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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 19:08:07 UTC

Update Date

2023-02-21 17:24:10 UTC

HMDB ID

HMDB0034324

Secondary Accession Numbers

HMDB34324

Metabolite Identification

Common Name

S-Propyl-L-cysteine

Description

S-Propyl-L-cysteine belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. S-Propyl-L-cysteine has been detected, but not quantified in, several different foods, such as red onion, onion-family vegetables, green onion, welsh onions (Allium fistulosum), and garden onions (Allium cepa). This could make S-propyl-L-cysteine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on S-Propyl-L-cysteine.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
S-Propylcysteine	HMDB
2-Amino-3-(propylsulfanyl)propanoate	Generator
2-Amino-3-(propylsulphanyl)propanoate	Generator
2-Amino-3-(propylsulphanyl)propanoic acid	Generator
S-Propylcysteine, (L-cys)-isomer	MeSH

Chemical Formula

C₆H₁₃NO₂S

Average Molecular Weight

163.238

Monoisotopic Molecular Weight

163.066699355

IUPAC Name

2-amino-3-(propylsulfanyl)propanoic acid

Traditional Name

2-amino-3-(propylsulfanyl)propanoic acid

CAS Registry Number

1115-93-1

SMILES

CCCSCC(N)C(O)=O

InChI Identifier

InChI=1S/C6H13NO2S/c1-2-3-10-4-5(7)6(8)9/h5H,2-4,7H2,1H3,(H,8,9)

InChI Key

WAAGBMYUYFBZIW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Cysteine and derivatives

Alternative Parents

Substituents

Cysteine or derivatives
Alpha-amino acid
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Thioether
Sulfenyl compound
Dialkylthioether
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

Extracellular (HMDB: HMDB0034324)
Cytoplasm (HMDB: HMDB0034324)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034324)

Source

Exogenous

Exogenous (HMDB: HMDB0034324)

Food

Food (HMDB: HMDB0034324)

Herb and spice

Herb

Welsh onion (FooDB: FOOD00241)

Vegetable

Onion-family vegetable

Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Endogenous

Plant

Plant (HMDB: HMDB0034324)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034324)

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
Water Solubility	13 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-1.6	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	2.62	ChemAxon
pKa (Strongest Basic)	9.14	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	42.2 m³·mol⁻¹	ChemAxon
Polarizability	17.85 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]+	135.682	31661259
DarkChem	[M-H]-	130.404	31661259
DeepCCS	[M+H]+	139.878	30932474
DeepCCS	[M-H]-	136.921	30932474
DeepCCS	[M-2H]-	173.738	30932474
DeepCCS	[M+Na]+	148.434	30932474
AllCCS	[M+H]+	136.8	32859911
AllCCS	[M+H-H2O]+	133.1	32859911
AllCCS	[M+NH4]+	140.3	32859911
AllCCS	[M+Na]+	141.3	32859911
AllCCS	[M-H]-	137.4	32859911
AllCCS	[M+Na-2H]-	139.8	32859911
AllCCS	[M+HCOO]-	142.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.8 minutes	32390414
Predicted by Siyang on May 30, 2022	10.3616 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	7.22 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	252.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	996.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	320.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	73.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	187.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	71.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	291.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	316.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	582.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	725.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	196.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	899.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	210.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	217.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	441.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	320.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	205.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
S-Propyl-L-cysteine	CCCSCC(N)C(O)=O	2412.2	Standard polar	33892256
S-Propyl-L-cysteine	CCCSCC(N)C(O)=O	1376.6	Standard non polar	33892256
S-Propyl-L-cysteine	CCCSCC(N)C(O)=O	1496.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
S-Propyl-L-cysteine,1TMS,isomer #1	CCCSCC(N)C(=O)O[Si](C)(C)C	1475.5	Semi standard non polar	33892256
S-Propyl-L-cysteine,1TMS,isomer #2	CCCSCC(N[Si](C)(C)C)C(=O)O	1528.7	Semi standard non polar	33892256
S-Propyl-L-cysteine,2TMS,isomer #1	CCCSCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1565.5	Semi standard non polar	33892256
S-Propyl-L-cysteine,2TMS,isomer #1	CCCSCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1556.7	Standard non polar	33892256
S-Propyl-L-cysteine,2TMS,isomer #2	CCCSCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1681.2	Semi standard non polar	33892256
S-Propyl-L-cysteine,2TMS,isomer #2	CCCSCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1646.7	Standard non polar	33892256
S-Propyl-L-cysteine,3TMS,isomer #1	CCCSCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1714.8	Semi standard non polar	33892256
S-Propyl-L-cysteine,3TMS,isomer #1	CCCSCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1703.8	Standard non polar	33892256
S-Propyl-L-cysteine,1TBDMS,isomer #1	CCCSCC(N)C(=O)O[Si](C)(C)C(C)(C)C	1709.5	Semi standard non polar	33892256
S-Propyl-L-cysteine,1TBDMS,isomer #2	CCCSCC(N[Si](C)(C)C(C)(C)C)C(=O)O	1754.5	Semi standard non polar	33892256
S-Propyl-L-cysteine,2TBDMS,isomer #1	CCCSCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2024.6	Semi standard non polar	33892256
S-Propyl-L-cysteine,2TBDMS,isomer #1	CCCSCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1988.4	Standard non polar	33892256
S-Propyl-L-cysteine,2TBDMS,isomer #2	CCCSCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2124.2	Semi standard non polar	33892256
S-Propyl-L-cysteine,2TBDMS,isomer #2	CCCSCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2083.1	Standard non polar	33892256
S-Propyl-L-cysteine,3TBDMS,isomer #1	CCCSCC(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	2396.1	Semi standard non polar	33892256
S-Propyl-L-cysteine,3TBDMS,isomer #1	CCCSCC(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	2327.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - S-Propyl-L-cysteine GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9000000000-e39ec4e849d5a92c13c6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - S-Propyl-L-cysteine GC-MS (1 TMS) - 70eV, Positive	splash10-00r5-9600000000-3d81cacecf28ee1bb9cb	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - S-Propyl-L-cysteine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - S-Propyl-L-cysteine 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 - S-Propyl-L-cysteine 10V, Positive-QTOF	splash10-02tm-5900000000-880175a4a4bcb6c6c48f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Propyl-L-cysteine 20V, Positive-QTOF	splash10-004l-9300000000-d6caeaeb4d132799c54c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Propyl-L-cysteine 40V, Positive-QTOF	splash10-0006-9000000000-df9962adbf588239e20e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Propyl-L-cysteine 10V, Negative-QTOF	splash10-03fr-6900000000-9b8367bc94192a4ade27	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Propyl-L-cysteine 20V, Negative-QTOF	splash10-004i-9200000000-d2412e10aa3c4d9e1ad6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Propyl-L-cysteine 40V, Negative-QTOF	splash10-001c-9000000000-fc547b97a274ae1fe56a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Propyl-L-cysteine 10V, Negative-QTOF	splash10-004i-9000000000-e7c25eb55afb7cceba91	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Propyl-L-cysteine 20V, Negative-QTOF	splash10-004i-9000000000-03f7245b990680eea644	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Propyl-L-cysteine 40V, Negative-QTOF	splash10-05di-9000000000-c82f8ca718ba1a536f21	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Propyl-L-cysteine 10V, Positive-QTOF	splash10-004j-8900000000-2d6631ef33b64740fec9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Propyl-L-cysteine 20V, Positive-QTOF	splash10-004i-9100000000-253a091a1117bfe23635	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Propyl-L-cysteine 40V, Positive-QTOF	splash10-00fv-9000000000-5e0bd7e3e983fa5cf41d	2021-09-22	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

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Asthma	33739820	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Asthma	33739820	details

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

FDB012677

KNApSAcK ID

Not Available

Chemspider ID

111437

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

125198

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 S-Propyl-L-cysteine (HMDB0034324)

MOL for HMDB0034324 (S-Propyl-L-cysteine)

3D MOL for HMDB0034324 (S-Propyl-L-cysteine)

3D SDF for HMDB0034324 (S-Propyl-L-cysteine)

3D-SDF for HMDB0034324 (S-Propyl-L-cysteine)

PDB for HMDB0034324 (S-Propyl-L-cysteine)

3D PDB for HMDB0034324 (S-Propyl-L-cysteine)

SMILES for HMDB0034324 (S-Propyl-L-cysteine)

INCHI for HMDB0034324 (S-Propyl-L-cysteine)

Structure for HMDB0034324 (S-Propyl-L-cysteine)

3D Structure for HMDB0034324 (S-Propyl-L-cysteine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra