S-ALLYLCYSTEINE

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27373435 | https://www.ncbi.nlm.nih.gov/pubmed/22685624/ |

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

Primary Target	Pharmacology	Condition	Potency
MAPK signaling pathway 26 Target ID: map04010 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19157822/	Inhibitor 8504
reactive species, •OH and ROO• 1 Target ID: reactive species, •OH and ROO• Sources: https://www.ncbi.nlm.nih.gov/pubmed/21995683/	Chelating Agent 139

Conditions

Condition	Modality	Highest Phase	Product
Ovarian cancer 160 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24362328	Primary	Basic research	Unknown Approved Use Unknown
Hepatocellular carcinoma 83 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22389672	Primary	Basic research	Unknown Approved Use Unknown
Oral cancer 13 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22011514	Primary	Preclinical	Unknown Approved Use Unknown
Prostate cancer 186 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22052207	Primary	Basic research	Unknown Approved Use Unknown
Type 2 diabetes mellitus 262 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27373435	Preventing	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Protective effects of cysteine analogues on acute myocardial ischemia: novel modulators of endogenous H(2)S production.	2010-05-15	19842912
Antioxidant strategy to rescue synaptosomes from oxidative damage and energy failure in neurotoxic models in rats: protective role of S-allylcysteine.	2010-01	19866339
S-allylcysteine modulates the expression of E-cadherin and inhibits the malignant progression of human oral cancer.	2009-12	19157822
A gas chromatography-mass spectrometry method for the quantitation of N-nitrosoproline and N-acetyl-S-allylcysteine in human urine: application to a study of the effects of garlic consumption on nitrosation.	2009-11-15	19643074
S-propargyl-cysteine protects both adult rat hearts and neonatal cardiomyocytes from ischemia/hypoxia injury: the contribution of the hydrogen sulfide-mediated pathway.	2009-08	19546814
S-allylcysteine attenuates renal injury by altering the expressions of iNOS and matrix metallo proteinase-2 during cyclosporine-induced nephrotoxicity in Wistar rats.	2009-08	19391111
Enabling olefin metathesis on proteins: chemical methods for installation of S-allyl cysteine.	2009-07-07	19557258
Protein carbonylation in THP-1 cells induced by cigarette smoke extract via a copper-catalyzed pathway.	2009-07	19456128
S-allyl L-cysteine diminishes cerebral ischemia-induced mitochondrial dysfunctions in hippocampus.	2009-04-10	19401183
Preventive effect of S-allylcysteine on membrane-bound enzymes and glycoproteins in normal and isoproterenol-induced cardiac toxicity in male Wistar rats.	2008-12	19067678
Purification and characterization of flavin-containing monooxygenase isoform 3 from rat kidney microsomes.	2008-12	18775983
Protective effect of S-allylcysteine against cyclophosphamide-induced bladder hemorrhagic cystitis in mice.	2008-11	18786597
Alleviative effects of s-allyl cysteine and s-ethyl cysteine on MCD diet-induced hepatotoxicity in mice.	2008-11	18786595
Multitargeted prevention and therapy of cancer by diallyl trisulfide and related Allium vegetable-derived organosulfur compounds.	2008-10-08	18579286
Lipid peroxidation, mitochondrial dysfunction and neurochemical and behavioural deficits in different neurotoxic models: protective role of S-allylcysteine.	2008-10	18985488
Chromium (VI)-induced oxidative stress and apoptosis is reduced by garlic and its derivative S-allylcysteine through the activation of Nrf2 in the hepatocytes of Wistar rats.	2008-10	18548744
Abeta mediated diminution of MTT reduction--an artefact of single cell culture?	2008-09-18	18800168
Allyl sulfides are privileged substrates in aqueous cross-metathesis: application to site-selective protein modification.	2008-07-30	18593118
S-allylcysteine ameliorates ischemia and reperfusion induced renal damage.	2008-06	18381751
Antioxidant and iron-binding properties of curcumin, capsaicin, and S-allylcysteine reduce oxidative stress in rat brain homogenate.	2008-05-14	18422331
S-Allylcysteine reduces breast tumor cell adhesion and invasion.	2008-03-07	18190785
Cytoplasmic calcium mediates oxidative damage in an excitotoxic /energetic deficit synergic model in rats.	2008-03	18364032
Prevention of N-nitrosodiethylamine-induced hepatocarcinogenesis by S-allylcysteine.	2008-03	18185914
Naringenin reduces tumor size and weight lost in N-methyl-N'-nitro-N-nitrosoguanidine-induced gastric carcinogenesis in rats.	2008-02	19083396
Anti-amyloidogenic activity of S-allyl-L-cysteine and its activity to destabilize Alzheimer's beta-amyloid fibrils in vitro.	2007-12-18	18023978
Hypoglycemic effect of aqueous shallot and garlic extracts in rats with fructose-induced insulin resistance.	2007-11	18299719
Role of garlic in the prevention of ischemia-reperfusion injury.	2007-11	17966137
Hydrogen sulfide preconditioning by garlic when it starts to smell.	2007-11	17873010
S-allylcysteine mediates cardioprotection in an acute myocardial infarction rat model via a hydrogen sulfide-mediated pathway.	2007-11	17766469
Renoprotective and antihypertensive effects of S-allylcysteine in 5/6 nephrectomized rats.	2007-11	17686953
S-allylcysteine scavenges singlet oxygen and hypochlorous acid and protects LLC-PK(1) cells of potassium dichromate-induced toxicity.	2007-10	17576034
Protective and alleviative effects from 4 cysteine-containing compounds on ethanol-induced acute liver injury through suppression of oxidation and inflammation.	2007-09	17995665
Amyloid beta-protein potentiates tunicamycin-induced neuronal death in organotypic hippocampal slice cultures.	2007-07-13	17560726
Role of caspase-12 in amyloid beta-peptide-induced toxicity in organotypic hippocampal slices cultured for long periods.	2007-05	17452809
Aged garlic extract and S-allyl cysteine prevent formation of advanced glycation endproducts.	2007-04-30	17321518
S-allyl cysteine prevents CCl(4)-induced acute liver injury in rats.	2007-04	17454131
S-allylcysteine, a water-soluble garlic derivative, suppresses the growth of a human androgen-independent prostate cancer xenograft, CWR22R, under in vivo conditions.	2007-04	17155983
Effect of heating on peroxynitrite scavenging capacity of garlic.	2007-04	17126976
S-allylcysteine ameliorates isoproterenol-induced cardiac toxicity in rats by stabilizing cardiac mitochondrial and lysosomal enzymes.	2007-02-13	17182065
Effect of aged garlic extract on APP processing and tau phosphorylation in Alzheimer's transgenic model Tg2576.	2006-12-06	16842945
A novel anticancer effect of garlic derivatives: inhibition of cancer cell invasion through restoration of E-cadherin expression.	2006-11	16675472
Increased expression of heat shock protein 72 protects renal proximal tubular cells from gentamicin-induced injury.	2006-10	17043427
Structure-activity relationship of neuroprotective and reactive oxygen species scavenging activities for allium organosulfur compounds.	2006-09-06	16939308
S-Allylcysteine prevents the rat from 3-nitropropionic acid-induced hyperactivity, early markers of oxidative stress and mitochondrial dysfunction.	2006-09	16806549
S-Allyl-L-cysteine attenuates cerebral ischemic injury by scavenging peroxynitrite and inhibiting the activity of extracellular signal-regulated kinase.	2006-08	17015261
Dietary S-allyl-L-cysteine reduces mortality with decreased incidence of stroke and behavioral changes in stroke-prone spontaneously hypertensive rats.	2006-08	16926510
Preventive effect of S-allylcysteine on lipid peroxides and antioxidants in normal and isoproterenol-induced cardiotoxicity in rats: a histopathological study.	2006-07-05	16757080
N-acetylcysteine selectively protects cerebellar granule cells from 4-hydroxynonenal-induced cell death.	2006-07	16675054
The antioxidant properties of garlic compounds: allyl cysteine, alliin, allicin, and allyl disulfide.	2006	16822206
Chemoprotection against N-methyl-n'-nitro-N-nitrosoguanidine-induced oxidative stress by s-allylcysteine, a garlic constituent, in wistar rats.	2003	20021185

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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 `Mon Mar 31 19:41:26 GMT 2025` Edited by `admin` on `Mon Mar 31 19:41:26 GMT 2025`
Record UNII	81R3X99M15
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

S-ALLYL-L-CYSTEINE

Preferred Name

English

S-ALLYLCYSTEINE

Systematic Name

English

(2R)-3-(ALLYLTHIO)-2-AMINOPROPANOIC ACID

Systematic Name

English

S-(2-PROPENYL)-L-CYSTEINE

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

(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