Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:44:15 UTC
Update Date2021-10-13 06:37:05 UTC
HMDB IDHMDB0033963
Secondary Accession Numbers
  • HMDB33963
Metabolite Identification
Common NameAllicin
DescriptionAllicin 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). Allicin is found, on average, in the highest concentration within soft-necked garlics (Allium sativum L. var. sativum). Allicin has also been detected, but not quantified in, several different foods, such as wakames (Undaria pinnatifida), black raspberries (Rubus occidentalis), bamboo shoots (Phyllostachys edulis), spinaches (Spinacia oleracea), and chinese chestnuts (Castanea mollissima). This could make allicin a potential biomarker for the consumption of these foods. Allicin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Allicin.
Structure
Data?1563862488
Synonyms
ValueSource
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, MeSH
AllitridiHMDB
AllylthiosulfinateHMDB, MeSH
Allylthiosulphinic acid allyl esterHMDB
DadsoHMDB
Diallyl disulfide-oxideHMDB, MeSH
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
Chemical FormulaC6H10OS2
Average Molecular Weight162.273
Monoisotopic Molecular Weight162.017306322
IUPAC Name3-[(prop-2-ene-1-sulfinyl)sulfanyl]prop-1-ene
Traditional Nameallicin
CAS Registry Number539-86-6
SMILES
C=CCSS(=O)CC=C
InChI Identifier
InChI=1S/C6H10OS2/c1-3-5-8-9(7)6-4-2/h3-4H,1-2,5-6H2
InChI KeyJDLKFOPOAOFWQN-UHFFFAOYSA-N
Chemical Taxonomy
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
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point25 °CNot Available
Boiling Point248.60 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility24 mg/mL at 10 °CNot Available
LogP1.133 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility6.13 g/LALOGPS
logP10(1.16) g/LALOGPS
logP10(2.02) g/LChemAxon
logS10(-1.4) g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+134.91931661259
DarkChem[M-H]-131.99131661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AllicinC=CCSS(=O)CC=C1788.2Standard polar33892256
AllicinC=CCSS(=O)CC=C1236.7Standard non polar33892256
AllicinC=CCSS(=O)CC=C1183.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Allicin GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9100000000-afcc42c2c1bd90b0e3842017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Allicin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Allicin 6V, Positive-QTOFsplash10-03di-5900000000-c7e9724fe1ff5ad98c3f2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allicin 10V, Negative-QTOFsplash10-0229-1900000000-a892e3c38e5a1381bfd62015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allicin 20V, Negative-QTOFsplash10-00di-8900000000-5679f84e236fe52171f12015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allicin 40V, Negative-QTOFsplash10-000l-9100000000-938b07f1d7929cac2c102015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allicin 10V, Negative-QTOFsplash10-00di-9000000000-cab08c5e5fb2515b21e02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allicin 20V, Negative-QTOFsplash10-00di-9000000000-783053aa8c1ac33a048a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allicin 40V, Negative-QTOFsplash10-00di-9000000000-38be7df051153b3a0b982021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allicin 10V, Positive-QTOFsplash10-03k9-9700000000-734a318e76fb991aae762015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allicin 20V, Positive-QTOFsplash10-00dl-9500000000-31a6285b63158ade86a32015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allicin 40V, Positive-QTOFsplash10-0096-9000000000-554fb97cc2ab4464f9482015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allicin 10V, Positive-QTOFsplash10-00di-9000000000-41d89692da06c3b22ce42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allicin 20V, Positive-QTOFsplash10-00di-9000000000-5573a83f7ab84f282f3c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allicin 40V, Positive-QTOFsplash10-00du-9000000000-04d80516e1e44b95f8992021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB11780
Phenol Explorer Compound IDNot Available
FooDB IDFDB012190
KNApSAcK IDC00001242
Chemspider ID58548
KEGG Compound IDC07600
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAllicin
METLIN IDNot Available
PubChem Compound65036
PDB IDNot Available
ChEBI ID28411
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1009901
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Luo DQ, Guo JH, Wang FJ, Jin ZX, Cheng XL, Zhu JC, Peng CQ, Zhang C: Anti-fungal efficacy of polybutylcyanoacrylate nanoparticles of allicin and comparison with pure allicin. J Biomater Sci Polym Ed. 2009;20(1):21-31. doi: 10.1163/156856208X393473. [PubMed:19105898 ]
  2. Younis F, Mirelman D, Rabinkov A, Rosenthal T: S-allyl-mercapto-captopril: a novel compound in the treatment of Cohen-Rosenthal diabetic hypertensive rats. J Clin Hypertens (Greenwich). 2010 Jun;12(6):451-5. doi: 10.1111/j.1751-7176.2010.00270.x. [PubMed:20591093 ]
  3. Makheja AN, Bailey JM: Antiplatelet constituents of garlic and onion. Agents Actions. 1990 Mar;29(3-4):360-3. [PubMed:2111084 ]
  4. Hasan N, Siddiqui MU, Toossi Z, Khan S, Iqbal J, Islam N: Allicin-induced suppression of Mycobacterium tuberculosis 85B mRNA in human monocytes. Biochem Biophys Res Commun. 2007 Apr 6;355(2):471-6. Epub 2007 Feb 7. [PubMed:17303073 ]
  5. Park SY, Cho SJ, Kwon HC, Lee KR, Rhee DK, Pyo S: Caspase-independent cell death by allicin in human epithelial carcinoma cells: involvement of PKA. Cancer Lett. 2005 Jun 16;224(1):123-32. Epub 2004 Nov 14. [PubMed:15911108 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .