Showing Compound (R)C(S)S-Alliin (FDB011674)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:46 UTC

Update date

2019-11-26 03:05:15 UTC

Primary ID

FDB011674

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(R)C(S)S-Alliin

Description

(R)C(S)S-Alliin, also known as isoalliin or PCSO, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon) (R)C(S)S-Alliin has been detected, but not quantified in, several different foods, such as welsh onions (Allium fistulosum), garden onion (var.), red onion, garden onions (Allium cepa), and green onion. This could make (R)C(S)S-alliin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (R)C(S)S-Alliin.

CAS Number

556-27-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
2-Amino-3-(prop-2-ene-1-sulfinyl)propanoate	HMDB
2-Amino-3-(prop-2-ene-1-sulphinyl)propanoate	HMDB
2-Amino-3-(prop-2-ene-1-sulphinyl)propanoic acid	HMDB
3-(Allylsulphinyl)-L-alanine	HMDB
Alliin	HMDB
Alliin, (L-ala)-(R)-isomer	HMDB
Alliin, (L-ala)-(S)-isomer	HMDB
Alliin, (L-ala)-isomer	HMDB
Isoalliin	HMDB
PCSO	HMDB

Showing 1 to 10 of 12 entries

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	17.2 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

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)

InChI Key

XUHLIQGRKRUKPH-UHFFFAOYSA-N

Isomeric SMILES

NC(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 alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Biological role:

Nutrient

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	Mp 163° dec.	DFC
Optical Rotation	[a]21D +67.7 (c, 2.0 in H2O)	DFC

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	(R)C(S)S-Alliin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9000000000-5d9a21e27ef3f517dd6d	Spectrum
Predicted GC-MS	(R)C(S)S-Alliin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9400000000-4437cf48a71215d0979e	Spectrum
Predicted GC-MS	(R)C(S)S-Alliin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(R)C(S)S-Alliin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(R)C(S)S-Alliin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(R)C(S)S-Alliin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(R)C(S)S-Alliin, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(R)C(S)S-Alliin, TBDMS_1_2, 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	splash10-03gi-1900000000-c555ee84b1ef7b497188	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000x-9700000000-fceeacb69e8f54ed59f7	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-57ef07206642af998090	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004r-2900000000-2e1124856d7e7fb193c7	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9600000000-f2d686842e93754c87d2	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00ks-9200000000-40481bee5ec83e05c2b7	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03gi-1900000000-c555ee84b1ef7b497188	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000x-9700000000-fceeacb69e8f54ed59f7	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-57ef07206642af998090	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004r-2900000000-2e1124856d7e7fb193c7	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9600000000-f2d686842e93754c87d2	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00ks-9200000000-40481bee5ec83e05c2b7	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-4ac0c68cb3c192b2e052	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-02c6e2c53f6107e27313	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-9000000000-93497b521a88141008ec	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000f-9500000000-8ea3f234c3bfe3df2b0d	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9100000000-a5db6938dd6bc4d086ac	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006y-9000000000-5688c056fa4f9896d8fd	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

108767

ChEMBL ID

Not Available

KEGG Compound ID

C08265

Pubchem Compound ID

121922

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB33592

CRC / DFC (Dictionary of Food Compounds) ID

BDM42-Z:GXW16-F

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

C00001336

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

Not Available

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

— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Showing Compound (R)C(S)S-Alliin (FDB011674)

Structure for FDB011674 ((R)C(S)S-Alliin)