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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 of DIALLYL SULFIDE

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

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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: p53/Puma signaling pathway
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
A pleiotropic response to phenobarbital-type enzyme inducers in the F344/NCr rat. Effects of chemicals of varied structure.
1992 Mar 3
Garlic ameliorates hyperlipidemia in chronic aminonucleoside nephrosis.
2000 Aug
Removal of glutathione produces apoptosis and necrosis in HepG2 cells overexpressing CYP2E1.
2001 Apr
Plant foods and risk of gastric cancer: a case-control study in Uruguay.
2001 Aug
[Status of and prospect on experimental studies of single Chinese herb inducing tumor cell apoptosis].
2001 Jan
CYP2E1-dependent toxicity and up-regulation of antioxidant genes.
2001 Jan-Feb
In-vitro antimicrobial activity of four diallyl sulphides occurring naturally in garlic and Chinese leek oils.
2001 Jul
Screening of organosulfur compounds as inhibitors of human CYP2A6.
2001 Jul
Diallyl sulfide--a flavour component from garlic (Allium sativum) attenuates lipid peroxidation in mice infected with Trichinella spiralis.
2001 May
Effect of diallyl sulfide and diallyl disulfide, the active principles of garlic, on the aflatoxin B(1)-induced DNA damage in primary rat hepatocytes.
2001 May 31
Etiology and chemoprevention of esophageal squamous cell carcinoma.
2001 Nov
Chemopreventive allylthiopyridazine derivatives induce apoptosis in SK-Hep-1 hepatocarcinoma cells through a caspase-3-dependent mechanism.
2001 Nov
A pilot study to determine the effectiveness of garlic oil capsules in the treatment of dyspeptic patients with Helicobacter pylori.
2001 Sep
Anti-tumour-promoting action of Allium constituents.
2002
Alleviation of cyclophosphamide-induced urotoxicity by naturally occurring sulphur compounds.
2002 Dec
Antioxidant and pro-oxidant effects of a manganese porphyrin complex against CYP2E1-dependent toxicity.
2002 Jul 1
Cyclosporine A protects against arachidonic acid toxicity in rat hepatocytes: role of CYP2E1 and mitochondria.
2002 Jun
Effects of food materials on removal of Allium-specific volatile sulfur compounds.
2002 Jun 19
Cytochrome P450 phenotypic ratios for predicting herb-drug interactions in humans.
2002 Sep
Prevention of chemical carcinogen DNA binding and inhibition of nuclear RNA polymerase activity by organosulfur compounds as the possible mechanisms for their anticancer initiation and proliferation effects.
2003
Antigenotoxic potential of certain dietary constituents.
2003
Protective effect of diallyl sulfide on oxidative stress and nephrotoxicity induced by gentamicin in rats.
2003 Dec
Garlic extract and two diallyl sulphides inhibit methicillin-resistant Staphylococcus aureus infection in BALB/cA mice.
2003 Dec
The combined effects of garlic oil and fish oil on the hepatic antioxidant and drug-metabolizing enzymes of rats.
2003 Feb
Cytochrome P450 2E1 responsiveness in the promoter of glutamate-cysteine ligase catalytic subunit.
2003 Jan
Protective action on human LDL against oxidation and glycation by four organosulfur compounds derived from garlic.
2003 Mar
The inhibition of superoxide production in EL4 lymphoma cells overexpressing growth hormone.
2003 May
Comparative study of extraction techniques for determination of garlic flavor components by gas chromatography-mass spectrometry.
2003 Oct
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
Post-initiation modulating effects of allyl sulfides in rat hepatocarcinogenesis.
2004 Sep
Patents

Sample Use Guides

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
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 UTC 2023
Edited
by admin
on Fri Dec 15 19:12:51 UTC 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
FHFI   HSDB   MI   USP-RS  
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
Created by admin on Fri Dec 15 19:12:51 UTC 2023 , Edited by admin on Fri Dec 15 19:12:51 UTC 2023
JECFA EVALUATION ALLYL SULFIDE
Created by admin on Fri Dec 15 19:12:51 UTC 2023 , Edited by admin on Fri Dec 15 19:12:51 UTC 2023
CFR 21 CFR 172.515
Created by admin on Fri Dec 15 19:12:51 UTC 2023 , Edited by admin on Fri Dec 15 19:12:51 UTC 2023
Code System Code Type Description
ECHA (EC/EINECS)
209-775-1
Created by admin on Fri Dec 15 19:12:51 UTC 2023 , Edited by admin on Fri Dec 15 19:12:51 UTC 2023
PRIMARY
RXCUI
17376
Created by admin on Fri Dec 15 19:12:51 UTC 2023 , Edited by admin on Fri Dec 15 19:12:51 UTC 2023
PRIMARY RxNorm
FDA UNII
60G7CF7CWZ
Created by admin on Fri Dec 15 19:12:51 UTC 2023 , Edited by admin on Fri Dec 15 19:12:51 UTC 2023
PRIMARY
RS_ITEM_NUM
1636800
Created by admin on Fri Dec 15 19:12:51 UTC 2023 , Edited by admin on Fri Dec 15 19:12:51 UTC 2023
PRIMARY
EPA CompTox
DTXSID6060470
Created by admin on Fri Dec 15 19:12:51 UTC 2023 , Edited by admin on Fri Dec 15 19:12:51 UTC 2023
PRIMARY
MERCK INDEX
m1558
Created by admin on Fri Dec 15 19:12:51 UTC 2023 , Edited by admin on Fri Dec 15 19:12:51 UTC 2023
PRIMARY Merck Index
MESH
C038491
Created by admin on Fri Dec 15 19:12:51 UTC 2023 , Edited by admin on Fri Dec 15 19:12:51 UTC 2023
PRIMARY
CAS
592-88-1
Created by admin on Fri Dec 15 19:12:51 UTC 2023 , Edited by admin on Fri Dec 15 19:12:51 UTC 2023
PRIMARY
NSC
20947
Created by admin on Fri Dec 15 19:12:51 UTC 2023 , Edited by admin on Fri Dec 15 19:12:51 UTC 2023
PRIMARY
JECFA MONOGRAPH
105
Created by admin on Fri Dec 15 19:12:51 UTC 2023 , Edited by admin on Fri Dec 15 19:12:51 UTC 2023
PRIMARY
HSDB
7333
Created by admin on Fri Dec 15 19:12:51 UTC 2023 , Edited by admin on Fri Dec 15 19:12:51 UTC 2023
PRIMARY
PUBCHEM
11617
Created by admin on Fri Dec 15 19:12:51 UTC 2023 , Edited by admin on Fri Dec 15 19:12:51 UTC 2023
PRIMARY
NCI_THESAURUS
C68524
Created by admin on Fri Dec 15 19:12:51 UTC 2023 , Edited by admin on Fri Dec 15 19:12:51 UTC 2023
PRIMARY
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