Record Information
Version2.0
Creation Date2012-05-31 14:02:03 -0600
Update Date2015-06-03 15:54:37 -0600
Secondary Accession Numbers
  • ECMDB04011
Identification
Name:Galactose 1-phosphate
Description:Galactose 1-phosphate is an intermediate in the Galactose metabolism
Structure
Thumb
Synonyms:
  • α-D-Gal-1-P
  • α-D-galactopyranose 1-phosphate
  • α-D-galactopyranose 1-phosphoric acid
  • 1-(Dihydrogen phosphate) Galactitol
  • 1-(Dihydrogen phosphoric acid) galactitol
  • 1-phosphate a-D-Galactopyranose
  • 1-Phosphate alpha-D-Galactopyranose
  • 1-Phosphate α-D-galactopyranose
  • 1-Phosphoric acid a-D-galactopyranose
  • 1-Phosphoric acid alpha-D-galactopyranose
  • 1-Phosphoric acid α-D-galactopyranose
  • A-D-1-(Dihydrogen phosphate) Galactopyranose
  • a-D-1-(Dihydrogen phosphoric acid) galactopyranose
  • a-D-Gal-1-P
  • a-D-Galactopyranose 1-phosphate
  • a-D-Galactopyranose 1-phosphoric acid
  • A-D-Galactopyranosyl phosphate
  • a-D-Galactopyranosyl phosphoric acid
  • A-D-Galactose 1-phosphate
  • a-D-Galactose 1-phosphoric acid
  • A-D-Galactosyl phosphate
  • a-D-Galactosyl phosphoric acid
  • Alpha-D-1-(Dihydrogen phosphate) Galactopyranose
  • alpha-D-1-(Dihydrogen phosphoric acid) galactopyranose
  • Alpha-D-Gal-1-P
  • Alpha-D-Galactopyranose 1-phosphate
  • alpha-D-Galactopyranose 1-phosphoric acid
  • Alpha-D-Galactopyranosyl phosphate
  • alpha-D-Galactopyranosyl phosphoric acid
  • Alpha-D-Galactose 1-phosphate
  • alpha-D-Galactose 1-phosphoric acid
  • Alpha-D-Galactosyl phosphate
  • alpha-D-Galactosyl phosphoric acid
  • D-Galactose 1-phosphate
  • D-Galactose 1-phosphoric acid
  • D-Galactose-1-phosphate
  • D-Galactose-1-phosphoric acid
  • Galactopyranose 1-phosphate
  • Galactopyranose 1-phosphoric acid
  • Galactose 1-phosphate
  • Galactose 1-phosphoric acid
  • Galactose-1-P
  • α-D-1-(Dihydrogen phosphate) galactopyranose
  • α-D-1-(Dihydrogen phosphoric acid) galactopyranose
  • α-D-Gal-1-P
  • α-D-Galactopyranose 1-phosphate
  • α-D-Galactopyranose 1-phosphoric acid
  • α-D-Galactopyranosyl phosphate
  • α-D-Galactopyranosyl phosphoric acid
  • α-D-Galactose 1-phosphate
  • α-D-Galactose 1-phosphoric acid
  • α-D-Galactosyl phosphate
  • α-D-Galactosyl phosphoric acid
Chemical Formula:C6H13O9P
Weight:Average: 260.1358
Monoisotopic: 260.029718526
InChI Key:HXXFSFRBOHSIMQ-FPRJBGLDSA-N
InChI:InChI=1S/C6H13O9P/c7-1-2-3(8)4(9)5(10)6(14-2)15-16(11,12)13/h2-10H,1H2,(H2,11,12,13)/t2-,3+,4+,5-,6-/m1/s1
CAS number:2255-14-3
IUPAC Name:{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid
Traditional IUPAC Name:glucose 1-phosphate
SMILES:OC[C@H]1O[C@H](OP(O)(O)=O)[C@H](O)[C@@H](O)[C@H]1O
Chemical Taxonomy
Description belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharide phosphates
Alternative Parents
Substituents
  • Hexose monosaccharide
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Oxane
  • Alkyl phosphate
  • Phosphoric acid ester
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Primary alcohol
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility32.3 g/LALOGPS
logP-2ALOGPS
logP-3.1ChemAxon
logS-0.91ALOGPS
pKa (Strongest Acidic)1.16ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area156.91 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity46.8 m³·mol⁻¹ChemAxon
Polarizability20.66 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Amino sugar and nucleotide sugar metabolism IIPW000887 ThumbThumb?image type=greyscaleThumb?image type=simple
Amino sugar and nucleotide sugar metabolism IIIPW000895 ThumbThumb?image type=greyscaleThumb?image type=simple
Galactitol and galactonate degradationPW000820 ThumbThumb?image type=greyscaleThumb?image type=simple
Galactose metabolismPW000821 ThumbThumb?image type=greyscaleThumb?image type=simple
Starch and sucrose metabolismPW000941 ThumbThumb?image type=greyscaleThumb?image type=simple
galactose degradation/Leloir PathwayPW000884 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9110000000-ee60e23a7f8053dae6d3View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-003r-5591470000-4932aa0d35a53458633dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0a4i-0390000000-9e3307d6125b74ed8579View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-05mk-2960000000-4950cd68ef81b4267967View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0230-5970000000-4c2745937c6f87f89f17View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9240000000-0a7885872856fe43526bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9240000000-b437590c213fb263989dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0532-9100000000-97504a02d14244b901cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-9360000000-98c3aee1d36863dc12abView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9110000000-92ad15ffc9eae3eed039View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-dfc211275bafe42581aeView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Barbouth D, Slepak T, Klapper H, Lai K, Elsas LJ: Prevention of a molecular misdiagnosis in galactosemia. Genet Med. 2006 Mar;8(3):178-82. Pubmed: 16540753
  • Barth CA, Kopra N: Oral intake of glucose plus galactose and erythrocyte galactose-1-phosphate. A nutritional evaluation of hydrolyzed lactose. Z Ernahrungswiss. 1986 Sep;25(3):171-9. Pubmed: 3776241
  • Berry GT, Palmieri M, Gross KC, Acosta PB, Henstenburg JA, Mazur A, Reynolds R, Segal S: The effect of dietary fruits and vegetables on urinary galactitol excretion in galactose-1-phosphate uridyltransferase deficiency. J Inherit Metab Dis. 1993;16(1):91-100. Pubmed: 8487507
  • Bozkowa K, Duchnowska A, Chojnacki T, Mankowski T: [New radioisotope method of quantitative determination of galactose-1-phosphate in red blood cells in galactosemia] Pol Tyg Lek. 1975 Dec 22;30(51):2123-6. Pubmed: 1197109
  • Bozkowa K, Zbieg-Sendecka E, Grodzka Z, Cabalska B: [Clinical and biochemical diagnosis of galactosemia among our cases] Probl Med Wieku Rozwoj. 1979;8:63-9. Pubmed: 263527
  • Dahlqvist A: A fluorometric method for the assay of galactose-1-phosphate in red blood cells. J Lab Clin Med. 1971 Dec;78(6):931-8. Pubmed: 5131857
  • Endres W: Inherited metabolic diseases affecting the carrier. J Inherit Metab Dis. 1997 Mar;20(1):9-20. Pubmed: 9061562
  • Gitzelmann R, Steinmann B, Mitchell B, Haigis E: Uridine diphosphate galactose 4'-epimerase deficiency. IV. Report of eight cases in three families. Helv Paediatr Acta. 1977 Apr;31(6):441-52. Pubmed: 404274
  • Guerrero NV, Singh RH, Manatunga A, Berry GT, Steiner RD, Elsas LJ 2nd: Risk factors for premature ovarian failure in females with galactosemia. J Pediatr. 2000 Dec;137(6):833-41. Pubmed: 11113841
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Mankowski T, Radomyska B, Zbieg-Sendecka E: Preliminary results of UDP galactose pyrophosphorylase in the erythrocytes of healthy persons and in patients with galactosaemia. Mater Med Pol. 1990 Jul-Sep;22(3):191-3. Pubmed: 2132425
  • Moller HE, Ullrich K, Vermathen P, Schuierer G, Koch HG: In vivo study of brain metabolism in galactosemia by 1H and 31P magnetic resonance spectroscopy. Eur J Pediatr. 1995;154(7 Suppl 2):S8-13. Pubmed: 7671972
  • Ning C, Reynolds R, Chen J, Yager C, Berry GT, McNamara PD, Leslie N, Segal S: Galactose metabolism by the mouse with galactose-1-phosphate uridyltransferase deficiency. Pediatr Res. 2000 Aug;48(2):211-7. Pubmed: 10926297
  • Ono H, Mawatari H, Mizoguchi N, Eguchi T, Sakura N, Hamakawa M: Transient galactosemia detected by neonatal mass screening. Pediatr Int. 1999 Jun;41(3):281-4. Pubmed: 10365579
  • Pesce MA, Bodourian SH, Nicholson JF: A new microfluorometric method for the measurement of galactose-1-phosphate in erythrocytes. Clin Chim Acta. 1982 Feb 5;118(2-3):177-89. Pubmed: 7055979
  • Pesce MA, Bodourian SH: Clinical significance of plasma galactose and erythrocyte galactose-1-phosphate measurements in transferase-deficient galactosemia and in individuals with below-normal transferase activity. Clin Chem. 1982 Feb;28(2):301-5. Pubmed: 6276048
  • Schadewaldt P, Kamalanathan L, Hammen HW, Wendel U: Age dependence of endogenous galactose formation in Q188R homozygous galactosemic patients. Mol Genet Metab. 2004 Jan;81(1):31-44. Pubmed: 14728989
  • Schaub J, Remberger K, Endres W, Bremer HJ: Galactosemia with endogenous production of galactose-1-phosphate and with cystic fibrosis-like appearance at autopsy. Helv Paediatr Acta. 1976 Jun;31(1):67-76. Pubmed: 939702
  • Wharton CH, Berry HK, Bofinger MK: Galactose-1-phosphate accumulation by a Duarte-transferase deficiency double heterozygote. Clin Genet. 1978 Feb;13(2):171-5. Pubmed: 627109
Synthesis Reference:Chen Jie; Yager Claire; Reynolds Robert; Palmieri Michael; Segal Stanton Erythrocyte galactose 1-phosphate quantified by isotope-dilution gas chromatography-mass spectrometry. Clinical chemistry (2002), 48(4), 604-12.
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID16077
HMDB IDHMDB00645
Pubchem Compound ID439995
Kegg IDC00446
ChemSpider ID110443
WikipediaGalactose 1-phosphate
BioCyc IDGALACTOSE-1P
EcoCyc IDGALACTOSE-1P
Ligand ExpoGL1

Enzymes

General function:
Involved in hydrolase activity
Specific function:
Degradation of external UDP-glucose to uridine monophosphate and glucose-1-phosphate, which can then be used by the cell
Gene Name:
ushA
Uniprot ID:
P07024
Molecular weight:
60824
Reactions
UDP-sugar + H(2)O = UMP + alpha-D-aldose 1-phosphate.
A 5'-ribonucleotide + H(2)O = a ribonucleoside + phosphate.
General function:
Involved in UDP-glucose:hexose-1-phosphate uridylyltransferase activity
Specific function:
UDP-glucose + alpha-D-galactose 1-phosphate = alpha-D-glucose 1-phosphate + UDP-galactose
Gene Name:
galT
Uniprot ID:
P09148
Molecular weight:
39645
Reactions
UDP-glucose + alpha-D-galactose 1-phosphate = alpha-D-glucose 1-phosphate + UDP-galactose.
General function:
Involved in galactokinase activity
Specific function:
ATP + D-galactose = ADP + alpha-D-galactose 1- phosphate
Gene Name:
galK
Uniprot ID:
P0A6T3
Molecular weight:
41442
Reactions
ATP + D-galactose = ADP + alpha-D-galactose 1-phosphate.
General function:
Involved in zinc ion binding
Specific function:
Converts galactitol 1-phosphate to tagatose 6-phosphate
Gene Name:
gatD
Uniprot ID:
P0A9S3
Molecular weight:
37390
Reactions
Galactitol-1-phosphate + NAD(+) = L-tagatose 6-phosphate + NADH.
General function:
Involved in acid phosphatase activity
Specific function:
Absolutely required for the growth of E.coli in a high- phosphate medium containing G-1-P as the sole carbon source
Gene Name:
agp
Uniprot ID:
P19926
Molecular weight:
45683
Reactions
Alpha-D-glucose 1-phosphate + H(2)O = D-glucose + phosphate.
General function:
Involved in sugar:hydrogen symporter activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in galactitol transport
Gene Name:
gatB
Uniprot ID:
P37188
Molecular weight:
10222
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.
General function:
Involved in transporter activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in galactitol transport
Gene Name:
gatA
Uniprot ID:
P69828
Molecular weight:
16907
Reactions
Protein EIIA N(pi)-phospho-L-histidine + protein EIIB = protein EIIA + protein EIIB N(pi)-phospho-L-histidine/cysteine.
General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in galactitol transport
Gene Name:
gatC
Uniprot ID:
P69831
Molecular weight:
48365
General function:
Involved in transferase activity
Specific function:
Specific function unknown
Gene Name:
wcaK
Uniprot ID:
P71242
Molecular weight:
47343

Transporters

General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in galactitol transport
Gene Name:
gatC
Uniprot ID:
P69831
Molecular weight:
48365
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368