AFCDB: Alliin (FDB000558)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:37 UTC

Update date

2019-11-26 02:54:59 UTC

Primary ID

FDB000558

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Alliin

Description

Alliin, also known as (S)-S-allyl-L-cysteine sulfoxide or (S)-3-(allylsulphinyl)-L-alanine, is a member of the class of compounds known as L-alpha-amino acids. L-alpha-amino acids are alpha amino acids which have the L-configuration of the alpha-carbon atom. Alliin is soluble (in water) and a moderately acidic compound (based on its pKa). Alliin can be found in a number of food items such as red rice, mandarin orange (clementine, tangerine), ceylon cinnamon, and olive, which makes alliin a potential biomarker for the consumption of these food products. Garlic has been used since antiquity as a therapeutic remedy for certain conditions now associated with oxygen toxicity, and, when this was investigated, garlic did indeed show strong antioxidant and hydroxyl radical-scavenging properties, it is presumed owing to the alliin contained within. Alliin has also been found to affect immune responses in blood .

CAS Number

556-27-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

Predicted Properties

Property	Value	Source
Water Solubility	38.5 g/L	ALOGPS
logP	-2.1	ALOGPS
logP	-3.7	ChemAxon
logS	-0.66	ALOGPS
pKa (Strongest Acidic)	1.84	ChemAxon
pKa (Strongest Basic)	8.45	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	80.39 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	43.72 m³·mol⁻¹	ChemAxon
Polarizability	17.46 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C6H11NO3S

IUPAC name

(2R)-2-amino-3-(prop-2-ene-1-sulfinyl)propanoic acid

InChI Identifier

InChI=1S/C6H11NO3S/c1-2-3-11(10)4-5(7)6(8)9/h2,5H,1,3-4,7H2,(H,8,9)/t5-,11?/m0/s1

InChI Key

XUHLIQGRKRUKPH-ITZCMCNPSA-N

Isomeric SMILES

N[C@@H](CS(=O)CC=C)C(O)=O

Average Molecular Weight

177.221

Monoisotopic Molecular Weight

177.045963913

Classification

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Sulfoxide
Amino acid
Allyl sulfur compound
Sulfinyl compound
Monocarboxylic acid or derivatives
Carboxylic acid
Carbonyl group
Amine
Hydrocarbon derivative
Organic nitrogen compound
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

non-proteinogenic alpha-amino acid (CHEBI:2596 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 40.66%; H 6.26%; N 7.90%; O 27.08%; S 18.09%	DFC
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Alliin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9100000000-102d9a5a1f1fa625f97d	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01si-2900000000-24acd7b523ee4a606a36	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000x-9700000000-e75bf2d8b03149e961c6	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-f3eb54e254975ddaec90	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004r-2900000000-4945f8ea6edf677c1cd7	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9500000000-78b8b7ac8907d004f235	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000j-9100000000-67dfec97d77e9d943fc5	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000f-9500000000-8ea3f234c3bfe3df2b0d	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9100000000-a5db6938dd6bc4d086ac	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006y-9000000000-5688c056fa4f9896d8fd	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-4ac0c68cb3c192b2e052	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-02c6e2c53f6107e27313	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-9000000000-93497b521a88141008ec	2021-10-21	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

BDM42-Z:BDM42-Z

EAFUS ID

Not Available

Dr. Duke ID

S-ALLYL-CYSTEINE-SULFOXIDE|2-PROPENYL-L-CYSTEINE-SULFOXIDE|ALLIN|S-ALLYL-CYSTEINE-SULPHOXIDE|ALLIIN

BIGG ID

Not Available

KNApSAcK ID

Not Available

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

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
anti aggregant			DUKE
anti atherogenic	38070	A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.	DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti diabetic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti hepatotoxic	62868	Any compound that is able to prevent damage to the liver.	DUKE
anti neuralgic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti peroxidant			DUKE
anti platelet			DUKE
anti radicular			DUKE
anti sarcomic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE

Showing 1 to 10 of 22 entries

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).

Alliin (FDB000558)

Structure for FDB000558 (Alliin)