7
Schwere Atome	32
Formalladung	0
Komplexität	638
Schmelzpunkt	214 °C
Physical Description	Solid

Sicherheit & Vorschriften

Toxizitätsübersicht	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).

Toxizitätsübersicht

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).

CAS No.

1173199-73-9

Summenformel

C20H27NO11

Durchschnittliche Molmasse

457,4 g/mol

Monoisotopische Masse

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

XLogP

-2,7

Polarare Oberfläche (TPSA)

202

H-Brücken-Donoren

H-Brücken-Akzeptoren

Frei drehbare Bindungen

Schwere Atome

Formalladung

Komplexität

638

Schmelzpunkt

214 °C

Physical Description

Solid

Sicherheit & Vorschriften

Toxizitätsübersicht	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).

Toxizitätsübersicht

Carcinogen Classification

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