AFCDB: Neolinustatin (FDB017846)

Record Information

Version

1.0

Creation date

2010-04-08 22:13:21 UTC

Update date

2019-11-26 03:15:19 UTC

Primary ID

FDB017846

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Neolinustatin

Description

Neolinustatin belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group. Neolinustatin is found, on average, in the highest concentration within flaxseeds (Linum usitatissimum). Neolinustatin has also been detected, but not quantified in, several different foods, such as chinese bayberries (Myrica rubra), wasabis (Wasabia japonica), dills (Anethum graveolens), bitter gourds (Momordica charantia), and parsnips (Pastinaca sativa). This could make neolinustatin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Neolinustatin.

CAS Number

72229-42-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	75.9 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-3	ChemAxon
logS	-0.75	ALOGPS
pKa (Strongest Acidic)	11.91	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	202.32 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	91.88 m³·mol⁻¹	ChemAxon
Polarizability	41.19 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C17H29NO11

IUPAC name

2-methyl-2-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}butanenitrile

InChI Identifier

InChI=1S/C17H29NO11/c1-3-17(2,6-18)29-16-14(25)12(23)10(21)8(28-16)5-26-15-13(24)11(22)9(20)7(4-19)27-15/h7-16,19-25H,3-5H2,1-2H3

InChI Key

WOSYVGNDRYBQCQ-UHFFFAOYSA-N

Isomeric SMILES

CCC(C)(OC1OC(COC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O)C#N

Average Molecular Weight

423.4123

Monoisotopic Molecular Weight

423.174060775

Classification

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
Disaccharide
O-glycosyl compound
Oxane
Secondary alcohol
Organoheterocyclic compound
Polyol
Acetal
Nitrile
Carbonitrile
Oxacycle
Primary alcohol
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant:

Animal

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Biological role:

Nutrient

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 48.22%; H 6.90%; N 3.31%; O 41.57%	DFC
Melting Point	Mp 190-192°	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]25D -37 (c, 0.37 in H2O)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Neolinustatin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0btc-5649400000-c9cfa48ce823aa8f25a7	Spectrum
Predicted GC-MS	Neolinustatin, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00e9-5150139000-e6d3dc33e23b181ea9b8	Spectrum
Predicted GC-MS	Neolinustatin, TBDMS_4_31, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Neolinustatin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Neolinustatin, "Neolinustatin,4TBDMS,#31" TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0zgi-6921700000-f7467844ef757d579d62	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ue9-9710000000-324a9709af2f022b6e4f	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f89-9700000000-b2f76afcb60030a8ad85	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0231-9421500000-e137b3d6e4ee11a61577	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-9300100000-46138695857e0d86b6bd	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-9100000000-9d89440459efbfc7dbe5	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0003900000-17ecf9299d82aff008ce	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0mbc-9447200000-6799fe334ed32cb5b75b	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-99b8207765b85b23d475	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00e9-5033900000-6d8756bd340b0e562a73	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9100000000-3fdcbd3cd72fb072c876	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pb9-9100000000-365a14e4b3ca43f2650d	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

3677427

ChEMBL ID

Not Available

KEGG Compound ID

C08336

Pubchem Compound ID

4479452

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB38482

CRC / DFC (Dictionary of Food Compounds) ID

DBZ32-R:LBL58-V

EAFUS ID

Not Available

Dr. Duke ID

NEOLINUSTATIN

BIGG ID

Not Available

KNApSAcK ID

C00001450

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
cyanogenic			DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Neolinustatin (FDB017846)

Structure for FDB017846 (Neolinustatin)