AFCDB: L-Methionine (FDB012683)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:18 UTC

Update date

2024-11-29 22:28:11 UTC

Primary ID

FDB012683

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

L-Methionine

Description

L-Methionine, also known as acimethin or H-met-H, 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. The L-enantiomer of methionine. 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 is a very strong basic compound (based on its pKa). L-Methionine exists in all living species, ranging from bacteria to humans. Outside of the human body, L-Methionine is found, on average, in the highest concentration within a few different foods, such as milk (cow), beluga whales, and smelts and in a lower concentration in white cabbages, wax gourds, and coconuts. L-Methionine has also been detected, but not quantified in, several different foods, such as pepper (c. chinense), acerola, grass pea, oxheart cabbages, and sherries. This could make L-methionine a potential biomarker for the consumption of these foods. L-Methionine is a potentially toxic compound. L-Methionine, with regard to humans, has been found to be associated with several diseases such as autism, leukemia, obesity, and heart failure; L-methionine has also been linked to the inborn metabolic disorder celiac disease.

CAS Number

63-68-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	23.9 g/L	ALOGPS
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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C5H11NO2S

IUPAC name

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

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

Isomeric SMILES

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

Average Molecular Weight

149.211

Monoisotopic Molecular Weight

149.051049291

Classification

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 )

Ontology

Physiological effect

Health effect:

Health condition:

Blood and lymphatic system disorders:

Anemia

Cardiac disorders:

Heart failure

Cancer:

Leukemia

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Role

Indirect biological role:

Industrial application:

Food and nutrition:

Nutritional supplement

Pharmaceutical industry:

Pharmaceutical

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 40.25%; H 7.43%; N 9.39%; O 21.44%; S 21.49%	DFC
Melting Point	Mp 283° dec.	DFC
Boiling Point	Not Available
Experimental Water Solubility	56.6 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	-1.87	HANSCH,C ET AL. (1995)
Experimental pKa	pKa2 9.2 (20°, 0.15M NaClO4)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]25D -14.9 (H2O); [a]D +34.6 (5M HCl)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	L-Methionine, 2 TMS, GC-MS Spectrum	splash10-004i-0920000000-945c85aa7c9f5eb2dfbb	Spectrum
GC-MS	L-Methionine, non-derivatized, GC-MS Spectrum	splash10-004i-0910000000-b837ee0f4413856560f1	Spectrum
GC-MS	L-Methionine, 2 TMS, GC-MS Spectrum	splash10-00b9-7910000000-5a1558fbb2f5e86edc9b	Spectrum
GC-MS	L-Methionine, 1 TMS, GC-MS Spectrum	splash10-0udi-1900000000-1a97567ce4f25c4e8263	Spectrum
GC-MS	L-Methionine, 2 TMS, GC-MS Spectrum	splash10-004i-0910000000-1b0477118cb20549bf4d	Spectrum
GC-MS	L-Methionine, non-derivatized, GC-MS Spectrum	splash10-004i-0920000000-8ffae5d87508e0704903	Spectrum
GC-MS	L-Methionine, non-derivatized, GC-MS Spectrum	splash10-004i-0920000000-945c85aa7c9f5eb2dfbb	Spectrum
GC-MS	L-Methionine, non-derivatized, GC-MS Spectrum	splash10-004i-0910000000-b837ee0f4413856560f1	Spectrum
GC-MS	L-Methionine, non-derivatized, GC-MS Spectrum	splash10-01bc-2692000000-c6a4af434abaeea2de87	Spectrum
GC-MS	L-Methionine, non-derivatized, GC-MS Spectrum	splash10-00b9-7910000000-5a1558fbb2f5e86edc9b	Spectrum
GC-MS	L-Methionine, non-derivatized, GC-MS Spectrum	splash10-0udi-1900000000-1a97567ce4f25c4e8263	Spectrum
GC-MS	L-Methionine, non-derivatized, GC-MS Spectrum	splash10-004i-0910000000-1b0477118cb20549bf4d	Spectrum
Predicted GC-MS	L-Methionine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0mbd-9200000000-77e5cfb78936ad02d71c	Spectrum
Predicted GC-MS	L-Methionine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-9510000000-c03dec8575710eed861e	Spectrum
Predicted GC-MS	L-Methionine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Methionine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Methionine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Methionine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0uea-1900000000-b991859b2c5bed6592a8	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-08fr-9000000000-66855ace60e59837f131	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-08fr-9000000000-56a567791c824c6a9da6	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0fe0-0900000000-d680295f21b2e2b40366	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0006-9000000000-062d3540db4db22da836	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-0900000000-84467513e2c9ec1a6851	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-88dc2bebb198eea550ef	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0udi-0920000000-b444ad79abeb16acde43	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-6e24a8df417e5f3db58c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-0900000000-c60ef880eb9a816a274b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0900000000-a7b7d1a3481c0c691a5b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0002-0900000000-9156f088f4cc9eafa892	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0002-9200000000-f78ba2aab8d5a0e0b135	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0002-9000000000-e7b819fd2d0ac3862860	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0002-9000000000-b61396e720381bd5ff85	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0002-9000000000-b61396e720381bd5ff85	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0udi-0900000000-c3557cb41fd6fe268819	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0udi-6900000000-6bf5af2d1c561013948a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-08fr-9000000000-63c9b1c138f9a27490e5	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-03di-9000000000-e133c47b0efe4992589f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-03di-9000000000-dee78b4f34f8732fedb0	2012-08-31	View Spectrum
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
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 MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-2900000000-305916dde72c899993b6	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-9800000000-47e0a34a2ec02bd762bf	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	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)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

16643

Phenol-Explorer ID

Not Available

DrugBank ID

DB00134

HMDB ID

HMDB00696

CRC / DFC (Dictionary of Food Compounds) ID

EAFUS ID

Dr. Duke ID

BIGG ID

KNApSAcK ID

HET ID

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Methionine

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti cataract	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
antidote	50247	Any protective agent counteracting or neutralizing the action of poisons.	DUKE
anti eczemic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti hepatotic	62868	Any compound that is able to prevent damage to the liver.	DUKE
antioxidant	22586	A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.	DUKE
anti Parkinsonian	48407	A drug used in the treatment of Parkinson's disease.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
emetic			DUKE
essential			DUKE
glutathionigenic			DUKE
hepatoprotective	62868	Any compound that is able to prevent damage to the liver.	DUKE
lipotropic			DUKE
urine acidifier			DUKE
urine deodorant			DUKE

Enzymes

Name	Gene Name	UniProt ID
Tyrosine aminotransferase	TAT	P17735
Kynurenine--oxoglutarate transaminase 3	CCBL2	Q6YP21
Methionine-R-sulfoxide reductase B1	MSRB1	Q9NZV6
Kynurenine--oxoglutarate transaminase 1	CCBL1	Q16773
Glutamine synthetase	GLUL	P15104
Methionine--tRNA ligase, cytoplasmic	MARS	P56192
Methionine--tRNA ligase, mitochondrial	MARS2	Q96GW9
Mitochondrial peptide methionine sulfoxide reductase	MSRA	Q9UJ68
Methionine-R-sulfoxide reductase B2, mitochondrial	MSRB2	Q9Y3D2
Methionine-R-sulfoxide reductase B3	MSRB3	Q8IXL7

Pathways

Name	SMPDB Link	KEGG Link
Betaine Metabolism	SMP00123	map00260
Glycine and Serine Metabolism	SMP00004	map00260
Methionine Metabolism	SMP00033	map00270
Spermidine and Spermine Biosynthesis	SMP00445	Not Available
Transcription/Translation	SMP00019	Not Available
Metabolism and Physiological Effects of Homocysteine	SMP0123280	Not Available
Metabolism and Physiological Effects of Dimethylglycine	SMP0124873	Not Available
Metabolism and Physiological Effects of N-Acetylmethionine	SMP0126707	Not Available
Metabolism and Physiological Effects of N-Formyl-L-Methionine	SMP0126765	Not Available
Metabolism and Physiological Effects of S-Adenosylhomocysteine	SMP0127690	Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

L-Methionine (FDB012683)

Structure for FDB012683 (L-Methionine)