Canmetcon
Record Information
Version1.0
Creation date2010-04-08 22:10:02 UTC
Update date2018-05-28 23:34:50 UTC
Primary IDFDB012190
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAllicin
DescriptionIsolated from garlic (Allium sativum). Nutriceutical Allicin is an organic compound obtained from garlic. It is also obtainable from onions, and other species in the family Alliaceae. It was first isolated and studied in the laboratory by Chester J. Cavallito in 1944. This colourless liquid has a distinctively pungent smell. This compound exhibits antibacterial and anti-fungal properties. Allicin is garlic's defence mechanism against attacks by pests. Allicin is found in many foods, some of which are saskatoon berry, arrowroot, summer savory, and devilfish.
CAS Number539-86-6
Structure
Thumb
Synonyms
SynonymSource
2-Propene-1-sulfinothioic acid S-2-propenyl esterChEBI
Thio-2-propene-1-sulfinic acid S-allyl esterChEBI
2-Propene-1-sulfinothioate S-2-propenyl esterGenerator
2-Propene-1-sulphinothioate S-2-propenyl esterGenerator
2-Propene-1-sulphinothioic acid S-2-propenyl esterGenerator
Thio-2-propene-1-sulfinate S-allyl esterGenerator
Thio-2-propene-1-sulphinate S-allyl esterGenerator
Thio-2-propene-1-sulphinic acid S-allyl esterGenerator
2-Propene-1-sulfinic acid, thio-, S-allyl esterHMDB
2-Propene-1-sulfinothioic acid, S-2-propenyl esterHMDB
2-Propene-1-sulfinothioic acid, S-2-propenyl ester (9ci)HMDB
AlliminHMDB
AllitridiHMDB
AllylthiosulfinateHMDB
Allylthiosulphinic acid allyl esterHMDB
DadsoHMDB
Diallyl disulfide-oxideHMDB
Diallyl thiosulfinateHMDB
Diallyldisulfid-S-oxidHMDB
S-2-Propenyl 2-propene-1-sulfinothioate, 9ciHMDB
S-Allyl 2-propene-1-sulfinothioateHMDB
S-Allyl acrylo-1-sulphinothioateHMDB
S-Allyl prop-2-ene-1-sulfinothioateHMDB
S-Prop-2-en-1-yl prop-2-ene-1-sulfinothioateHMDB
2-Propene-1-sulfinothioic acid, S-2-propenyl ester (9CI)biospider
Diallyldisulfid-s-oxidbiospider
S-2-Propenyl 2-propene-1-sulfinothioate, 9CIdb_source
S-allyl 2-propene-1-sulfinothioatebiospider
S-allyl prop-2-ene-1-sulfinothioatebiospider
S-prop-2-en-1-yl prop-2-ene-1-sulfinothioatebiospider
thio-2-propene-1-sulfinic acid S-allyl esterbiospider
Predicted Properties
PropertyValueSource
Water Solubility6.13 g/LALOGPS
logP1.16ALOGPS
logP2.02ChemAxon
logS-1.4ALOGPS
pKa (Strongest Basic)-5.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity44.93 m³·mol⁻¹ChemAxon
Polarizability17.01 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC6H10OS2
IUPAC name3-[(prop-2-ene-1-sulfinyl)sulfanyl]prop-1-ene
InChI IdentifierInChI=1S/C6H10OS2/c1-3-5-8-9(7)6-4-2/h3-4H,1-2,5-6H2
InChI KeyJDLKFOPOAOFWQN-UHFFFAOYSA-N
Isomeric SMILESC=CCSS(=O)CC=C
Average Molecular Weight162.273
Monoisotopic Molecular Weight162.017306322
Classification
Description belongs to the class of organic compounds known as thiosulfinic acid esters. These are organic compounds containing an ester of thiosulfinic acid with the general structure RS(=S)OR' (R, R'=alkyl, aryl).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassThiosulfinic acid esters
Sub ClassNot Available
Direct ParentThiosulfinic acid esters
Alternative Parents
Substituents
  • Thiosulfinic acid ester
  • Allyl sulfur compound
  • Sulfenyl compound
  • Sulfinyl compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 44.41%; H 6.21%; O 9.86%; S 39.52%DFC
Melting Point<25 °C
Boiling PointNot Available
Experimental Water Solubility24 mg/mL at 10 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data240 () (MeOH) (Berdy)DFC
Densityd 1.11DFC
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9100000000-afcc42c2c1bd90b0e384View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0229-1900000000-a892e3c38e5a1381bfd6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-8900000000-5679f84e236fe52171f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000l-9100000000-938b07f1d7929cac2c10View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03k9-9700000000-734a318e76fb991aae76View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-9500000000-31a6285b63158ade86a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0096-9000000000-554fb97cc2ab4464f948View in MoNA
ChemSpider ID58548
ChEMBL IDNot Available
KEGG Compound IDC07600
Pubchem Compound ID65036
Pubchem Substance IDNot Available
ChEBI ID28411
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB33963
CRC / DFC (Dictionary of Food Compounds) IDHDZ34-Z:HDZ34-Z
EAFUS IDNot Available
Dr. Duke IDALLICIN
BIGG IDNot Available
KNApSAcK IDC00001242
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDAllicin
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
alcohol dehydrogenase inhibitor50269 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of alcohol dehydrogenase (EC 1.1.1.1).DUKE
allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.DUKE
amebicide33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti helmintic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti aggregantDUKE
anti atherosclerotic38070 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 cholinesterase37733 An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of cholinesterase (EC 3.1.1.8).DUKE
anti diabetic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti flu22587 A substance that destroys or inhibits replication of viruses.DUKE
anti glaucomicDUKE
anti herpetic22587 A substance that destroys or inhibits replication of viruses.DUKE
anti hypertensive52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti leukemic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti leukotriene35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti lymphomicDUKE
anti mutagenicDUKE
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 plateletDUKE
anti proliferantDUKE
anti prostaglandin49020 A chemical substance which inhibits the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites.DUKE
anti radicularDUKE
anti sarcomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti shigellic33282 A substance that kills or slows the growth of bacteria.DUKE
anti staphylococcic33282 A substance that kills or slows the growth of bacteria.DUKE
anti triglyceride35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti tubercular33282 A substance that kills or slows the growth of bacteria.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
apoptoticDUKE
calcium antagonist48706 Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.DUKE
candidicideDUKE
cyclooxygenase inhibitor35544 A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
Gram(+)icide33282 A substance that kills or slows the growth of bacteria.DUKE
Gram(-)icide33282 A substance that kills or slows the growth of bacteria.DUKE
hepatotoxic50908 A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals.DUKE
hypocholesterolemicDUKE
hypoglycemic35526 A drug which lowers the blood glucose level.DUKE
hypolipidemicDUKE
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
insecticide24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
insulin-sparingDUKE
larvicideDUKE
lipolyticDUKE
lipoxygenase inhibitor35856 A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes.DUKE
mucokineticDUKE
mycobactericideDUKE
nematicide25491 A substance used to destroy pests of the phylum Nematoda (roundworms).DUKE
nitric-oxide inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
papain 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
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
prooxidantDUKE
prostaglandin-synthetase 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
succinate-dehydrogenase 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
trichomonicideDUKE
urease inhibitor50635 EC 3.5.1.* (non-peptide linear amide C-N hydrolase) inhibitor that interferes with the activity of urease (EC 3.5.1.5), reducing hydrolysis.DUKE
vibriocideDUKE
xanthine oxidase inhibitor35634 An EC 1.17.3.* (oxidoreductase acting on CH or CH2 with oxygen as acceptor) inhibitor that interferes with the action of xanthine oxidase (EC 1.17.3.2).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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.