Human Metabolome Database Version 3.5

Showing metabocard for Mannose 6-phosphate (HMDB01078)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:30:19 -0600
HMDB ID HMDB01078
Secondary Accession Numbers None
Metabolite Identification
Common Name Mannose 6-phosphate
Description Mannose-6-phosphate is a potent competitive inhibitor of pinocytosis of human platelet beta-glucuronidase and it is a necessary component of the recognition marker on the enzyme for pinocytosis by human fibroblasts as well (PMID 908752 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. alpha-D-Mannose-6-P
  2. alpha-D-Mannose-6-phosphate
  3. alpha-delta-Mannose-6-P
  4. alpha-delta-Mannose-6-phosphate
  5. D-Mannose 6-phosphate
  6. delta-Mannose 6-phosphate
  7. Man-6-p
  8. Mannose 6-phosphate
  9. Mannose-6-phosphate
Chemical Formula C6H13O9P
Average Molecular Weight 260.1358
Monoisotopic Molecular Weight 260.029718526
IUPAC Name {[(2R,3S,4S,5S,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name [(2R,3S,4S,5S,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxyphosphonic acid
CAS Registry Number 3672-15-9
SMILES O[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@@H]1O
InChI Identifier InChI=1S/C6H13O9P/c7-3-2(1-14-16(11,12)13)15-6(10)5(9)4(3)8/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5+,6-/m1/s1
InChI Key NBSCHQHZLSJFNQ-RWOPYEJCSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Monosaccharides
Sub Class Hexoses
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
  • Carbohydrates and Carbohydrate Conjugates
  • D-glucopyranose 6-phosphate(ChEBI)
Substituents
  • 1,2 Diol
  • Hemiacetal
  • Monosaccharide Phosphate
  • Organic Hypophosphite
  • Organic Phosphite
  • Oxane
  • Phosphoric Acid Ester
  • Secondary Alcohol
Direct Parent Hexoses
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Fructose and mannose metabolism
Application Not Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 31.4 g/L ALOGPS
LogP -2.06 ALOGPS
LogP -3.1 ChemAxon
LogS -0.92 ALOGPS
pKa (strongest acidic) 1.22 ChemAxon
pKa (strongest basic) -3.6 ChemAxon
Hydrogen Acceptor Count 8 ChemAxon
Hydrogen Donor Count 6 ChemAxon
Polar Surface Area 156.91 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 46.8 ChemAxon
Polarizability 20.43 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations Not Available
Tissue Location
  • Fibroblasts
  • Intestine
  • Testes
  • Liver
  • Prostate
  • Spleen
Pathways
Name SMPDB Link KEGG Link
Fructose and Mannose Degradation SMP00064 map00051 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022411
KNApSAcK ID Not Available
Chemspider ID 388338 Link_out
KEGG Compound ID C00275 Link_out
BioCyc ID MANNOSE-6P Link_out
BiGG ID 34471 Link_out
Wikipedia Link Mannose 6-phosphate Link_out
NuGOwiki Link HMDB01078 Link_out
Metagene Link HMDB01078 Link_out
METLIN ID 5987 Link_out
PubChem Compound 439198 Link_out
PDB ID M6D Link_out
ChEBI ID 49728 Link_out
References
Synthesis Reference Pascual, C.; Herrera, L. Use of permeabilized yeast cells as a system of enzyme immobilization. Its use for the preparation of mannose 6-phosphate. Folia Microbiologica (Prague, Czech Republic) (1981), 26(2), 103-6.
