Record Information
Version1.0
Creation date2010-04-08 22:04:37 UTC
Update date2025-11-18 22:19:39 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
(2R)-2-Amino-3-(prop-2-ene-1-sulfinyl)propanoateGenerator
(2R)-2-Amino-3-(prop-2-ene-1-sulphinyl)propanoateGenerator
(2R)-2-Amino-3-(prop-2-ene-1-sulphinyl)propanoic acidGenerator
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
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.
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
OntologyNo ontology term
Physico-Chemical Properties
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSAlliin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9100000000-102d9a5a1f1fa625f97dSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01si-2900000000-24acd7b523ee4a606a362016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000x-9700000000-e75bf2d8b03149e961c62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-f3eb54e254975ddaec902016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004r-2900000000-4945f8ea6edf677c1cd72016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9500000000-78b8b7ac8907d004f2352016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000j-9100000000-67dfec97d77e9d943fc52016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000f-9500000000-8ea3f234c3bfe3df2b0d2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9100000000-a5db6938dd6bc4d086ac2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006y-9000000000-5688c056fa4f9896d8fd2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-4ac0c68cb3c192b2e0522021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-02c6e2c53f6107e273132021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-93497b521a88141008ec2021-10-21View Spectrum
NMRNot Available
ChemSpider ID78760
ChEMBL IDCHEMBL464166
KEGG Compound IDC08265
Pubchem Compound ID25200619
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
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDAlliin
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-aggregantAn agent that prevents platelet aggregation, reducing blood clot formation. Its biological role is to inhibit platelet activation, and its therapeutic applications include preventing thrombosis and stroke. Key medical uses include treating cardiovascular diseases, such as myocardial infarction and atrial fibrillation, and managing conditions that increase the risk of blood clots.DUKE
Anti-atherogenic38070 An agent that prevents or reduces the formation of atheromas (plaques) in arteries, thereby lowering the risk of cardiovascular disease. It inhibits the biological processes leading to atherosclerosis, and has therapeutic applications in managing hyperlipidemia, hypertension, and cardiovascular disease, with key medical uses including reducing inflammation and improving lipid profiles.DUKE
Anti bacterial33282 An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.DUKE
Antibiotic22582 An agent that inhibits the growth of or destroys microorganisms, particularly bacteria. Therapeutically, antibiotics are used to treat bacterial infections, such as pneumonia, tuberculosis, and skin infections, by targeting specific biochemical processes essential for microbial survival.DUKE
Anti-diabetic52217 An agent that regulates blood sugar levels, enhancing insulin sensitivity or secretion. Therapeutically, it's used to manage diabetes, reducing symptoms and complications, and commonly prescribed to treat type 1 and 2 diabetes, as well as gestational diabetes.DUKE
Anti hepatotoxic62868 An agent that protects the liver from damage, reducing toxicity and promoting liver health. It plays a biological role in preventing liver injury and supporting liver function. Therapeutically, it is used to treat liver diseases, such as hepatitis and cirrhosis, and to counteract liver-damaging effects of certain medications and toxins.DUKE
Anti neuralgic52217 An agent that relieves nerve pain, reducing inflammation and discomfort. It plays a biological role in blocking pain pathways, and has therapeutic applications in managing conditions like trigeminal neuralgia, shingles, and diabetic neuropathy. Key medical uses include treating severe nerve pain, numbness, and tingling sensations.DUKE
Anti-oxidant22586 An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.DUKE
Anti peroxidantAn agent that prevents oxygen atom and peroxide formation, reducing oxidative stress and cell damage. It plays a biological role in protecting cells from free radicals. Therapeutically, it's used to manage conditions like cancer, Alzheimer's, and atherosclerosis, with key medical applications in neuroprotection, cardiovascular health, and anti-aging.DUKE
Anti plateletAn agent that prevents blood clot formation by inhibiting platelet aggregation, used to treat and prevent heart disease, stroke, and other cardiovascular conditions.DUKE
Anti radicularAn agent that relieves inflammation or irritation of the nerve root of a tooth, reducing pain and discomfort. Its biological role is to target and alleviate radicular pain, with therapeutic applications in endodontics and key medical uses in root canal treatments and tooth sensitivity management.DUKE
Anti sarcomic35610 An agent that targets sarcomas, a type of cancer that arises from connective tissue. It plays a biological role in inhibiting tumor growth and proliferation. Therapeutically, it is used to manage soft tissue sarcomas, with key medical applications in oncology, particularly in treating rare and aggressive sarcoma subtypes.DUKE
Anti thrombotic50248 An agent that prevents blood clot formation, reducing the risk of thrombosis. Its biological role is to inhibit platelet aggregation and blood coagulation. Therapeutically, it is used to prevent and treat conditions such as stroke, heart attack, and deep vein thrombosis, as well as to manage atrial fibrillation and peripheral artery disease.DUKE
Antitumor35610 An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.DUKE
Hepatoprotective62868 An agent that protects the liver from damage, promoting liver health and function. It plays a biological role in reducing oxidative stress and inflammation, and has therapeutic applications in managing liver diseases, such as hepatitis and cirrhosis, and key medical uses in treating drug-induced liver injury and toxicities.DUKE
HypocholesterolemicAn agent that lowers cholesterol levels in the blood, playing a crucial role in preventing cardiovascular disease. Therapeutically, it is used to manage hyperlipidemia and reduce the risk of heart disease, with key medical applications including the treatment of high cholesterol, atherosclerosis, and coronary artery disease.DUKE
Hypoglycemic35526 An agent that lowers blood glucose levels, playing a crucial role in glucose metabolism. Therapeutically, it is used to manage diabetes and insulin resistance, with key medical applications in treating type 1 and 2 diabetes, and preventing diabetic complications.DUKE
Immunostimulant50847 An agent that stimulates the immune system, enhancing its response to infections and diseases. Therapeutically, it boosts the body's natural defenses, commonly used to treat immunodeficiency disorders, prevent infections, and support cancer treatment, as well as manage chronic conditions like hepatitis and HIV.DUKE
LipolyticAn agent that stimulates hydrolysis of fats into fatty acids and glycerol, playing a key biological role in fat metabolism. Therapeutically, lipolytics have applications in managing obesity and hypertriglyceridemia, with medical uses including weight loss and improving lipid profiles.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
PhagocytoticAn agent that engulfs and internalizes solid particles or cells through phagocytosis, playing a key role in immune defense. Therapeutically, it aids in removing pathogens and debris, with medical applications in treating infections and inflammatory disorders.DUKE
Squalene-monooxygenase inhibitor23924 An agent that blocks the activity of squalene-monooxygenase, an enzyme involved in cholesterol biosynthesis. It reduces cholesterol production, with therapeutic applications in managing hypercholesterolemia and related cardiovascular diseases, and key medical uses in treating high cholesterol and preventing atherosclerosis.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).