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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

enzymes (2) Show 2 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:36 UTC

Update Date

2023-02-21 17:16:10 UTC

HMDB ID

HMDB0002108

Secondary Accession Numbers

HMDB02108

Metabolite Identification

Common Name

Methylcysteine

Description

Methylcysteine is one of the identified number of bioactive substances in garlic that are water soluble (PMID 16484549 ). It has been suggested that the use of these organosulfur agents derived from garlic could protect partially oxidized and glycated LDL or plasma against further oxidative and glycative deterioration, which might benefit patients with diabetic-related vascular diseases (PMID 15161248 ). It may also exert some chemopreventive effects on chemical carcinogenesis. However, it should be borne in mind that may also demonstrate promotion potential, depending on the organ examined (PMID 9591199 ). Methylcystein is a biomarker for the consumption of dried and cooked beans.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2R)-2-Amino-3-(methylsulfanyl)propanoic acid	HMDB
(R)-2-Amino-3-(methylthio)propanoic acid	HMDB
3-(Methylthio)-L-alanine	HMDB
L-Methylcysteine	HMDB
S-Methyl-L-cysteine	HMDB
(2R)-2-Amino-3-(methylsulfanyl)propanoate	HMDB
(2R)-2-Amino-3-(methylsulphanyl)propanoate	HMDB
(2R)-2-Amino-3-(methylsulphanyl)propanoic acid	HMDB
(R)-2-Amino-3-(methylthio)propanoate	HMDB
3-(Methylthio)-L-(8ci)alanine	HMDB
Acm-thiopropionate	HMDB
Acm-thiopropionic acid	HMDB
L-Aspartic acid dimethyl ester	HMDB
S-Acetamidomethyl-deamino-cysteine	HMDB
S-Methyl-(9ci)-L-cysteine	HMDB
S-Methyl-cysteine	HMDB
S-Methyl-DL-cysteine	HMDB
S-Methylcysteine	HMDB
S-11C-Methyl-L-cysteine	HMDB
S-Methylcysteine, (DL-cys)-isomer	HMDB
S-Methylcysteine, hydrochloride, (L-cys)-isomer	HMDB
S-Methylcysteine, (L-cys)-isomer	HMDB

Chemical Formula

C₄H₉NO₂S

Average Molecular Weight

135.18

Monoisotopic Molecular Weight

135.035399708

IUPAC Name

(2S)-2-amino-3-(methylsulfanyl)propanoic acid

Traditional Name

(2S)-2-amino-3-(methylsulfanyl)propanoic acid

CAS Registry Number

1187-84-4

SMILES

CSC[C@@H](N)C(O)=O

InChI Identifier

InChI=1S/C4H9NO2S/c1-8-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m1/s1

InChI Key

IDIDJDIHTAOVLG-GSVOUGTGSA-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
S-alkyl-l-cysteine
Alpha-amino acid
D-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

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 508804)

Organ

Placenta (HMDB: HMDB0002108)

Excreta

Biofluid or Excreta

Urine (PMID: 27012787)
Feces (PMID: 27543620)

Source

Exogenous

Food

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Pulse

Bean

Pulses (FooDB: FOOD00867)

Herb and spice

Herb

Welsh onion (FooDB: FOOD00241)
Soft-necked garlic (FooDB: FOOD00850)

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)

