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Details

Stereochemistry ABSOLUTE
Molecular Formula C6H11NO2S
Molecular Weight 161.222
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of S-ALLYLCYSTEINE

SMILES

N[C@@H](CSCC=C)C(O)=O

InChI

InChIKey=ZFAHNWWNDFHPOH-YFKPBYRVSA-N
InChI=1S/C6H11NO2S/c1-2-3-10-4-5(7)6(8)9/h2,5H,1,3-4,7H2,(H,8,9)/t5-/m0/s1

HIDE SMILES / InChI

Molecular Formula C6H11NO2S
Molecular Weight 161.222
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

S-Allylcysteine (SAC), the most abundant organosulfur compound in aged garlic extract, has multifunctional activity via different mechanisms and neuroprotective effects that are exerted probably via its antioxidant or free radical scavenger action. Anticancer effects of SAC were reported in prostate cancer, breast cancer, oral cavity cancer, non-small cell lung cancer, neuroblastoma, and hepatocellular carcinoma through the restoration of E-cadherin, the reduction of Slug and matrix metalloproteinase (MMP) protein expression, and stimulating apoptotic pathways. In addition, recently was revealed, that SAC might have imperative implications for the deterrence and early treatment of type 2 diabetes by reducing the influx of glucose in the polyol pathway, thereby elevating the GSH level and reducing the activities of aldose reductase (AR) and sorbitol dehydrogenase (SDH).

