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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:18:04 UTC
Update Date2022-03-07 02:53:46 UTC
HMDB IDHMDB0033566
Secondary Accession Numbers
  • HMDB33566
Metabolite Identification
Common NameAjoene
DescriptionAjoene is found in onion-family vegetables. Ajoene is isolated from garlic (Allium sativum) extracts. Nutriceutical with anti-cancer properties Ajoene is a chemical compound available from garlic (Allium sativum). The name (and pronunciation) is derived from "ajo", the Spanish word for garlic. It is found as a mixture of two isomers, E-, and Z- 4,5,9-trithiadodeca-1,6,11-triene 9-oxide. Ajoene, an unsaturated disulfide, is formed from the bonding of three allicin molecules. Allicin is a sulfinyl compound that gives garlic its strong odor and flavor. The release of allicin occurs after a garlic clove is crushed or finely chopped. Subsequent formation of ajoene occurs when allicin is dissolved in various solvents including edible oils. Ajoene is also found in garlic extract. Ajoene is most stable and most abundant in macerate of garlic (chopped garlic in edible oil)
Structure
Data?1563862425
Synonyms
ValueSource
2-Propenyl 3-(2-propenylsulfinyl)-1-propenyl disulfide, 9ciHMDB
2-Propenyl-3-(2-propenylsulfinyl)-1-propenyl disulfideHMDB
4,5,9-Trithia-1,6,11-dodecatriene 9-oxideHMDB
4,5,9-Trithiadodeca-1,6,11-triene 9-oxideHMDB
Allyl 3-allylsulfinyl-1-propenyl disulfideHMDB
Disulfide, 2-propenyl 3-(2-propenylsulfinyl)-1-propenylHMDB
trans-AjoeneHMDB
Chemical FormulaC9H14OS3
Average Molecular Weight234.402
Monoisotopic Molecular Weight234.02067714
IUPAC Name3-{[(1Z)-3-(prop-2-ene-1-sulfinyl)prop-1-en-1-yl]disulfanyl}prop-1-ene
Traditional Name3-{[(1Z)-3-(prop-2-ene-1-sulfinyl)prop-1-en-1-yl]disulfanyl}prop-1-ene
CAS Registry Number92285-01-3
SMILES
C=CCSS\C=C/CS(=O)CC=C
InChI Identifier
InChI=1S/C9H14OS3/c1-3-6-11-12-7-5-9-13(10)8-4-2/h3-5,7H,1-2,6,8-9H2/b7-5-
InChI KeyIXELFRRANAOWSF-ALCCZGGFSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sulfoxides. Sulfoxides are compounds containing a sulfoxide functional group, with the structure RS(=O)R' (R,R' not H).
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassSulfoxides
Sub ClassNot Available
Direct ParentSulfoxides
Alternative Parents
Substituents
  • Allyl sulfur compound
  • Sulfoxide
  • Organic disulfide
  • Sulfenyl compound
  • Sulfinyl compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Biological roleIndustrial application
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.44 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.4 g/LALOGPS
logP2.58ALOGPS
logP1.66ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)16.01ChemAxon
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity69 m³·mol⁻¹ChemAxon
Polarizability24.81 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+154.1231661259
DarkChem[M-H]-149.83731661259
DeepCCS[M+H]+146.63930932474
DeepCCS[M-H]-143.74830932474
DeepCCS[M-2H]-180.42530932474
DeepCCS[M+Na]+155.86130932474
AllCCS[M+H]+150.732859911
AllCCS[M+H-H2O]+147.532859911
AllCCS[M+NH4]+153.732859911
AllCCS[M+Na]+154.632859911
AllCCS[M-H]-149.232859911
AllCCS[M+Na-2H]-150.732859911
AllCCS[M+HCOO]-152.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AjoeneC=CCSS\C=C/CS(=O)CC=C2776.1Standard polar33892256
AjoeneC=CCSS\C=C/CS(=O)CC=C1854.2Standard non polar33892256
AjoeneC=CCSS\C=C/CS(=O)CC=C1781.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Ajoene GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-38a71ef9ab244c72057d2017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ajoene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ajoene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ajoene 10V, Positive-QTOFsplash10-000l-7890000000-11928f7c30159af165e82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ajoene 20V, Positive-QTOFsplash10-0006-9600000000-c607fc1496412765e8c52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ajoene 40V, Positive-QTOFsplash10-006x-9200000000-a2836ecdf1469af5047c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ajoene 10V, Negative-QTOFsplash10-0016-6960000000-e17a4526d3baecc4e3882016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ajoene 20V, Negative-QTOFsplash10-0079-9300000000-d62719e8491d22e01b5c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ajoene 40V, Negative-QTOFsplash10-0f72-9300000000-e0cce5cae13d413bf2942016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ajoene 10V, Positive-QTOFsplash10-000i-5940000000-2ff7b7a62d176c1fb3832021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ajoene 20V, Positive-QTOFsplash10-0079-9400000000-cb9a19f42f5eeb7c89082021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ajoene 40V, Positive-QTOFsplash10-00di-9000000000-c468260d51fc7a1b3b0d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ajoene 10V, Negative-QTOFsplash10-00di-9310000000-a37b89564227f0a2bab02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ajoene 20V, Negative-QTOFsplash10-00dr-9200000000-110a3f385d2a123a74ca2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ajoene 40V, Negative-QTOFsplash10-000i-9100000000-1d553532a99796a2a70b2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003580
KNApSAcK IDC00052510
Chemspider ID8056824
KEGG Compound IDC16757
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAjoene
METLIN IDNot Available
PubChem Compound9881148
PDB IDNot Available
ChEBI ID80707
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1631421
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Naganawa R, Iwata N, Ishikawa K, Fukuda H, Fujino T, Suzuki A: Inhibition of microbial growth by ajoene, a sulfur-containing compound derived from garlic. Appl Environ Microbiol. 1996 Nov;62(11):4238-42. [PubMed:8900018 ]
  2. Ledezma E, Apitz-Castro R: [Ajoene the main active compound of garlic (Allium sativum): a new antifungal agent]. Rev Iberoam Micol. 2006 Jun;23(2):75-80. [PubMed:16854181 ]
  3. Urbina JA, Marchan E, Lazardi K, Visbal G, Apitz-Castro R, Gil F, Aguirre T, Piras MM, Piras R: Inhibition of phosphatidylcholine biosynthesis and cell proliferation in Trypanosoma cruzi by ajoene, an antiplatelet compound isolated from garlic. Biochem Pharmacol. 1993 Jun 22;45(12):2381-7. [PubMed:8328978 ]
  4. Kaschula CH, Hunter R, Parker MI: Garlic-derived anticancer agents: structure and biological activity of ajoene. Biofactors. 2010 Jan-Feb;36(1):78-85. doi: 10.1002/biof.76. [PubMed:20108330 ]
  5. Srivastava KC, Tyagi OD: Effects of a garlic-derived principle (ajoene) on aggregation and arachidonic acid metabolism in human blood platelets. Prostaglandins Leukot Essent Fatty Acids. 1993 Aug;49(2):587-95. [PubMed:8415808 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .