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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:20:15 UTC

Update Date

2022-03-07 02:53:47 UTC

HMDB ID

HMDB0033592

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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
PCSO	HMDB
S-(2-Propenyl)cysteine sulfoxide	HMDB
S-Allylcysteine sulfoxide	HMDB
Alliin, (L-ala)-(R)-isomer	HMDB
Alliin, (L-ala)-(S)-isomer	HMDB
Alliin, (L-ala)-isomer	HMDB
Isoalliin	HMDB
3-(Allylsulphinyl)-L-alanine	HMDB
Alliin	HMDB
2-Amino-3-(prop-2-ene-1-sulfinyl)propanoate	HMDB
2-Amino-3-(prop-2-ene-1-sulphinyl)propanoate	HMDB
2-Amino-3-(prop-2-ene-1-sulphinyl)propanoic acid	HMDB

Chemical Formula

C₆H₁₁NO₃S

Average Molecular Weight

177.221

Monoisotopic Molecular Weight

177.045963913

IUPAC Name

2-amino-3-(prop-2-ene-1-sulfinyl)propanoic acid

Traditional Name

allin

CAS Registry Number

556-27-4

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 Key

XUHLIQGRKRUKPH-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).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha 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 Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	163 °C	Not Available
Boiling Point	416.13 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	1000000 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-0.478 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	38.5 g/L	ALOGPS
logP	-2.1	ALOGPS
logP	-3.7	ChemAxon
logS	-0.66	ALOGPS
pKa (Strongest Acidic)	1.84	ChemAxon
pKa (Strongest Basic)	8.45	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	80.39 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	43.72 m³·mol⁻¹	ChemAxon
Polarizability	17.2 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	139.039	31661259
DarkChem	[M-H]-	132.63	31661259
DeepCCS	[M+H]+	131.15	30932474
DeepCCS	[M-H]-	127.351	30932474
DeepCCS	[M-2H]-	164.727	30932474
DeepCCS	[M+Na]+	139.959	30932474
AllCCS	[M+H]+	139.9	32859911
AllCCS	[M+H-H2O]+	136.2	32859911
AllCCS	[M+NH4]+	143.3	32859911
AllCCS	[M+Na]+	144.3	32859911
AllCCS	[M-H]-	135.8	32859911
AllCCS	[M+Na-2H]-	137.8	32859911
AllCCS	[M+HCOO]-	140.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(R)C(S)S-Alliin	NC(CS(=O)CC=C)C(O)=O	2652.8	Standard polar	33892256
(R)C(S)S-Alliin	NC(CS(=O)CC=C)C(O)=O	1408.5	Standard non polar	33892256
(R)C(S)S-Alliin	NC(CS(=O)CC=C)C(O)=O	1625.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(R)C(S)S-Alliin,1TMS,isomer #1	C=CCS(=O)CC(N)C(=O)O[Si](C)(C)C	1500.4	Semi standard non polar	33892256
(R)C(S)S-Alliin,1TMS,isomer #2	C=CCS(=O)CC(N[Si](C)(C)C)C(=O)O	1587.9	Semi standard non polar	33892256
(R)C(S)S-Alliin,2TMS,isomer #1	C=CCS(=O)CC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1641.0	Semi standard non polar	33892256
(R)C(S)S-Alliin,2TMS,isomer #1	C=CCS(=O)CC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1818.7	Standard non polar	33892256
(R)C(S)S-Alliin,2TMS,isomer #2	C=CCS(=O)CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1738.6	Semi standard non polar	33892256
(R)C(S)S-Alliin,2TMS,isomer #2	C=CCS(=O)CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1885.4	Standard non polar	33892256
(R)C(S)S-Alliin,3TMS,isomer #1	C=CCS(=O)CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1769.5	Semi standard non polar	33892256
(R)C(S)S-Alliin,3TMS,isomer #1	C=CCS(=O)CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1995.3	Standard non polar	33892256
(R)C(S)S-Alliin,1TBDMS,isomer #1	C=CCS(=O)CC(N)C(=O)O[Si](C)(C)C(C)(C)C	1747.1	Semi standard non polar	33892256
(R)C(S)S-Alliin,1TBDMS,isomer #2	C=CCS(=O)CC(N[Si](C)(C)C(C)(C)C)C(=O)O	1848.4	Semi standard non polar	33892256
(R)C(S)S-Alliin,2TBDMS,isomer #1	C=CCS(=O)CC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2081.3	Semi standard non polar	33892256
(R)C(S)S-Alliin,2TBDMS,isomer #1	C=CCS(=O)CC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2365.6	Standard non polar	33892256
(R)C(S)S-Alliin,2TBDMS,isomer #2	C=CCS(=O)CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2212.1	Semi standard non polar	33892256
(R)C(S)S-Alliin,2TBDMS,isomer #2	C=CCS(=O)CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2379.1	Standard non polar	33892256
(R)C(S)S-Alliin,3TBDMS,isomer #1	C=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)C	2475.3	Semi standard non polar	33892256
(R)C(S)S-Alliin,3TBDMS,isomer #1	C=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)C	2711.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (R)C(S)S-Alliin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-5d9a21e27ef3f517dd6d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)C(S)S-Alliin GC-MS (1 TMS) - 70eV, Positive	splash10-0006-9400000000-4437cf48a71215d0979e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)C(S)S-Alliin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)C(S)S-Alliin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)C(S)S-Alliin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)C(S)S-Alliin GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)C(S)S-Alliin GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)C(S)S-Alliin GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)C(S)S-Alliin 10V, Positive-QTOF	splash10-03gi-1900000000-c555ee84b1ef7b497188	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)C(S)S-Alliin 20V, Positive-QTOF	splash10-000x-9700000000-fceeacb69e8f54ed59f7	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)C(S)S-Alliin 40V, Positive-QTOF	splash10-0006-9000000000-57ef07206642af998090	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)C(S)S-Alliin 10V, Negative-QTOF	splash10-004r-2900000000-2e1124856d7e7fb193c7	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)C(S)S-Alliin 20V, Negative-QTOF	splash10-000i-9600000000-f2d686842e93754c87d2	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)C(S)S-Alliin 40V, Negative-QTOF	splash10-00ks-9200000000-40481bee5ec83e05c2b7	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)C(S)S-Alliin 10V, Positive-QTOF	splash10-03gi-1900000000-c555ee84b1ef7b497188	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)C(S)S-Alliin 20V, Positive-QTOF	splash10-000x-9700000000-fceeacb69e8f54ed59f7	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)C(S)S-Alliin 40V, Positive-QTOF	splash10-0006-9000000000-57ef07206642af998090	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)C(S)S-Alliin 10V, Negative-QTOF	splash10-004r-2900000000-2e1124856d7e7fb193c7	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)C(S)S-Alliin 20V, Negative-QTOF	splash10-000i-9600000000-f2d686842e93754c87d2	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)C(S)S-Alliin 40V, Negative-QTOF	splash10-00ks-9200000000-40481bee5ec83e05c2b7	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)C(S)S-Alliin 10V, Negative-QTOF	splash10-000i-9000000000-4ac0c68cb3c192b2e052	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)C(S)S-Alliin 20V, Negative-QTOF	splash10-000i-9000000000-02c6e2c53f6107e27313	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)C(S)S-Alliin 40V, Negative-QTOF	splash10-0002-9000000000-93497b521a88141008ec	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)C(S)S-Alliin 10V, Positive-QTOF	splash10-000f-9500000000-8ea3f234c3bfe3df2b0d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)C(S)S-Alliin 20V, Positive-QTOF	splash10-0006-9100000000-a5db6938dd6bc4d086ac	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)C(S)S-Alliin 40V, Positive-QTOF	splash10-006y-9000000000-5688c056fa4f9896d8fd	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

121922

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1592041

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for (R)C(S)S-Alliin (HMDB0033592)

MOL for HMDB0033592 ((R)C(S)S-Alliin)

3D MOL for HMDB0033592 ((R)C(S)S-Alliin)

3D SDF for HMDB0033592 ((R)C(S)S-Alliin)

3D-SDF for HMDB0033592 ((R)C(S)S-Alliin)

PDB for HMDB0033592 ((R)C(S)S-Alliin)

3D PDB for HMDB0033592 ((R)C(S)S-Alliin)

SMILES for HMDB0033592 ((R)C(S)S-Alliin)

INCHI for HMDB0033592 ((R)C(S)S-Alliin)

Structure for HMDB0033592 ((R)C(S)S-Alliin)

3D Structure for HMDB0033592 ((R)C(S)S-Alliin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra