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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2009-03-03 12:04:46 UTC
Update Date2022-09-22 18:34:20 UTC
HMDB IDHMDB0011745
Secondary Accession Numbers
  • HMDB11745
Metabolite Identification
Common NameN-Acetyl-L-methionine
DescriptionN-Acetyl-L-methionine or N-Acetylmethionine, belongs to the class of organic compounds known as N-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. N-Acetylmethionine can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-Acetylmethionine is a biologically available N-terminal capped form of the proteinogenic alpha amino acid L-methionine. N-acetyl amino acids can be produced either via direct synthesis of specific N-acetyltransferases or via the proteolytic degradation of N-acetylated proteins by specific hydrolases. N-terminal acetylation of proteins is a widespread and highly conserved process in eukaryotes that is involved in protection and stability of proteins (PMID: 16465618 ). About 85% of all human proteins and 68% of all yeast proteins are acetylated at their N-terminus (PMID: 21750686 ). Several proteins from prokaryotes and archaea are also modified by N-terminal acetylation. The majority of eukaryotic N-terminal-acetylation reactions occur through N-acetyltransferase enzymes or NAT’s (PMID: 30054468 ). These enzymes consist of three main oligomeric complexes NatA, NatB, and NatC, which are composed of at least a unique catalytic subunit and one unique ribosomal anchor. The substrate specificities of different NAT enzymes are mainly determined by the identities of the first two N-terminal residues of the target protein. The human NatA complex co-translationally acetylates N-termini that bear a small amino acid (A, S, T, C, and occasionally V and G) (PMID: 30054468 ). NatA also exists in a monomeric state and can post-translationally acetylate acidic N-termini residues (D-, E-). NatB and NatC acetylate N-terminal methionine with further specificity determined by the identity of the second amino acid. N-acetylated amino acids, such as N-acetylmethionine can be released by an N-acylpeptide hydrolase from peptides generated by proteolytic degradation (PMID: 16465618 ). In addition to the NAT enzymes and protein-based acetylation, N-acetylation of free methionine can also occur. In particular, N-Acetylmethionine can be biosynthesized from L-methionine and acetyl-CoA by the enzyme methionine N-acetyltransferase (EC 2.3.1.66). Excessive amounts N-acetyl amino acids including N-acetylmethionine (as well as N-acetylglycine, N-acetylserine, N-acetylglutamine, N-acetylglutamate, N-acetylalanine, N-acetylleucine and smaller amounts of N-acetylthreonine, N-acetylisoleucine, and N-acetylvaline) can be detected in the urine with individuals with acylase I deficiency, a genetic disorder (PMID: 16465618 ). Aminoacylase I is a soluble homodimeric zinc binding enzyme that catalyzes the formation of free aliphatic amino acids from N-acetylated precursors. In humans, Aminoacylase I is encoded by the aminoacylase 1 gene (ACY1) on chromosome 3p21 that consists of 15 exons (OMIM 609924 ). Individuals with aminoacylase I deficiency will experience convulsions, hearing loss and difficulty feeding (PMID: 16465618 ). ACY1 can also catalyze the reverse reaction, the synthesis of acetylated amino acids. Many N-acetylamino acids, including N-acetylmethionine are classified as uremic toxins if present in high abundance in the serum or plasma (PMID: 26317986 ; PMID: 20613759 ). Uremic toxins are a diverse group of endogenously produced molecules that, if not properly cleared or eliminated by the kidneys, can cause kidney damage, cardiovascular disease and neurological deficits (PMID: 18287557 ).
