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Human Metabolome Database Version 2.5

 

Showing metabocard for Methionine sulfoxide (HMDB02005)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2006-05-22 15:17:31
Update Date 2010-04-26 12:47:17
Accession Number HMDB02005
Secondary Accession Numbers Not Available
Common Name Methionine sulfoxide
Description Methionine sulfoxide is an oxidation product of methionine with reactive oxygen species via 2-electron-dependent mechanism. Such oxidants can be generated from activated neutrophils; therefore, methionine sulfoxide can be regarded as a biomarker of oxidative stress in vivo. (PMID 12576054)
Synonyms
  1. DL-Methionine sulfoxide
  2. L-Methionine sulfoxide
  3. S-oxide-methionine
  4. alpha-amino-gamma-(methylsulfinyl)-Butyric acid
  5. 2-amino-4-(methylsulfinyl)-Butanoic acid
  6. 2-amino-4-(methylsulfinyl)-Butanoate
  7. L-methionine R-oxide;L-methionine (S)-S-oxide
Chemical IUPAC Name 2-amino-4-methylsulfinyl-butanoic acid
Chemical Formula C5H11NO3S
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Amino acids and Amino Acid conjugates
Class
  • Amino Acids
Sub Class
  • NA
Family
  • Mammalian Metabolite
Species
  • primary amine
  • primary aliphatic amine (alkylamine)
  • carboxylic acid
  • sulfoxide
  • alpha-aminoacid
Biofunction
  • Protein synthesis, amino acid biosynthesis
Application
—
Source
  • Endogenous
Average Molecular Weight 165.211
Monoisotopic Molecular Weight 165.045959
Isomeric SMILES CS(=O)CCC(N)C(O)=O
Canonical SMILES CS(=O)CCC(N)C(O)=O
KEGG Compound ID Not Available
BioCyc ID L-METHIONINE_SULFOXIDE Link Image
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB02005 Link Image
Metagene Link HMDB02005 Link Image
METLIN ID 6428 Link Image
PubChem Compound 847 Link Image
PubChem Substance 10487164 Link Image
ChEBI ID Not Available
CAS Registry Number 62697-73-8
InChI Identifier InChI=1/C5H11NO3S/c1-10(9)3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)
Synthesis Reference Not Available
Melting Point (Experimental) 232 - 234 oC
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 54.0 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -2.40 [Predicted by ALOGPS]; -3.9 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
Download FID (Varian)
Show Experimental Conditions Link Image
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
Download FID (Bruker)
Show Experimental Conditions Link Image
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum
Low Energy
Download File
Show Experimental Conditions Link Image
Medium Energy
Download File
Show Experimental Conditions Link Image
High Energy
Download File
Show Experimental Conditions Link Image
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm (Predicted from LogP)
Biofluid Location
  • Blood
  • Urine
Tissue Location
Tissue References
Epidermis —
Concentrations (Normal)
Biofluid Blood
Value 4.0 (3.0-5.0) uM
Age Adult:>18 yrs old
Sex N/A
Patient information Normal
Comments Not Available
References
  • Doctor's Data
Biofluid Urine
Value < 0.132 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Doctor's Data
Concentrations (Abnormal) Not Available
Associated Disorders Not Available
OMIM ID Not Available
Pathways
Name SMPDB Link KEGG Link
Methionine Metabolism SMP00033 Link Image map00270 Link Image
General References
  1. Schallreuter KU: Functioning methionine-S-sulfoxide reductases A and B are present in human skin. J Invest Dermatol. 2006 May;126(5):947-9. [PubMed Link Image]
  2. O'Donohue TL, Charlton CG, Thoa NB, Helke CJ, Moody TW, Pert A, Williams A, Miller RL, Jacobowitz DM: Release of alpha-melanocyte stimulating hormone into rat and human cerebrospinal fluid in vivo and from rat hypothalamus slices in vitro. Peptides. 1981 Spring;2(1):93-100. [PubMed Link Image]
  3. Boudier C, Cadene M, Bieth JG: Inhibition of neutrophil cathepsin G by oxidized mucus proteinase inhibitor. Effect of heparin. Biochemistry. 1999 Jun 29;38(26):8451-7. [PubMed Link Image]
  4. Mashima R, Nakanishi-Ueda T, Yamamoto Y: Simultaneous determination of methionine sulfoxide and methionine in blood plasma using gas chromatography-mass spectrometry. Anal Biochem. 2003 Feb 1;313(1):28-33. [PubMed Link Image]
Metabolic Enzymes
  1. Peptide methionine sulfoxide reductase
  2. Methionine-R-sulfoxide reductase B2, mitochondrial
  3. Methionine-R-sulfoxide reductase B3, mitochondrial
Enzyme 1 [top]
Enzyme 1 ID 5769
Enzyme 1 Name Peptide methionine sulfoxide reductase
Enzyme 1 Synonyms
  1. Protein- methionine-S-oxide reductase
  2. PMSR
  3. Peptide-methionine
  4. S-S-oxide reductase
  5. Peptide Met(Oreductase
Enzyme 1 Gene Name MSRA
Enzyme 1 Protein Sequence >Peptide methionine sulfoxide reductase 
MLSATRRACQLLLLHSLFPVPRMGNSASNIVSPQEALPGRKEQTPVAAKHHVNGNRTVEP
FPEGTQMAVFGMGCFWGAERKFWVLKGVYSTQVGFAGGYTSNPTYKEVCSEKTGHAEVVR
VVYQPEHMSFEELLKVFWENHDPTQGMRQGNDHGTQYRSAIYPTSAKQMEAALSSKENYQ
KVLSEHGFGPITTDIREGQTFYYAEDYHQQYLSKNPNGYCGLGGTGVSCPVGIKK
Enzyme 1 Number of Residues 235
Enzyme 1 Molecular Weight 26133
Enzyme 1 Theoretical pI 8.21
Enzyme 1 GO Classification
Function
  • catalytic activity
  • oxidoreductase activity
  • oxidoreductase activity, acting on sulfur group of donors
  • oxidoreductase activity, acting on sulfur group of donors, disulfide as acceptor
  • protein-methionine-S-oxide reductase activity
Process
  • macromolecule metabolism
  • metabolism
  • physiological process
  • protein metabolism
Component
—
Enzyme 1 General Function Posttranslational modification, protein turnover, chaperones
Enzyme 1 Specific Function Has an important function as a repair enzyme for proteins that have been inactivated by oxidation. Catalyzes the reversible oxidation-reduction of methionine sulfoxide in proteins to methionine
Enzyme 1 Pathways Not Available
Enzyme 1 Reactions Not Available
Enzyme 1 Pfam Domain Function
Enzyme 1 Signals
  • 1-26
Enzyme 1 Transmembrane Regions Not Available
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 6136945 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID Q9UJ68 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name MSRA_HUMAN Link Image
Enzyme 1 PDB ID Not Available
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence >708 bp 
ATGCTCTCGGCCACCCGGAGGGCTTGCCAGCTCCTCCTCCTCCACAGCCTCTTTCCCGTC
CCGAGGATGGGCAACTCGGCCTCGAACATCGTCAGCCCCCAGGAGGCCTTGCCGGGCCGG
AAGGAACAGACCCCTGTAGCGGCCAAACATCATGTCAATGGCAACAGAACAGTCGAACCT
TTCCCAGAGGGAACACAGATGGCTGTATTTGGAATGGGATGTTTCTGGGGAGCTGAAAGG
AAATTCTGGGTCTTGAAAGGAGTGTATTCAACTCAAGTTGGTTTTGCAGGAGGCTATACT
TCAAATCCTACTTATAAAGAAGTCTGCTCAGAAAAAACTGGCCATGCAGAAGTCGTCCGA
GTGGTGTACCAGCCAGAACACATGAGTTTTGAGGAACTGCTCAAGGTCTTCTGGGAGAAT
CACGACCCGACCCAAGGTATGCGCCAGGGGAACGACCATGGCACTCAGTACCGCTCGGCC
ATCTACCCGACCTCTGCCAAGCAAATGGAGGCAGCCCTGAGCTCCAAAGAGAACTACCAA
AAGGTTCTTTCAGAGCACGGCTTCGGCCCCATCACTACCGACATCCGGGAGGGACAGACT
TTCTACTATGCGGAAGACTACCACCAGCAGTACCTGAGCAAGAACCCCAATGGCTACTGC
GGCCTTGGGGGCACCGGCGTGTCCTGCCCAGTGGGTATTAAAAAATAA
Enzyme 1 GenBank Gene ID AJ242973 Link Image
Enzyme 1 GeneCard ID MSRA Link Image
Enzyme 1 GenAtlas ID MSRA Link Image
Enzyme 1 HGNC ID HGNC:7377 Link Image
Enzyme 1 Chromosome Location 8
Enzyme 1 Locus 8p23.1
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References
  1. Kuschel L, Hansel A, Schonherr R, Weissbach H, Brot N, Hoshi T, Heinemann SH: Molecular cloning and functional expression of a human peptide methionine sulfoxide reductase (hMsrA). FEBS Lett. 1999 Jul 30;456(1):17-21. [PubMed Link Image]
Enzyme 1 Metabolite References Not Available
Enzyme 2 [top]
Enzyme 2 ID 14940
Enzyme 2 Name Methionine-R-sulfoxide reductase B2, mitochondrial
Enzyme 2 Synonyms Not Available
Enzyme 2 Gene Name MSRB2
Enzyme 2 Protein Sequence >Methionine-R-sulfoxide reductase B2, mitochondrial 
MARLLWLLRGLTLGTAPRRAVRGQAGGGGPGTGPGLGEAGSLATCELPLAKSEWQKKLTP
EQFYVTREKGTEPPFSGIYLNNKEAGMYHCVCCDSPLFSSEKKYCSGTGWPSFSEAHGTS
GSDESHTGILRRLDTSLGSARTEVVCKQCEAHLGHVFPDGPGPNGQRFCINSVALKFKPR
KH
Enzyme 2 Number of Residues 182
Enzyme 2 Molecular Weight 19536
Enzyme 2 Theoretical pI 8.76
Enzyme 2 GO Classification Not Available
Enzyme 2 General Function Posttranslational modification, protein turnover, chaperones
Enzyme 2 Specific Function Catalyzes the reduction of free and protein-bound methionine sulfoxide to methionine
Enzyme 2 Pathways Not Available
Enzyme 2 Reactions Not Available
Enzyme 2 Pfam Domain Function
Enzyme 2 Signals
  • None
Enzyme 2 Transmembrane Regions
  • None
Enzyme 2 Essentiality Not Available
Enzyme 2 GenBank ID Protein 5059062 Link Image
Enzyme 2 UniProtKB/Swiss-Prot ID Q9Y3D2 Link Image
Enzyme 2 UniProtKB/Swiss-Prot Entry Name MSRB2_HUMAN Link Image
Enzyme 2 PDB ID Not Available
Enzyme 2 Cellular Location Not Available
Enzyme 2 Gene Sequence >549 bp 
ATGGCGCGGCTCCTCTGGTTGCTCCGGGGCCTGACCCTCGGAACTGCGCCTCGGCGGGCG
GTGCGGGGCCAAGCGGGCGGCGGCGGGCCCGGCACCGGGCCGGGACTGGGGGAGGCAGGG
TCTCTTGCAACGTGTGAGCTGCCTCTTGCCAAGAGTGAGTGGCAAAAGAAACTAACCCCG
GAGCAGTTCTACGTCACAAGAGAAAAGGGAACGGAACCGCCTTTCAGTGGGATCTACCTG
AATAACAAGGAAGCAGGAATGTATCATTGCGTGTGCTGCGACAGTCCACTCTTCAGTTCT
GAGAAAAAGTACTGCTCTGGCACTGGGTGGCCTTCGTTTTCCGAGGCTCATGGTACGTCT
GGCTCTGATGAAAGCCACACAGGGATCCTGAGACGTCTGGATACCTCGTTAGGATCAGCT
CGCACAGAGGTTGTCTGCAAGCAGTGTGAAGCTCATCTAGGTCACGTGTTTCCTGATGGA
CCTGGGCCCAATGGTCAGAGGTTTTGCATCAACAGTGTGGCTTTGAAGTTCAAACCAAGG
AAACACTGA
Enzyme 2 GenBank Gene ID AF122004 Link Image
Enzyme 2 GeneCard ID Q9Y3D2 Link Image
Enzyme 2 GenAtlas ID MSRB2 Link Image
Enzyme 2 HGNC ID HGNC:17061 Link Image
Enzyme 2 Chromosome Location 10
Enzyme 2 Locus 10p12
Enzyme 2 SNPs SNPJam Report Link Image
Enzyme 2 General References
  1. Lai CH, Chou CY, Ch'ang LY, Liu CS, Lin W: Identification of novel human genes evolutionarily conserved in Caenorhabditis elegans by comparative proteomics. Genome Res. 2000 May;10(5):703-13. [PubMed Link Image]
Enzyme 2 Metabolite References Not Available
Enzyme 3 [top]
Enzyme 3 ID 14941
Enzyme 3 Name Methionine-R-sulfoxide reductase B3, mitochondrial
Enzyme 3 Synonyms
  1. MsrB3
Enzyme 3 Gene Name MSRB3
Enzyme 3 Protein Sequence >Methionine-R-sulfoxide reductase B3, mitochondrial 
MSAFNLLHLVTKSQPVALRACGLPSGSCRDKKNCKVVFSQQELRKRLTPLQYHVTQEKGT
ESAFEGEYTHHKDPGIYKCVVCGTPLFKSETKFDSGSGWPSFHDVINSEAITFTDDFSYG
MHRVETSCSQCGAHLGHIFDDGPRPTGKRYCINSAALSFTPADSSGTAEGGSGVASPAQA
DKAEL
Enzyme 3 Number of Residues 185
Enzyme 3 Molecular Weight 20010
Enzyme 3 Theoretical pI 7.18
Enzyme 3 GO Classification Not Available
Enzyme 3 General Function Posttranslational modification, protein turnover, chaperones
Enzyme 3 Specific Function Catalyzes the reduction of free and protein-bound methionine sulfoxide to methionine
Enzyme 3 Pathways Not Available
Enzyme 3 Reactions Not Available
Enzyme 3 Pfam Domain Function
Enzyme 3 Signals
  • None
Enzyme 3 Transmembrane Regions
  • None
Enzyme 3 Essentiality Not Available
Enzyme 3 GenBank ID Protein 37181574 Link Image
Enzyme 3 UniProtKB/Swiss-Prot ID Q8IXL7 Link Image
Enzyme 3 UniProtKB/Swiss-Prot Entry Name MSRB3_HUMAN Link Image
Enzyme 3 PDB ID Not Available
Enzyme 3 Cellular Location Not Available
Enzyme 3 Gene Sequence >579 bp 
ATGAGCCCGCGGCGGACCCTCCCGCGCCCCCTCTCGCTCTGCCTCTCCCTCTGCCTCTGC
CTCTGCCTGGCCGCGGCTCTGGGAAGTGCGCAGTCCGGGTCGTGTAGGGATAAAAAGAAC
TGTAAGGTGGTCTTTTCCCAGCAGGAACTGAGGAAGCGGCTAACACCCCTGCAGTACCAT
GTCACTCAGGAGAAAGGGACCGAAAGTGCCTTTGAAGGAGAATACACACATCACAAAGAT
CCTGGAATATATAAATGTGTTGTTTGTGGAACTCCATTGTTTAAGTCAGAAACCAAATTT
GACTCCGGTTCAGGTTGGCCTTCATTCCACGATGTGATCAATTCTGAGGCAATCACATTC
ACAGATGACTTTTCCTATGGGATGCACAGGGTGGAAACAAGCTGCTCTCAGTGTGGTGCT
CACCTTGGGCACATTTTTGATGATGGGCCTCGTCCAACTGGGAAAAGATACTGCATAAAT
TCGGCTGCCTTGTCTTTTACACCTGCGGATAGCAGTGGCACCGCCGAGGGAGGCAGTGGG
GTCGCCAGCCCGGCCCAGGCAGACAAAGCGGAGCTCTAG
Enzyme 3 GenBank Gene ID AY358229 Link Image
Enzyme 3 GeneCard ID Q8IXL7 Link Image
Enzyme 3 GenAtlas ID MSRB3 Link Image
Enzyme 3 HGNC ID HGNC:27375 Link Image
Enzyme 3 Chromosome Location 12
Enzyme 3 Locus 12q14.3
Enzyme 3 SNPs SNPJam Report Link Image
Enzyme 3 General References
  1. Clark HF, Gurney AL, Abaya E, Baker K, Baldwin D, Brush J, Chen J, Chow B, Chui C, Crowley C, Currell B, Deuel B, Dowd P, Eaton D, Foster J, Grimaldi C, Gu Q, Hass PE, Heldens S, Huang A, Kim HS, Klimowski L, Jin Y, Johnson S, Lee J, Lewis L, Liao D, Mark M, Robbie E, Sanchez C, Schoenfeld J, Seshagiri S, Simmons L, Singh J, Smith V, Stinson J, Vagts A, Vandlen R, Watanabe C, Wieand D, Woods K, Xie MH, Yansura D, Yi S, Yu G, Yuan J, Zhang M, Zhang Z, Goddard A, Wood WI, Godowski P, Gray A: The secreted protein discovery initiative (SPDI), a large-scale effort to identify novel human secreted and transmembrane proteins: a bioinformatics assessment. Genome Res. 2003 Oct;13(10):2265-70. Epub 2003 Sep 15. [PubMed Link Image]
Enzyme 3 Metabolite References Not Available