Showing Compound Card for Galactose (CDB000101)

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Record Information
Version1.0
Created at2020-03-18 23:24:48 UTC
Updated at2020-11-18 16:34:46 UTC
CannabisDB IDCDB000101
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameGalactose
DescriptionGalactose, also known as galactopyranose, 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 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. Galactose is a monosaccharid found in cannabis plants (PMID: 6991645 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2R,3S,4S,5R)-2,3,4,5,6-PentahydroxyhexanalChEBI
GalactopyranoseMeSH
D GalactoseMeSH
D-GalactoseMeSH
GalactopyranosideMeSH
Chemical FormulaC6H12O6
Average Molecular Weight180.16
Monoisotopic Molecular Weight180.0634
IUPAC Name(2R,3S,4S,5R)-2,3,4,5,6-pentahydroxyhexanal
Traditional Namealdehydo-D-galactose
CAS Registry Number59-23-4
SMILES
OC[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)C=O
InChI Identifier
InChI=1S/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h1,3-6,8-12H,2H2/t3-,4+,5+,6-/m0/s1
InChI KeyGZCGUPFRVQAUEE-KCDKBNATSA-N
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 Parents
Substituents
  • Hexose monosaccharide
  • Medium-chain aldehyde
  • Beta-hydroxy aldehyde
  • Alpha-hydroxyaldehyde
  • Secondary alcohol
  • Polyol
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Carbonyl group
  • Aldehyde
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point168–170 °CWikipedia
Boiling PointNot AvailableNot Available
Water Solubility650 g/LWikipedia
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.4ALOGPS
logP-3.6ChemAxon
logS0.16ALOGPS
pKa (Strongest Acidic)12.26ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area118.22 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity37.35 m³·mol⁻¹ChemAxon
Polarizability16.13 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSGalactose, 1 MEOX; 5 TMS, GC-MS Spectrumsplash10-066r-1963000000-20f964d19542821e3092Spectrum
GC-MSGalactose, 1 MEOX; 5 TMS, GC-MS Spectrumsplash10-066r-1963000000-9b4d2187359e4427fc63Spectrum
Predicted GC-MSGalactose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-06xx-9700000000-ceca0a9339feb50332b7Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-014i-0190000000-5f9700d2fb9d3803b3152020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-014i-1290000000-4a2f118de83c3fd895762020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 12V, negativesplash10-004i-2900000000-41882e175ed558fdcbde2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 12V, positivesplash10-0udi-0900000000-869a46d7f04b5bc961502020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 4V, positivesplash10-01p7-9400000000-4b357e4a105f58144fc22020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 5V, positivesplash10-01vy-9300000000-da35c11fce45fe7a740d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 7V, positivesplash10-01w3-9100000000-1dff5e1a4031702a876e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-03du-9000000000-cd0856e2038752b33c5c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-03k9-9000000000-d2d96a2104f7536b62f52020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 17V, positivesplash10-03dj-9000000000-ba0af57d2c1268059cd92020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-03k9-9000000000-34675ae85736565c23c92020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 1V, positivesplash10-03di-0900000000-4f0478f40b72c7d11a3f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 2V, positivesplash10-03di-0900000000-acdab0035233d01ec7612020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 3V, positivesplash10-03di-0900000000-3c5697f764858966d8b32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 4V, positivesplash10-03di-1900000000-e9c3ce484a8b2dd253502020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 5V, positivesplash10-03dm-3900000000-48616d3ba50de6aeef682020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 6V, positivesplash10-01oy-7900000000-010b62191ab8df7359822020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 7V, positivesplash10-0007-9600000000-1c7767154c8d716c27942020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 8V, positivesplash10-0006-9300000000-609ae946204045022a832020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 9V, positivesplash10-000f-9200000000-a4866a9de898c3169b602020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 10V, positivesplash10-000f-9100000000-225070d62a4fceacc3712020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 11V, positivesplash10-01vx-9100000000-1bff987ed1fcd84b3d072020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 12V, positivesplash10-01vx-9000000000-f524900cff88cdc7ced62020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 13V, positivesplash10-03l3-9000000000-8f119ef7525c9894bcc82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 14V, positivesplash10-03kl-9000000000-faa1027b0b4385eff7b72020-07-22View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDDB11735
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00019681
Chemspider IDNot Available
KEGG Compound IDC01582
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGalactose
METLIN IDNot Available
PubChem Compound3037556
PDB IDNot Available
ChEBI ID17118
References
General References
  1. Lai K, Klapa MI: Alternative pathways of galactose assimilation: could inverse metabolic engineering provide an alternative to galactosemic patients? Metab Eng. 2004 Jul;6(3):239-44. doi: 10.1016/j.ymben.2004.01.001. [PubMed:15256214 ]
  2. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]