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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:20:15 UTC
Update Date2022-03-07 02:53:47 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 isoalliin or PCSO, 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 onion-family vegetables, green onion, garlics (Allium sativum), red onion, and garden onions (Allium cepa). 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
PCSOHMDB
S-(2-Propenyl)cysteine sulfoxideHMDB
S-Allylcysteine sulfoxideHMDB
Alliin, (L-ala)-(R)-isomerHMDB
Alliin, (L-ala)-(S)-isomerHMDB
Alliin, (L-ala)-isomerHMDB
IsoalliinHMDB
3-(Allylsulphinyl)-L-alanineHMDB
AlliinHMDB
2-Amino-3-(prop-2-ene-1-sulfinyl)propanoateHMDB
2-Amino-3-(prop-2-ene-1-sulphinyl)propanoateHMDB
2-Amino-3-(prop-2-ene-1-sulphinyl)propanoic acidHMDB
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

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point163 °CNot Available
Boiling Point416.13 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1000000 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-0.478 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot 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 Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+139.03931661259
DarkChem[M-H]-132.6331661259
DeepCCS[M+H]+131.1530932474
DeepCCS[M-H]-127.35130932474
DeepCCS[M-2H]-164.72730932474
DeepCCS[M+Na]+139.95930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(R)C(S)S-AlliinNC(CS(=O)CC=C)C(O)=O2652.8Standard polar33892256
(R)C(S)S-AlliinNC(CS(=O)CC=C)C(O)=O1408.5Standard non polar33892256
(R)C(S)S-AlliinNC(CS(=O)CC=C)C(O)=O1625.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(R)C(S)S-Alliin,1TMS,isomer #1C=CCS(=O)CC(N)C(=O)O[Si](C)(C)C1500.4Semi standard non polar33892256
(R)C(S)S-Alliin,1TMS,isomer #2C=CCS(=O)CC(N[Si](C)(C)C)C(=O)O1587.9Semi standard non polar33892256
(R)C(S)S-Alliin,2TMS,isomer #1C=CCS(=O)CC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C1641.0Semi standard non polar33892256
(R)C(S)S-Alliin,2TMS,isomer #1C=CCS(=O)CC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C1818.7Standard non polar33892256
(R)C(S)S-Alliin,2TMS,isomer #2C=CCS(=O)CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1738.6Semi standard non polar33892256
(R)C(S)S-Alliin,2TMS,isomer #2C=CCS(=O)CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1885.4Standard non polar33892256
(R)C(S)S-Alliin,3TMS,isomer #1C=CCS(=O)CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1769.5Semi standard non polar33892256
(R)C(S)S-Alliin,3TMS,isomer #1C=CCS(=O)CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1995.3Standard non polar33892256
(R)C(S)S-Alliin,1TBDMS,isomer #1C=CCS(=O)CC(N)C(=O)O[Si](C)(C)C(C)(C)C1747.1Semi standard non polar33892256
(R)C(S)S-Alliin,1TBDMS,isomer #2C=CCS(=O)CC(N[Si](C)(C)C(C)(C)C)C(=O)O1848.4Semi standard non polar33892256
(R)C(S)S-Alliin,2TBDMS,isomer #1C=CCS(=O)CC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2081.3Semi standard non polar33892256
(R)C(S)S-Alliin,2TBDMS,isomer #1C=CCS(=O)CC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2365.6Standard non polar33892256
(R)C(S)S-Alliin,2TBDMS,isomer #2C=CCS(=O)CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2212.1Semi standard non polar33892256
(R)C(S)S-Alliin,2TBDMS,isomer #2C=CCS(=O)CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2379.1Standard non polar33892256
(R)C(S)S-Alliin,3TBDMS,isomer #1C=CCS(=O)CC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2475.3Semi standard non polar33892256
(R)C(S)S-Alliin,3TBDMS,isomer #1C=CCS(=O)CC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2711.7Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (R)C(S)S-Alliin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-5d9a21e27ef3f517dd6d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)C(S)S-Alliin GC-MS (1 TMS) - 70eV, Positivesplash10-0006-9400000000-4437cf48a71215d0979e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)C(S)S-Alliin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)C(S)S-Alliin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)C(S)S-Alliin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)C(S)S-Alliin GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)C(S)S-Alliin GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)C(S)S-Alliin GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)C(S)S-Alliin 10V, Positive-QTOFsplash10-03gi-1900000000-c555ee84b1ef7b4971882015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)C(S)S-Alliin 20V, Positive-QTOFsplash10-000x-9700000000-fceeacb69e8f54ed59f72015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)C(S)S-Alliin 40V, Positive-QTOFsplash10-0006-9000000000-57ef07206642af9980902015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)C(S)S-Alliin 10V, Negative-QTOFsplash10-004r-2900000000-2e1124856d7e7fb193c72015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)C(S)S-Alliin 20V, Negative-QTOFsplash10-000i-9600000000-f2d686842e93754c87d22015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)C(S)S-Alliin 40V, Negative-QTOFsplash10-00ks-9200000000-40481bee5ec83e05c2b72015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)C(S)S-Alliin 10V, Positive-QTOFsplash10-03gi-1900000000-c555ee84b1ef7b4971882015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)C(S)S-Alliin 20V, Positive-QTOFsplash10-000x-9700000000-fceeacb69e8f54ed59f72015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)C(S)S-Alliin 40V, Positive-QTOFsplash10-0006-9000000000-57ef07206642af9980902015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)C(S)S-Alliin 10V, Negative-QTOFsplash10-004r-2900000000-2e1124856d7e7fb193c72015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)C(S)S-Alliin 20V, Negative-QTOFsplash10-000i-9600000000-f2d686842e93754c87d22015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)C(S)S-Alliin 40V, Negative-QTOFsplash10-00ks-9200000000-40481bee5ec83e05c2b72015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)C(S)S-Alliin 10V, Negative-QTOFsplash10-000i-9000000000-4ac0c68cb3c192b2e0522021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)C(S)S-Alliin 20V, Negative-QTOFsplash10-000i-9000000000-02c6e2c53f6107e273132021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)C(S)S-Alliin 40V, Negative-QTOFsplash10-0002-9000000000-93497b521a88141008ec2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)C(S)S-Alliin 10V, Positive-QTOFsplash10-000f-9500000000-8ea3f234c3bfe3df2b0d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)C(S)S-Alliin 20V, Positive-QTOFsplash10-0006-9100000000-a5db6938dd6bc4d086ac2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)C(S)S-Alliin 40V, Positive-QTOFsplash10-006y-9000000000-5688c056fa4f9896d8fd2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView 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
Good Scents IDrw1592041
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.. .