Milk Composition Database: Showing metabocard for L-Methionine (BMDB0000696)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

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Record Information

Version

1.0

Creation Date

2016-09-30 22:35:03 UTC

Update Date

2020-06-04 21:42:04 UTC

MCDB ID

BMDB0000696

Secondary Accession Numbers

BMDB00696

Metabolite Identification

Common Name

L-Methionine

Description

L-Methionine, also known as liquimeth or pedameth, belongs to the class of organic compounds known as methionine and derivatives. Methionine and derivatives are compounds containing methionine or a derivative thereof resulting from reaction of methionine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Methionine is a drug which is used for protein synthesis including the formation of same, l-homocysteine, l-cysteine, taurine, and sulfate. L-Methionine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Methionine exists in all living species, ranging from bacteria to humans. L-Methionine is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S)-2-Amino-4-(methylsulfanyl)butanoic acid	ChEBI
(S)-2-Amino-4-(methylthio)butanoic acid	ChEBI
(S)-2-Amino-4-(methylthio)butyric acid	ChEBI
(S)-Methionine	ChEBI
L-(-)-Methionine	ChEBI
L-alpha-Amino-gamma-methylmercaptobutyric acid	ChEBI
L-Methionin	ChEBI
M	ChEBI
Met	ChEBI
METHIONINE	ChEBI
L-2-Amino-4methylthiobutyric acid	Kegg
L-Methionine Z	Kegg
(2S)-2-Amino-4-(methylsulfanyl)butanoate	Generator
(2S)-2-Amino-4-(methylsulphanyl)butanoate	Generator
(2S)-2-Amino-4-(methylsulphanyl)butanoic acid	Generator
(S)-2-Amino-4-(methylthio)butanoate	Generator
(S)-2-Amino-4-(methylthio)butyrate	Generator
L-a-Amino-g-methylmercaptobutyrate	Generator
L-a-Amino-g-methylmercaptobutyric acid	Generator
L-alpha-Amino-gamma-methylmercaptobutyrate	Generator
L-Α-amino-γ-methylmercaptobutyrate	Generator
L-Α-amino-γ-methylmercaptobutyric acid	Generator
L-2-Amino-4methylthiobutyrate	Generator
(L)-Methionine	HMDB
(S)-(+)-Methionine	HMDB
(S)-2-Amino-4-(methylthio)-butanoate	HMDB
(S)-2-Amino-4-(methylthio)-butanoic acid	HMDB
2-Amino-4-(methylthio)butyrate	HMDB
2-Amino-4-(methylthio)butyric acid	HMDB
2-Amino-4-methylthiobutanoate	HMDB
2-Amino-4-methylthiobutanoic acid	HMDB
a-Amino-g-methylmercaptobutyrate	HMDB
a-Amino-g-methylmercaptobutyric acid	HMDB
Acimethin	HMDB
alpha-Amino-alpha-aminobutyric acid	HMDB
alpha-Amino-gamma-methylmercaptobutyrate	HMDB
alpha-Amino-gamma-methylmercaptobutyric acid	HMDB
Cymethion	HMDB
g-Methylthio-a-aminobutyrate	HMDB
g-Methylthio-a-aminobutyric acid	HMDB
gamma-Methylthio-alpha-aminobutyrate	HMDB
gamma-Methylthio-alpha-aminobutyric acid	HMDB
H-Met-H	HMDB
H-Met-OH	HMDB
L(-)-Amino-alpha-amino-alpha-aminobutyric acid	HMDB
L(-)-Amino-gamma-methylthiobutyric acid	HMDB
L-2-Amino-4-(methylthio)butyric acid	HMDB
L-2-Amino-4-methylthiobutyric acid	HMDB
L-a-Amino-g-methylthiobutyrate	HMDB
L-a-Amino-g-methylthiobutyric acid	HMDB
L-alpha-Amino-gamma-methylthiobutyrate	HMDB
L-alpha-Amino-gamma-methylthiobutyric acid	HMDB
L-gamma-Methylthio-alpha-aminobutyric acid	HMDB
L-Methioninum	HMDB
Liquimeth	HMDB
Mepron	HMDB
Methilanin	HMDB
Methioninum	HMDB
Metionina	HMDB
Neo-methidin	HMDB
Poly-L-methionine	HMDB
Polymethionine	HMDB
S-Methionine	HMDB
S-Methyl-L-homocysteine	HMDB
Toxin war	HMDB
L-Isomer methionine	HMDB
Methionine, L-isomer	HMDB
Pedameth	HMDB
Methionine, L isomer	HMDB
(3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-BETA,BETA-carotene-3,3'-diol	ChEBI
Bo-xan	ChEBI
e 161b	ChEBI
Xanthophyll	ChEBI
(3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-b,b-carotene-3,3'-diol	Generator
(3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-β,β-carotene-3,3'-diol	Generator

Chemical Formula

C₅H₁₁NO₂S

Average Molecular Weight

149.211

Monoisotopic Molecular Weight

149.051049291

IUPAC Name

(2S)-2-amino-4-(methylsulfanyl)butanoic acid

Traditional Name

L-methionine

CAS Registry Number

63-68-3

SMILES

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

InChI Identifier

InChI=1S/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1

InChI Key

FFEARJCKVFRZRR-BYPYZUCNSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as methionine and derivatives. Methionine and derivatives are compounds containing methionine or a derivative thereof resulting from reaction of methionine 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

Methionine and derivatives

Alternative Parents

Substituents

Methionine or derivatives
Alpha-amino acid
L-alpha-amino acid
Thia fatty acid
Fatty acid
Fatty acyl
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Thioether
Sulfenyl compound
Dialkylthioether
Amine
Organic oxygen compound
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Primary aliphatic amine
Carbonyl group
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

aspartate family amino acid (CHEBI:16643 )
proteinogenic amino acid (CHEBI:16643 )
L-alpha-amino acid (CHEBI:16643 )
methionine (CHEBI:16643 )
Common amino acids (C00073 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	284 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	56.6 mg/mL	YALKOWSKY,SH & DANNENFELSER,RM (1992)
LogP	-1.87	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	-1.8	ALOGPS
logP	-2.2	ChemAxon
logS	-0.8	ALOGPS
pKa (Strongest Acidic)	2.53	ChemAxon
pKa (Strongest Basic)	9.5	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	37.59 m³·mol⁻¹	ChemAxon
Polarizability	15.5 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	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
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-004i-0920000000-945c85aa7c9f5eb2dfbb	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-004i-0910000000-b837ee0f4413856560f1	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00b9-7910000000-5a1558fbb2f5e86edc9b	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-0udi-1900000000-1a97567ce4f25c4e8263	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-004i-0910000000-1b0477118cb20549bf4d	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-0920000000-8ffae5d87508e0704903	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004i-0920000000-945c85aa7c9f5eb2dfbb	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004i-0910000000-b837ee0f4413856560f1	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-QQ (Non-derivatized)	splash10-01bc-2692000000-c6a4af434abaeea2de87	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00b9-7910000000-5a1558fbb2f5e86edc9b	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0udi-1900000000-1a97567ce4f25c4e8263	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004i-0910000000-1b0477118cb20549bf4d	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0mbd-9200000000-77e5cfb78936ad02d71c	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9510000000-c03dec8575710eed861e	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0uea-1900000000-b991859b2c5bed6592a8	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-08fr-9000000000-66855ace60e59837f131	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-08fr-9000000000-56a567791c824c6a9da6	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0fe0-0900000000-d680295f21b2e2b40366	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0006-9000000000-062d3540db4db22da836	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-0900000000-84467513e2c9ec1a6851	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-88dc2bebb198eea550ef	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0udi-0920000000-b444ad79abeb16acde43	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-6e24a8df417e5f3db58c	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-0900000000-c60ef880eb9a816a274b	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0900000000-a7b7d1a3481c0c691a5b	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0002-0900000000-9156f088f4cc9eafa892	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0002-9200000000-f78ba2aab8d5a0e0b135	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0002-9000000000-e7b819fd2d0ac3862860	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0002-9000000000-b61396e720381bd5ff85	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0002-9000000000-b61396e720381bd5ff85	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0udi-0900000000-c3557cb41fd6fe268819	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0udi-6900000000-6bf5af2d1c561013948a	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-08fr-9000000000-63c9b1c138f9a27490e5	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-03di-9000000000-e133c47b0efe4992589f	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-03di-9000000000-dee78b4f34f8732fedb0	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , Positive	splash10-0udi-0900000000-d3f03ff5e8eacc8b6c8e	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0udi-0900000000-e0dd5ff44b7962f6a2d2	2012-08-31	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-2900000000-305916dde72c899993b6	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-9800000000-47e0a34a2ec02bd762bf	2016-09-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Not Available	2021-10-10	View Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Not Available	2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected but not Quantified	Not Applicable	PMID: 23497994	details
Detected but not Quantified	Not Applicable	PMID: 25087032	details
Detected and Quantified	5898 uM	Fooddata+, T...	details
Detected and Quantified	5898 uM	Fooddata+, T...	details
Detected and Quantified	5898 uM	Fooddata+, T...	details
Detected and Quantified	5898 uM	Fooddata+, T...	details
Detected and Quantified	5764 uM	Fooddata+, T...	details
Detected and Quantified	5764 uM	Fooddata+, T...	details
Detected and Quantified	5764 uM	Fooddata+, T...	details
Detected and Quantified	1.0 +/- 0.1 uM	PMID: 30994344	details
Detected and Quantified	0.9 +/- 0.1 uM	PMID: 30994344	details
Detected and Quantified	1.0 +/- 0.1 uM	PMID: 30994344	details
Detected and Quantified	1.0 +/- 0.1 uM	PMID: 30994344	details

External Links

HMDB ID

HMDB0000696

DrugBank ID

DB00134

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

16643

References

Synthesis Reference

Boy, Matthias; Klein, Daniela; Schroeder, Hartwig. Method for the production and recovery of methionine. PCT Int. Appl. (2005), 34 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
Fooddata+, The Technical University of Denmark (DTU) [Link]

Showing metabocard for L-Methionine (BMDB0000696)

Structure for BMDB0000696 (L-Methionine)