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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:30:25 UTC

Update Date

2023-02-21 17:18:46 UTC

HMDB ID

HMDB0029440

Secondary Accession Numbers

HMDB29440

Metabolite Identification

Common Name

trans-S-(1-Propenyl)-L-cysteine

Description

trans-S-(1-Propenyl)-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. trans-S-(1-Propenyl)-L-cysteine has been detected, but not quantified in, soft-necked garlics (Allium sativum L. var. sativum). This could make trans-S-(1-propenyl)-L-cysteine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on trans-S-(1-Propenyl)-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
L-trans-S-(1-Propenyl)cysteine, 9ci	HMDB
2-Amino-3-[(1Z)-prop-1-en-1-ylsulfanyl]propanoate	Generator
2-Amino-3-[(1Z)-prop-1-en-1-ylsulphanyl]propanoate	Generator
2-Amino-3-[(1Z)-prop-1-en-1-ylsulphanyl]propanoic acid	Generator

Chemical Formula

C₆H₁₁NO₂S

Average Molecular Weight

161.222

Monoisotopic Molecular Weight

161.051049291

IUPAC Name

2-amino-3-[(1Z)-prop-1-en-1-ylsulfanyl]propanoic acid

Traditional Name

2-amino-3-[(1Z)-prop-1-en-1-ylsulfanyl]propanoic acid

CAS Registry Number

Not Available

SMILES

C\C=C/SCC(N)C(O)=O

InChI Identifier

InChI=1S/C6H11NO2S/c1-2-3-10-4-5(7)6(8)9/h2-3,5H,4,7H2,1H3,(H,8,9)/b3-2-

InChI Key

HYGGRRPFVXHQQW-IHWYPQMZSA-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
Thioenolether
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Sulfenyl 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

Extracellular (HMDB: HMDB0029440)
Cytoplasm (HMDB: HMDB0029440)

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)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	195 °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	12.2 g/L	ALOGPS
logP	-1.8	ALOGPS
logP	-1.9	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	2.5	ChemAxon
pKa (Strongest Basic)	9.1	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	4	ChemAxon
Refractivity	42.48 m³·mol⁻¹	ChemAxon
Polarizability	16.32 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]+	136.508	31661259
DarkChem	[M-H]-	129.779	31661259
DeepCCS	[M+H]+	133.688	30932474
DeepCCS	[M-H]-	130.339	30932474
DeepCCS	[M-2H]-	167.387	30932474
DeepCCS	[M+Na]+	142.474	30932474
AllCCS	[M+H]+	137.0	32859911
AllCCS	[M+H-H2O]+	133.1	32859911
AllCCS	[M+NH4]+	140.5	32859911
AllCCS	[M+Na]+	141.5	32859911
AllCCS	[M-H]-	136.0	32859911
AllCCS	[M+Na-2H]-	138.4	32859911
AllCCS	[M+HCOO]-	141.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
trans-S-(1-Propenyl)-L-cysteine	C\C=C/SCC(N)C(O)=O	2410.3	Standard polar	33892256
trans-S-(1-Propenyl)-L-cysteine	C\C=C/SCC(N)C(O)=O	1366.3	Standard non polar	33892256
trans-S-(1-Propenyl)-L-cysteine	C\C=C/SCC(N)C(O)=O	1537.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
trans-S-(1-Propenyl)-L-cysteine,1TMS,isomer #1	C/C=C\SCC(N)C(=O)O[Si](C)(C)C	1469.8	Semi standard non polar	33892256
trans-S-(1-Propenyl)-L-cysteine,1TMS,isomer #2	C/C=C\SCC(N[Si](C)(C)C)C(=O)O	1543.3	Semi standard non polar	33892256
trans-S-(1-Propenyl)-L-cysteine,2TMS,isomer #1	C/C=C\SCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1591.6	Semi standard non polar	33892256
trans-S-(1-Propenyl)-L-cysteine,2TMS,isomer #1	C/C=C\SCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1567.5	Standard non polar	33892256
trans-S-(1-Propenyl)-L-cysteine,2TMS,isomer #2	C/C=C\SCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1706.6	Semi standard non polar	33892256
trans-S-(1-Propenyl)-L-cysteine,2TMS,isomer #2	C/C=C\SCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1674.8	Standard non polar	33892256
trans-S-(1-Propenyl)-L-cysteine,3TMS,isomer #1	C/C=C\SCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1742.4	Semi standard non polar	33892256
trans-S-(1-Propenyl)-L-cysteine,3TMS,isomer #1	C/C=C\SCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1707.6	Standard non polar	33892256
trans-S-(1-Propenyl)-L-cysteine,1TBDMS,isomer #1	C/C=C\SCC(N)C(=O)O[Si](C)(C)C(C)(C)C	1713.9	Semi standard non polar	33892256
trans-S-(1-Propenyl)-L-cysteine,1TBDMS,isomer #2	C/C=C\SCC(N[Si](C)(C)C(C)(C)C)C(=O)O	1773.6	Semi standard non polar	33892256
trans-S-(1-Propenyl)-L-cysteine,2TBDMS,isomer #1	C/C=C\SCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2020.1	Semi standard non polar	33892256
trans-S-(1-Propenyl)-L-cysteine,2TBDMS,isomer #1	C/C=C\SCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2024.2	Standard non polar	33892256
trans-S-(1-Propenyl)-L-cysteine,2TBDMS,isomer #2	C/C=C\SCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2123.6	Semi standard non polar	33892256
trans-S-(1-Propenyl)-L-cysteine,2TBDMS,isomer #2	C/C=C\SCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2107.4	Standard non polar	33892256
trans-S-(1-Propenyl)-L-cysteine,3TBDMS,isomer #1	C/C=C\SCC(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	2406.2	Semi standard non polar	33892256
trans-S-(1-Propenyl)-L-cysteine,3TBDMS,isomer #1	C/C=C\SCC(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	2344.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - trans-S-(1-Propenyl)-L-cysteine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00fu-9100000000-dd6a7db23894a31316ae	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - trans-S-(1-Propenyl)-L-cysteine GC-MS (1 TMS) - 70eV, Positive	splash10-01dr-9300000000-647ca38f22c685b7df73	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - trans-S-(1-Propenyl)-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 - trans-S-(1-Propenyl)-L-cysteine 10V, Positive-QTOF	splash10-02tl-5900000000-16b46b5bb60f757bea8f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-S-(1-Propenyl)-L-cysteine 20V, Positive-QTOF	splash10-00fu-9200000000-751de25c8ac7e83deb58	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-S-(1-Propenyl)-L-cysteine 40V, Positive-QTOF	splash10-006x-9000000000-d9f3ace7156bc45c851c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-S-(1-Propenyl)-L-cysteine 10V, Negative-QTOF	splash10-03k9-6900000000-6b54748286363878d7bc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-S-(1-Propenyl)-L-cysteine 20V, Negative-QTOF	splash10-00di-9200000000-0a4eb244aa0632b18518	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-S-(1-Propenyl)-L-cysteine 40V, Negative-QTOF	splash10-0080-9000000000-a497aba1bb6e105d6ea7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-S-(1-Propenyl)-L-cysteine 10V, Negative-QTOF	splash10-00di-9000000000-6ba7b0193ed0d1ba6340	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-S-(1-Propenyl)-L-cysteine 20V, Negative-QTOF	splash10-00di-9000000000-6ba7b0193ed0d1ba6340	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-S-(1-Propenyl)-L-cysteine 40V, Negative-QTOF	splash10-05fr-9000000000-d42422bf201e4c45d96c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-S-(1-Propenyl)-L-cysteine 10V, Positive-QTOF	splash10-00di-9100000000-ae91da66bdf5baa37d70	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-S-(1-Propenyl)-L-cysteine 20V, Positive-QTOF	splash10-00di-9000000000-e68dce878f8c7dd52caa	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-S-(1-Propenyl)-L-cysteine 40V, Positive-QTOF	splash10-00dl-9000000000-1fae11e6e036a0dc162a	2021-09-24	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

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX 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

FDB000547

KNApSAcK ID

Not Available

Chemspider ID

35032870

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

87194674

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 trans-S-(1-Propenyl)-L-cysteine (HMDB0029440)

MOL for HMDB0029440 (trans-S-(1-Propenyl)-L-cysteine)

3D MOL for HMDB0029440 (trans-S-(1-Propenyl)-L-cysteine)

3D SDF for HMDB0029440 (trans-S-(1-Propenyl)-L-cysteine)

3D-SDF for HMDB0029440 (trans-S-(1-Propenyl)-L-cysteine)

PDB for HMDB0029440 (trans-S-(1-Propenyl)-L-cysteine)

3D PDB for HMDB0029440 (trans-S-(1-Propenyl)-L-cysteine)

SMILES for HMDB0029440 (trans-S-(1-Propenyl)-L-cysteine)

INCHI for HMDB0029440 (trans-S-(1-Propenyl)-L-cysteine)

Structure for HMDB0029440 (trans-S-(1-Propenyl)-L-cysteine)

3D Structure for HMDB0029440 (trans-S-(1-Propenyl)-L-cysteine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra