MiMeDB: Showing metabocard for Methylcysteine (MMDBc0000407)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:37:03 UTC

Update Date

2024-04-30 19:32:16 UTC

Metabolite ID

MMDBc0000407

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

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

Molecular Formula

C₄H₉NO₂S

Average Mass

135.18

Monoisotopic Mass

135.035399708

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

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

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9000000000-e1d92d2a30bee517d754	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-9000000000-e1d92d2a30bee517d754	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-9000000000-e1d92d2a30bee517d754	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-3900000000-5cbf55ce6a100129ce26	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dj-9200000000-db00622b129035e9b4e3	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9000000000-b7d1bbbfc29f4c11b472	2021-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Placenta
Urine

Tissue Locations

Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0193392	Methylated-DNA--protein-cysteine methyltransferase	Unknown	P16455	Homo sapiens
MMDBp0193487	Cathepsin D	Enzyme	P07339	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1		Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified			0.0177	0.619	umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	21110385
Human Urine	Detected and Quantified			0.0796	0.717	umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	21110385
Human Urine	Detected and Quantified			0.34	0.82	umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	27012787
Human Urine	Detected and Quantified			0.34	0.82	umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	27012787
Human Urine	Detected and Quantified			0.35	0.63	umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	27012787
Human Urine	Detected and Quantified			0.35	0.63	umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	27012787
Human Blood	Detected and Quantified	3.9	1.9			uM	Adult (>18 years old)	Both	Normal	HMDB	508804
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0002108

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

References

Synthesis Reference

Not Available

General References

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 ]
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. doi: 10.1021/jf0307292. [PubMed:15161248 ]
Rivlin RS: Is garlic alternative medicine? J Nutr. 2006 Mar;136(3 Suppl):713S-715S. doi: 10.1093/jn/136.3.713S. [PubMed:16484549 ]
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 ]

Showing metabocard for Methylcysteine (MMDBc0000407)

MOL for #<Metabolite:0x00007fdb50ab68b8>

3D MOL for #<Metabolite:0x00007fdb50ab68b8>

3D SDF for #<Metabolite:0x00007fdb50ab68b8>

3D-SDF for #<Metabolite:0x00007fdb50ab68b8>

PDB for #<Metabolite:0x00007fdb50ab68b8>

3D PDB for #<Metabolite:0x00007fdb50ab68b8>

SMILES for #<Metabolite:0x00007fdb50ab68b8>

INCHI for #<Metabolite:0x00007fdb50ab68b8>

Structure for #<Metabolite:0x00007fdb50ab68b8>

3D Structure for #<Metabolite:0x00007fdb50ab68b8>