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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-04-23 20:55:42 UTC
HMDB IDHMDB0000645
Secondary Accession Numbers
  • HMDB0003359
  • HMDB0062705
  • HMDB00645
  • HMDB03359
  • HMDB62705
Metabolite Identification
Common NameGalactose 1-phosphate
DescriptionGalactose 1-phosphate, also known as alpha-D-gal-1-p or α-D-gal-1-p, belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. Galactose 1-phosphate is a drug. Galactose 1-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). D-Galactose-1-phosphate is an intermediate in the intraconversion of glucose and uridine diphosphate galactose. The improper metabolism of galactose-1-phosphate is a characteristic of galactosemia. Galactose 1-phosphate exists in all living species, ranging from bacteria to humans. It is formed from galactose by galactokinase. Within humans, galactose 1-phosphate participates in a number of enzymatic reactions. In particular, uridine diphosphate glucose and galactose 1-phosphate can be biosynthesized from uridine diphosphategalactose and glucose 1-phosphate; which is mediated by the enzyme galactose-1-phosphate uridylyltransferase. In addition, galactose 1-phosphate can be biosynthesized from D-galactose through the action of the enzyme galactokinase. In humans, galactose 1-phosphate is involved in the metabolic disorder called galactosemia II (galk). Outside of the human body, galactose 1-phosphate has been detected, but not quantified in, several different foods, such as gooseberries, anises, turmerics, caraway, and cumins. This could make galactose 1-phosphate a potential biomarker for the consumption of these foods.
Structure
Data?1582752146
Synonyms
ValueSource
1-O-Phosphono-alpha-D-galactopyranoseChEBI
alpha-D-Gal-1-pChEBI
alpha-D-Galactopyranose 1-phosphateChEBI
alpha-D-Galactopyranose, 1-(dihydrogen phosphate)ChEBI
alpha-D-Galactopyranosyl phosphateChEBI
alpha-D-Galactosyl phosphateChEBI
Galactose-1-phosphateChEBI
1-O-Phosphono-a-D-galactopyranoseGenerator
1-O-Phosphono-α-D-galactopyranoseGenerator
a-D-Gal-1-pGenerator
Α-D-gal-1-pGenerator
a-D-Galactopyranose 1-phosphateGenerator
a-D-Galactopyranose 1-phosphoric acidGenerator
alpha-D-Galactopyranose 1-phosphoric acidGenerator
Α-D-galactopyranose 1-phosphateGenerator
Α-D-galactopyranose 1-phosphoric acidGenerator
a-D-Galactopyranose, 1-(dihydrogen phosphate)Generator
a-D-Galactopyranose, 1-(dihydrogen phosphoric acid)Generator
alpha-D-Galactopyranose, 1-(dihydrogen phosphoric acid)Generator
Α-D-galactopyranose, 1-(dihydrogen phosphate)Generator
Α-D-galactopyranose, 1-(dihydrogen phosphoric acid)Generator
a-D-Galactopyranosyl phosphateGenerator
a-D-Galactopyranosyl phosphoric acidGenerator
alpha-D-Galactopyranosyl phosphoric acidGenerator
Α-D-galactopyranosyl phosphateGenerator
Α-D-galactopyranosyl phosphoric acidGenerator
a-D-Galactosyl phosphateGenerator
a-D-Galactosyl phosphoric acidGenerator
alpha-D-Galactosyl phosphoric acidGenerator
Α-D-galactosyl phosphateGenerator
Α-D-galactosyl phosphoric acidGenerator
Galactose-1-phosphoric acidGenerator
Galactose 1-phosphoric acidGenerator
a-D-Galactose-1-phosphateHMDB
a-D-Galactose-1-phosphoric acidHMDB
alpha-D-Galactose-1-phosphoric acidHMDB
Α-D-galactose-1-phosphateHMDB
Α-D-galactose-1-phosphoric acidHMDB
Galactose-1-phosphate, (beta-L-gal)-isomerHMDB
Galactose-1-phosphate, 14C-labeledHMDB
Galactose-1-phosphate, disilver (+1) salt, (D-gal)-isomerHMDB
Galactose-1-phosphate, sodium saltHMDB
Galactose-1-phosphate, (beta-D-gal)-isomerHMDB
1-(Dihydrogen phosphate) galactitolHMDB
1-Phosphate a-D-galactopyranoseHMDB
a-D-1-(Dihydrogen phosphate) galactopyranoseHMDB
a-D-Galactose 1-phosphateHMDB
alpha-D-1-(Dihydrogen phosphate) galactopyranoseHMDB
alpha-D-Galactose 1-phosphateHMDB
D-Galactose 1-phosphateHMDB
Galactopyranose 1-phosphateHMDB
D-Galactopyranose 1-phosphateHMDB
D-Galactopyranose 1-phosphoric acidHMDB
D-Galactose 1-phosphoric acidHMDB
Chemical FormulaC6H13O9P
Average Molecular Weight260.1358
Monoisotopic Molecular Weight260.029718526
IUPAC Name{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid
Traditional Namegalactose 1 phosphate
CAS Registry Number2255-14-3
SMILES
OC[C@H]1O[C@H](OP(O)(O)=O)[C@H](O)[C@@H](O)[C@H]1O
InChI Identifier
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
InChI KeyHXXFSFRBOHSIMQ-FPRJBGLDSA-N
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility32.3 g/LALOGPS
logP-3.1ChemAxon
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
Polarizability20.62 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9110000000-ee60e23a7f8053dae6d3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0fsi-5901370000-80b5e0114d382bd45e3fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-9030000000-7fff706c8ccfa4e8ee82Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-9030000000-7ea4c16f3c1f90045b95Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0002-9000000000-d23bc07bd7bdf7ddce46Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-03dl-1970000000-880e9f60970f0816b8c4Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-001i-0920000000-2cbd9f1121176bb271efSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0002-0090000000-f7a9704c507f87576963Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0002-0190000000-190752fd0e6fc6923351Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0f72-0490000000-14a970b0e103aee3ac86Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-000i-0950000000-791dd70d946defe0237dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-001r-0890000000-7333cc4fec9c480da18bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-000i-0920000000-b0116f36e8c1774e674fSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-000i-0900000000-ce07a8268e9be0a752eaSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-004l-9000000000-771382b82d73a025b900Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-03di-0900000000-75b95578eec10c7fb1a0Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-00di-0900000000-efd4d199381342fcfd6eSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-014i-0900000000-59a34fd931d5d3eb02adSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-0f6t-0290000000-e0994816c9da10e9884bSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-004i-0190000000-0871936f57509fe1ab16Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-00di-0049000000-b5229bec94bbe9e0fe04Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9240000000-4057005941a73b47e92bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9240000000-2b520b8d7520453613e5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9100000000-adafd3ed58bf5371e4a1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6s-9480000000-6d21f499da6e13bbe38dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9110000000-68aeffe1ebca2d4d4362Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-dfc211275bafe42581aeSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
Tissue Locations
  • Erythrocyte
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified31.0 (0.0-57.0) uMChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified65.0 +/- 31.0 uMNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02317
Phenol Explorer Compound IDNot Available
FooDB IDFDB031262
KNApSAcK IDC00007391
Chemspider IDNot Available
KEGG Compound IDC00446
BioCyc IDGALACTOSE-1P
BiGG IDNot Available
Wikipedia LinkGalactose_1-phosphate
METLIN IDNot Available
PubChem Compound123912
PDB IDNot Available
ChEBI ID17973
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceChen 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
General References
  1. Endres W: Inherited metabolic diseases affecting the carrier. J Inherit Metab Dis. 1997 Mar;20(1):9-20. [PubMed:9061562 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]
  14. 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 ]
  15. 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 ]
  16. 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 ]
  17. 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 ]
  18. 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 ]
  19. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

General function:
Involved in UDP-glucose:hexose-1-phosphate uridylyltransferase activity
Specific function:
Not Available
Gene Name:
GALT
Uniprot ID:
P07902
Molecular weight:
43362.83
Reactions
Uridine diphosphate glucose + Galactose 1-phosphate → Glucose 1-phosphate + Uridine diphosphategalactosedetails
General function:
Involved in galactokinase activity
Specific function:
Acts on GalNAc. Also acts as a galactokinase when galactose is present at high concentrations. May be involved in a salvage pathway for the reutilization of free GalNAc derived from the degradation of complex carbohydrates.
Gene Name:
GALK2
Uniprot ID:
Q01415
Molecular weight:
49234.57
Reactions
Adenosine triphosphate + beta-D-Galactose → ADP + Galactose 1-phosphatedetails
General function:
Involved in galactokinase activity
Specific function:
Major enzyme for galactose metabolism.
Gene Name:
GALK1
Uniprot ID:
P51570
Molecular weight:
42271.805
Reactions
Adenosine triphosphate + beta-D-Galactose → ADP + Galactose 1-phosphatedetails