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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2009-03-03 12:04:46 UTC
Update Date2020-03-02 16:05:15 UTC
HMDB IDHMDB0011745
Secondary Accession Numbers
  • HMDB11745
Metabolite Identification
Common NameN-Acetyl-L-methionine
DescriptionN-acetyl-L-methionine is nutritionally and metabolically equivalent to L-methionine. Methionine is a dietary indispensable amino acid required for normal growth and development of humans, other mammals, and avian species. In addition to being a substrate for protein synthesis, it is an intermediate in transmethylation reactions, serving as the major methyl group donor in vivo, including the methyl groups for DNA and RNA intermediates. Methionine is a methyl acceptor for 5-methyltetrahydrofolate-homocysteine methyltransferase (methionine synthase), the only reaction that allows for the recycling of this form of folate, and is also a methyl acceptor for the catabolism of betaine. Methionine is also required for the synthesis of cysteine. Methionine is accepted as the metabolic precursor for cysteine. Only the sulfur atom from methionine is transferred to cysteine; the carbon skeleton of cysteine is donated by serine (PMID: 16702340 ). The adequacy range of dietary requirements of specific amino acids in disease states is difficult to determine. Requirements may not be similar in diseases with regards to protein synthesis. Requirements for this purpose can be assessed only when such a function can be measured and related to clinical outcomes. There is apparent consensus concerning normal sulfur amino acid (SAA) requirements. WHO recommendations amount to 13 mg/kg per 24 h in healthy adults. This amount is roughly doubled in artificial nutrition regimens. In disease or after trauma, requirements may be altered for methionine, cysteine, and taurine. Although in specific cases of congenital enzyme deficiency, prematurity, or diminished liver function, hypermethioninemia or hyperhomocysteinemia may occur, SAA supplementation can be considered safe in amounts exceeding 2-3 times the minimum recommended daily intake. Apart from some very specific indications (e.g. acetaminophen poisoning) the usefulness of SAA supplementation is not yet established (PMID: 16702341 ). Methionine is known to exacerbate psychopathological symptoms in schizophrenic patients, there is no evidence of similar effects in healthy subjects. The role of methionine as a precursor of homocysteine is the most notable cause for concern. A "loading dose" of methionine (0.1 g/kg) has been given, and the resultant acute increase in plasma homocysteine has been used as an index of the susceptibility to cardiovascular disease. Although this procedure results in vascular dysfunction, this is acute and unlikely to result in permanent damage. However, a 10-fold larger dose, given mistakenly, resulted in death. Longer-term studies in adults have indicated no adverse consequences of moderate fluctuations in dietary methionine intake, but intakes higher than 5 times normal resulted in elevated homocysteine levels. These effects of methionine on homocysteine and vascular function are moderated by supplements of vitamins B-6, B-12, C, and folic acid. In infants, methionine intakes of 2 to 5 times normal resulted in impaired growth and extremely high plasma methionine levels, but no adverse long-term consequences were observed (PMID: 16702346 ).
Structure
Data?1582752946
Synonyms
ValueSource
(2S)-2-Acetamido-4-(methylsulfanyl)butanoic acidChEBI
Acetyl-L-methionineChEBI
AcetylmethionineChEBI
AcMetChEBI
L-(N-Acetyl)methionineChEBI
MethionamineChEBI
N-Ac-metChEBI
Nalpha-acetyl-L-methionineChEBI
N-Acetyl-L-methionineKegg
(2S)-2-Acetamido-4-(methylsulfanyl)butanoateGenerator
(2S)-2-Acetamido-4-(methylsulphanyl)butanoateGenerator
(2S)-2-Acetamido-4-(methylsulphanyl)butanoic acidGenerator
N-AcetylmethionineChEBI
N-Ac-L-methionineMeSH
N-Acetyl-methionineMeSH
N-Acetylmethionine monopotassium saltMeSH
N-Acetylmethionine monosodium saltMeSH
HepsanMeSH
N-Acetylmethionine, (D)-isomerMeSH
N-Acetylmethionine, (DL)-isomerMeSH
(2S)-2-Acetamido-4-methylsulfanylbutanoic acidHMDB
(S)-2-Acetamido-4-(methylthio)butanoic acidHMDB
MethioninHMDB
Chemical FormulaC7H13NO3S
Average Molecular Weight191.248
Monoisotopic Molecular Weight191.061613977
IUPAC Name(2S)-2-acetamido-4-(methylsulfanyl)butanoic acid
Traditional NameN-acetylmethionine
CAS Registry Number65-82-7
SMILES
CSCC[C@H](NC(C)=O)C(O)=O
InChI Identifier
InChI=1S/C7H13NO3S/c1-5(9)8-6(7(10)11)3-4-12-2/h6H,3-4H2,1-2H3,(H,8,9)(H,10,11)/t6-/m0/s1
InChI KeyXUYPXLNMDZIRQH-LURJTMIESA-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentMethionine and derivatives
Alternative Parents
Substituents
  • Methionine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-l-alpha-amino acid
  • Thia fatty acid
  • Fatty acid
  • Fatty acyl
  • Acetamide
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point105.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility307 at 25 °CNot Available
LogP-0.03MEYLAN,WM & HOWARD,PH (1995)
Predicted Properties
PropertyValueSource
Water Solubility6.84 g/LALOGPS
logP-0.15ALOGPS
logP-0.11ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)4.02ChemAxon
pKa (Strongest Basic)-1.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity47.03 m³·mol⁻¹ChemAxon
Polarizability19.59 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0v4j-2920000000-21fd3a4d7b12ac2aca3cSpectrum
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0002-6900000000-3e9fc6c1775a4e3d390aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-0900000000-08cead5b5b6a03d6ba5aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0005-1900000000-d059fe0be6d1a5b4b084Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9100000000-43df5a1503ce3f2cf758Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9000000000-b757a5078c71037ef5b6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9000000000-275fc8f00e0ba4f1dbeaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-0900000000-4826c0abe069970d9768Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udj-3900000000-947d106e4353bbea5449Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0k92-9500000000-5171045a6fc50c4963f9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-08fr-9100000000-2e49b493225ec50c951fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-9000000000-df7f02d0426ee253bc2bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-1900000000-15861132c8b2269198aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udj-2900000000-dfeda97a2049e74815ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0w2m-9400000000-6da930234f6033225c78Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0005-4900000000-fd1e8a8512a5adc4f78bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9500000000-ba3c2cf457f39b90d9b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-63ccb712a985eedfd16aSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
  • Saliva
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDDB01646
Phenol Explorer Compound IDNot Available
FooDB IDFDB001089
KNApSAcK IDNot Available
Chemspider ID395338
KEGG Compound IDC02712
BioCyc IDCPD0-2015
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID21557
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Ball RO, Courtney-Martin G, Pencharz PB: The in vivo sparing of methionine by cysteine in sulfur amino acid requirements in animal models and adult humans. J Nutr. 2006 Jun;136(6 Suppl):1682S-1693S. [PubMed:16702340 ]
  2. van de Poll MC, Dejong CH, Soeters PB: Adequate range for sulfur-containing amino acids and biomarkers for their excess: lessons from enteral and parenteral nutrition. J Nutr. 2006 Jun;136(6 Suppl):1694S-1700S. [PubMed:16702341 ]
  3. Garlick PJ: Toxicity of methionine in humans. J Nutr. 2006 Jun;136(6 Suppl):1722S-1725S. [PubMed:16702346 ]
  4. 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

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Photoreceptor required for image-forming vision at low light intensity. Required for photoreceptor cell viability after birth. Light-induced isomerization of 11-cis to all-trans retinal triggers a conformational change leading to G-protein activation and release of all-trans retinal
Gene Name:
RHO
Uniprot ID:
P08100
Molecular weight:
38892.3
References
  1. 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 ]