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. Beljaars L, Molema G, Weert B, Bonnema H, Olinga P, Groothuis GM, Meijer DK, Poelstra K: Albumin modified with mannose 6-phosphate: A potential carrier for selective delivery of antifibrotic drugs to rat and human hepatic stellate cells. Hepatology. 1999 May;29(5):1486-93. Pubmed: 10216133 Link_out
  2. van der Ploeg AT, van der Kraaij AM, Willemsen R, Kroos MA, Loonen MC, Koster JF, Reuser AJ: Rat heart perfusion as model system for enzyme replacement therapy in glycogenosis type II. Pediatr Res. 1990 Oct;28(4):344-7. Pubmed: 2235132 Link_out
  3. DeRossi C, Bode L, Eklund EA, Zhang F, Davis JA, Westphal V, Wang L, Borowsky AD, Freeze HH: Ablation of mouse phosphomannose isomerase (Mpi) causes mannose 6-phosphate accumulation, toxicity, and embryonic lethality. J Biol Chem. 2006 Mar 3;281(9):5916-27. Epub 2005 Dec 8. Pubmed: 16339137 Link_out
  4. Yatziv S, Barfi G, Newburg DS: Lysosomal hydrolases in blood-derived macrophages of patients with I-cell disease. J Lab Clin Med. 1986 Oct;108(4):365-8. Pubmed: 3093618 Link_out
  5. Tiede S, Muschol N, Reutter G, Cantz M, Ullrich K, Braulke T: Missense mutations in N-acetylglucosamine-1-phosphotransferase alpha/beta subunit gene in a patient with mucolipidosis III and a mild clinical phenotype. Am J Med Genet A. 2005 Sep 1;137(3):235-40. Pubmed: 16094673 Link_out
  6. Puolakkainen M, Kuo CC, Campbell LA: Chlamydia pneumoniae uses the mannose 6-phosphate/insulin-like growth factor 2 receptor for infection of endothelial cells. Infect Immun. 2005 Aug;73(8):4620-5. Pubmed: 16040974 Link_out
  7. Holtta-Vuori M, Maatta J, Ullrich O, Kuismanen E, Ikonen E: Mobilization of late-endosomal cholesterol is inhibited by Rab guanine nucleotide dissociation inhibitor. Curr Biol. 2000 Jan 27;10(2):95-8. Pubmed: 10662671 Link_out
  8. Harper J, Burns JL, Foulstone EJ, Pignatelli M, Zaina S, Hassan AB: Soluble IGF2 receptor rescues Apc(Min/+) intestinal adenoma progression induced by Igf2 loss of imprinting. Cancer Res. 2006 Feb 15;66(4):1940-8. Pubmed: 16488992 Link_out
  9. Saris JJ, Derkx FH, De Bruin RJ, Dekkers DH, Lamers JM, Saxena PR, Schalekamp MA, Jan Danser AH: High-affinity prorenin binding to cardiac man-6-P/IGF-II receptors precedes proteolytic activation to renin. Am J Physiol Heart Circ Physiol. 2001 Apr;280(4):H1706-15. Pubmed: 11247783 Link_out
  10. Bird CH, Sun J, Ung K, Karambalis D, Whisstock JC, Trapani JA, Bird PI: Cationic sites on granzyme B contribute to cytotoxicity by promoting its uptake into target cells. Mol Cell Biol. 2005 Sep;25(17):7854-67. Pubmed: 16107729 Link_out
  11. Adrian JE, Poelstra K, Scherphof GL, Molema G, Meijer DK, Reker-Smit C, Morselt HW, Kamps JA: Interaction of targeted liposomes with primary cultured hepatic stellate cells: Involvement of multiple receptor systems. J Hepatol. 2006 Mar;44(3):560-7. Epub 2005 Oct 19. Pubmed: 16368158 Link_out
  12. Ullrich K, Basner R, Gieselmann V, Von Figura K: Recognition of human urine alpha-N-acetylglucosaminidase by rat hepatocytes. Involvement of receptors specific for galactose, mannose 6-phosphate and mannose. Biochem J. 1979 May 15;180(2):413-9. Pubmed: 114170 Link_out
  13. Davis JA, Wu XH, Wang L, DeRossi C, Westphal V, Wu R, Alton G, Srikrishna G, Freeze HH: Molecular cloning, gene organization, and expression of mouse Mpi encoding phosphomannose isomerase. Glycobiology. 2002 Jul;12(7):435-42. Pubmed: 12122025 Link_out
  14. Kaplan A, Fischer D, Achord D, Sly W: Phosphohexosyl recognition is a general characteristic of pinocytosis of lysosomal glycosidases by human fibroblasts. J Clin Invest. 1977 Nov;60(5):1088-93. Pubmed: 908752 Link_out
  15. Lobel P, Dahms NM, Breitmeyer J, Chirgwin JM, Kornfeld S: Cloning of the bovine 215-kDa cation-independent mannose 6-phosphate receptor. Proc Natl Acad Sci U S A. 1987 Apr;84(8):2233-7. Pubmed: 2951738 Link_out
  16. Maguchi S, Taniguchi N, Makita A: Elevated activity and increased mannose-6-phosphate in the carbohydrate moiety of cathepsin D from human hepatoma. Cancer Res. 1988 Jan 15;48(2):362-7. Pubmed: 2825973 Link_out
  17. Sleat DE, Wang Y, Sohar I, Lackland H, Li Y, Li H, Zheng H, Lobel P: Identification and validation of mannose 6-phosphate glycoproteins in human plasma reveal a wide range of lysosomal and non-lysosomal proteins. Mol Cell Proteomics. 2006 Oct;5(10):1942-56. Epub 2006 May 17. Pubmed: 16709564 Link_out
  18. Sleat DE, Sohar I, Lackland H, Majercak J, Lobel P: Rat brain contains high levels of mannose-6-phosphorylated glycoproteins including lysosomal enzymes and palmitoyl-protein thioesterase, an enzyme implicated in infantile neuronal lipofuscinosis. J Biol Chem. 1996 Aug 9;271(32):19191-8. Pubmed: 8702598 Link_out
  19. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411 Link_out

Enzymes
Name: Glucokinase
Reactions: Not Available
Gene Name: GCK
Uniprot ID: P35557 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hexokinase-3
Reactions:
Adenosine triphosphate + D-Mannose unknown ADP + Mannose 6-phosphate details
Gene Name: HK3
Uniprot ID: P52790 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hexokinase-2
Reactions:
Adenosine triphosphate + D-Mannose unknown ADP + Mannose 6-phosphate details
Gene Name: HK2
Uniprot ID: P52789 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hexokinase-1
Reactions:
Adenosine triphosphate + D-Mannose unknown ADP + Mannose 6-phosphate details
Gene Name: HK1
Uniprot ID: P19367 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Mannose-6-phosphate isomerase
Reactions:
Mannose 6-phosphate unknown Fructose 6-phosphate details
Mannose 6-phosphate unknown Beta-D-Fructose 6-phosphate details
Gene Name: MPI
Uniprot ID: P34949 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphomannomutase 2
Reactions:
D-Mannose 1-phosphate unknown Mannose 6-phosphate details
Mannose 6-phosphate unknown D-Mannose 1-phosphate details
Gene Name: PMM2
Uniprot ID: O15305 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphomannomutase 1
Reactions:
D-Mannose 1-phosphate unknown Mannose 6-phosphate details
Mannose 6-phosphate unknown D-Mannose 1-phosphate details
Gene Name: PMM1
Uniprot ID: Q92871 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Perilipin-3
Reactions: Not Available
Gene Name: PLIN3
Uniprot ID: O60664 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cation-dependent mannose-6-phosphate receptor
Reactions: Not Available
Gene Name: M6PR
Uniprot ID: P20645 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cation-independent mannose-6-phosphate receptor
Reactions: Not Available
Gene Name: IGF2R
Uniprot ID: P11717 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphoglucomutase-2
Reactions: Not Available
Gene Name: PGM2
Uniprot ID: Q96G03 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphofurin acidic cluster sorting protein 1
Reactions: Not Available
Gene Name: PACS1
Uniprot ID: Q6VY07 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sortilin
Reactions: Not Available
Gene Name: SORT1
Uniprot ID: Q99523 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Kinesin-like protein KIF13A
Reactions: Not Available
Gene Name: KIF13A
Uniprot ID: Q9H1H9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: WD repeat domain phosphoinositide-interacting protein 1
Reactions: Not Available
Gene Name: WIPI1
Uniprot ID: Q5MNZ9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Putative hexokinase HKDC1
Reactions:
Adenosine triphosphate + D-Mannose unknown ADP + Mannose 6-phosphate details
Gene Name: HKDC1
Uniprot ID: Q2TB90 Link_out
Protein Sequence: FASTA