Showing Compound alpha-D-Galactose (FDB021787)

Record Information

Version

1.0

Creation date

2011-04-07 23:15:07 UTC

Update date

2025-11-19 02:39:38 UTC

Primary ID

FDB021787

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

alpha-D-Galactose

Description

D-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‚Äôs disease in rats (PMID: 29501615).

CAS Number

3646-73-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
ALPHA D-GALACTOSE	ChEBI
alpha-D-Gal	ChEBI
Gal-alpha	ChEBI
alpha-D-Galactose	Kegg
a D-GALACTOSE	Generator
Α D-galactose	Generator
a-D-Gal	Generator
Α-D-gal	Generator
Gal-a	Generator
Gal-α	Generator
a-D-Galactose	Generator
Α-D-galactose	Generator
(+)-Galactose	HMDB
5Abp	HMDB
8Abp	HMDB
alpha-D-Galactopyranose	HMDB
D-(+)-Galactose	HMDB
D-Hexose	HMDB
GAL	HMDB
Galactose	HMDB
Galactose (NF)	HMDB
GLA	HMDB
GLC	HMDB
Hexose	HMDB
SHU 508 a	MeSH, HMDB
SH-TA-508	MeSH, HMDB
SHU 508	MeSH, HMDB
Levovist	MeSH, HMDB
SHU-508	MeSH, HMDB

Predicted Properties

Property	Value	Source
Water Solubility	782 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-2.9	ChemAxon
logS	0.64	ALOGPS
pKa (Strongest Acidic)	11.3	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	110.38 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	35.92 m³·mol⁻¹	ChemAxon
Polarizability	16.13 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C6H12O6

IUPAC name

(2S,3R,4S,5R,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol

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 Key

WQZGKKKJIJFFOK-PHYPRBDBSA-N

Isomeric SMILES

OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O

Average Molecular Weight

180.1559

Monoisotopic Molecular Weight

180.063388116

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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Hexoses

Alternative Parents

Substituents

Hexose monosaccharide
Oxane
Secondary alcohol
Hemiacetal
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

D-galactopyranose (CHEBI:28061 )

Ontology

Ingestion

Source:

Biological:

Plant:

Animal

Biological location:

Organ and components:

Biofluid and excreta:

Cell and elements:

Extracellular

Subcellular:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	alpha-D-Galactose, non-derivatized, GC-MS Spectrum	splash10-066s-0941000000-8f1b68655e0a5ed179e3	Spectrum
GC-MS	alpha-D-Galactose, non-derivatized, GC-MS Spectrum	splash10-0ldj-0941000000-84c771fab416aa0a40d8	Spectrum
GC-MS	alpha-D-Galactose, non-derivatized, GC-MS Spectrum	splash10-0ktb-0931000000-6f37a774d1ab64585c8d	Spectrum
GC-MS	alpha-D-Galactose, non-derivatized, GC-MS Spectrum	splash10-066s-0931000000-9945093085ef7b0de618	Spectrum
GC-MS	alpha-D-Galactose, non-derivatized, GC-MS Spectrum	splash10-0ldj-0931000000-1ed532d5d2897be775df	Spectrum
GC-MS	alpha-D-Galactose, non-derivatized, GC-MS Spectrum	splash10-00di-9731000000-af5bd67ad0bbb2997839	Spectrum
GC-MS	alpha-D-Galactose, non-derivatized, GC-MS Spectrum	splash10-00di-9621000000-9dad5bd1760a891ace2a	Spectrum
GC-MS	alpha-D-Galactose, non-derivatized, GC-MS Spectrum	splash10-0fr2-0920000000-d0bbaf502997c43971ba	Spectrum
GC-MS	alpha-D-Galactose, non-derivatized, GC-MS Spectrum	splash10-0fr2-1920000000-f47f0b66263744db15ba	Spectrum
GC-MS	alpha-D-Galactose, non-derivatized, GC-MS Spectrum	splash10-066s-0941000000-8f1b68655e0a5ed179e3	Spectrum
GC-MS	alpha-D-Galactose, non-derivatized, GC-MS Spectrum	splash10-0ldj-0941000000-84c771fab416aa0a40d8	Spectrum
GC-MS	alpha-D-Galactose, non-derivatized, GC-MS Spectrum	splash10-0ktb-0931000000-6f37a774d1ab64585c8d	Spectrum
GC-MS	alpha-D-Galactose, non-derivatized, GC-MS Spectrum	splash10-066s-0931000000-9945093085ef7b0de618	Spectrum
GC-MS	alpha-D-Galactose, non-derivatized, GC-MS Spectrum	splash10-0ldj-0931000000-1ed532d5d2897be775df	Spectrum
GC-MS	alpha-D-Galactose, non-derivatized, GC-MS Spectrum	splash10-00di-9731000000-af5bd67ad0bbb2997839	Spectrum
GC-MS	alpha-D-Galactose, non-derivatized, GC-MS Spectrum	splash10-00di-9621000000-9dad5bd1760a891ace2a	Spectrum
GC-MS	alpha-D-Galactose, non-derivatized, GC-MS Spectrum	splash10-0fr2-0920000000-d0bbaf502997c43971ba	Spectrum
GC-MS	alpha-D-Galactose, non-derivatized, GC-MS Spectrum	splash10-0fr2-1920000000-f47f0b66263744db15ba	Spectrum
Predicted GC-MS	alpha-D-Galactose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0np0-9700000000-e8d638dc817e46b97d7b	Spectrum
Predicted GC-MS	alpha-D-Galactose, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004i-6122690000-eaf6f7adf34ccd0c667b	Spectrum
Predicted GC-MS	alpha-D-Galactose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	alpha-D-Galactose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	alpha-D-Galactose, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	alpha-D-Galactose, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	alpha-D-Galactose, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0f6t-0900000000-70d3989fddd34b894c77	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00ri-9700000000-d454170b4e3ed18ed2d9	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-007a-9300000000-81f5f12f84924a34e2c0	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 10V, negative	splash10-059i-9100000000-33aacf4c62b17cfa394e	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 20V, negative	splash10-0a4i-9000000000-79ea696263aaad168701	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 40V, negative	splash10-0a4i-9000000000-480461c1cdd9d138dce2	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-059i-9100000000-33aacf4c62b17cfa394e	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-79ea696263aaad168701	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-480461c1cdd9d138dce2	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01q9-0900000000-b0bc47623e7b2ca31c02	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03ea-3900000000-648e1637af29cf2a3518	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0007-9200000000-9e6f46a1cbf52d6e347a	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-2900000000-a4ec4f0b1e29e360a952	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01t9-6900000000-7b3ea9c64ecc8d4ac867	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9100000000-ec2bf4918640a0a36398	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-2900000000-2448926b508622464fe7	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056r-8900000000-4c073cb93b78120113e6	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-ece70093ab5d3c331ac4	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01qa-0900000000-04ceb34d441ff6a75763	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dl-9400000000-a8f1ceab155611f949c1	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ow-9000000000-358f68fc2b7a72c27546	2021-09-25	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C 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