Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:30:26 UTC

Update Date

2022-03-07 02:52:10 UTC

HMDB ID

HMDB0029442

Secondary Accession Numbers

HMDB29442

Metabolite Identification

Common Name

(R)C(R)S-S-Propylcysteine sulfoxide

Description

(R)C(R)S-S-Propylcysteine sulfoxide, also known as 2-amino-3-(propane-1-sulfinyl)propanoate, 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(R)S-S-Propylcysteine sulfoxide has been detected, but not quantified in, several different foods, such as green onion, onion-family vegetables, welsh onions (Allium fistulosum), red onion, and garden onions (Allium cepa). This could make (R)C(R)S-S-propylcysteine sulfoxide a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on (R)C(R)S-S-Propylcysteine sulfoxide.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(R)C(R)S-S-Propylcysteine sulphoxide	Generator
2-Amino-3-(propane-1-sulfinyl)propanoate	HMDB
2-Amino-3-(propane-1-sulphinyl)propanoate	HMDB
2-Amino-3-(propane-1-sulphinyl)propanoic acid	HMDB

Chemical Formula

C₆H₁₃NO₃S

Average Molecular Weight

179.237

Monoisotopic Molecular Weight

179.061613977

IUPAC Name

2-amino-3-(propane-1-sulfinyl)propanoic acid

Traditional Name

2-amino-3-(propane-1-sulfinyl)propanoic acid

CAS Registry Number

17935-27-2

SMILES

CCCS(=O)CC(N)C(O)=O

InChI Identifier

InChI=1S/C6H13NO3S/c1-2-3-11(10)4-5(7)6(8)9/h5H,2-4,7H2,1H3,(H,8,9)

InChI Key

JZKMSAGUCSIIAH-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
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

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0029442)
Extracellular (HMDB: HMDB0029442)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029442)

Source

Endogenous

Endogenous (HMDB: HMDB0029442)

Plant

Plant (HMDB: HMDB0029442)

Exogenous

Food

Food (HMDB: HMDB0029442)

