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Human Metabolome Database Version 2.5

 

Showing metabocard for 5'-Methylthioadenosine (HMDB01173)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2005-11-16 15:48:42
Update Date 2009-09-16 13:57:34
Accession Number HMDB01173
Secondary Accession Numbers Not Available
Common Name 5'-Methylthioadenosine
Description 5-Methylthioadenosine is a normal metabolite present in human urine. Elevated excretion appears in children with severe combined immunodeficiency syndrome (PMID 3987052)
Synonyms
  1. 1-(6-amino-9H-purin-9-yl)-1-deoxy-5-S-methyl-5-thio-beta-D-Ribofuranose
  2. 5'-(Methylthio)-5'-deoxyadenosine
  3. 5'-(Methylthio)adenosine
  4. 5'-Deoxy-5'-(methylthio)adenosine
  5. 5'-Methylthioadenosine
  6. 5'-S-Methyl-5'-thioadenosine
  7. 5'-S-methyl-5'-thio-Adenosine
  8. 5-Methylthioadenosine
  9. MTA
  10. Methylthioadenosine
  11. S-methyl-5-thioadenosine
  12. Thiomethyladenosine
  13. 1-(6-amino-9H-purin-9-yl)-1-deoxy-5-S-methyl-5-thio-beta-delta-Ribofuranose
  14. S-methyl-5'-thioadenosine
Chemical IUPAC Name 2-(6-aminopurin-9-yl)-5-(methylsulfanylmethyl)oxolane-3,4-diol
Chemical Formula C11H15N5O3S
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Nucleosides and Nucleoside conjugates
Class
  • Nucleoside Analogues
Sub Class
  • Methylated nucleosides
Family
  • Mammalian Metabolite
Species
  • secondary alcohol
  • 1,2-diol
  • thioether
  • primary amine
  • primary aromatic amine
  • aromatic compound
  • heterocyclic compound
Biofunction
  • Component of Arginine and proline metabolism
  • Component of beta-Alanine metabolism
Application
—
Source
  • Endogenous
Average Molecular Weight 297.333
Monoisotopic Molecular Weight 297.089569
Isomeric SMILES CSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N
Canonical SMILES CSCC1OC(C(O)C1O)N1C=NC2=C1N=CN=C2N
KEGG Compound ID C00170 Link Image
BioCyc ID 5-METHYLTHIOADENOSINE Link Image
BiGG ID 34127 Link Image
Wikipedia Link Not Available
NuGOwiki Link HMDB01173 Link Image
Metagene Link HMDB01173 Link Image
METLIN ID 3425 Link Image
PubChem Compound 149 Link Image
PubChem Substance 10428286 Link Image
ChEBI ID 17509 Link Image
CAS Registry Number 2457-80-9
InChI Identifier InChI=1/C11H15N5O3S/c1-20-2-5-7(17)8(18)11(19-5)16-4-15-6-9(12)13-3-14-10(6)16/h3-5,7-8,11,17-18H,2H2,1H3,(H2,12,13,14)/t5-,7-,8-,11-/m1/s1
Synthesis Reference Sufrin, Janice R.; Spiess, Arthur J.; Kramer, Debora L.; Libby, Paul R.; Porter, Carl W. Synthesis and antiproliferative effects of novel 5'-fluorinated analogs of 5'-deoxy-5'-(methylthio)adenosine. Journal of Medicinal Chemistry (1989), 32(5), 997-1001.
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 6.50 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -0.14 [Predicted by ALOGPS]; -0.1 [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
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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
  • Urine
Tissue Location
Tissue References
Fibroblasts —
Platelet —
Concentrations (Normal)
Biofluid Urine
Value 0.12 +/- 0.08 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Liebich HM, Di Stefano C, Wixforth A, Schmid HR: Quantitation of urinary nucleosides by high-performance liquid chromatography. J Chromatogr A. 1997 Feb 28;763(1-2):193-7. [PubMed Link Image]
Biofluid Urine
Value 0.13 +/- 0.11 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Female
Patient information Normal
Comments Not Available
References
  • Liebich HM, Di Stefano C, Wixforth A, Schmid HR: Quantitation of urinary nucleosides by high-performance liquid chromatography. J Chromatogr A. 1997 Feb 28;763(1-2):193-7. [PubMed Link Image]
Biofluid Urine
Value 0.12 +/- 0.05 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Male
Patient information Normal
Comments Not Available
References
  • Liebich HM, Di Stefano C, Wixforth A, Schmid HR: Quantitation of urinary nucleosides by high-performance liquid chromatography. J Chromatogr A. 1997 Feb 28;763(1-2):193-7. [PubMed Link Image]
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
Spermidine and Spermine Biosynthesis SMP00445 Link Image
General References
  1. Gerasimovskaya EV, Ahmad S, White CW, Jones PL, Carpenter TC, Stenmark KR: Extracellular ATP is an autocrine/paracrine regulator of hypoxia-induced adventitial fibroblast growth. Signaling through extracellular signal-regulated kinase-1/2 and the Egr-1 transcription factor. J Biol Chem. 2002 Nov 22;277(47):44638-50. Epub 2002 Sep 18. [PubMed Link Image]
  2. Mills GC, Mills JS: Urinary excretion of methylthioadenosine in immunodeficient children. Clin Chim Acta. 1985 Mar 30;147(1):15-23. [PubMed Link Image]
  3. Contreres JO, Dupuy E, Job B, Habib A, Bryckaert M, Rosa JP, Simoneau G, Herbert JM, Savi P, Levy-Toledano S: Effect of clopidogrel administration to healthy volunteers on platelet phosphorylation events triggered by ADP. Br J Haematol. 2003 Feb;120(4):633-42. [PubMed Link Image]
  4. Mills GC, Schmalstieg FC, Goldblum RM: Urinary excretion of modified purines and nucleosides in immunodeficient children. Biochem Med. 1985 Aug;34(1):37-51. [PubMed Link Image]
  5. Liebich HM, Di Stefano C, Wixforth A, Schmid HR: Quantitation of urinary nucleosides by high-performance liquid chromatography. J Chromatogr A. 1997 Feb 28;763(1-2):193-7. [PubMed Link Image]
Metabolic Enzymes
  1. Spermine synthase
  2. S-methyl-5-thioadenosine phosphorylase
  3. Spermidine synthase (Spermidine synthase, isoform CRA_a)
Enzyme 1 [top]
Enzyme 1 ID 5449
Enzyme 1 Name Spermine synthase
Enzyme 1 Synonyms
  1. Spermidine aminopropyltransferase
  2. SPMSY
Enzyme 1 Gene Name SMS
Enzyme 1 Protein Sequence >Spermine synthase 
MAAARHSTLDFMLGAKADGETILKGLQSIFQEQGMAESVHTWQDHGYLATYTNKNGSFAN
LRIYPHGLVLLDLQSYDGDAQGKEEIDSILNKVEERMKELSQDSTGRVKRLPPIVRGGAI
DRYWPTADGRLVEYDIDEVVYDEDSPYQNIKILHSKQFGNILILSGDVNLAESDLAYTRA
IMGSGKEDYTGKDVLILGGGDGGILCEIVKLKPKMVTMVEIDQMVIDGCKKYMRKTCGDV
LDNLKGDCYQVLIEDCIPVLKRYAKEGREFDYVINDLTAVPISTSPEEDSTWEFLRLILD
LSMKVLKQDGKYFTQGNCVNLTEALSLYEEQLGRLYCPVEFSKEIVCVPSYLELWVFYTV
WKKAKP
Enzyme 1 Number of Residues 366
Enzyme 1 Molecular Weight 41269
Enzyme 1 Theoretical pI 4.62
Enzyme 1 GO Classification
Function
  • catalytic activity
Process
—
Component
—
Enzyme 1 General Function Amino acid transport and metabolism
Enzyme 1 Specific Function S-adenosylmethioninamine + spermidine = 5'- methylthioadenosine + spermine
Enzyme 1 Pathways
Enzyme 1 Reactions
  • S-adenosylmethioninamine + spermidine = 5'-methylthioadenosine + spermine
Enzyme 1 Pfam Domain Function
Enzyme 1 Signals
  • None
Enzyme 1 Transmembrane Regions
  • None
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 791051 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID P52788 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name SPSY_HUMAN Link Image
Enzyme 1 PDB ID Not Available
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence >1107 bp 
ATGCCTGGGGCAGCAGCACGGCACAGCACGCTCGACTTCATGCTCGGCGCCAAAGCTGAT
GGTGAGACCATTCTAAAAGGCCTCCAGTCCATTTTCCAGGAGCAGGGGATGGCGGAGTCG
GTGCACACCTGGCAGGACCATGGCTATTTAGCAACCTACACAAACAAGAACGGCAGCTTT
GCCAATTTGAGAATTTACCCACATGGATTGGTGTTGCTGGACCTTCAGAGTTATGATGGT
GATGCGCAAGGCAAAGAAGAGATCGACAGTATTTTGAACAAAGTAGAGGAAAGAATGAAA
GAATTGAGTCAGGACAGTACTGGGCGGGTGAAACGATTACCACCCATAGTGCGAGGAGGA
GCCATCGACAGATACTGGCCCACCGCCGACGGGCGCCTGGTTGAATATGACATAGATGAA
GTGGTATATGACGAAGATTCACCTTATCAAAATATAAAAATTCTACACTCGAAGCAGTTT
GGAAATATTCTCATCCTTAGTGGGGATGTTAATTTGGCAGAGAGTGATTTGGCATATACC
CGGGCCATCATGGGCAGTGGCAAAGAAGATTACACTGGCAAAGATGTACTCATTCTGGGA
GGTGGAGACGGAGGCATATTGTGTGAAATAGTCAAACTAAAACCAAAGATGGTCACTATG
GTAGAGATTGACCAAATGGTGATTGATGGGTGTAAGAAATACATGCGAAAAACGTGTGGC
GATGTCTTAGACAATCTTAAAGGAGACTGCTATCAGGTTCTAATAGAAGACTGTATCCCG
GTACTGAAGAGGTACGCCAAAGAAGGGAGAGAATTTGATTATGTGATTAATGATTTGACA
GCTGTTCCAATCTCCACGTCTCCAGAAGAAGATTCCACATGGGAGTTTCTCAGACTGATT
CTTGACCTCTCAATGAAAGTGTTGAAACAGGATGGGAAATATTTTACACAGGGGAACTGT
GTCAATCTGACAGAAGCACTGTCGCTCTATGAAGAACAGCTGGGGCGCCTGTATTGTCCT
GTGGAATTTTCAAAGGAGATCGTCTGTGTCCCTTCATACTTGGAATTGTGGGTATTTTAC
ACTGTTTGGAAGAAAGCTAAACCCTGA
Enzyme 1 GenBank Gene ID Z49099 Link Image
Enzyme 1 GeneCard ID SMS Link Image
Enzyme 1 GenAtlas ID SMS Link Image
Enzyme 1 HGNC ID HGNC:11123 Link Image
Enzyme 1 Chromosome Location X
Enzyme 1 Locus Xp22.1
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References
  1. Korhonen VP, Halmekyto M, Kauppinen L, Myohanen S, Wahlfors J, Keinanen T, Hyvonen T, Alhonen L, Eloranta T, Janne J: Molecular cloning of a cDNA encoding human spermine synthase. DNA Cell Biol. 1995 Oct;14(10):841-7. [PubMed Link Image]
  2. Grieff M, Whyte MP, Thakker RV, Mazzarella R: Sequence analysis of 139 kb in Xp22.1 containing spermine synthase and the 5' region of PEX. Genomics. 1997 Sep 1;44(2):227-31. [PubMed Link Image]
  3. Gevaert K, Goethals M, Martens L, Van Damme J, Staes A, Thomas GR, Vandekerckhove J: Exploring proteomes and analyzing protein processing by mass spectrometric identification of sorted N-terminal peptides. Nat Biotechnol. 2003 May;21(5):566-9. Epub 2003 Mar 31. [PubMed Link Image]
Enzyme 1 Metabolite References Not Available
Enzyme 2 [top]
Enzyme 2 ID 5634
Enzyme 2 Name S-methyl-5-thioadenosine phosphorylase
Enzyme 2 Synonyms
  1. 5'- methylthioadenosine phosphorylase
  2. MTA phosphorylase
  3. MTAPase
Enzyme 2 Gene Name MTAP
Enzyme 2 Protein Sequence >S-methyl-5-thioadenosine phosphorylase 
MASGTTTTAVKIGIIGGTGLDDPEILEGRTEKYVDTPFGKPSDALILGKIKNVDCVLLAR
HGRQHTIMPSKVNYQANIWALKEEGCTHVIVTTACGSLREEIQPGDIVIIDQFIDRTTMR
PQSFYDGSHSCARGVCHIPMAEPFCPKTREVLIETAKKLGLRCHSKGTMVTIEGPRFSSR
AESFMFRTWGADVINMTTVPEVVLAKEAGICYASIAMATDYDCWKEHEEAVSVDRVLKTL
KENANKAKSLLLTTIPQIGSTEWSETLHNLKNMAQFSVLLPRH
Enzyme 2 Number of Residues 283
Enzyme 2 Molecular Weight 31236
Enzyme 2 Theoretical pI 7.21
Enzyme 2 GO Classification Not Available
Enzyme 2 General Function Nucleotide transport and metabolism
Enzyme 2 Specific Function Plays a major role in polyamine metabolism and is important for the salvage of both adenine and methionine
Enzyme 2 Pathways Not Available
Enzyme 2 Reactions
  • S-methyl-5-thioadenosine + phosphate = adenine + S-methyl-5-thio-alpha-D-ribose 1-phosphate
Enzyme 2 Pfam Domain Function Not Available
Enzyme 2 Signals
  • None
Enzyme 2 Transmembrane Regions
  • None
Enzyme 2 Essentiality Not Available
Enzyme 2 GenBank ID Protein 847724 Link Image
Enzyme 2 UniProtKB/Swiss-Prot ID Q13126 Link Image
Enzyme 2 UniProtKB/Swiss-Prot Entry Name MTAP_HUMAN Link Image
Enzyme 2 PDB ID 1SD2 Link Image
Enzyme 2 PDB File Show
Enzyme 2 3D Structure
Enzyme 2 Cellular Location Not Available
Enzyme 2 Gene Sequence >852 bp 
ATGGCCTCTGGCACCACCACCACCGCCGTGAAGATTGGAATAATTGGTGGAACAGGCCTG
GATGATCCAGAAATTTTAGAAGGAAGAACTGAAAAATATGTGGATACTCCATTTGGCAAG
CCATCTGATGCCTTAATTTTGGGGAAGATAAAAAATGTTGATTGCATCCTCCTTGCAAGG
CATGGAAGGCAGCACACCATCATGCCTTCAAAGGTCAACTACCAGGCGAACATCTGGGCT
TTGAAGGAAGAGGGCTGTACACATGTCATAGTGACCACAGCTTGTGGCTCCTTGAGGGAG
GAGATTCAGCCCGGCGATATTGTCATTATTGATCAGTTCATTGACAGGACCACTATGAGA
CCTCAGTCCTTCTATGATGGAAGTCATTCTTGTGCCAGAGGAGTGTGCCATATTCCAATG
GCTGAGCCGTTTTGCCCCAAAACGAGAGAGGTTCTTATAGAGACTGCTAAGAAGCTAGGA
CTCCGGTGCCACTCAAAGGGGACAATGGTCACAATCGAGGGACCTCGTTTTAGCTCCCGG
GCAGAAAGCTTCATGTTCCGCACCTGGGGGGCGGATGTTATCAACATGACCACAGTTCCA
GAGGTGGTTCTTGCTAAGGAGGCTGGAATTTGTTACGCAAGTATCGCCATGGCGACAGAT
TATGACTGCTGGAAGGAGCACGAGGAAGCAGTTTCGGTGGACCGGGTCTTAAAGACCCTG
AAAGAAAACGCTAATAAAGCCAAAAGCTTACTGCTCACTACCATACCTCAGATAGGGTCC
ACAGAATGGTCAGAAACCCTCCATAACCTGAAGAATATGGCCCAGTTTTCTGTTTTATTA
CCAAGACATTAA
Enzyme 2 GenBank Gene ID U22233 Link Image
Enzyme 2 GeneCard ID MTAP Link Image
Enzyme 2 GenAtlas ID MTAP Link Image
Enzyme 2 HGNC ID HGNC:7413 Link Image
Enzyme 2 Chromosome Location Not Available
Enzyme 2 Locus Not Available
Enzyme 2 SNPs SNPJam Report Link Image
Enzyme 2 General References
  1. Olopade OI, Pomykala HM, Hagos F, Sveen LW, Espinosa R 3rd, Dreyling MH, Gursky S, Stadler WM, Le Beau MM, Bohlander SK: Construction of a 2.8-megabase yeast artificial chromosome contig and cloning of the human methylthioadenosine phosphorylase gene from the tumor suppressor region on 9p21. Proc Natl Acad Sci U S A. 1995 Jul 3;92(14):6489-93. [PubMed Link Image]
  2. Nobori T, Takabayashi K, Tran P, Orvis L, Batova A, Yu AL, Carson DA: Genomic cloning of methylthioadenosine phosphorylase: a purine metabolic enzyme deficient in multiple different cancers. Proc Natl Acad Sci U S A. 1996 Jun 11;93(12):6203-8. [PubMed Link Image]
  3. Della Ragione F, Takabayashi K, Mastropietro S, Mercurio C, Oliva A, Russo GL, Della Pietra V, Borriello A, Nobori T, Carson DA, Zappia V: Purification and characterization of recombinant human 5'-methylthioadenosine phosphorylase: definite identification of coding cDNA. Biochem Biophys Res Commun. 1996 Jun 25;223(3):514-9. [PubMed Link Image]
  4. Appleby TC, Erion MD, Ealick SE: The structure of human 5'-deoxy-5'-methylthioadenosine phosphorylase at 1.7 A resolution provides insights into substrate binding and catalysis. Structure. 1999 Jun 15;7(6):629-41. [PubMed Link Image]
Enzyme 2 Metabolite References Not Available
Enzyme 3 [top]
Enzyme 3 ID 13000
Enzyme 3 Name Spermidine synthase (Spermidine synthase, isoform CRA_a)
Enzyme 3 Synonyms Not Available
Enzyme 3 Gene Name SRM
Enzyme 3 Protein Sequence >Spermidine synthase (Spermidine synthase, isoform CRA_a) 
MEPGPDGPAASGPAAIREGWFRETCSLWPGQALSLQVEQLLHHRRSRYQDILVFRSKTYG
NVLVLDGVIQCTERDEFSYQEMIANLPLCSHPNPRKVLIIGGGDGGVLREVVKHPSVESV
VQCEIDEDVIQVSKKFLPGMAIGYSSSKLTLHVGDGFEFMKQNQDAFDVIITDSSDPMGP
AESLFKESYYQLMKTALKEDGVLCCQGECQWLHLDLIKEMRQFCQSLFPVVAYAYCTIPT
YPSGQIGFMLCSKNPSTNFQEPVQPLTQQQVAQMQLKYYNSDVHRAAFVLPEFARKALND
VS
Enzyme 3 Number of Residues 302
Enzyme 3 Molecular Weight 33825
Enzyme 3 Theoretical pI Not Available
Enzyme 3 GO Classification Not Available
Enzyme 3 General Function Not Available
Enzyme 3 Specific Function Not Available
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 Not Available
Enzyme 3 UniProtKB/Swiss-Prot ID B1AKP9 Link Image
Enzyme 3 UniProtKB/Swiss-Prot Entry Name B1AKP9_HUMAN Link Image
Enzyme 3 PDB ID Not Available
Enzyme 3 Cellular Location Not Available
Enzyme 3 Gene Sequence Not Available
Enzyme 3 GenBank Gene ID Not Available
Enzyme 3 GeneCard ID B1AKP9 Link Image
Enzyme 3 GenAtlas ID Not Available
Enzyme 3 HGNC ID Not Available
Enzyme 3 Chromosome Location Not Available
Enzyme 3 Locus Not Available
Enzyme 3 SNPs SNPJam Report Link Image
Enzyme 3 General References Not Available
Enzyme 3 Metabolite References Not Available