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Showing Compound S-Allylcysteine (FDB012675)

Record Information
Version1.0
Creation date2010-04-08 22:10:18 UTC
Update date2019-11-26 03:07:21 UTC
Primary IDFDB012675
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameS-Allylcysteine
DescriptionS-Allylcysteine belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. S-Allylcysteine is a cooked and roasted tasting compound. S-Allylcysteine is found, on average, in the highest concentration within soft-necked garlics (Allium sativum L. var. sativum). S-Allylcysteine has also been detected, but not quantified in, several different foods, such as red onion, welsh onions (Allium fistulosum), garlics (Allium sativum), green onion, and onion-family vegetables. This could make S-allylcysteine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on S-Allylcysteine.
CAS Number21593-77-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
L-DeoxyallIInHMDB
S-2-Propenyl-L-cysteineHMDB, MeSH
S-Allyl-L -cysteineHMDB
Allyl cysteineMeSH, HMDB
2-Amino-3-(prop-2-en-1-ylsulfanyl)propanoateGenerator
2-Amino-3-(prop-2-en-1-ylsulphanyl)propanoateGenerator
2-Amino-3-(prop-2-en-1-ylsulphanyl)propanoic acidGenerator
S-AllylcysteineMeSH
L-Cysteine, S-2-propenyl-biospider
L-deoxyallIInbiospider
S-allyl-l -cysteinebiospider
Predicted Properties
PropertyValueSource
Water Solubility13.7 g/LALOGPS
logP-1.8ALOGPS
logP-1.8ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)2.53ChemAxon
pKa (Strongest Basic)9.14ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity42.09 m³·mol⁻¹ChemAxon
Polarizability16.85 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H11NO2S
IUPAC name2-amino-3-(prop-2-en-1-ylsulfanyl)propanoic acid
InChI IdentifierInChI=1S/C6H11NO2S/c1-2-3-10-4-5(7)6(8)9/h2,5H,1,3-4,7H2,(H,8,9)
InChI KeyZFAHNWWNDFHPOH-UHFFFAOYSA-N
Isomeric SMILESNC(CSCC=C)C(O)=O
Average Molecular Weight161.222
Monoisotopic Molecular Weight161.051049291
Classification
Description Belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentCysteine and derivatives
Alternative Parents
Substituents
  • Cysteine or derivatives
  • Alpha-amino acid
  • Amino acid
  • Allyl sulfur compound
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Thioether
  • Sulfenyl compound
  • Dialkylthioether
  • Carbonyl group
  • Amine
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Foods

Fruits and vegetables:

Herbs and spices:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 44.70%; H 6.88%; N 8.69%; O 19.85%; S 19.89%DFC
Melting PointMp 218°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -16.4 (H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSS-Allylcysteine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9000000000-6472ab7f2d2b13b42092Spectrum
Predicted GC-MSS-Allylcysteine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0007-9500000000-6130c45418f29c7eb2abSpectrum
Predicted GC-MSS-Allylcysteine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0296-5900000000-8c89fd146060416fb06f2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00fu-9300000000-9edb4d3a5be841c6a27e2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9000000000-8dde9c26474a4aa9cf9c2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0229-4900000000-5ea2674e8ab9863410c82017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9500000000-584904bc5c18c5d83a032017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0080-9100000000-847061c3a2deccc782b72017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dj-7900000000-cf1399bc43a29b3b3b3f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9200000000-ee198d96f7aa130ede352021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9000000000-55e1f534cff75732a9622021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-f82699e969ddcd674ff22021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0089-9100000000-9c1e17063ccb59bc374a2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-bfbf6eb00eab590319dc2021-09-23View Spectrum
NMRNot Available
ChemSpider ID88744
ChEMBL IDNot Available
KEGG Compound IDC16759
Pubchem Compound ID98280
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34323
CRC / DFC (Dictionary of Food Compounds) IDHJQ86-N:HJQ74-I
EAFUS ID103
Dr. Duke IDS-ALLYL-L-CYSTEINE|S-ALLYL-CYSTEINE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1593931
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Anti-aging52217 An agent that slows or reverses cellular aging, promoting youthful function. Its biological role involves protecting against oxidative stress and DNA damage. Therapeutically, it has applications in dermatology, gerontology, and regenerative medicine, with key medical uses including skin rejuvenation, reducing age-related diseases, and improving overall healthspan.DUKE
Anti-atherogenic38070 An agent that prevents or reduces the formation of atheromas (plaques) in arteries, thereby lowering the risk of cardiovascular disease. It inhibits the biological processes leading to atherosclerosis, and has therapeutic applications in managing hyperlipidemia, hypertension, and cardiovascular disease, with key medical uses including reducing inflammation and improving lipid profiles.DUKE
Anti-cancer35610 An agent that inhibits the growth and proliferation of cancer cells, used to treat and manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, to reduce tumor size, prevent metastasis, and improve patient survival.DUKE
Anti-cholesterogenicAn agent that inhibits cholesterol production, reducing total circulating cholesterol levels. It plays a biological role in lipid metabolism regulation. Therapeutically, it is used to manage hypercholesterolemia, preventing cardiovascular disease, and reducing the risk of heart attacks and strokes. Key medical uses include treating high cholesterol, atherosclerosis, and familial hypercholesterolemia.DUKE
Anti-diabetic52217 An agent that regulates blood sugar levels, enhancing insulin sensitivity or secretion. Therapeutically, it's used to manage diabetes, reducing symptoms and complications, and commonly prescribed to treat type 1 and 2 diabetes, as well as gestational diabetes.DUKE
Anti hepatotoxic62868 An agent that protects the liver from damage, reducing toxicity and promoting liver health. It plays a biological role in preventing liver injury and supporting liver function. Therapeutically, it is used to treat liver diseases, such as hepatitis and cirrhosis, and to counteract liver-damaging effects of certain medications and toxins.DUKE
Anti-melanomic35610 An agent that inhibits melanin production, reducing melanoma cell growth. It has therapeutic applications in treating skin cancers, particularly melanoma, and key medical uses include preventing tumor progression and metastasis, as well as managing pigmentation disorders.DUKE
Anti neuroblastomicAn agent that targets and inhibits the growth of neuroblastoma, a malignant tumor composed of neuroblasts, commonly found in the adrenal gland, used therapeutically to treat neuroblastoma, particularly in pediatric cancer patients.DUKE
Anti NF-kappa-B35222 An agent that inhibits the activity of NF-kappa-B, a protein complex involved in inflammation and immune responses. It reduces inflammation and has therapeutic applications in managing autoimmune diseases, cancer, and inflammatory disorders, with key medical uses including treatment of rheumatoid arthritis, asthma, and certain types of cancer.DUKE
Anti-oxidant22586 An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.DUKE
Anti proliferantAn agent that prevents or inhibits cell growth and division, used therapeutically to treat cancer, manage tumor growth, and prevent restenosis after angioplasty, reducing abnormal cell proliferation.DUKE
Anti radicularAn agent that relieves inflammation or irritation of the nerve root of a tooth, reducing pain and discomfort. Its biological role is to target and alleviate radicular pain, with therapeutic applications in endodontics and key medical uses in root canal treatments and tooth sensitivity management.DUKE
Antitumor35610 An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.DUKE
Chemopreventive35610 An agent that prevents or delays the development of cancer, reducing the risk of tumor formation and progression. It plays a biological role in inhibiting carcinogenesis, and has therapeutic applications in cancer prevention, with key medical uses including reducing the risk of colorectal, breast, and prostate cancers.DUKE
Glutathione-sparingAn agent that conserves or increases glutathione levels, a crucial antioxidant in cells. It plays a biological role in protecting against oxidative stress and cell damage. Therapeutically, glutathione-sparing agents have applications in managing neurodegenerative diseases, cancer, and liver disorders, with key medical uses including reducing chemotherapy side effects and treating liver diseases.DUKE
Hepatoprotective62868 An agent that protects the liver from damage, promoting liver health and function. It plays a biological role in reducing oxidative stress and inflammation, and has therapeutic applications in managing liver diseases, such as hepatitis and cirrhosis, and key medical uses in treating drug-induced liver injury and toxicities.DUKE
HypocholesterolemicAn agent that lowers cholesterol levels in the blood, playing a crucial role in preventing cardiovascular disease. Therapeutically, it is used to manage hyperlipidemia and reduce the risk of heart disease, with key medical applications including the treatment of high cholesterol, atherosclerosis, and coronary artery disease.DUKE
Immunostimulant50847 An agent that stimulates the immune system, enhancing its response to infections and diseases. Therapeutically, it boosts the body's natural defenses, commonly used to treat immunodeficiency disorders, prevent infections, and support cancer treatment, as well as manage chronic conditions like hepatitis and HIV.DUKE
MucokineticAn agent that aids in the clearance of mucus from the airways, lungs, bronchi, and trachea, playing a biological role in maintaining respiratory health. Therapeutically, it is used to manage respiratory disorders, with key medical applications in treating conditions such as chronic bronchitis, asthma, and COPD.DUKE
Squalene-monooxygenase inhibitor23924 An agent that blocks the activity of squalene-monooxygenase, an enzyme involved in cholesterol biosynthesis. It reduces cholesterol production, with therapeutic applications in managing hypercholesterolemia and related cardiovascular diseases, and key medical uses in treating high cholesterol and preventing atherosclerosis.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
cooked
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
roasted
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).