Milk Composition Database: Showing metabocard for Galactose 1-phosphate (BMDB0000645)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:34:12 UTC

Update Date

2020-06-04 20:29:23 UTC

MCDB ID

BMDB0000645

Secondary Accession Numbers

BMDB00645

Metabolite Identification

Common Name

Galactose 1-phosphate

Description

Galactose 1-phosphate, also known as delta-glucose 1-phosphate or cori ester, belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. Galactose 1-phosphate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Galactose 1-phosphate exists in all living species, ranging from bacteria to humans. Galactose 1-phosphate participates in a number of enzymatic reactions, within cattle. In particular, Uridine diphosphate glucose and galactose 1-phosphate can be biosynthesized from uridine diphosphategalactose and glucose 1-phosphate through its interaction with the enzyme galactose-1-phosphate uridylyltransferase. Furthermore, Galactose 1-phosphate can be biosynthesized from D-galactose through the action of the enzyme galactokinase. Finally, Uridine diphosphate glucose and galactose 1-phosphate can be biosynthesized from uridine diphosphategalactose and glucose 1-phosphate; which is mediated by the enzyme galactose-1-phosphate uridylyltransferase. In cattle, galactose 1-phosphate is involved in a couple of metabolic pathways, which include the nucleotide sugars metabolism pathway and lactose synthesis pathway. Galactose 1-phosphate is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-O-Phosphono-alpha-D-galactopyranose	ChEBI
alpha-D-Gal-1-p	ChEBI
alpha-D-Galactopyranose 1-phosphate	ChEBI
alpha-D-Galactopyranose, 1-(dihydrogen phosphate)	ChEBI
alpha-D-Galactopyranosyl phosphate	ChEBI
alpha-D-Galactosyl phosphate	ChEBI
Galactose-1-phosphate	ChEBI
1-O-Phosphono-a-D-galactopyranose	Generator
1-O-Phosphono-α-D-galactopyranose	Generator
a-D-Gal-1-p	Generator
Α-D-gal-1-p	Generator
a-D-Galactopyranose 1-phosphate	Generator
a-D-Galactopyranose 1-phosphoric acid	Generator
alpha-D-Galactopyranose 1-phosphoric acid	Generator
Α-D-galactopyranose 1-phosphate	Generator
Α-D-galactopyranose 1-phosphoric acid	Generator
a-D-Galactopyranose, 1-(dihydrogen phosphate)	Generator
a-D-Galactopyranose, 1-(dihydrogen phosphoric acid)	Generator
alpha-D-Galactopyranose, 1-(dihydrogen phosphoric acid)	Generator
Α-D-galactopyranose, 1-(dihydrogen phosphate)	Generator
Α-D-galactopyranose, 1-(dihydrogen phosphoric acid)	Generator
a-D-Galactopyranosyl phosphate	Generator
a-D-Galactopyranosyl phosphoric acid	Generator
alpha-D-Galactopyranosyl phosphoric acid	Generator
Α-D-galactopyranosyl phosphate	Generator
Α-D-galactopyranosyl phosphoric acid	Generator
a-D-Galactosyl phosphate	Generator
a-D-Galactosyl phosphoric acid	Generator
alpha-D-Galactosyl phosphoric acid	Generator
Α-D-galactosyl phosphate	Generator
Α-D-galactosyl phosphoric acid	Generator
Galactose-1-phosphoric acid	Generator
Galactose 1-phosphoric acid	Generator
a-D-Galactose-1-phosphate	HMDB
a-D-Galactose-1-phosphoric acid	HMDB
alpha-D-Galactose-1-phosphoric acid	HMDB
Α-D-galactose-1-phosphate	HMDB
Α-D-galactose-1-phosphoric acid	HMDB
Galactose-1-phosphate, (beta-L-gal)-isomer	HMDB
Galactose-1-phosphate, 14C-labeled	HMDB
Galactose-1-phosphate, disilver (+1) salt, (D-gal)-isomer	HMDB
Galactose-1-phosphate, sodium salt	HMDB
Galactose-1-phosphate, (beta-D-gal)-isomer	HMDB
1-(Dihydrogen phosphate) galactitol	HMDB
1-Phosphate a-D-galactopyranose	HMDB
a-D-1-(Dihydrogen phosphate) galactopyranose	HMDB
a-D-Galactose 1-phosphate	HMDB
alpha-D-1-(Dihydrogen phosphate) galactopyranose	HMDB
alpha-D-Galactose 1-phosphate	HMDB
D-Galactose 1-phosphate	HMDB
Galactopyranose 1-phosphate	HMDB
D-Galactopyranose 1-phosphate	HMDB
D-Galactopyranose 1-phosphoric acid	HMDB
D-Galactose 1-phosphoric acid	HMDB

Chemical Formula

C₆H₁₃O₉P

Average Molecular Weight

260.1358

Monoisotopic Molecular Weight

260.029718526

IUPAC Name

{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid

Traditional Name

galactose 1 phosphate

CAS Registry Number

2255-14-3

SMILES

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

InChI Identifier

InChI=1S/C6H13O9P/c7-1-2-3(8)4(9)5(10)6(14-2)15-16(11,12)13/h2-10H,1H2,(H2,11,12,13)/t2-,3+,4+,5-,6-/m1/s1

InChI Key

HXXFSFRBOHSIMQ-FPRJBGLDSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Monosaccharide phosphates

Alternative Parents

Substituents

Hexose monosaccharide
Monosaccharide phosphate
Monoalkyl phosphate
Organic phosphoric acid derivative
Oxane
Alkyl phosphate
Phosphoric acid ester
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Alcohol
Hydrocarbon derivative
Primary alcohol
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

D-galactopyranose 1-phosphate (CHEBI:17973 )
alpha-D-hexose 1-phosphate (CHEBI:17973 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-2	ALOGPS
logP	-3.1	ChemAxon
logS	-0.91	ALOGPS
pKa (Strongest Acidic)	1.16	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	156.91 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	46.8 m³·mol⁻¹	ChemAxon
Polarizability	20.62 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9110000000-ee60e23a7f8053dae6d3	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-0fsi-5901370000-80b5e0114d382bd45e3f	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_5) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-004i-9030000000-7fff706c8ccfa4e8ee82	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-004i-9030000000-7ea4c16f3c1f90045b95	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-0002-9000000000-d23bc07bd7bdf7ddce46	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 18V, positive	splash10-03dl-1970000000-880e9f60970f0816b8c4	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 18V, positive	splash10-001i-0920000000-2cbd9f1121176bb271ef	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-0002-0090000000-f7a9704c507f87576963	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-0002-0190000000-190752fd0e6fc6923351	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-0f72-0490000000-14a970b0e103aee3ac86	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, positive	splash10-000i-0950000000-791dd70d946defe0237d	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-001r-0890000000-7333cc4fec9c480da18b	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, positive	splash10-000i-0920000000-b0116f36e8c1774e674f	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 18V, positive	splash10-000i-0900000000-ce07a8268e9be0a752ea	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 18V, positive	splash10-004l-9000000000-771382b82d73a025b900	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 18V, positive	splash10-03di-0900000000-75b95578eec10c7fb1a0	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 18V, positive	splash10-00di-0900000000-efd4d199381342fcfd6e	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 18V, positive	splash10-014i-0900000000-59a34fd931d5d3eb02ad	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 18V, positive	splash10-0f6t-0290000000-e0994816c9da10e9884b	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 18V, positive	splash10-004i-0190000000-0871936f57509fe1ab16	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 7V, positive	splash10-00di-0049000000-b5229bec94bbe9e0fe04	2020-07-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9240000000-4057005941a73b47e92b	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9240000000-2b520b8d7520453613e5	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9100000000-adafd3ed58bf5371e4a1	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a6s-9480000000-6d21f499da6e13bbe38d	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9110000000-68aeffe1ebca2d4d4362	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-dfc211275bafe42581ae	2015-09-15	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected but not Quantified	Not Applicable	PMID: 23497994	details
Detected but not Quantified	Not Applicable	PMID: 23738862	details
Detected but not Quantified	Not Applicable	PMID: 25087032	details
Detected and Quantified	561 - 2070 uM	PMID: 22098372	details

External Links

HMDB ID

HMDB0000645

DrugBank ID

DB02317

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001159

KNApSAcK ID

C00007391

Chemspider ID

Not Available

KEGG Compound ID

C00446

BioCyc ID

GALACTOSE-1P

BiGG ID

Not Available

Wikipedia Link

Galactose_1-phosphate

METLIN ID

Not Available

PubChem Compound

123912

PDB ID

Not Available

ChEBI ID

17973

References

Synthesis Reference

Chen Jie; Yager Claire; Reynolds Robert; Palmieri Michael; Segal Stanton Erythrocyte galactose 1-phosphate quantified by isotope-dilution gas chromatography-mass spectrometry. Clinical chemistry (2002), 48(4), 604-12.

Material Safety Data Sheet (MSDS)

Not Available

General References

Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9. [PubMed:22098372 ]
Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30. [PubMed:25087032 ]
Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15. [PubMed:23497994 ]
Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5. [PubMed:23738862 ]
Antunes-Fernandes EC, van Gastelen S, Dijkstra J, Hettinga KA, Vervoort J: Milk metabolome relates enteric methane emission to milk synthesis and energy metabolism pathways. J Dairy Sci. 2016 Aug;99(8):6251-6262. doi: 10.3168/jds.2015-10248. Epub 2016 May 26. [PubMed:27236769 ]

Showing metabocard for Galactose 1-phosphate (BMDB0000645)

Structure for BMDB0000645 (Galactose 1-phosphate)