ChemFOnt: Showing chemical card for cis-Ajoene (CFc000333201)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:13:04 UTC

Chemfont ID

CFc000333201

Molecule Identification

Common Name

cis-Ajoene

Definition

Ajoene is a member of the class of compounds known as sulfoxides. Sulfoxides are compounds containing a sulfoxide functional group, with the structure RS(=O)R' (R,R' not H). Ajoene is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). Ajoene can be found in garlic, onion-family vegetables, and soft-necked garlic, which makes ajoene a potential biomarker for the consumption of these food products. The name (and pronunciation) is derived from "ajo", the Spanish word for garlic. It is found as a mixture of up to four isomers, which differ in terms of the stereochemistry of central alkene (E- vs Z-) and the chirality of the sulfoxide .

Structure

MOL SDF PDB SMILES InChI

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

92285-00-2

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 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0033566)
Cell membrane (HMDB: HMDB0033566)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033566)

Source

Exogenous

Exogenous (HMDB: HMDB0033566)

Food

Food (HMDB: HMDB0033566)

Herb and spice

Herb

Garlic (FooDB: FOOD00008)
Soft-necked garlic (FooDB: FOOD00850)

Endogenous

Plant

Plant (HMDB: HMDB0033566)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Antineoplastic agent

Anticancer agent (HMDB: HMDB0033566)

Antimicrobial agent (HMDB: HMDB0033566)

Manufacturing industry

Laboratory chemical

Laboratory chemical (HMDB: HMDB0033566)

Biological role

Nutrient (HMDB: HMDB0033566)

Physical Properties

Predicted 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