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Showing Compound alpha-D-Galactose (FDB021787)

Record Information
Version1.0
Creation date2011-04-07 23:15:07 UTC
Update date2020-09-17 15:41:19 UTC
Primary IDFDB021787
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namealpha-D-Galactose
DescriptionD-galactose, also known as galactopyranose, is an aldohexose is a C4-epimer of glucose. It is as sweet as glucose and only 65% as sweet as sucrose. When D-galactose condenses with glucose, lactose if formed. In humans and other species, galactose is metabolized to glucose largely by the Leloir pathway. D-galactose is converted to UDP-glucose and glucose-1-phosphate by three enzymes (PMID: 1292318): 1) Galactokinase (GALK; KEGG enzyme E.C. 2.7.1.6) phosphorylates D-galactose to D-galactose-1-phosphate; 2) Then D-galactose-1-phosphate uridyltransferase (GALT; KEGG enzyme E.C. 2.7.7.12) transfers a UMP from UDP-glucose to D-galactose-1-phosphate to form UDP-galactose and glucose-1-phosphate. Glucose-1-phosphate will then enter the glycolytic pathway for energy production. 3) UDP-galactose epimerase (GALE) then interconverts UDP-galactose to UDP-glucose. Lactose in mammalian milk is the main source of D-galactose. Galactose in the urine is a biomarker for the consumption of milk. Galactose can also be found in some fruits and vegetables such as in banana, orange, papaya, bell pepper, avocado and sugar beets ( http://www.thegoodscentscompany.com/data/rw1233801.html#tooccur). It is also found in fig leaves, sesame, carob bean, caraway seeds and beet, cocoa, chive, potato. In addition to D-Galactose providing energy for the body, it is also a necessary substrate for the biosynthesis of many macromolecules such as cerebrosides, gangliosides, and mucoproteins. Galactose is a component of the antigens of the ABO blood group (PMID: 15373665). Metabolic pathways for D-galactose are important not only for the provision of these pathways but also for the prevention of D-galactose accumulation. There are diseases resulting from the deficiencies of the three enzymes of the Leloir pathway. Classic galactosemia, or the accumulation of D-galactose in the blood, is the rare inborn error of D-galactose metabolism, caused by the deficiency of the second enzyme GALT, (from mutations in the GALT gene; PMID: 10408771). As galactose accumulation is associated with health problems (PMID: 26001656), particularly involving the liver (PMID: 29502917), the discovery of alternative metabolic pathways to the Leloir in fungi and bacteria (PMID:15256214) could lead to discovery of analogous genes in humans. D-galactose was also be protective against pancreatitis (PMID: 2989374) and streptozotocin-induced model of Alzheimer’s disease in rats (PMID: 29501615).
CAS Number3646-73-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
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
Chemical FormulaC6H12O6
IUPAC name(2S,3R,4S,5R,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
InChI IdentifierInChI=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
Isomeric SMILESOC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O
Average Molecular Weight180.1559
Monoisotopic Molecular Weight180.063388116
Classification
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 Parents
Substituents
  • Hexose monosaccharide
  • Oxane
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSalpha-D-Galactose, non-derivatized, GC-MS Spectrumsplash10-066s-0941000000-8f1b68655e0a5ed179e3Spectrum
GC-MSalpha-D-Galactose, non-derivatized, GC-MS Spectrumsplash10-0ldj-0941000000-84c771fab416aa0a40d8Spectrum
GC-MSalpha-D-Galactose, non-derivatized, GC-MS Spectrumsplash10-0ktb-0931000000-6f37a774d1ab64585c8dSpectrum
GC-MSalpha-D-Galactose, non-derivatized, GC-MS Spectrumsplash10-066s-0931000000-9945093085ef7b0de618Spectrum
GC-MSalpha-D-Galactose, non-derivatized, GC-MS Spectrumsplash10-0ldj-0931000000-1ed532d5d2897be775dfSpectrum
GC-MSalpha-D-Galactose, non-derivatized, GC-MS Spectrumsplash10-00di-9731000000-af5bd67ad0bbb2997839Spectrum
GC-MSalpha-D-Galactose, non-derivatized, GC-MS Spectrumsplash10-00di-9621000000-9dad5bd1760a891ace2aSpectrum
GC-MSalpha-D-Galactose, non-derivatized, GC-MS Spectrumsplash10-0fr2-0920000000-d0bbaf502997c43971baSpectrum
GC-MSalpha-D-Galactose, non-derivatized, GC-MS Spectrumsplash10-0fr2-1920000000-f47f0b66263744db15baSpectrum
GC-MSalpha-D-Galactose, non-derivatized, GC-MS Spectrumsplash10-066s-0941000000-8f1b68655e0a5ed179e3Spectrum
GC-MSalpha-D-Galactose, non-derivatized, GC-MS Spectrumsplash10-0ldj-0941000000-84c771fab416aa0a40d8Spectrum
GC-MSalpha-D-Galactose, non-derivatized, GC-MS Spectrumsplash10-0ktb-0931000000-6f37a774d1ab64585c8dSpectrum
GC-MSalpha-D-Galactose, non-derivatized, GC-MS Spectrumsplash10-066s-0931000000-9945093085ef7b0de618Spectrum
GC-MSalpha-D-Galactose, non-derivatized, GC-MS Spectrumsplash10-0ldj-0931000000-1ed532d5d2897be775dfSpectrum
GC-MSalpha-D-Galactose, non-derivatized, GC-MS Spectrumsplash10-00di-9731000000-af5bd67ad0bbb2997839Spectrum
GC-MSalpha-D-Galactose, non-derivatized, GC-MS Spectrumsplash10-00di-9621000000-9dad5bd1760a891ace2aSpectrum
GC-MSalpha-D-Galactose, non-derivatized, GC-MS Spectrumsplash10-0fr2-0920000000-d0bbaf502997c43971baSpectrum
GC-MSalpha-D-Galactose, non-derivatized, GC-MS Spectrumsplash10-0fr2-1920000000-f47f0b66263744db15baSpectrum
Predicted GC-MSalpha-D-Galactose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0np0-9700000000-e8d638dc817e46b97d7bSpectrum
Predicted GC-MSalpha-D-Galactose, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-6122690000-eaf6f7adf34ccd0c667bSpectrum
Predicted GC-MSalpha-D-Galactose, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSalpha-D-Galactose, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSalpha-D-Galactose, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSalpha-D-Galactose, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSalpha-D-Galactose, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0f6t-0900000000-70d3989fddd34b894c772012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00ri-9700000000-d454170b4e3ed18ed2d92012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-007a-9300000000-81f5f12f84924a34e2c02012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, negativesplash10-059i-9100000000-33aacf4c62b17cfa394e2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, negativesplash10-0a4i-9000000000-79ea696263aaad1687012020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, negativesplash10-0a4i-9000000000-480461c1cdd9d138dce22020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-059i-9100000000-33aacf4c62b17cfa394e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-79ea696263aaad1687012021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-480461c1cdd9d138dce22021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0900000000-b0bc47623e7b2ca31c022016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ea-3900000000-648e1637af29cf2a35182016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9200000000-9e6f46a1cbf52d6e347a2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2900000000-a4ec4f0b1e29e360a9522016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-6900000000-7b3ea9c64ecc8d4ac8672016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9100000000-ec2bf4918640a0a363982016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2900000000-2448926b508622464fe72021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-8900000000-4c073cb93b78120113e62021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-ece70093ab5d3c331ac42021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01qa-0900000000-04ceb34d441ff6a757632021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-9400000000-a8f1ceab155611f949c12021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ow-9000000000-358f68fc2b7a72c275462021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 400 MHz, H2O, experimental)Spectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC00984
Pubchem Compound ID439357
Pubchem Substance IDNot Available
ChEBI ID28061
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDGZN85-U:HJZ10-F
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDGalactose
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference