Record Information
Version1.0
Created at2020-04-17 19:22:52 UTC
Updated at2020-11-18 16:39:35 UTC
CannabisDB IDCDB005235
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameD-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 ( Ref:DOI ). It is also found in fig leaves, sesame, carob bean, caraway seeds and beet, cocoa, chive, potato, and cannabis plants (PMID: 6991645 ). 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 ). D-Galactose is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
Synonyms
ValueSource
ALPHA D-GALACTOSEChEBI
alpha-D-GalChEBI
Gal-alphaChEBI
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 Molecular Weight180.16
Monoisotopic Molecular Weight180.0634
IUPAC Name(2S,3R,4S,5R,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
Traditional Namegalactose
CAS Registry Number3646-73-9
SMILES
OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O
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
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
  • 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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point170 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility683 mg/mLNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSD-Galactose, non-derivatized, GC-MS Spectrumsplash10-066s-0941000000-8f1b68655e0a5ed179e3Spectrum
GC-MSD-Galactose, non-derivatized, GC-MS Spectrumsplash10-0ldj-0941000000-84c771fab416aa0a40d8Spectrum
GC-MSD-Galactose, non-derivatized, GC-MS Spectrumsplash10-0ktb-0931000000-6f37a774d1ab64585c8dSpectrum
GC-MSD-Galactose, non-derivatized, GC-MS Spectrumsplash10-066s-0931000000-9945093085ef7b0de618Spectrum
GC-MSD-Galactose, non-derivatized, GC-MS Spectrumsplash10-0ldj-0931000000-1ed532d5d2897be775dfSpectrum
GC-MSD-Galactose, non-derivatized, GC-MS Spectrumsplash10-00di-9731000000-af5bd67ad0bbb2997839Spectrum
GC-MSD-Galactose, non-derivatized, GC-MS Spectrumsplash10-00di-9621000000-9dad5bd1760a891ace2aSpectrum
GC-MSD-Galactose, non-derivatized, GC-MS Spectrumsplash10-0fr2-0920000000-d0bbaf502997c43971baSpectrum
GC-MSD-Galactose, non-derivatized, GC-MS Spectrumsplash10-0fr2-1920000000-f47f0b66263744db15baSpectrum
GC-MSD-Galactose, non-derivatized, GC-MS Spectrumsplash10-066s-0941000000-8f1b68655e0a5ed179e3Spectrum
GC-MSD-Galactose, non-derivatized, GC-MS Spectrumsplash10-0ldj-0941000000-84c771fab416aa0a40d8Spectrum
GC-MSD-Galactose, non-derivatized, GC-MS Spectrumsplash10-0ktb-0931000000-6f37a774d1ab64585c8dSpectrum
GC-MSD-Galactose, non-derivatized, GC-MS Spectrumsplash10-066s-0931000000-9945093085ef7b0de618Spectrum
GC-MSD-Galactose, non-derivatized, GC-MS Spectrumsplash10-0ldj-0931000000-1ed532d5d2897be775dfSpectrum
GC-MSD-Galactose, non-derivatized, GC-MS Spectrumsplash10-00di-9731000000-af5bd67ad0bbb2997839Spectrum
GC-MSD-Galactose, non-derivatized, GC-MS Spectrumsplash10-00di-9621000000-9dad5bd1760a891ace2aSpectrum
GC-MSD-Galactose, non-derivatized, GC-MS Spectrumsplash10-0fr2-0920000000-d0bbaf502997c43971baSpectrum
GC-MSD-Galactose, non-derivatized, GC-MS Spectrumsplash10-0fr2-1920000000-f47f0b66263744db15baSpectrum
Predicted GC-MSD-Galactose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0np0-9700000000-e8d638dc817e46b97d7bSpectrum
Predicted GC-MSD-Galactose, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-6122690000-eaf6f7adf34ccd0c667bSpectrum
Predicted GC-MSD-Galactose, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-Galactose, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-Galactose, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-Galactose, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-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
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Aldose reductaseAKR1B17q35P15121 details
Hexokinase-3HK35q35.2P52790 details
Hexokinase-2HK22p13P52789 details
Hexokinase-1HK110q22P19367 details
GalactocerebrosidaseGALC14q31P54803 details
Lactase-phlorizin hydrolaseLCT2q21P09848 details
Alpha-galactosidase AGLAP06280 details
Beta-galactosidaseGLB1P16278 details
N-acetylgalactosamine kinaseGALK215q21.1-q21.2Q01415 details
GalactokinaseGALK117q24P51570 details
N-acetylgalactosamine-6-sulfataseGALNSP34059 details
Maltase-glucoamylase, intestinalMGAMO43451 details
Neutral alpha-glucosidase CGANCQ8TET4 details
Putative hexokinase HKDC1HKDC110q22.1Q2TB90 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
N-acetylgalactosamine-6-sulfataseGALNSP34059 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Alpha-galactosidase AGLAP06280 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0000143
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021787
KNApSAcK IDC00001119
Chemspider IDNot Available
KEGG Compound IDC00984
BioCyc IDALPHA-D-GALACTOSE
BiGG IDNot Available
Wikipedia LinkGalactose
METLIN IDNot Available
PubChem Compound439357
PDB IDNot Available
ChEBI ID28061
References
General References
  1. 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 ]
  2. Tyfield L, Reichardt J, Fridovich-Keil J, Croke DT, Elsas LJ 2nd, Strobl W, Kozak L, Coskun T, Novelli G, Okano Y, Zekanowski C, Shin Y, Boleda MD: Classical galactosemia and mutations at the galactose-1-phosphate uridyl transferase (GALT) gene. Hum Mutat. 1999;13(6):417-30. doi: 10.1002/(SICI)1098-1004(1999)13:6<417::AID-HUMU1>3.0.CO;2-0. [PubMed:10408771 ]
  3. 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 ]
  4. Blumenreich GA: The standard of care. AANA J. 1992 Dec;60(6):529-31. [PubMed:1292318 ]
  5. Yamamoto F: Review: ABO blood group system--ABH oligosaccharide antigens, anti-A and anti-B, A and B glycosyltransferases, and ABO genes. Immunohematology. 2004;20(1):3-22. [PubMed:15373665 ]
  6. Coelho AI, Berry GT, Rubio-Gozalbo ME: Galactose metabolism and health. Curr Opin Clin Nutr Metab Care. 2015 Jul;18(4):422-7. doi: 10.1097/MCO.0000000000000189. [PubMed:26001656 ]
  7. Demirbas D, Brucker WJ, Berry GT: Inborn Errors of Metabolism with Hepatopathy: Metabolism Defects of Galactose, Fructose, and Tyrosine. Pediatr Clin North Am. 2018 Apr;65(2):337-352. doi: 10.1016/j.pcl.2017.11.008. [PubMed:29502917 ]
  8. Van Meel FC, Steenbakkers PG, Oomen JC: Human and chimpanzee monoclonal antibodies. J Immunol Methods. 1985 Jun 25;80(2):267-76. doi: 10.1016/0022-1759(85)90027-4. [PubMed:2989374 ]
  9. Knezovic A, Osmanovic Barilar J, Babic A, Bagaric R, Farkas V, Riederer P, Salkovic-Petrisic M: Glucagon-like peptide-1 mediates effects of oral galactose in streptozotocin-induced rat model of sporadic Alzheimer's disease. Neuropharmacology. 2018 Jun;135:48-62. doi: 10.1016/j.neuropharm.2018.02.027. Epub 2018 Feb 28. [PubMed:29501615 ]

Only showing the first 10 proteins. There are 16 proteins in total.

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the NADPH-dependent reduction of a wide variety of carbonyl-containing compounds to their corresponding alcohols with a broad range of catalytic efficiencies.
Gene Name:
AKR1B1
Uniprot ID:
P15121
Molecular weight:
35853.125
General function:
Involved in ATP binding
Specific function:
Not Available
Gene Name:
HK3
Uniprot ID:
P52790
Molecular weight:
99024.56
General function:
Involved in ATP binding
Specific function:
Not Available
Gene Name:
HK2
Uniprot ID:
P52789
Molecular weight:
102379.06
General function:
Involved in ATP binding
Specific function:
Not Available
Gene Name:
HK1
Uniprot ID:
P19367
Molecular weight:
102485.1
General function:
Involved in galactosylceramidase activity
Specific function:
Hydrolyzes the galactose ester bonds of galactosylceramide, galactosylsphingosine, lactosylceramide, and monogalactosyldiglyceride. Enzyme with very low activity responsible for the lysosomal catabolism of galactosylceramide, a major lipid in myelin, kidney and epithelial cells of small intestine and colon.
Gene Name:
GALC
Uniprot ID:
P54803
Molecular weight:
77062.86
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
LPH splits lactose in the small intestine.
Gene Name:
LCT
Uniprot ID:
P09848
Molecular weight:
218584.77
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
GLA
Uniprot ID:
P06280
Molecular weight:
Not Available
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Cleaves beta-linked terminal galactosyl residues from gangliosides, glycoproteins, and glycosaminoglycans. Isoform 2 has no beta-galactosidase catalytic activity, but plays functional roles in the formation of extracellular elastic fibers (elastogenesis) and in the development of connective tissue. Seems to be identical to the elastin-binding protein (EBP), a major component of the non-integrin cell surface receptor expressed on fibroblasts, smooth muscle cells, chondroblasts, leukocytes, and certain cancer cell types. In elastin producing cells, associates with tropoelastin intracellularly and functions as a recycling molecular chaperone which facilitates the secretions of tropoelastin and its assembly into elastic fibers.
Gene Name:
GLB1
Uniprot ID:
P16278
Molecular weight:
Not Available
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
General function:
Involved in galactokinase activity
Specific function:
Major enzyme for galactose metabolism.
Gene Name:
GALK1
Uniprot ID:
P51570
Molecular weight:
42271.805

Only showing the first 10 proteins. There are 16 proteins in total.