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: reactive species, •OH and ROO•
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Antiproliferative effects of S-allylmercaptocysteine on colon cancer cells when tested alone or in combination with sulindac sulfide.
2001 Jan 15
Induction of histone acetylation and inhibition of growth of mouse erythroleukemia cells by S-allylmercaptocysteine.
2002
Effect of naturally occurring organosulfur compounds on nitric oxide production in lipopolysaccharide-activated macrophages.
2002 Jun 14
Effect of garlic on cardiovascular disorders: a review.
2002 Nov 19
Effect of S-allylcysteine on oxidant-antioxidant status during N-methyl-N'-nitro-N-nitrosoguanidine and saturated sodium chloride-induced gastric carcinogenesis in Wistar rats.
2003
S-allyl-L-cysteine selectively protects cultured rat hippocampal neurons from amyloid beta-protein- and tunicamycin-induced neuronal death.
2003
Antioxidant S-allylcysteine prevents gentamicin-induced oxidative stress and renal damage.
2003 Aug 1
Garlic [Allium sativum]: a review of its potential use as an anti-cancer agent.
2003 Feb
S-allylcysteine inhibits circulatory lipid peroxidation and promotes antioxidants in N-nitrosodiethylamine-induced carcinogenesis.
2003 Jan-Feb
High-performance ion-pair chromatography method for simultaneous analysis of alliin, deoxyalliin, allicin and dipeptide precursors in garlic products using multiple mass spectrometry and UV detection.
2003 Mar 28
Protective effect of S-allyl-L-cysteine, a garlic compound, on amyloid beta-protein-induced cell death in nerve growth factor-differentiated PC12 cells.
2003 May
Neurotoxicity induced by amyloid beta-peptide and ibotenic acid in organotypic hippocampal cultures: protection by S-allyl-L-cysteine, a garlic compound.
2003 Sep 19
Altered cytokeratin expression during chemoprevention of hamster buccal pouch carcinogenesis by S-allylcysteine.
2003 Sep-Oct
S-Allylcysteine prevents amyloid-beta peptide-induced oxidative stress in rat hippocampus and ameliorates learning deficits.
2004 Apr 12
S-allylmercaptocysteine scavenges hydroxyl radical and singlet oxygen in vitro and attenuates gentamicin-induced oxidative and nitrosative stress and renal damage in vivo.
2004 Apr 30
S-Allylcysteine, a garlic-derived antioxidant, ameliorates quinolinic acid-induced neurotoxicity and oxidative damage in rats.
2004 Dec
Influence of organosulphur compounds from garlic on the secretion of matrix metalloproteinases and their inhibitor TIMP-1 by cultured HUVEC cells.
2004 Jul
Antioxidative and antiglycative effects of six organosulfur compounds in low-density lipoprotein and plasma.
2004 Jun 2
Protective effect of S-allylcysteine and lycopene in combination against N-methyl-N'-nitro-N-nitrosoguanidine-induced genotoxicity.
2004 Mar-Apr
Effect of five cysteine-containing compounds on three lipogenic enzymes in Balb/cA mice consuming a high saturated fat diet.
2004 Sep
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
Peroxynitrite decomposition catalyst ameliorates renal damage and protein nitration in cisplatin-induced nephrotoxicity in rats.
2004 Sep 30
Bench-to-bedside review: Amelioration of acute renal impairment using ethyl pyruvate.
2005
Combination of S-allylcysteine and lycopene induces apoptosis by modulating Bcl-2, Bax, Bim and caspases during experimental gastric carcinogenesis.
2005 Aug
Synthesis of the flavour precursor, alliin, in garlic tissue cultures.
2005 Jan
Aminotransferase, L-amino acid oxidase and beta-lyase reactions involving L-cysteine S-conjugates found in allium extracts. Relevance to biological activity?
2005 Jan 15
Combination chemoprevention of experimental gastric carcinogenesis by s-allylcysteine and lycopene: modulatory effects on glutathione redox cycle antioxidants.
2005 Winter
Effect of aged garlic extract on APP processing and tau phosphorylation in Alzheimer's transgenic model Tg2576.
2006 Dec 6
Protective effect of S-allylcysteine on 3-nitropropionic acid-induced lipid peroxidation and mitochondrial dysfunction in rat brain synaptosomes.
2006 Jan 30
1H-15N NMR studies of the complex bis(S-allyl-L-cysteinate)palladium(II).
2006 May 15
Increased expression of heat shock protein 72 protects renal proximal tubular cells from gentamicin-induced injury.
2006 Oct
Structure-activity relationship of neuroprotective and reactive oxygen species scavenging activities for allium organosulfur compounds.
2006 Sep 6
S-allylcysteine, a water-soluble garlic derivative, suppresses the growth of a human androgen-independent prostate cancer xenograft, CWR22R, under in vivo conditions.
2007 Apr
Effect of heating on peroxynitrite scavenging capacity of garlic.
2007 Apr
Aged garlic extract and S-allyl cysteine prevent formation of advanced glycation endproducts.
2007 Apr 30
S-allylcysteine ameliorates isoproterenol-induced cardiac toxicity in rats by stabilizing cardiac mitochondrial and lysosomal enzymes.
2007 Feb 13
Amyloid beta-protein potentiates tunicamycin-induced neuronal death in organotypic hippocampal slice cultures.
2007 Jul 13
Renoprotective and antihypertensive effects of S-allylcysteine in 5/6 nephrectomized rats.
2007 Nov
S-allylcysteine scavenges singlet oxygen and hypochlorous acid and protects LLC-PK(1) cells of potassium dichromate-induced toxicity.
2007 Oct
Preventive effect of S-allylcysteine on membrane-bound enzymes and glycoproteins in normal and isoproterenol-induced cardiac toxicity in male Wistar rats.
2008 Dec
S-Allylcysteine reduces breast tumor cell adhesion and invasion.
2008 Mar 7
Antioxidant and iron-binding properties of curcumin, capsaicin, and S-allylcysteine reduce oxidative stress in rat brain homogenate.
2008 May 14
Abeta mediated diminution of MTT reduction--an artefact of single cell culture?
2008 Sep 18
S-allyl L-cysteine diminishes cerebral ischemia-induced mitochondrial dysfunctions in hippocampus.
2009 Apr 10
S-allylcysteine attenuates renal injury by altering the expressions of iNOS and matrix metallo proteinase-2 during cyclosporine-induced nephrotoxicity in Wistar rats.
2009 Aug
Antioxidant strategy to rescue synaptosomes from oxidative damage and energy failure in neurotoxic models in rats: protective role of S-allylcysteine.
2010 Jan
Patents