Vegetable

Onion-family vegetable

Allium (FooDB: FOOD00005)
Garden onion (FooDB: FOOD00006)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	161 - 162 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	33.3 g/L	ALOGPS
logP	-2	ALOGPS
logP	-3.6	ChemAxon
logS	-0.73	ALOGPS
pKa (Strongest Acidic)	1.92	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	43.83 m³·mol⁻¹	ChemAxon
Polarizability	18.15 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]+	139.336	31661259
DarkChem	[M-H]-	135.897	31661259
DeepCCS	[M+H]+	135.023	30932474
DeepCCS	[M-H]-	131.412	30932474
DeepCCS	[M-2H]-	168.502	30932474
DeepCCS	[M+Na]+	143.763	30932474
AllCCS	[M+H]+	139.8	32859911
AllCCS	[M+H-H2O]+	136.1	32859911
AllCCS	[M+NH4]+	143.2	32859911
AllCCS	[M+Na]+	144.2	32859911
AllCCS	[M-H]-	136.5	32859911
AllCCS	[M+Na-2H]-	138.5	32859911
AllCCS	[M+HCOO]-	140.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(R)C(R)S-S-Propylcysteine sulfoxide	CCCS(=O)CC(N)C(O)=O	2699.5	Standard polar	33892256
(R)C(R)S-S-Propylcysteine sulfoxide	CCCS(=O)CC(N)C(O)=O	1471.9	Standard non polar	33892256
(R)C(R)S-S-Propylcysteine sulfoxide	CCCS(=O)CC(N)C(O)=O	1615.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(R)C(R)S-S-Propylcysteine sulfoxide,1TMS,isomer #1	CCCS(=O)CC(N)C(=O)O[Si](C)(C)C	1565.7	Semi standard non polar	33892256
(R)C(R)S-S-Propylcysteine sulfoxide,1TMS,isomer #2	CCCS(=O)CC(N[Si](C)(C)C)C(=O)O	1633.0	Semi standard non polar	33892256
(R)C(R)S-S-Propylcysteine sulfoxide,2TMS,isomer #1	CCCS(=O)CC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1659.5	Semi standard non polar	33892256
(R)C(R)S-S-Propylcysteine sulfoxide,2TMS,isomer #1	CCCS(=O)CC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1908.8	Standard non polar	33892256
(R)C(R)S-S-Propylcysteine sulfoxide,2TMS,isomer #2	CCCS(=O)CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1791.6	Semi standard non polar	33892256
(R)C(R)S-S-Propylcysteine sulfoxide,2TMS,isomer #2	CCCS(=O)CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1921.2	Standard non polar	33892256
(R)C(R)S-S-Propylcysteine sulfoxide,3TMS,isomer #1	CCCS(=O)CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1808.1	Semi standard non polar	33892256
(R)C(R)S-S-Propylcysteine sulfoxide,3TMS,isomer #1	CCCS(=O)CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2054.1	Standard non polar	33892256
(R)C(R)S-S-Propylcysteine sulfoxide,1TBDMS,isomer #1	CCCS(=O)CC(N)C(=O)O[Si](C)(C)C(C)(C)C	1810.3	Semi standard non polar	33892256
(R)C(R)S-S-Propylcysteine sulfoxide,1TBDMS,isomer #2	CCCS(=O)CC(N[Si](C)(C)C(C)(C)C)C(=O)O	1866.7	Semi standard non polar	33892256
(R)C(R)S-S-Propylcysteine sulfoxide,2TBDMS,isomer #1	CCCS(=O)CC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2101.8	Semi standard non polar	33892256
(R)C(R)S-S-Propylcysteine sulfoxide,2TBDMS,isomer #1	CCCS(=O)CC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2473.5	Standard non polar	33892256
(R)C(R)S-S-Propylcysteine sulfoxide,2TBDMS,isomer #2	CCCS(=O)CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2222.2	Semi standard non polar	33892256
(R)C(R)S-S-Propylcysteine sulfoxide,2TBDMS,isomer #2	CCCS(=O)CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2434.1	Standard non polar	33892256
(R)C(R)S-S-Propylcysteine sulfoxide,3TBDMS,isomer #1	CCCS(=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	2489.3	Semi standard non polar	33892256
(R)C(R)S-S-Propylcysteine sulfoxide,3TBDMS,isomer #1	CCCS(=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	2829.6	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(R)S-S-Propylcysteine sulfoxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9100000000-54e74d4eb36c315a0e93	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)C(R)S-S-Propylcysteine sulfoxide GC-MS (1 TMS) - 70eV, Positive	splash10-006x-9310000000-57666e34138768771113	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)C(R)S-S-Propylcysteine sulfoxide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)C(R)S-S-Propylcysteine sulfoxide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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(R)S-S-Propylcysteine sulfoxide 10V, Positive-QTOF	splash10-001i-2900000000-4e31073766aec703b0c8	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)C(R)S-S-Propylcysteine sulfoxide 20V, Positive-QTOF	splash10-000x-9700000000-9f6de32e6f9b5083d407	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)C(R)S-S-Propylcysteine sulfoxide 40V, Positive-QTOF	splash10-0006-9000000000-1542761cf15e9d3ef63e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)C(R)S-S-Propylcysteine sulfoxide 10V, Negative-QTOF	splash10-004i-2900000000-7564d6c23ffef025aaff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)C(R)S-S-Propylcysteine sulfoxide 20V, Negative-QTOF	splash10-000l-9500000000-976fec14f8d3f1d0922b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)C(R)S-S-Propylcysteine sulfoxide 40V, Negative-QTOF	splash10-00rm-9200000000-3b615057cdf0430dbc39	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)C(R)S-S-Propylcysteine sulfoxide 10V, Positive-QTOF	splash10-001c-9800000000-9f05862babcc07618b65	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)C(R)S-S-Propylcysteine sulfoxide 20V, Positive-QTOF	splash10-006x-9100000000-bb3fa7aa24b91886c786	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)C(R)S-S-Propylcysteine sulfoxide 40V, Positive-QTOF	splash10-0007-9000000000-3ba065cb7950c87b9e76	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)C(R)S-S-Propylcysteine sulfoxide 10V, Negative-QTOF	splash10-000f-9500000000-e064a58bc35f24cf4ccb	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)C(R)S-S-Propylcysteine sulfoxide 20V, Negative-QTOF	splash10-000i-9000000000-eb2058c7b367ec5fde19	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)C(R)S-S-Propylcysteine sulfoxide 40V, Negative-QTOF	splash10-00di-9000000000-a634a471cac0c3cfdbfe	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹³C 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

FDB000551

KNApSAcK ID

Not Available

Chemspider ID

311305

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25202184

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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(R)S-S-Propylcysteine sulfoxide (HMDB0029442)

MOL for HMDB0029442 ((R)C(R)S-S-Propylcysteine sulfoxide)

3D MOL for HMDB0029442 ((R)C(R)S-S-Propylcysteine sulfoxide)

3D SDF for HMDB0029442 ((R)C(R)S-S-Propylcysteine sulfoxide)

3D-SDF for HMDB0029442 ((R)C(R)S-S-Propylcysteine sulfoxide)

PDB for HMDB0029442 ((R)C(R)S-S-Propylcysteine sulfoxide)

3D PDB for HMDB0029442 ((R)C(R)S-S-Propylcysteine sulfoxide)

SMILES for HMDB0029442 ((R)C(R)S-S-Propylcysteine sulfoxide)

INCHI for HMDB0029442 ((R)C(R)S-S-Propylcysteine sulfoxide)

Structure for HMDB0029442 ((R)C(R)S-S-Propylcysteine sulfoxide)

3D Structure for HMDB0029442 ((R)C(R)S-S-Propylcysteine sulfoxide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra