Showing Compound S-Allylcysteine (FDB012675)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:18 UTC

Update date

2019-11-26 03:07:21 UTC

Primary ID

FDB012675

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

S-Allylcysteine

Description

S-Allylcysteine, also known as L-deoxyalliin, belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. S-Allylcysteine is a very strong basic compound (based on its pKa). S-Allylcysteine is a cooked and roasted tasting compound. S-Allylcysteine is found, on average, in the highest concentration within soft-necked garlics. S-Allylcysteine has also been detected, but not quantified in, garden onions and onion-family vegetables. This could make S-allylcysteine a potential biomarker for the consumption of these foods.

CAS Number

21593-77-1

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
L-DeoxyallIIn	HMDB
S-2-Propenyl-L-cysteine	HMDB
S-Allyl-L -cysteine	HMDB
Allyl cysteine	HMDB
2-Amino-3-(prop-2-en-1-ylsulfanyl)propanoate	Generator
2-Amino-3-(prop-2-en-1-ylsulphanyl)propanoate	Generator
2-Amino-3-(prop-2-en-1-ylsulphanyl)propanoic acid	Generator
S-Allylcysteine	MeSH
L-Cysteine, S-2-propenyl-	biospider
L-deoxyallIIn	biospider
S-allyl-l -cysteine	biospider

Predicted Properties

Property	Value	Source
Water Solubility	13.7 g/L	ALOGPS
logP	-1.8	ALOGPS
logP	-1.8	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	2.53	ChemAxon
pKa (Strongest Basic)	9.14	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	42.09 m³·mol⁻¹	ChemAxon
Polarizability	16.85 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

C6H11NO2S

IUPAC name

2-amino-3-(prop-2-en-1-ylsulfanyl)propanoic acid

InChI Identifier

InChI=1S/C6H11NO2S/c1-2-3-10-4-5(7)6(8)9/h2,5H,1,3-4,7H2,(H,8,9)

InChI Key

ZFAHNWWNDFHPOH-UHFFFAOYSA-N

Isomeric SMILES

NC(CSCC=C)C(O)=O

Average Molecular Weight

161.222

Monoisotopic Molecular Weight

161.051049291

Classification

Description

Belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Cysteine and derivatives

Alternative Parents

Substituents

Cysteine or derivatives
Alpha-amino acid
Amino acid
Allyl sulfur compound
Carboxylic acid
Monocarboxylic acid or derivatives
Thioether
Sulfenyl compound
Dialkylthioether
Carbonyl group
Amine
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Primary aliphatic amine
Hydrocarbon derivative
Organic oxygen compound
Organopnictogen compound
Organic oxide
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

Foods

Fruits and vegetables:

Vegetables:

Onion family vegetables

Herbs and spices:

Herbs:

Garlic

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 44.70%; H 6.88%; N 8.69%; O 19.85%; S 19.89%	DFC
Melting Point	Mp 218°	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]D -16.4 (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	S-Allylcysteine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9000000000-6472ab7f2d2b13b42092	Spectrum
Predicted GC-MS	S-Allylcysteine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0007-9500000000-6130c45418f29c7eb2ab	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0296-5900000000-8c89fd146060416fb06f	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00fu-9300000000-9edb4d3a5be841c6a27e	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006x-9000000000-8dde9c26474a4aa9cf9c	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0229-4900000000-5ea2674e8ab9863410c8	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9500000000-584904bc5c18c5d83a03	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0080-9100000000-847061c3a2deccc782b7	Spectrum

NMR

Not Available

External Links

ChemSpider ID

88744

ChEMBL ID

Not Available

KEGG Compound ID

C16759

Pubchem Compound ID

98280

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB34323

CRC / DFC (Dictionary of Food Compounds) ID

HJQ86-N:HJQ74-I

EAFUS ID

103

Dr. Duke ID

S-ALLYL-L-CYSTEINE|S-ALLYL-CYSTEINE

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

rw1593931

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
anti aging	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	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 cancer	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti cholesterogenic			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 melanomic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti neuroblastomic			DUKE
anti NF-kappa-B	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
antioxidant	22586	A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.	DUKE
anti proliferant			DUKE
anti radicular			DUKE
antitumor	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
chemopreventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
glutathione-sparing			DUKE
hepatoprotective	62868	Any compound that is able to prevent damage to the liver.	DUKE
hypocholesterolemic			DUKE
immunostimulant	50847	A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.	DUKE
mucokinetic			DUKE
squalene-monooxygenase inhibitor	23924	A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
cooked	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
roasted	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

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).