Patents

Sample Use Guides

in rats: Diabetes was induced in male albino Wistar rats by intraperitoneal administration of STZ (55 mg kg-1 bw-1) and NA (110 mg kg-1 bw-1). S-allylcysteine (SAC) (150 mg kg-1 bw-1) was orally administered to the rats with diabetes for 45 days to assess its effects on blood glucose, insulin, insulin resistance, glycated hemoglobin, aldose reductase (AR), sorbitol dehydrogenase (SDH), sorbitol, fructose, thiobarbituric acid-reactive substances (TBARS), hydroperoxide, hemoglobin and glutathione (GSH).
Route of Administration: Oral
S-allylcysteine (SAC) suppressed proliferation and induced apoptosis in human ovarian cancer cells in vitro. SAC (1-100 mmol/L) inhibited the proliferation of A2780 cells in dose- and time-dependent manners (the IC50 value was approximately 25 mmol/L at 48 h, and less than 6.25 mmol/L at 96 h). Furthermore, SAC dose-dependently inhibited the colony formation of A2780 cells. Treatment of A2780 cells with SAC resulted in G1/S phase arrest and induced apoptosis, accompanied by decreased expression of pro-caspase-3, Parp-1 and Bcl-2, and increased expression of active caspase-3 and Bax. SAC treatment significantly reduced the migration of A2780 cells, and markedly decreased the protein expression of Wnt5a, p-AKT and c-Jun, which were the key proteins involved in proliferation and metastasis.
Substance Class Chemical
Created
by admin
on Thu Jul 06 02:23:39 UTC 2023
Edited
by admin
on Thu Jul 06 02:23:39 UTC 2023
Record UNII
81R3X99M15
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
S-ALLYLCYSTEINE
Systematic Name English
(2R)-3-(ALLYLTHIO)-2-AMINOPROPANOIC ACID
Systematic Name English
S-(2-PROPENYL)-L-CYSTEINE
Systematic Name English
S-ALLYL-L-CYSTEINE
FHFI  
Systematic Name English
DEOXYALLIIN
Systematic Name English
S-ALLYL-LAEVO-CYSTEINE
Common Name English
S-ALLYL-L-CYSTEINE [USP-RS]
Common Name English
L-CYSTEINE, S-2-PROPENYL-
Systematic Name English
ALANINE, 3-(ALLYLTHIO)-
Systematic Name English
(2R)-2-AMINO-3-(PROP-2-EN-1-YLSULFANYL) PROPANOIC ACID
Systematic Name English
S-ALLYLCYSTEINE [INCI]
Common Name English
(R)-ALLYLTHIO-2-AMINOPROPANOIC ACID
Systematic Name English
NSC-96449
Code English
3-(ALLYLTHIO)-L-ALANINE
Systematic Name English
FEMA NO. 4322
Code English
ALANINE, 3-(ALLYLTHIO)-, L-
Systematic Name English
S-ALLYL-L-CYSTEINE [FHFI]
Common Name English
S-ALLYL-L-CYSTEINE (CONSTITUENT OF GARLIC) [DSC]
Common Name English
(+)-S-ALLYLCYSTEINE
Systematic Name English
L-CYSTEINE, S-2-PROPEN-1-YL-
Systematic Name English
Classification Tree Code System Code
JECFA EVALUATION S-ALLYL-L-CYSTEINE
Created by admin on Thu Jul 06 02:23:39 UTC 2023 , Edited by admin on Thu Jul 06 02:23:39 UTC 2023
NCI_THESAURUS C68520
Created by admin on Thu Jul 06 02:23:39 UTC 2023 , Edited by admin on Thu Jul 06 02:23:39 UTC 2023
NCI_THESAURUS C275
Created by admin on Thu Jul 06 02:23:39 UTC 2023 , Edited by admin on Thu Jul 06 02:23:39 UTC 2023
DSLD 4106 (Number of products:1)
Created by admin on Thu Jul 06 02:23:39 UTC 2023 , Edited by admin on Thu Jul 06 02:23:39 UTC 2023
Code System Code Type Description
WIKIPEDIA
S-Allylcysteine
Created by admin on Thu Jul 06 02:23:39 UTC 2023 , Edited by admin on Thu Jul 06 02:23:39 UTC 2023
PRIMARY
NCI_THESAURUS
C63658
Created by admin on Thu Jul 06 02:23:39 UTC 2023 , Edited by admin on Thu Jul 06 02:23:39 UTC 2023
PRIMARY
CHEBI
74077
Created by admin on Thu Jul 06 02:23:39 UTC 2023 , Edited by admin on Thu Jul 06 02:23:39 UTC 2023
PRIMARY
RS_ITEM_NUM
1013057
Created by admin on Thu Jul 06 02:23:39 UTC 2023 , Edited by admin on Thu Jul 06 02:23:39 UTC 2023
PRIMARY
NSC
96449
Created by admin on Thu Jul 06 02:23:39 UTC 2023 , Edited by admin on Thu Jul 06 02:23:39 UTC 2023
PRIMARY
EPA CompTox
DTXSID20894862
Created by admin on Thu Jul 06 02:23:39 UTC 2023 , Edited by admin on Thu Jul 06 02:23:39 UTC 2023
PRIMARY
CAS
21593-77-1
Created by admin on Thu Jul 06 02:23:39 UTC 2023 , Edited by admin on Thu Jul 06 02:23:39 UTC 2023
PRIMARY
MESH
C065299
Created by admin on Thu Jul 06 02:23:39 UTC 2023 , Edited by admin on Thu Jul 06 02:23:39 UTC 2023
PRIMARY
FDA UNII
81R3X99M15
Created by admin on Thu Jul 06 02:23:39 UTC 2023 , Edited by admin on Thu Jul 06 02:23:39 UTC 2023
PRIMARY
PUBCHEM
9793905
Created by admin on Thu Jul 06 02:23:39 UTC 2023 , Edited by admin on Thu Jul 06 02:23:39 UTC 2023
PRIMARY
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