ChemFOnt: Showing chemical card for 6-[cyano(phenyl)methoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid (CFc000158450)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 23:45:46 UTC

Chemfont ID

CFc000158450

Molecule Identification

Common Name

6-[cyano(phenyl)methoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

Definition

Laetrile, also known as amygdalin or vitamin B17, belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group. Based on a literature review a significant number of articles have been published on Laetrile.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Mandelonitrile-beta-gentiobioside	MeSH
Amygdalin	MeSH
Neoamygdalin	MeSH
Amygdaloside	MeSH
Mandelonitrile beta gentiobioside	MeSH
Vitamin b17	MeSH
Cyano(phenyl)methyl hexopyranosiduronate	Generator

Chemical Formula

C₁₄H₁₅NO₇

Average Molecular Weight

309.274

Monoisotopic Molecular Weight

309.084851827

IUPAC Name

6-[cyano(phenyl)methoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

6-[cyano(phenyl)methoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC1C(O)C(OC(C#N)C2=CC=CC=C2)OC(C1O)C(O)=O

InChI Identifier

InChI=1S/C14H15NO7/c15-6-8(7-4-2-1-3-5-7)21-14-11(18)9(16)10(17)12(22-14)13(19)20/h1-5,8-12,14,16-18H,(H,19,20)

InChI Key

XLSLFPQAPYONPW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Cyanogenic glycosides

Alternative Parents

Substituents

Cyanogenic glycoside
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Hexose monosaccharide
O-glycosyl compound
Beta-hydroxy acid
Monocyclic benzene moiety
Hydroxy acid
Benzenoid
Pyran
Monosaccharide
Oxane
Secondary alcohol
Acetal
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Polyol
Carbonitrile
Nitrile
Hydrocarbon derivative
Organic nitrogen compound
Organopnictogen compound
Carbonyl group
Alcohol
Organic oxide
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	16.4 g/L	ALOGPS
logP	-0.56	ALOGPS
logP	-0.5	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	2.28	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	140.24 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	69.96 m³·mol⁻¹	ChemAxon
Polarizability	29.41 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0178042

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

233826

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Amygdalin

METLIN ID

Not Available

PubChem Compound

266052

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 6-[cyano(phenyl)methoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid (CFc000158450)

MOL for CFc000158450 (6-[cyano(phenyl)methoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D MOL for CFc000158450 (6-[cyano(phenyl)methoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D SDF for CFc000158450 (6-[cyano(phenyl)methoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D-SDF for CFc000158450 (6-[cyano(phenyl)methoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

PDB for CFc000158450 (6-[cyano(phenyl)methoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D PDB for CFc000158450 (6-[cyano(phenyl)methoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

SMILES for CFc000158450 (6-[cyano(phenyl)methoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

INCHI for CFc000158450 (6-[cyano(phenyl)methoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

Structure for CFc000158450 (6-[cyano(phenyl)methoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D Structure for CFc000158450 (6-[cyano(phenyl)methoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)