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
N-AcetylmethionineChEBI
Nalpha-acetyl-L-methionineChEBI
(2S)-2-Acetamido-4-(methylsulfanyl)butanoateGenerator
(2S)-2-Acetamido-4-(methylsulphanyl)butanoateGenerator
(2S)-2-Acetamido-4-(methylsulphanyl)butanoic acidGenerator
N-Ac-L-methionineMeSH, HMDB
N-Acetyl-methionineMeSH, HMDB
N-Acetylmethionine monopotassium saltMeSH, HMDB
N-Acetylmethionine monosodium saltMeSH, HMDB
HepsanMeSH, HMDB
N-Acetylmethionine, (D)-isomerMeSH, HMDB
N-Acetylmethionine, (DL)-isomerMeSH, HMDB
N-Acetyl-L-methionineKEGG
(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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point105.5 °CNot Available
Boiling Point453.60 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility307 at 25 °CNot Available
LogP-0.03MEYLAN,WM & HOWARD,PH (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Astarita_neg139.030932474
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+139.97330932474
DeepCCS[M-H]-136.14630932474
DeepCCS[M-2H]-173.34230932474
DeepCCS[M+Na]+148.8930932474
AllCCS[M+H]+142.732859911
AllCCS[M+H-H2O]+139.132859911
AllCCS[M+NH4]+146.132859911
AllCCS[M+Na]+147.032859911
AllCCS[M-H]-142.232859911
AllCCS[M+Na-2H]-143.932859911
AllCCS[M+HCOO]-145.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-Acetyl-L-methionineCSCC[C@H](NC(C)=O)C(O)=O2591.2Standard polar33892256
N-Acetyl-L-methionineCSCC[C@H](NC(C)=O)C(O)=O1643.4Standard non polar33892256
N-Acetyl-L-methionineCSCC[C@H](NC(C)=O)C(O)=O1704.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Acetyl-L-methionine,1TMS,isomer #1CSCC[C@H](NC(C)=O)C(=O)O[Si](C)(C)C1652.8Semi standard non polar33892256
N-Acetyl-L-methionine,1TMS,isomer #2CSCC[C@@H](C(=O)O)N(C(C)=O)[Si](C)(C)C1653.0Semi standard non polar33892256
N-Acetyl-L-methionine,2TMS,isomer #1CSCC[C@@H](C(=O)O[Si](C)(C)C)N(C(C)=O)[Si](C)(C)C1671.5Semi standard non polar33892256
N-Acetyl-L-methionine,2TMS,isomer #1CSCC[C@@H](C(=O)O[Si](C)(C)C)N(C(C)=O)[Si](C)(C)C1683.1Standard non polar33892256
N-Acetyl-L-methionine,2TMS,isomer #1CSCC[C@@H](C(=O)O[Si](C)(C)C)N(C(C)=O)[Si](C)(C)C1996.3Standard polar33892256
N-Acetyl-L-methionine,1TBDMS,isomer #1CSCC[C@H](NC(C)=O)C(=O)O[Si](C)(C)C(C)(C)C1888.8Semi standard non polar33892256
N-Acetyl-L-methionine,1TBDMS,isomer #2CSCC[C@@H](C(=O)O)N(C(C)=O)[Si](C)(C)C(C)(C)C1896.9Semi standard non polar33892256
N-Acetyl-L-methionine,2TBDMS,isomer #1CSCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(C)=O)[Si](C)(C)C(C)(C)C2146.4Semi standard non polar33892256
N-Acetyl-L-methionine,2TBDMS,isomer #1CSCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(C)=O)[Si](C)(C)C(C)(C)C2140.3Standard non polar33892256
N-Acetyl-L-methionine,2TBDMS,isomer #1CSCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(C)=O)[Si](C)(C)C(C)(C)C2228.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - N-Acetyl-L-methionine GC-MS (2 TMS)splash10-0v4j-2920000000-21fd3a4d7b12ac2aca3c2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-Acetyl-L-methionine GC-MS (1 TMS)splash10-0002-6900000000-3e9fc6c1775a4e3d390a2014-06-16HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetyl-L-methionine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-L-methionine LC-ESI-QQ , negative-QTOFsplash10-0006-0900000000-08cead5b5b6a03d6ba5a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-L-methionine LC-ESI-QQ , negative-QTOFsplash10-0005-1900000000-d059fe0be6d1a5b4b0842017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-L-methionine LC-ESI-QQ , negative-QTOFsplash10-0002-9100000000-43df5a1503ce3f2cf7582017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-L-methionine LC-ESI-QQ , negative-QTOFsplash10-0002-9000000000-b757a5078c71037ef5b62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-L-methionine LC-ESI-QQ , negative-QTOFsplash10-0002-9000000000-275fc8f00e0ba4f1dbea2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-L-methionine LC-ESI-QQ , positive-QTOFsplash10-0006-0900000000-4826c0abe069970d97682017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-L-methionine LC-ESI-QQ , positive-QTOFsplash10-0udj-3900000000-947d106e4353bbea54492017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-L-methionine LC-ESI-QQ , positive-QTOFsplash10-0k92-9500000000-5171045a6fc50c4963f92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-L-methionine LC-ESI-QQ , positive-QTOFsplash10-08fr-9100000000-2e49b493225ec50c951f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-L-methionine LC-ESI-QQ , positive-QTOFsplash10-03di-9000000000-df7f02d0426ee253bc2b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-L-methionine 30V, Positive-QTOFsplash10-0006-9000000000-c95070994ff6981f31be2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-L-methionine 10V, Negative-QTOFsplash10-0005-8900000000-00ef889f3b4f112d8d2e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-L-methionine 40V, Negative-QTOFsplash10-0002-9000000000-7616747f5e52c0cfcb212021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-L-methionine 30V, Negative-QTOFsplash10-0002-9000000000-832ee5d6104ffe5e03432021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-L-methionine 20V, Negative-QTOFsplash10-0002-9000000000-253c94d8794c74656d122021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-L-methionine 10V, Positive-QTOFsplash10-0k97-9700000000-c475f07ae6596a5bd16c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-L-methionine 0V, Positive-QTOFsplash10-0006-0900000000-3c38449e27fee255c0e62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-L-methionine 10V, Positive-QTOFsplash10-0udm-6900000000-8def9e0a4df7dda943182021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-L-methionine 30V, Positive-QTOFsplash10-08fu-9000000000-c048830a23b089c34b542021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-L-methionine 10V, Positive-QTOFsplash10-0006-1900000000-15861132c8b2269198ae2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-L-methionine 20V, Positive-QTOFsplash10-0udj-2900000000-dfeda97a2049e74815ce2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-L-methionine 40V, Positive-QTOFsplash10-0w2m-9400000000-6da930234f6033225c782015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-L-methionine 10V, Negative-QTOFsplash10-0005-4900000000-fd1e8a8512a5adc4f78b2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-L-methionine 20V, Negative-QTOFsplash10-0002-9500000000-ba3c2cf457f39b90d9b02015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-L-methionine 40V, Negative-QTOFsplash10-0002-9000000000-63ccb712a985eedfd16a2015-09-15Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 500 MHz, H2O, experimental)2019-11-14Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation 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 Compound448580
PDB IDNot Available
ChEBI ID21557
Food Biomarker OntologyNot Available
VMH IDC02712
MarkerDB IDNot Available
Good Scents IDrw1265521
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Sass JO, Mohr V, Olbrich H, Engelke U, Horvath J, Fliegauf M, Loges NT, Schweitzer-Krantz S, Moebus R, Weiler P, Kispert A, Superti-Furga A, Wevers RA, Omran H: Mutations in ACY1, the gene encoding aminoacylase 1, cause a novel inborn error of metabolism. Am J Hum Genet. 2006 Mar;78(3):401-9. Epub 2006 Jan 18. [PubMed:16465618 ]
  2. 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 ]
  3. 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 ]
  4. Garlick PJ: Toxicity of methionine in humans. J Nutr. 2006 Jun;136(6 Suppl):1722S-1725S. [PubMed:16702346 ]
  5. 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 ]
  6. Tanaka H, Sirich TL, Plummer NS, Weaver DS, Meyer TW: An Enlarged Profile of Uremic Solutes. PLoS One. 2015 Aug 28;10(8):e0135657. doi: 10.1371/journal.pone.0135657. eCollection 2015. [PubMed:26317986 ]
  7. Van Damme P, Hole K, Pimenta-Marques A, Helsens K, Vandekerckhove J, Martinho RG, Gevaert K, Arnesen T: NatF contributes to an evolutionary shift in protein N-terminal acetylation and is important for normal chromosome segregation. PLoS Genet. 2011 Jul;7(7):e1002169. doi: 10.1371/journal.pgen.1002169. Epub 2011 Jul 7. [PubMed:21750686 ]
  8. Ree R, Varland S, Arnesen T: Spotlight on protein N-terminal acetylation. Exp Mol Med. 2018 Jul 27;50(7):1-13. doi: 10.1038/s12276-018-0116-z. [PubMed:30054468 ]
  9. Toyohara T, Akiyama Y, Suzuki T, Takeuchi Y, Mishima E, Tanemoto M, Momose A, Toki N, Sato H, Nakayama M, Hozawa A, Tsuji I, Ito S, Soga T, Abe T: Metabolomic profiling of uremic solutes in CKD patients. Hypertens Res. 2010 Sep;33(9):944-52. doi: 10.1038/hr.2010.113. Epub 2010 Jul 8. [PubMed:20613759 ]
  10. Vanholder R, Baurmeister U, Brunet P, Cohen G, Glorieux G, Jankowski J: A bench to bedside view of uremic toxins. J Am Soc Nephrol. 2008 May;19(5):863-70. doi: 10.1681/ASN.2007121377. Epub 2008 Feb 20. [PubMed:18287557 ]

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 ]