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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 23:58:35 UTC
NP-MRD IDNP0000923
Secondary Accession NumbersNone
Natural Product Identification
Common NameD-Galactose
DescriptionD-Galactose is an aldohexose that occurs naturally in the D-form in lactose, cerebrosides, gangliosides, and mucoproteins. D-Galactose is an energy-providing nutrient and also a necessary basic substrate for the biosynthesis of many macromolecules in the body. Metabolic pathways for D-Galactose are important not only for the provision of these pathways but also for the prevention of D-Galactose and D-Galactose metabolite accumulation. The main source of D-Galactose is lactose in the milk of mammals, but it can also be found in some fruits and vegetables. Utilization of D-Galactose in all living cells is initiated by the phosphorylation of the hexose by the enzyme galactokinase (E.C. 2.7.1.6) (GALK) to form D-Galactose-1-phosphate. In the presence of D-Galactose-1-phosphate uridyltransferase (E.C. 2.7.7.12) (GALT) D-Galactose-1-phosphate is exchanged with glucose-1-phosphate in UDP-glucose to form UDP-galactose. Glucose-1-phosphate will then enter the glycolytic pathway for energy production. Deficiency of the enzyme GALT in galactosemic patients leads to the accumulation of D-Galactose-1-phosphate. Classic galactosemia-a term that denotes the presence of D-Galactose in the blood is the rare inborn error of D-Galactose metabolism, diagnosed by the deficiency of the second enzyme of the D-Galactose assimilation pathway, GALT, which, in turn, is caused by mutations at the GALT gene. (PMID: 15256214 , 11020650 , 10408771 ). Galactose in the urine is a biomarker for the consumption of milk.
Structure
Data?1628564082
Synonyms
ValueSource
ALPHA D-GALACTOSEChEBI
alpha-D-GalChEBI
Gal-alphaChEBI
WURCS=2.0/1,1,0/[a2112h-1a_1-5]/1/ChEBI
alpha-D-GalactoseKegg
a D-GALACTOSEGenerator
Α D-galactoseGenerator
a-D-GalGenerator
Α-D-galGenerator
Gal-aGenerator
Gal-αGenerator
a-D-GalactoseGenerator
Α-D-galactoseGenerator
(+)-GalactoseHMDB
5AbpHMDB
8AbpHMDB
alpha-D-GalactopyranoseHMDB
D-(+)-GalactoseHMDB
D-HexoseHMDB
GALHMDB
GalactoseHMDB
Galactose (NF)HMDB
GLAHMDB
GLCHMDB
HexoseHMDB
SHU 508 aMeSH, HMDB
SH-TA-508MeSH, HMDB
SHU 508MeSH, HMDB
LevovistMeSH, HMDB
SHU-508MeSH, HMDB
Chemical FormulaC6H12O6
Average Mass180.1559 Da
Monoisotopic Mass180.06339 Da
IUPAC Name(2S,3R,4S,5R,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
Traditional Namegalactose
CAS Registry Number59-23-4
SMILES
[H]OC([H])([H])[C@@]1([H])O[C@]([H])(O[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@@]1([H])O[H]
InChI Identifier
InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3+,4+,5-,6+/m1/s1
InChI KeyWQZGKKKJIJFFOK-PHYPRBDBSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 1H] 2D NMR Spectrum (experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 400 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)V.dorna832021-08-08View Spectrum
Species
Species of Origin
Species NameSourceReference
Acacia tortuosaKNApSAcK Database
Brassica oleracea L. ssp. BotrytisKNApSAcK Database
Carica papayaKNApSAcK Database
Cassia angustifoliaKNApSAcK Database
Hibiscus sabdariffa L.KNApSAcK Database
Laminaria japonicaKNApSAcK Database
Oryza sativaKNApSAcK Database
Paeonia peregrinaKNApSAcK Database
Phyllanthus sellowianusKNApSAcK Database
Prunus aviumKNApSAcK Database
Solanum lycopersicum L.KNApSAcK Database
Species Where Detected
Species NameSourceReference
Escherichia coliKNApSAcK Database
Homo sapiens (Serum)KNApSAcK Database
Homo sapiens (Urine)KNApSAcK Database
Phoma medicaginisKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexoses
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point170 °CNot Available
Boiling Point410.80 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility683 mg/mLNot Available
LogP-2.490 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility782 g/LALOGPS
logP-2.6ALOGPS
logP-2.9ChemAxon
logS0.64ALOGPS
pKa (Strongest Acidic)11.3ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area110.38 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.92 m³·mol⁻¹ChemAxon
Polarizability16.13 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
External Links
HMDB IDHMDB0000143
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021787
KNApSAcK IDC00019681
Chemspider ID388480
KEGG Compound IDC00984
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGalactose
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID28061
Good Scents IDrw1233801
References
General References
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  2. 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. doi: 10.1038/nature07762. [PubMed:19212411 ]
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  5. Ning C, Segal S: Plasma galactose and galactitol concentration in patients with galactose-1-phosphate uridyltransferase deficiency galactosemia: determination by gas chromatography/mass spectrometry. Metabolism. 2000 Nov;49(11):1460-6. [PubMed:11092512 ]
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  14. 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 ]
  15. Tamamori A, Fujimoto A, Okano Y, Kobayashi K, Saheki T, Tagami Y, Takei H, Shigematsu Y, Hata I, Ozaki H, Tokuhara D, Nishimura Y, Yorifuji T, Igarashi N, Ohura T, Shimizu T, Inui K, Sakai N, Abukawa D, Miyakawa T, Matsumori M, Ban K, Kaneko H, Yamano T: Effects of citrin deficiency in the perinatal period: feasibility of newborn mass screening for citrin deficiency. Pediatr Res. 2004 Oct;56(4):608-14. Epub 2004 Aug 4. [PubMed:15295082 ]
  16. Wang ZJ, Berry GT, Dreha SF, Zhao H, Segal S, Zimmerman RA: Proton magnetic resonance spectroscopy of brain metabolites in galactosemia. Ann Neurol. 2001 Aug;50(2):266-9. [PubMed:11506413 ]
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  18. Schmidt LE, Ott P, Tygstrup N: Galactose elimination capacity as a prognostic marker in patients with severe acetaminophen-induced hepatotoxicity: 10 years' experience. Clin Gastroenterol Hepatol. 2004 May;2(5):418-24. [PubMed:15118981 ]
  19. Vironen J, Kellokumpu S, Andersson LC, Kellokumpu I: Comparison of a peanut agglutinin test and an immunochemical faecal occult blood test in detecting colorectal neoplasia in symptomatic patients. Scand J Clin Lab Invest. 2004 Apr;64(2):140-5. [PubMed:15115252 ]
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  21. Chen J, Yager C, Reynolds R, Palmieri M, Segal S: Erythrocyte galactose 1-phosphate quantified by isotope-dilution gas chromatography-mass spectrometry. Clin Chem. 2002;48(4):604-12. [PubMed:11901058 ]
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  23. Cavalli C, Teng C, Battaglia FC, Bevilacqua G: Free sugar and sugar alcohol concentrations in human breast milk. J Pediatr Gastroenterol Nutr. 2006 Feb;42(2):215-21. [PubMed:16456418 ]
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  25. Wan CC, Muldrey JE, Li SC, Li YT: beta-Mannosidase from the mushroom Polyporus sulfureus. J Biol Chem. 1976 Jul 25;251(14):4384-8. [PubMed:6478 ]
  26. Redaelli CA, Dufour JF, Wagner M, Schilling M, Husler J, Krahenbuhl L, Buchler MW, Reichen J: Preoperative galactose elimination capacity predicts complications and survival after hepatic resection. Ann Surg. 2002 Jan;235(1):77-85. [PubMed:11753045 ]
  27. Rudzeviciene O, Narkeviciute I, Eidukevicius R: Lactose malabsorption in young Lithuanian children with atopic dermatitis. Acta Paediatr. 2004 Apr;93(4):482-6. [PubMed:15188975 ]
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