Brassica

Brassicas (FooDB: FOOD00857)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	300.30 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	225200 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.380 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	65.8 g/L	ALOGPS
logP	-2.2	ALOGPS
logP	-2.4	ChemAxon
logS	-0.31	ALOGPS
pKa (Strongest Acidic)	2.44	ChemAxon
pKa (Strongest Basic)	9.15	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	3	ChemAxon
Refractivity	32.87 m³·mol⁻¹	ChemAxon
Polarizability	13.56 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
DeepCCS	[M+H]+	122.847	30932474
DeepCCS	[M-H]-	119.617	30932474
DeepCCS	[M-2H]-	156.523	30932474
DeepCCS	[M+Na]+	131.483	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methylcysteine	CSC[C@@H](N)C(O)=O	2127.7	Standard polar	33892256
Methylcysteine	CSC[C@@H](N)C(O)=O	1217.3	Standard non polar	33892256
Methylcysteine	CSC[C@@H](N)C(O)=O	1481.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Methylcysteine,1TMS,isomer #1	CSC[C@@H](N)C(=O)O[Si](C)(C)C	1298.5	Semi standard non polar	33892256
Methylcysteine,1TMS,isomer #2	CSC[C@@H](N[Si](C)(C)C)C(=O)O	1385.2	Semi standard non polar	33892256
Methylcysteine,2TMS,isomer #1	CSC[C@@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1412.7	Semi standard non polar	33892256
Methylcysteine,2TMS,isomer #1	CSC[C@@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1384.5	Standard non polar	33892256
Methylcysteine,2TMS,isomer #1	CSC[C@@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1733.0	Standard polar	33892256
Methylcysteine,2TMS,isomer #2	CSC[C@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1555.3	Semi standard non polar	33892256
Methylcysteine,2TMS,isomer #2	CSC[C@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1468.1	Standard non polar	33892256
Methylcysteine,2TMS,isomer #2	CSC[C@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1866.4	Standard polar	33892256
Methylcysteine,3TMS,isomer #1	CSC[C@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1570.9	Semi standard non polar	33892256
Methylcysteine,3TMS,isomer #1	CSC[C@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1532.6	Standard non polar	33892256
Methylcysteine,3TMS,isomer #1	CSC[C@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1610.7	Standard polar	33892256
Methylcysteine,1TBDMS,isomer #1	CSC[C@@H](N)C(=O)O[Si](C)(C)C(C)(C)C	1536.6	Semi standard non polar	33892256
Methylcysteine,1TBDMS,isomer #2	CSC[C@@H](N[Si](C)(C)C(C)(C)C)C(=O)O	1634.6	Semi standard non polar	33892256
Methylcysteine,2TBDMS,isomer #1	CSC[C@@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1881.6	Semi standard non polar	33892256
Methylcysteine,2TBDMS,isomer #1	CSC[C@@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1819.3	Standard non polar	33892256
Methylcysteine,2TBDMS,isomer #1	CSC[C@@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1939.1	Standard polar	33892256
Methylcysteine,2TBDMS,isomer #2	CSC[C@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1990.8	Semi standard non polar	33892256
Methylcysteine,2TBDMS,isomer #2	CSC[C@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1907.8	Standard non polar	33892256
Methylcysteine,2TBDMS,isomer #2	CSC[C@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2006.7	Standard polar	33892256
Methylcysteine,3TBDMS,isomer #1	CSC[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	2255.4	Semi standard non polar	33892256
Methylcysteine,3TBDMS,isomer #1	CSC[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	2160.7	Standard non polar	33892256
Methylcysteine,3TBDMS,isomer #1	CSC[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	2001.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Methylcysteine 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 - Methylcysteine 10V, Negative-QTOF	splash10-0002-9000000000-e1d92d2a30bee517d754	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylcysteine 20V, Negative-QTOF	splash10-0002-9000000000-e1d92d2a30bee517d754	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylcysteine 40V, Negative-QTOF	splash10-0002-9000000000-e1d92d2a30bee517d754	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylcysteine 10V, Positive-QTOF	splash10-014i-3900000000-5cbf55ce6a100129ce26	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylcysteine 20V, Positive-QTOF	splash10-00dj-9200000000-db00622b129035e9b4e3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylcysteine 40V, Positive-QTOF	splash10-0002-9000000000-b7d1bbbfc29f4c11b472	2021-09-23	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

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	3.9 +/- 1.9 uM	Adult (>18 years old)	Both	Normal	508804	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Urine	Detected and Quantified	0.34-0.82 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	27012787	details
Urine	Detected and Quantified	0.35-0.63 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	27012787	details
Urine	Detected and Quantified	0.0796-0.717 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	21110385	details
Urine	Detected and Quantified	0.0177-0.619 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	21110385	details
Urine	Detected and Quantified	0.34-0.82 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	27012787	details
Urine	Detected and Quantified	0.35-0.63 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	27012787	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

FDB003689

KNApSAcK ID

C00000747

Chemspider ID

79551

KEGG Compound ID

Not Available

BioCyc ID

S-METHYL-L-CYSTEINE

BiGG ID

Not Available

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

ChEBI ID

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1281351

References

Synthesis Reference

Ma, Chengjun; Yao, Fei; Zhang, Guanyong. Synthesis of S-methyl-L-cysteine. Huaxue Shijie (2003), 44(7), 370-372.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Huang CN, Horng JS, Yin MC: Antioxidative and antiglycative effects of six organosulfur compounds in low-density lipoprotein and plasma. J Agric Food Chem. 2004 Jun 2;52(11):3674-8. [PubMed:15161248 ]
Rivlin RS: Is garlic alternative medicine? J Nutr. 2006 Mar;136(3 Suppl):713S-715S. [PubMed:16484549 ]
Fukushima S, Takada N, Hori T, Wanibuchi H: Cancer prevention by organosulfur compounds from garlic and onion. J Cell Biochem Suppl. 1997;27:100-5. [PubMed:9591199 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

Enzyme Details

1. Methylated-DNA--protein-cysteine methyltransferase

General function:: Involved in methylated-DNA-[protein]-cysteine S-methyltransferase activity
Specific function:: Involved in the cellular defense against the biological effects of O6-methylguanine (O6-MeG) in DNA. Repairs alkylated guanine in DNA by stoichiometrically transferring the alkyl group at the O-6 position to a cysteine residue in the enzyme. This is a suicide reaction:the enzyme is irreversibly inactivated
Gene Name:: MGMT
Uniprot ID:: P16455
Molecular weight:: 21645.8

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Enzyme Details

2. Cathepsin D

General function:: Involved in aspartic-type endopeptidase activity
Specific function:: Acid protease active in intracellular protein breakdown. Involved in the pathogenesis of several diseases such as breast cancer and possibly Alzheimer disease
Gene Name:: CTSD
Uniprot ID:: P07339
Molecular weight:: 44551.8

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Showing metabocard for Methylcysteine (HMDB0002108)

MOL for HMDB0002108 (Methylcysteine)

3D MOL for HMDB0002108 (Methylcysteine)

3D SDF for HMDB0002108 (Methylcysteine)

3D-SDF for HMDB0002108 (Methylcysteine)

PDB for HMDB0002108 (Methylcysteine)

3D PDB for HMDB0002108 (Methylcysteine)

SMILES for HMDB0002108 (Methylcysteine)

INCHI for HMDB0002108 (Methylcysteine)

Structure for HMDB0002108 (Methylcysteine)

3D Structure for HMDB0002108 (Methylcysteine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

References

References