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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:18:04 UTC

Update Date

2022-03-07 02:53:46 UTC

HMDB ID

HMDB0033566

Secondary Accession Numbers

HMDB33566

Metabolite Identification

Common Name

Ajoene

Description

Ajoene 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -4.977   4.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.358   0.151   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.644   4.771   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.025  -0.619   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.025   4.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.310   4.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.691   4.771   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.691   0.151   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.025   2.461   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.357   2.461   0.000  0.00  0.00           O+0
HETATM   11  S   UNK     0      -0.976   4.771   0.000  0.00  0.00           S+0
HETATM   12  S   UNK     0       0.357   4.001   0.000  0.00  0.00           S+0
HETATM   13  S   UNK     0       1.691   1.691   0.000  0.00  0.00           S+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    6                                                       
CONECT    4    2    8                                                       
CONECT    5    7    9                                                       
CONECT    6    3   11                                                       
CONECT    7    5   12                                                       
CONECT    8    4   13                                                       
CONECT    9    5   13                                                       
CONECT   10   13                                                            
CONECT   11    6   12                                                       
CONECT   12    7   11                                                       
CONECT   13    8    9   10                                                  
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

COMPND    HMDB0033566
HETATM    1  C1  UNL     1       6.114   0.340   1.434  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.471  -0.164   0.403  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.029   0.072   0.259  1.00  0.00           C  
HETATM    4  S1  UNL     1       3.151  -1.518   0.251  1.00  0.00           S  
HETATM    5  S2  UNL     1       1.065  -1.270   0.047  1.00  0.00           S  
HETATM    6  C4  UNL     1       0.543  -1.259  -1.655  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.434  -0.444  -1.997  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.027   0.409  -0.937  1.00  0.00           C  
HETATM    9  S3  UNL     1      -2.785  -0.046  -0.867  1.00  0.00           S  
HETATM   10  O1  UNL     1      -2.863  -1.526  -0.555  1.00  0.00           O  
HETATM   11  C7  UNL     1      -3.630   0.922   0.391  1.00  0.00           C  
HETATM   12  C8  UNL     1      -5.047   0.498   0.388  1.00  0.00           C  
HETATM   13  C9  UNL     1      -5.591  -0.014   1.476  1.00  0.00           C  
HETATM   14  H1  UNL     1       5.616   0.926   2.184  1.00  0.00           H  
HETATM   15  H2  UNL     1       7.190   0.180   1.569  1.00  0.00           H  
HETATM   16  H3  UNL     1       5.971  -0.753  -0.351  1.00  0.00           H  
HETATM   17  H4  UNL     1       3.860   0.518  -0.751  1.00  0.00           H  
HETATM   18  H5  UNL     1       3.611   0.782   0.983  1.00  0.00           H  
HETATM   19  H6  UNL     1       1.034  -1.914  -2.354  1.00  0.00           H  
HETATM   20  H7  UNL     1      -0.812  -0.381  -3.035  1.00  0.00           H  
HETATM   21  H8  UNL     1      -0.538   0.296   0.030  1.00  0.00           H  
HETATM   22  H9  UNL     1      -0.997   1.490  -1.203  1.00  0.00           H  
HETATM   23  H10 UNL     1      -3.191   0.700   1.374  1.00  0.00           H  
HETATM   24  H11 UNL     1      -3.497   2.000   0.207  1.00  0.00           H  
HETATM   25  H12 UNL     1      -5.617   0.614  -0.507  1.00  0.00           H  
HETATM   26  H13 UNL     1      -6.639  -0.338   1.505  1.00  0.00           H  
HETATM   27  H14 UNL     1      -4.987  -0.119   2.368  1.00  0.00           H  
CONECT    1    2    2   14   15
CONECT    2    3   16
CONECT    3    4   17   18
CONECT    4    5
CONECT    5    6
CONECT    6    7    7   19
CONECT    7    8   20
CONECT    8    9   21   22
CONECT    9   10   10   11
CONECT   11   12   23   24
CONECT   12   13   13   25
CONECT   13   26   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Propenyl 3-(2-propenylsulfinyl)-1-propenyl disulfide, 9ci	HMDB
2-Propenyl-3-(2-propenylsulfinyl)-1-propenyl disulfide	HMDB
4,5,9-Trithia-1,6,11-dodecatriene 9-oxide	HMDB
4,5,9-Trithiadodeca-1,6,11-triene 9-oxide	HMDB
Allyl 3-allylsulfinyl-1-propenyl disulfide	HMDB
Disulfide, 2-propenyl 3-(2-propenylsulfinyl)-1-propenyl	HMDB
trans-Ajoene	HMDB

Chemical Formula

C₉H₁₄OS₃

Average Molecular Weight

234.402

Monoisotopic Molecular Weight

234.02067714

IUPAC Name

3-{[(1Z)-3-(prop-2-ene-1-sulfinyl)prop-1-en-1-yl]disulfanyl}prop-1-ene

Traditional Name

3-{[(1Z)-3-(prop-2-ene-1-sulfinyl)prop-1-en-1-yl]disulfanyl}prop-1-ene

CAS Registry Number

92285-01-3

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 Key

IXELFRRANAOWSF-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).

Kingdom

Organic compounds

Super Class

Organosulfur compounds

Class

Sulfoxides

Sub Class

Not Available

Direct Parent

Sulfoxides

Alternative Parents

Substituents

Allyl sulfur compound
Sulfoxide
Organic disulfide
Sulfenyl compound
Sulfinyl compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

sulfoxide (CHEBI:80707 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0033566)

Onion-family vegetable

Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Not Available

cyclooxygenase 2 inhibitor (HMDB: HMDB0033566)
EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor (HMDB: HMDB0033566)
cyclooxygenase inhibitor (HMDB: HMDB0033566)
lipoxygenase inhibitor (HMDB: HMDB0033566)
nitric-oxide inhibitor (HMDB: HMDB0033566)
prostaglandin inhibitor (HMDB: HMDB0033566)
prostaglandin-synthetase inhibitor (HMDB: HMDB0033566)

Industrial application

Manufacturing industry

Material processing agent

pesticide (HMDB: HMDB0033566)
protisticide (HMDB: HMDB0033566)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	3.44 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.4 g/L	ALOGPS
logP	2.58	ALOGPS
logP	1.66	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	16.01	ChemAxon
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	69 m³·mol⁻¹	ChemAxon
Polarizability	24.81 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	154.12	31661259
DarkChem	[M-H]-	149.837	31661259
DeepCCS	[M+H]+	146.639	30932474
DeepCCS	[M-H]-	143.748	30932474
DeepCCS	[M-2H]-	180.425	30932474
DeepCCS	[M+Na]+	155.861	30932474
AllCCS	[M+H]+	150.7	32859911
AllCCS	[M+H-H2O]+	147.5	32859911
AllCCS	[M+NH4]+	153.7	32859911
AllCCS	[M+Na]+	154.6	32859911
AllCCS	[M-H]-	149.2	32859911
AllCCS	[M+Na-2H]-	150.7	32859911
AllCCS	[M+HCOO]-	152.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ajoene	C=CCSS\C=C/CS(=O)CC=C	2776.1	Standard polar	33892256
Ajoene	C=CCSS\C=C/CS(=O)CC=C	1854.2	Standard non polar	33892256
Ajoene	C=CCSS\C=C/CS(=O)CC=C	1781.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ajoene GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9300000000-38a71ef9ab244c72057d	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ajoene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ajoene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ajoene 10V, Positive-QTOF	splash10-000l-7890000000-11928f7c30159af165e8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ajoene 20V, Positive-QTOF	splash10-0006-9600000000-c607fc1496412765e8c5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ajoene 40V, Positive-QTOF	splash10-006x-9200000000-a2836ecdf1469af5047c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ajoene 10V, Negative-QTOF	splash10-0016-6960000000-e17a4526d3baecc4e388	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ajoene 20V, Negative-QTOF	splash10-0079-9300000000-d62719e8491d22e01b5c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ajoene 40V, Negative-QTOF	splash10-0f72-9300000000-e0cce5cae13d413bf294	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ajoene 10V, Positive-QTOF	splash10-000i-5940000000-2ff7b7a62d176c1fb383	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ajoene 20V, Positive-QTOF	splash10-0079-9400000000-cb9a19f42f5eeb7c8908	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ajoene 40V, Positive-QTOF	splash10-00di-9000000000-c468260d51fc7a1b3b0d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ajoene 10V, Negative-QTOF	splash10-00di-9310000000-a37b89564227f0a2bab0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ajoene 20V, Negative-QTOF	splash10-00dr-9200000000-110a3f385d2a123a74ca	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ajoene 40V, Negative-QTOF	splash10-000i-9100000000-1d553532a99796a2a70b	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ajoene

METLIN ID

Not Available

PubChem Compound

9881148

PDB ID

Not Available

ChEBI ID

80707

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1631421

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
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 ]
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 ]
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 ]
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 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Ajoene (HMDB0033566)

MOL for HMDB0033566 (Ajoene)

3D MOL for HMDB0033566 (Ajoene)

3D SDF for HMDB0033566 (Ajoene)

3D-SDF for HMDB0033566 (Ajoene)

PDB for HMDB0033566 (Ajoene)

3D PDB for HMDB0033566 (Ajoene)

SMILES for HMDB0033566 (Ajoene)

INCHI for HMDB0033566 (Ajoene)

Structure for HMDB0033566 (Ajoene)

3D Structure for HMDB0033566 (Ajoene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra