DIALLYL SULFIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H10S
Molecular Weight	114.209
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C=CCSCC=C

InChI

InChIKey=UBJVUCKUDDKUJF-UHFFFAOYSA-N

InChI=1S/C6H10S/c1-3-5-7-6-4-2/h3-4H,1-2,5-6H2

HIDE SMILES / InChI

Molecular Formula	C6H10S
Molecular Weight	114.209
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22397993 | https://www.ncbi.nlm.nih.gov/pubmed/29266336 | https://www.ncbi.nlm.nih.gov/pubmed/25488545

Allyl sulfide or diallyl sulfide, a natural organosulfur compound, which is mostly obtained from the genus Allium plants, exhibits anticancer activities. This compound also possesses a protective role in cisplatin-induced nephrotoxicity via suppressing NF-κB downstream inflammatory proteins and p53/Puma signaling pathway. Besides, diallyl sulfide exerts protective properties in experimental Inflammatory bowel disease (IBD), an incurable disease which affects millions of people. It was also discovered, that diallyl sulfide may be effective in reducing ethanol-induced injury of cells thereby suggesting its potential to be used in drug formulations.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
p53/Puma signaling pathway 1 Target ID: p53/Puma signaling pathway Sources: https://www.ncbi.nlm.nih.gov/pubmed/29266336	Modulator 828

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cisplatin-induced nephrotoxicity 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29266336	Preventing		Preclinical	Unknown Approved Use Unknown
Inflammatory bowel disease 19 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25488545	Preventing		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
A pleiotropic response to phenobarbital-type enzyme inducers in the F344/NCr rat. Effects of chemicals of varied structure.	1992 Mar 3	1372805
Activation of cytochrome P450 gene expression in the rat brain by phenobarbital-like inducers.	2000 Sep	10945841
Relative activities of organosulfur compounds derived from onions and garlic in increasing tissue activities of quinone reductase and glutathione transferase in rat tissues.	2001	11962257
Inhibition of carcinogenesis and toxicity by dietary constituents.	2001	11764996
Antioxidants in chemoprevention of skin cancer.	2001	11225193
Removal of glutathione produces apoptosis and necrosis in HepG2 cells overexpressing CYP2E1.	2001 Apr	11329505
Effects of the garlic compound diallyl disulfide on the metabolism, adherence and cell cycle of HT-29 colon carcinoma cells: evidence of sensitive and resistant sub-populations.	2001 Aug	11470743
Cytochrome P4502E1 induction increases thioacetamide liver injury in diet-restricted rats.	2001 Aug	11454726
Antimutagenic activity of organosulfur compounds from Allium is associated with phase II enzyme induction.	2001 Aug 22	11448651
[Status of and prospect on experimental studies of single Chinese herb inducing tumor cell apoptosis].	2001 Jan	12577383
Ethanol enhances retinoic acid metabolism into polar metabolites in rat liver via induction of cytochrome P4502E1.	2001 Jan	11208727
CYP2E1-dependent toxicity and up-regulation of antioxidant genes.	2001 Jan-Feb	11173976
In-vitro antimicrobial activity of four diallyl sulphides occurring naturally in garlic and Chinese leek oils.	2001 Jul	11444776
Screening of organosulfur compounds as inhibitors of human CYP2A6.	2001 Jul	11408364
Diallyl sulfide--a flavour component from garlic (Allium sativum) attenuates lipid peroxidation in mice infected with Trichinella spiralis.	2001 May	11417909
In vitro activity of garlic oil and four diallyl sulphides against antibiotic-resistant Pseudomonas aeruginosa and Klebsiella pneumoniae.	2001 May	11328781
Anti-tumour-promoting action of Allium constituents.	2002	12484213
Use of factorial designs to optimize animal experiments and reduce animal use.	2002	12391398
In vivo effect of diallyl sulfide and cimetidine on phenacetin metabolism and bioavailability in rat.	2002	12136947
Spontaneous oxidative stress and liver tumors in mice lacking methionine adenosyltransferase 1A.	2002 Aug	12060674
Inhibition of human low density lipoprotein oxidation by active principles from spices.	2002 Jan	11936843
Effect of naturally occurring organosulfur compounds on nitric oxide production in lipopolysaccharide-activated macrophages.	2002 Jun 14	12044841
Inhibition of heterocyclic aromatic amine formation in fried ground beef patties by garlic and selected garlic-related sulfur compounds.	2002 Nov	12430700
Effect of garlic on cardiovascular disorders: a review.	2002 Nov 19	12537594
Cytochrome P450 phenotypic ratios for predicting herb-drug interactions in humans.	2002 Sep	12235448
Enhancement of glutathione and g-glutamylcysteine synthetase, the rate limiting enzyme of glutathione synthesis, by chemoprotective plant-derived food and beverage components in the human hepatoma cell line HepG2.	2003	12791507
Short-term acetaldehyde exposure depresses ventricular myocyte contraction: role of cytochrome P450 oxidase, xanthine oxidase, and lipid peroxidation.	2003 Apr	12711919
Interactions of herbs with cytochrome P450.	2003 Feb	12635815
The combined effects of garlic oil and fish oil on the hepatic antioxidant and drug-metabolizing enzymes of rats.	2003 Feb	12575903
Cytochrome P450 2E1 responsiveness in the promoter of glutamate-cysteine ligase catalytic subunit.	2003 Jan	12500194
Protective action on human LDL against oxidation and glycation by four organosulfur compounds derived from garlic.	2003 Mar	12784861
Comparative study of extraction techniques for determination of garlic flavor components by gas chromatography-mass spectrometry.	2003 Oct	12923610
Inhibition by allyl sulfides and phenethyl isothiocyanate of methyl-n-pentylnitrosamine depentylation by rat esophageal microsomes, human and rat CYP2E1, and Rat CYP2A3.	2004	15203378
Garlic metabolites fail to inhibit the activation of the transcription factor NF-kappaB and subsequent expression of the adhesion molecule E-selectin in human endothelial cells.	2004 Feb	14991270
Inhibition of N-acetyltransferase activity and gene expression in human colon cancer cell lines by diallyl sulfide.	2004 Feb	14667466
Reversal of P-glycoprotein-mediated multidrug resistance by diallyl sulfide in K562 leukemic cells and in mouse liver.	2004 Jun	14729595
Inhibitory activity of essential oils of garlic and onion against bacteria and yeasts.	2004 Mar	15035364
Signal transduction pathways leading to cell cycle arrest and apoptosis induction in cancer cells by Allium vegetable-derived organosulfur compounds: a review.	2004 Nov 2	15476856
Role of chemopreventive agents in cancer therapy.	2004 Nov 25	15488631
Involvement of cytochrome P450 2E1 in the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced mouse model of Parkinson's disease.	2004 Oct	15447662
Garlic's ability to prevent in vitro Cu2+-induced lipoprotein oxidation in human serum is preserved in heated garlic: effect unrelated to Cu2+-chelation.	2004 Sep 1	15341661

Patents

Sample Use Guides

In Vivo Use Guide

cisplatin-induced nephrotoxicity in rats: diallyl sulfide (DAS) was given at two dose levels; 50 and 100 mg/kg, orally for 4 consecutive days, starting one hour after administration of single dose of cisplatin (3.5 mg/kg, i.p.).

Route of Administration: Oral

In Vitro Use Guide

Diallyl sulfide (DAS), diallyl disulfide (DADS) and diallyl trisulfide (DATS) at 25 μM for 24-h and 48-h incubations promoted expression of drug resistant genes in colo 205 human colon cancer cells. Cells were treated with 25 uM DAS, DADS and DATS for 24 and 48 h and gene expression levels in colo 205 cells were determined for MRP1, MRP3, MRP4 and MRP6. Results indicated that DAS and DADS enhanced Mdr3 gene expression at the 48-h treatment, but did not affect MRP1, MRP4 and MRP6 gene expression in colo 205 cells. However, DAS and DADS inhibited the gene expressions of MRPs at 24 and 48-h treatment, and both inhibited MRP3 at 24-h treatment and inhibited MRP4 at 48 h treatment in colo 205 cells.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:12:51 GMT 2023` Edited by `admin` on `Fri Dec 15 19:12:51 GMT 2023`
Record UNII	60G7CF7CWZ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIALLYL SULFIDE

Systematic Name

English

DIALLYL SULPHIDE

Systematic Name

English

ALLYL SULFIDE [FHFI]

Common Name

English

DIALLYL MONOSULPHIDE

Common Name

English

ALLYL SULPHIDE

Systematic Name

English

ALLYL SULFIDE [MI]

Common Name

English

NSC-20947

Code

English

ALLYL SULFIDE [USP-RS]

Common Name

English

BIS(2-PROPENYL) SULPHIDE

Systematic Name

English

ALLYL SULFIDE

Systematic Name

English

1-PROPENE, 3,3'-THIOBIS-

Systematic Name

English

DIALLYL MONOSULFIDE

Common Name

English

DI(2-PROPENYL) SULPHIDE

Systematic Name

English

DIALLYL THIOETHER

Systematic Name

English

BIS(2-PROPENYL) SULFIDE

Systematic Name

English

ALLYL SULFIDE [HSDB]

Common Name

English

FEMA NO. 2042

Code

English

DI(2-PROPENYL) SULFIDE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C68520