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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:20:15 UTC
Update Date2021-09-14 15:00:49 UTC
HMDB IDHMDB0033592
Secondary Accession Numbers
  • HMDB33592
Metabolite Identification
Common Name(R)C(S)S-Alliin
Description(R)C(S)S-Alliin, also known as PCSO or isoalliin, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon) (R)C(S)S-Alliin has been detected, but not quantified in, several different foods, such as garden onions (Allium cepa), green onion, garden onion (var.), welsh onions (Allium fistulosum), and onion-family vegetables. This could make (R)C(S)S-alliin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (R)C(S)S-Alliin.
Structure
Data?1563862429
Synonyms
ValueSource
PCSOMeSH
S-(2-Propenyl)cysteine sulfoxideMeSH
S-Allylcysteine sulfoxideMeSH
Alliin, (L-ala)-(R)-isomerMeSH
Alliin, (L-ala)-(S)-isomerMeSH
Alliin, (L-ala)-isomerMeSH
IsoalliinMeSH
3-(Allylsulphinyl)-L-alanineHMDB
AlliinHMDB
2-Amino-3-(prop-2-ene-1-sulfinyl)propanoateGenerator
2-Amino-3-(prop-2-ene-1-sulphinyl)propanoateGenerator
2-Amino-3-(prop-2-ene-1-sulphinyl)propanoic acidGenerator
Chemical FormulaC6H11NO3S
Average Molecular Weight177.221
Monoisotopic Molecular Weight177.045963913
IUPAC Name2-amino-3-(prop-2-ene-1-sulfinyl)propanoic acid
Traditional Nameallin
CAS Registry Number556-27-4
SMILES
NC(CS(=O)CC=C)C(O)=O
InChI Identifier
InChI=1S/C6H11NO3S/c1-2-3-11(10)4-5(7)6(8)9/h2,5H,1,3-4,7H2,(H,8,9)
InChI KeyXUHLIQGRKRUKPH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Sulfoxide
  • Allyl sulfur compound
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Sulfinyl compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point163 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility38.5 g/LALOGPS
logP-2.1ALOGPS
logP-3.7ChemAxon
logS-0.66ALOGPS
pKa (Strongest Acidic)1.84ChemAxon
pKa (Strongest Basic)8.45ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.39 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity43.72 m³·mol⁻¹ChemAxon
Polarizability17.2 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available139.03931661259
DarkChem[M-H]-PredictedNot Available132.6331661259

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
(R)C(S)S-Alliin,1TMS,#11500.4296https://arxiv.org/abs/1905.12712
(R)C(S)S-Alliin,1TMS,#21587.8762https://arxiv.org/abs/1905.12712
(R)C(S)S-Alliin,1TBDMS,#11747.0776https://arxiv.org/abs/1905.12712
(R)C(S)S-Alliin,1TBDMS,#21848.4004https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-5d9a21e27ef3f517dd6d2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-9400000000-4437cf48a71215d0979e2017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-5d9a21e27ef3f517dd6d2021-09-05View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03gi-1900000000-c555ee84b1ef7b4971882015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000x-9700000000-fceeacb69e8f54ed59f72015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-57ef07206642af9980902015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004r-2900000000-2e1124856d7e7fb193c72015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9600000000-f2d686842e93754c87d22015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ks-9200000000-40481bee5ec83e05c2b72015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03gi-1900000000-c555ee84b1ef7b4971882015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000x-9700000000-fceeacb69e8f54ed59f72015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-57ef07206642af9980902015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004r-2900000000-2e1124856d7e7fb193c72015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9600000000-f2d686842e93754c87d22015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ks-9200000000-40481bee5ec83e05c2b72015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-4ac0c68cb3c192b2e0522021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-02c6e2c53f6107e273132021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-93497b521a88141008ec2021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000f-9500000000-8ea3f234c3bfe3df2b0d2021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9100000000-a5db6938dd6bc4d086ac2021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006y-9000000000-5688c056fa4f9896d8fd2021-09-07View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB011674
KNApSAcK IDC00001336
Chemspider ID108767
KEGG Compound IDC08265
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound121922
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .