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Human Metabolome Database Version 2.5

 

Showing metabocard for 5-Methylthioribose 1-phosphate (HMDB00963)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-05 20:58:24
Accession Number HMDB00963
Secondary Accession Numbers Not Available
Common Name 5-Methylthioribose 1-phosphate
Description 5-Methylthioribose 1-phosphate is an intermediate in methionine biosynthesis. It is converted from 5'-Deoxy-5'-methylthioadenosine by 5'-Deoxy-5'-methylthioadenosine phosphorylase. Then it is converted to methionine (PMID 2153115). In the methionine salvage pathway 5-methylthioribose 1-phosphate isomerase (M1Pi) catalyzes the conversion of 5-methylthioribose 1-phosphate (MTR-1-P) to 5-methylthioribulose 1-phosphate (MTRu-1-P)
Synonyms
  1. 1-phospho-5-S-methylthioribose
  2. 1-phosphomethylthioribose
  3. 5-Methylthioribose 1-phosphate
  4. 5-Methylthioribose 1-phosphic acid
  5. 5-methylthio-5-deoxy-D-ribose-1-phosphate
  6. 5-Methylthio-5-deoxy-D-ribose 1-phosphate
  7. 5-methylthio-D-ribose-1-phosphate
  8. 5-methylthioribose-1-phosphate
  9. D-ribofuranoside
  10. S5-methyl-5-thio-D-ribose-1-phosphate
  11. S-methyl-5-thio-alpha-D-ribose 1-phosphate
Chemical IUPAC Name [3,4-dihydroxy-5-(methylsulfanylmethyl)oxolan-2-yl]oxyphosphonic acid
Chemical Formula C6H13O7PS
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Carbohydrates and Carbohydrate conjugates
Class
  • Sugar Phosphates
Sub Class
  • Monosaccharide phosphates
Family
  • Mammalian Metabolite
Species
  • secondary alcohol
  • 1,2-diol
  • thioether
  • phosphoric acid ester
  • heterocyclic compound
Biofunction
—
Application
—
Source
  • Endogenous
Average Molecular Weight 260.202
Monoisotopic Molecular Weight 260.011963
Isomeric SMILES CSCC1OC(OP(O)(O)=O)[C@H](O)[C@@H]1O
Canonical SMILES CSCC1OC(OP(O)(O)=O)C(O)C1O
KEGG Compound ID C04188 Link Image
BioCyc ID CPD-444 Link Image
BiGG ID 43318 Link Image
Wikipedia Link Not Available
NuGOwiki Link HMDB00963 Link Image
Metagene Link HMDB00963 Link Image
METLIN ID 5909 Link Image
PubChem Compound 465 Link Image
PubChem Substance 2407 Link Image
ChEBI ID 27859 Link Image
CAS Registry Number 72843-83-5
InChI Identifier InChI=1/C6H13O7PS/c1-15-2-3-4(7)5(8)6(12-3)13-14(9,10)11/h3-8H,2H2,1H3,(H2,9,10,11)/t3-,4+,5+,6?/m0/s1
Synthesis Reference Della Ragione, Fulvio; Carteni-Farina, Maria; Gragnaniello, Vincenzo; Schettino, Maria Irene; Zappia, Vincenzo. Purification and characterization of 5'-deoxy-5'-methylthioadenosine phosphorylase from human placenta. Journal of Biological Chemistry (1986), 261(26), 12324-9.
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 28.699999 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -2
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -1.16 [Predicted by ALOGPS]; -1.8 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm
Biofluid Location Not Available
Tissue Location Not Available
Concentrations (Normal) Not Available
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. Avila MA, Garcia-Trevijano ER, Lu SC, Corrales FJ, Mato JM: Methylthioadenosine. Int J Biochem Cell Biol. 2004 Nov;36(11):2125-30. [PubMed Link Image]
  2. Savarese TM, Ghoda LY, Dexter DL, Parks RE Jr: Conversion of 5'-deoxy-5'-methylthioadenosine and 5'-deoxy-5'-methylthioinosine to methionine in cultured human leukemic cells. Cancer Res. 1983 Oct;43(10):4699-702. [PubMed Link Image]
  3. Tisdale MJ: Methionine synthesis from 5'-methylthioadenosine by tumour cells. Biochem Pharmacol. 1983 Oct 1;32(19):2915-20. [PubMed Link Image]
  4. Savarese TM, Cannistra AJ, Parks RE Jr, Secrist JA 3rd, Shortnacy AT, Montgomery JA: 5'-deoxy-5'-methylthioadenosine phosphorylase--IV. Biological activity of 2-fluoroadenine-substituted 5'-deoxy-5'-methylthioadenosine analogs. Biochem Pharmacol. 1987 Jun 15;36(12):1881-93. [PubMed Link Image]
  5. Ghoda LY, Savarese TM, Dexter DL, Parks RE Jr, Trackman PC, Abeles RH: Characterization of a defect in the pathway for converting 5'-deoxy-5'-methylthioadenosine to methionine in a subline of a cultured heterogeneous human colon carcinoma. J Biol Chem. 1984 Jun 10;259(11):6715-9. [PubMed Link Image]
  6. Gianotti AJ, Tower PA, Sheley JH, Conte PA, Spiro C, Ferro AJ, Fitchen JH, Riscoe MK: Selective killing of Klebsiella pneumoniae by 5-trifluoromethylthioribose. Chemotherapeutic exploitation of the enzyme 5-methylthioribose kinase. J Biol Chem. 1990 Jan 15;265(2):831-7. [PubMed Link Image]
Metabolic Enzymes
  1. S-methyl-5-thioadenosine phosphorylase
Enzyme 1 [top]
Enzyme 1 ID 5634
Enzyme 1 Name S-methyl-5-thioadenosine phosphorylase
Enzyme 1 Synonyms
  1. 5'- methylthioadenosine phosphorylase
  2. MTA phosphorylase
  3. MTAPase
Enzyme 1 Gene Name MTAP
Enzyme 1 Protein Sequence >S-methyl-5-thioadenosine phosphorylase 
MASGTTTTAVKIGIIGGTGLDDPEILEGRTEKYVDTPFGKPSDALILGKIKNVDCVLLAR
HGRQHTIMPSKVNYQANIWALKEEGCTHVIVTTACGSLREEIQPGDIVIIDQFIDRTTMR
PQSFYDGSHSCARGVCHIPMAEPFCPKTREVLIETAKKLGLRCHSKGTMVTIEGPRFSSR
AESFMFRTWGADVINMTTVPEVVLAKEAGICYASIAMATDYDCWKEHEEAVSVDRVLKTL
KENANKAKSLLLTTIPQIGSTEWSETLHNLKNMAQFSVLLPRH
Enzyme 1 Number of Residues 283
Enzyme 1 Molecular Weight 31236
Enzyme 1 Theoretical pI 7.21
Enzyme 1 GO Classification Not Available
Enzyme 1 General Function Nucleotide transport and metabolism
Enzyme 1 Specific Function Plays a major role in polyamine metabolism and is important for the salvage of both adenine and methionine
Enzyme 1 Pathways Not Available
Enzyme 1 Reactions
  • S-methyl-5-thioadenosine + phosphate = adenine + S-methyl-5-thio-alpha-D-ribose 1-phosphate
Enzyme 1 Pfam Domain Function Not Available
Enzyme 1 Signals
  • None
Enzyme 1 Transmembrane Regions
  • None
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 847724 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID Q13126 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name MTAP_HUMAN Link Image
Enzyme 1 PDB ID 1SD2 Link Image
Enzyme 1 PDB File Show
Enzyme 1 3D Structure
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence >852 bp 
ATGGCCTCTGGCACCACCACCACCGCCGTGAAGATTGGAATAATTGGTGGAACAGGCCTG
GATGATCCAGAAATTTTAGAAGGAAGAACTGAAAAATATGTGGATACTCCATTTGGCAAG
CCATCTGATGCCTTAATTTTGGGGAAGATAAAAAATGTTGATTGCATCCTCCTTGCAAGG
CATGGAAGGCAGCACACCATCATGCCTTCAAAGGTCAACTACCAGGCGAACATCTGGGCT
TTGAAGGAAGAGGGCTGTACACATGTCATAGTGACCACAGCTTGTGGCTCCTTGAGGGAG
GAGATTCAGCCCGGCGATATTGTCATTATTGATCAGTTCATTGACAGGACCACTATGAGA
CCTCAGTCCTTCTATGATGGAAGTCATTCTTGTGCCAGAGGAGTGTGCCATATTCCAATG
GCTGAGCCGTTTTGCCCCAAAACGAGAGAGGTTCTTATAGAGACTGCTAAGAAGCTAGGA
CTCCGGTGCCACTCAAAGGGGACAATGGTCACAATCGAGGGACCTCGTTTTAGCTCCCGG
GCAGAAAGCTTCATGTTCCGCACCTGGGGGGCGGATGTTATCAACATGACCACAGTTCCA
GAGGTGGTTCTTGCTAAGGAGGCTGGAATTTGTTACGCAAGTATCGCCATGGCGACAGAT
TATGACTGCTGGAAGGAGCACGAGGAAGCAGTTTCGGTGGACCGGGTCTTAAAGACCCTG
AAAGAAAACGCTAATAAAGCCAAAAGCTTACTGCTCACTACCATACCTCAGATAGGGTCC
ACAGAATGGTCAGAAACCCTCCATAACCTGAAGAATATGGCCCAGTTTTCTGTTTTATTA
CCAAGACATTAA
Enzyme 1 GenBank Gene ID U22233 Link Image
Enzyme 1 GeneCard ID MTAP Link Image
Enzyme 1 GenAtlas ID MTAP Link Image
Enzyme 1 HGNC ID HGNC:7413 Link Image
Enzyme 1 Chromosome Location Not Available
Enzyme 1 Locus Not Available
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 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 1 Metabolite References Not Available