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

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 16:02:08 UTC

Update Date

2021-09-23 16:02:08 UTC

HMDB ID

HMDB0302213

Secondary Accession Numbers

None

Metabolite Identification

Common Name

S-Propylcysteine sulphoxide

Description

S-propylcysteine sulphoxide, also known as pcso, is a member of the class of compounds known as L-alpha-amino acids. L-alpha-amino acids are alpha amino acids which have the L-configuration of the alpha-carbon atom. S-propylcysteine sulphoxide is soluble (in water) and a moderately acidic compound (based on its pKa). S-propylcysteine sulphoxide can be found in soft-necked garlic, which makes S-propylcysteine sulphoxide a potential biomarker for the consumption of this food product.

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-(Propylsulfinyl)-L-alanine	Generator
S-Propylcysteine sulfoxide	Generator

Chemical Formula

C₆H₁₃NO₃S

Average Molecular Weight

179.237

Monoisotopic Molecular Weight

179.061613977

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CCCS(=O)C[C@H](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)/t5-,11?/m0/s1

InChI Key

JZKMSAGUCSIIAH-ITZCMCNPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Sulfoxide
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Sulfinyl compound
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Primary aliphatic amine
Organic nitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0302213)

Food

Herb and spice

Herb

Soft-necked garlic (FooDB: FOOD00850)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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
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	18.22 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
AllCCS	[M+H]+	139.765	32859911
AllCCS	[M+H-H2O]+	136.097	32859911
AllCCS	[M+Na]+	144.157	32859911
AllCCS	[M+NH4]+	143.175	32859911
AllCCS	[M-H]-	136.47	32859911
AllCCS	[M+Na-2H]-	138.467	32859911
AllCCS	[M+HCOO]-	140.717	32859911
DeepCCS	[M+H]+	137.323	30932474
DeepCCS	[M-H]-	133.495	30932474
DeepCCS	[M-2H]-	170.49	30932474
DeepCCS	[M+Na]+	146.066	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
S-Propylcysteine sulphoxide,2TMS,isomer #1	CCCS(=O)C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1642.1	Semi standard non polar	33892256
S-Propylcysteine sulphoxide,2TMS,isomer #1	CCCS(=O)C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1986.1	Standard non polar	33892256
S-Propylcysteine sulphoxide,2TMS,isomer #1	CCCS(=O)C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1940.6	Standard polar	33892256
S-Propylcysteine sulphoxide,2TMS,isomer #2	CCCS(=O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1740.3	Semi standard non polar	33892256
S-Propylcysteine sulphoxide,2TMS,isomer #2	CCCS(=O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1939.6	Standard non polar	33892256
S-Propylcysteine sulphoxide,2TMS,isomer #2	CCCS(=O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2123.6	Standard polar	33892256
S-Propylcysteine sulphoxide,3TMS,isomer #1	CCCS(=O)C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1769.7	Semi standard non polar	33892256
S-Propylcysteine sulphoxide,3TMS,isomer #1	CCCS(=O)C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2086.1	Standard non polar	33892256
S-Propylcysteine sulphoxide,3TMS,isomer #1	CCCS(=O)C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1858.5	Standard polar	33892256
S-Propylcysteine sulphoxide,2TBDMS,isomer #1	CCCS(=O)C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2073.1	Semi standard non polar	33892256
S-Propylcysteine sulphoxide,2TBDMS,isomer #1	CCCS(=O)C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2538.6	Standard non polar	33892256
S-Propylcysteine sulphoxide,2TBDMS,isomer #1	CCCS(=O)C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2171.3	Standard polar	33892256
S-Propylcysteine sulphoxide,2TBDMS,isomer #2	CCCS(=O)C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2200.4	Semi standard non polar	33892256
S-Propylcysteine sulphoxide,2TBDMS,isomer #2	CCCS(=O)C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2467.6	Standard non polar	33892256
S-Propylcysteine sulphoxide,2TBDMS,isomer #2	CCCS(=O)C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2264.3	Standard polar	33892256
S-Propylcysteine sulphoxide,3TBDMS,isomer #1	CCCS(=O)C[C@@H](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	2465.0	Semi standard non polar	33892256
S-Propylcysteine sulphoxide,3TBDMS,isomer #1	CCCS(=O)C[C@@H](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	2850.2	Standard non polar	33892256
S-Propylcysteine sulphoxide,3TBDMS,isomer #1	CCCS(=O)C[C@@H](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	2235.0	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Propylcysteine sulphoxide 10V, Positive-QTOF	splash10-001i-2900000000-4e31073766aec703b0c8	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Propylcysteine sulphoxide 20V, Positive-QTOF	splash10-000x-9700000000-9f6de32e6f9b5083d407	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Propylcysteine sulphoxide 40V, Positive-QTOF	splash10-0006-9000000000-1542761cf15e9d3ef63e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Propylcysteine sulphoxide 10V, Negative-QTOF	splash10-004i-2900000000-7564d6c23ffef025aaff	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Propylcysteine sulphoxide 20V, Negative-QTOF	splash10-000l-9500000000-976fec14f8d3f1d0922b	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Propylcysteine sulphoxide 40V, Negative-QTOF	splash10-00rm-9200000000-3b615057cdf0430dbc39	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Propylcysteine sulphoxide 10V, Positive-QTOF	splash10-001c-9800000000-9f05862babcc07618b65	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Propylcysteine sulphoxide 20V, Positive-QTOF	splash10-006x-9100000000-bb3fa7aa24b91886c786	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Propylcysteine sulphoxide 40V, Positive-QTOF	splash10-0007-9000000000-3ba065cb7950c87b9e76	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Propylcysteine sulphoxide 10V, Negative-QTOF	splash10-000f-9500000000-e064a58bc35f24cf4ccb	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Propylcysteine sulphoxide 20V, Negative-QTOF	splash10-000i-9000000000-eb2058c7b367ec5fde19	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Propylcysteine sulphoxide 40V, Negative-QTOF	splash10-00di-9000000000-a634a471cac0c3cfdbfe	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB003691

KNApSAcK ID

Not Available

Chemspider ID

78759

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

87309

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

Not Available

Showing metabocard for S-Propylcysteine sulphoxide (HMDB0302213)

MOL for HMDB0302213 (S-Propylcysteine sulphoxide)

3D MOL for HMDB0302213 (S-Propylcysteine sulphoxide)

3D SDF for HMDB0302213 (S-Propylcysteine sulphoxide)

3D-SDF for HMDB0302213 (S-Propylcysteine sulphoxide)

PDB for HMDB0302213 (S-Propylcysteine sulphoxide)

3D PDB for HMDB0302213 (S-Propylcysteine sulphoxide)

SMILES for HMDB0302213 (S-Propylcysteine sulphoxide)

INCHI for HMDB0302213 (S-Propylcysteine sulphoxide)

Structure for HMDB0302213 (S-Propylcysteine sulphoxide)

3D Structure for HMDB0302213 (S-Propylcysteine sulphoxide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra