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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 19:08:04 UTC

Update Date

2023-02-21 17:24:10 UTC

HMDB ID

HMDB0034323

Secondary Accession Numbers

HMDB34323

Metabolite Identification

Common Name

S-Allylcysteine

Description

S-Allylcysteine 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-Allylcysteine is a cooked and roasted tasting compound. S-Allylcysteine is found, on average, in the highest concentration within soft-necked garlics (Allium sativum L. var. sativum). S-Allylcysteine has also been detected, but not quantified in, several different foods, such as onion-family vegetables, welsh onions (Allium fistulosum), garden onion (var.), garden onions (Allium cepa), and green onion. This could make S-allylcysteine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on S-Allylcysteine.

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-DeoxyallIIn	HMDB
S-2-Propenyl-L-cysteine	HMDB, MeSH
S-Allyl-L -cysteine	HMDB
Allyl cysteine	MeSH, HMDB
2-Amino-3-(prop-2-en-1-ylsulfanyl)propanoate	Generator
2-Amino-3-(prop-2-en-1-ylsulphanyl)propanoate	Generator
2-Amino-3-(prop-2-en-1-ylsulphanyl)propanoic acid	Generator
S-Allylcysteine	MeSH

Chemical Formula

C₆H₁₁NO₂S

Average Molecular Weight

161.222

Monoisotopic Molecular Weight

161.051049291

IUPAC Name

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

Traditional Name

S-allyl cysteine

CAS Registry Number

21593-77-1

SMILES

NC(CSCC=C)C(O)=O

InChI Identifier

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

InChI Key

ZFAHNWWNDFHPOH-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
Allyl sulfur compound
Carboxylic acid
Monocarboxylic acid or derivatives
Thioether
Sulfenyl compound
Dialkylthioether
Carbonyl group
Amine
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Primary aliphatic amine
Hydrocarbon derivative
Organic oxygen compound
Organopnictogen compound
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0034323)
Cytoplasm (HMDB: HMDB0034323)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034323)

Source

Exogenous

Food

Food (HMDB: HMDB0034323)

Herb and spice

Herb

Vegetable

Onion-family vegetable

Onion family vegetables (HMDB: HMDB0034323)
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: HMDB0034323)

Process

Not Available

Role

Industrial applicationBiological role

Nutrient (HMDB: HMDB0034323)
Anti aging (HMDB: HMDB0034323)
Anti atherogenic (HMDB: HMDB0034323)
Anti cancer (HMDB: HMDB0034323)
Anti cholesterogenic (HMDB: HMDB0034323)
Anti diabetic (HMDB: HMDB0034323)
Anti hepatotoxic (HMDB: HMDB0034323)
Anti melanomic (HMDB: HMDB0034323)
Anti neuroblastomic (HMDB: HMDB0034323)
Anti NF-kappa-B (HMDB: HMDB0034323)
Anti proliferant (HMDB: HMDB0034323)
Anti radicular (HMDB: HMDB0034323)
Glutathione-sparing (HMDB: HMDB0034323)
Hypocholesterolemic (HMDB: HMDB0034323)
Mucokinetic (HMDB: HMDB0034323)

Modulator

Inhibitor

Enzyme inhibitor

Squalene-monooxygenase inhibitor (HMDB: HMDB0034323)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	218 °C	Not Available
Boiling Point	300.00 to 301.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0	The Good Scents Company Information System
LogP	1.310	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	13.7 g/L	ALOGPS
logP	-1.8	ALOGPS
logP	-1.8	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	2.53	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	42.09 m³·mol⁻¹	ChemAxon
Polarizability	16.85 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]+	134.134	31661259
DarkChem	[M-H]-	129.034	31661259
DeepCCS	[M+H]+	130.584	30932474
DeepCCS	[M-H]-	127.821	30932474
DeepCCS	[M-2H]-	164.273	30932474
DeepCCS	[M+Na]+	139.056	30932474
AllCCS	[M+H]+	136.3	32859911
AllCCS	[M+H-H2O]+	132.6	32859911
AllCCS	[M+NH4]+	139.9	32859911
AllCCS	[M+Na]+	140.9	32859911
AllCCS	[M-H]-	135.7	32859911
AllCCS	[M+Na-2H]-	138.1	32859911
AllCCS	[M+HCOO]-	140.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
S-Allylcysteine	NC(CSCC=C)C(O)=O	2402.2	Standard polar	33892256
S-Allylcysteine	NC(CSCC=C)C(O)=O	1320.3	Standard non polar	33892256
S-Allylcysteine	NC(CSCC=C)C(O)=O	1548.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
S-Allylcysteine,1TMS,isomer #1	C=CCSCC(N)C(=O)O[Si](C)(C)C	1433.3	Semi standard non polar	33892256
S-Allylcysteine,1TMS,isomer #2	C=CCSCC(N[Si](C)(C)C)C(=O)O	1501.9	Semi standard non polar	33892256
S-Allylcysteine,2TMS,isomer #1	C=CCSCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1541.2	Semi standard non polar	33892256
S-Allylcysteine,2TMS,isomer #1	C=CCSCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1545.2	Standard non polar	33892256
S-Allylcysteine,2TMS,isomer #2	C=CCSCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1657.9	Semi standard non polar	33892256
S-Allylcysteine,2TMS,isomer #2	C=CCSCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1623.4	Standard non polar	33892256
S-Allylcysteine,3TMS,isomer #1	C=CCSCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1698.2	Semi standard non polar	33892256
S-Allylcysteine,3TMS,isomer #1	C=CCSCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1696.2	Standard non polar	33892256
S-Allylcysteine,1TBDMS,isomer #1	C=CCSCC(N)C(=O)O[Si](C)(C)C(C)(C)C	1654.9	Semi standard non polar	33892256
S-Allylcysteine,1TBDMS,isomer #2	C=CCSCC(N[Si](C)(C)C(C)(C)C)C(=O)O	1717.2	Semi standard non polar	33892256
S-Allylcysteine,2TBDMS,isomer #1	C=CCSCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1976.8	Semi standard non polar	33892256
S-Allylcysteine,2TBDMS,isomer #1	C=CCSCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1972.9	Standard non polar	33892256
S-Allylcysteine,2TBDMS,isomer #2	C=CCSCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2077.2	Semi standard non polar	33892256
S-Allylcysteine,2TBDMS,isomer #2	C=CCSCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2056.7	Standard non polar	33892256
S-Allylcysteine,3TBDMS,isomer #1	C=CCSCC(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	2373.5	Semi standard non polar	33892256
S-Allylcysteine,3TBDMS,isomer #1	C=CCSCC(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	2312.6	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - S-Allylcysteine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-6472ab7f2d2b13b42092	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - S-Allylcysteine GC-MS (1 TMS) - 70eV, Positive	splash10-0007-9500000000-6130c45418f29c7eb2ab	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - S-Allylcysteine 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-Allylcysteine 10V, Positive-QTOF	splash10-0296-5900000000-8c89fd146060416fb06f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Allylcysteine 20V, Positive-QTOF	splash10-00fu-9300000000-9edb4d3a5be841c6a27e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Allylcysteine 40V, Positive-QTOF	splash10-006x-9000000000-8dde9c26474a4aa9cf9c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Allylcysteine 10V, Negative-QTOF	splash10-0229-4900000000-5ea2674e8ab9863410c8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Allylcysteine 20V, Negative-QTOF	splash10-00di-9500000000-584904bc5c18c5d83a03	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Allylcysteine 40V, Negative-QTOF	splash10-0080-9100000000-847061c3a2deccc782b7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Allylcysteine 10V, Positive-QTOF	splash10-00dj-7900000000-cf1399bc43a29b3b3b3f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Allylcysteine 20V, Positive-QTOF	splash10-00di-9200000000-ee198d96f7aa130ede35	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Allylcysteine 40V, Positive-QTOF	splash10-006x-9000000000-55e1f534cff75732a962	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Allylcysteine 10V, Negative-QTOF	splash10-00di-9000000000-f82699e969ddcd674ff2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Allylcysteine 20V, Negative-QTOF	splash10-0089-9100000000-9c1e17063ccb59bc374a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Allylcysteine 40V, Negative-QTOF	splash10-00di-9000000000-bfbf6eb00eab590319dc	2021-09-23	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

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

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

S-Allyl cysteine

METLIN ID

Not Available

PubChem Compound

98280

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1593931

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-Allylcysteine (HMDB0034323)

MOL for HMDB0034323 (S-Allylcysteine)

3D MOL for HMDB0034323 (S-Allylcysteine)

3D SDF for HMDB0034323 (S-Allylcysteine)

3D-SDF for HMDB0034323 (S-Allylcysteine)

PDB for HMDB0034323 (S-Allylcysteine)

3D PDB for HMDB0034323 (S-Allylcysteine)

SMILES for HMDB0034323 (S-Allylcysteine)

INCHI for HMDB0034323 (S-Allylcysteine)

Structure for HMDB0034323 (S-Allylcysteine)

3D Structure for HMDB0034323 (S-Allylcysteine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra