Record Information
Version1.0
Creation date2010-04-08 22:04:37 UTC
Update date2018-05-28 23:02:08 UTC
Primary IDFDB000558
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAlliin
DescriptionAlliin, 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 Number556-27-4
Structure
Thumb
Synonyms
SynonymSource
Alliin, (L-ala)-(R)-isomerMeSH
IsoalliinMeSH
Alliin, (L-ala)-(S)-isomerMeSH
S-(2-Propenyl)cysteine sulfoxideMeSH
PCSOMeSH
S-Allylcysteine sulfoxideMeSH
Alliin, (L-ala)-isomerMeSH
3-(2-Propenylsulfinyl)alanine, 9CIdb_source
b-Allysulfenylalaninedb_source
Predicted Properties
PropertyValueSource
Water Solubility38.5 g/LALOGPS
logP-2.1ALOGPS
logP-3.7ChemAxon
logS-0.66ALOGPS
pKa (Strongest Acidic)1.84ChemAxon
pKa (Strongest Basic)8.45ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.39 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity43.72 m³·mol⁻¹ChemAxon
Polarizability17.46 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC6H11NO3S
IUPAC name(2R)-2-amino-3-(prop-2-ene-1-sulfinyl)propanoic acid
InChI IdentifierInChI=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 KeyXUHLIQGRKRUKPH-ITZCMCNPSA-N
Isomeric SMILESN[C@@H](CS(=O)CC=C)C(O)=O
Average Molecular Weight177.221
Monoisotopic Molecular Weight177.045963913
Classification
DescriptionThis compound 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
OntologyShould have ontology for this compound
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 40.66%; H 6.26%; N 7.90%; O 27.08%; S 18.09%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9100000000-102d9a5a1f1fa625f97dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01si-2900000000-24acd7b523ee4a606a36View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000x-9700000000-e75bf2d8b03149e961c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-f3eb54e254975ddaec90View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004r-2900000000-4945f8ea6edf677c1cd7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9500000000-78b8b7ac8907d004f235View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000j-9100000000-67dfec97d77e9d943fc5View in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDBDM42-Z:BDM42-Z
EAFUS IDNot Available
Dr. Duke IDS-ALLYL-CYSTEINE-SULFOXIDE|2-PROPENYL-L-CYSTEINE-SULFOXIDE|ALLIN|S-ALLYL-CYSTEINE-SULPHOXIDE|ALLIIN
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti aggregantDUKE
anti atherogenic38070 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 bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
antibiotic22582 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti diabetic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti hepatotoxic62868 Any compound that is able to prevent damage to the liver.DUKE
anti neuralgic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antioxidant22586 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 peroxidantDUKE
anti plateletDUKE
anti radicularDUKE
anti sarcomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti thrombotic50248 Drug that acts on blood and blood-forming organs and those that affect the hemostatic system.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
hypocholesterolemicDUKE
hypoglycemic35526 A drug which lowers the blood glucose level.DUKE
immunostimulant50847 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
lipolyticDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
phagocytoticDUKE
squalene-monooxygenase inhibitor23924 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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).