Record Information |
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Version | 2.0 |
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Created at | 2005-11-16 15:48:42 UTC |
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Updated at | 2024-09-17 15:44:47 UTC |
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NP-MRD ID | NP0001292 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Galactose 1-phosphate |
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Description | Galactose 1-phosphate, also known as D-Galactose-1-phosphate or alpha-D-gal-1-P, belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphate group linked to the carbohydrate unit. Galactose-1-phosphate is an intermediate in the interconversion of glucose and uridine diphosphate galactose. Galactose 1-phosphate exists in all living species, ranging from bacteria to plants to humans. Within humans, galactose 1-phosphate participates in a number of enzymatic reactions. In particular, 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 (GALT). In addition, galactose 1-phosphate can be biosynthesized from D-galactose through the action of the enzyme galactokinase. The improper metabolism of galactose-1-phosphate is a characteristic of a condition known as galactosemia (PMID: 7671964 ). Type I galactosemia is a genetic disorder that is caused by the impairment of galactose-1-phosphate uridylyltransferase (EC 2.7.7.12). Evidence suggests that misfolding of the galactose 1-phosphate uridylyltransferase enzyme is the underlying cause of type I galactosemia (PMID: 23583749 ). Outside of the human body, galactose 1-phosphate has been detected, but not quantified in, several different foods, such as gooseberries, anises, turmerics, caraway, and cumins. |
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Structure | OC[C@H]1O[C@H](OP(O)(O)=O)[C@H](O)[C@@H](O)[C@H]1O 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 |
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Synonyms | Value | Source |
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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 |
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Chemical Formula | C6H13O9P |
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Average Mass | 260.1358 Da |
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Monoisotopic Mass | 260.02972 Da |
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IUPAC Name | {[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid |
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Traditional Name | galactose 1 phosphate |
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CAS Registry Number | 2255-14-3 |
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SMILES | OC[C@H]1O[C@H](OP(O)(O)=O)[C@H](O)[C@@H](O)[C@H]1O |
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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 |
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InChI Key | HXXFSFRBOHSIMQ-FPRJBGLDSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Species Where Detected | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbohydrates and carbohydrate conjugates |
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Direct Parent | Monosaccharide phosphates |
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Alternative Parents | |
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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
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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General References | - Ning C, Reynolds R, Chen J, Yager C, Berry GT, McNamara PD, Leslie N, Segal S: Galactose metabolism by the mouse with galactose-1-phosphate uridyltransferase deficiency. Pediatr Res. 2000 Aug;48(2):211-7. [PubMed:10926297 ]
- Berry GT, Palmieri M, Gross KC, Acosta PB, Henstenburg JA, Mazur A, Reynolds R, Segal S: The effect of dietary fruits and vegetables on urinary galactitol excretion in galactose-1-phosphate uridyltransferase deficiency. J Inherit Metab Dis. 1993;16(1):91-100. [PubMed:8487507 ]
- Ono H, Mawatari H, Mizoguchi N, Eguchi T, Sakura N, Hamakawa M: Transient galactosemia detected by neonatal mass screening. Pediatr Int. 1999 Jun;41(3):281-4. [PubMed:10365579 ]
- Endres W: Inherited metabolic diseases affecting the carrier. J Inherit Metab Dis. 1997 Mar;20(1):9-20. [PubMed:9061562 ]
- Guerrero NV, Singh RH, Manatunga A, Berry GT, Steiner RD, Elsas LJ 2nd: Risk factors for premature ovarian failure in females with galactosemia. J Pediatr. 2000 Dec;137(6):833-41. [PubMed:11113841 ]
- Schaub J, Remberger K, Endres W, Bremer HJ: Galactosemia with endogenous production of galactose-1-phosphate and with cystic fibrosis-like appearance at autopsy. Helv Paediatr Acta. 1976 Jun;31(1):67-76. [PubMed:939702 ]
- Bozkowa K, Zbieg-Sendecka E, Grodzka Z, Cabalska B: [Clinical and biochemical diagnosis of galactosemia among our cases]. Probl Med Wieku Rozwoj. 1979;8:63-9. [PubMed:263527 ]
- Dahlqvist A: A fluorometric method for the assay of galactose-1-phosphate in red blood cells. J Lab Clin Med. 1971 Dec;78(6):931-8. [PubMed:5131857 ]
- Bozkowa K, Duchnowska A, Chojnacki T, Mankowski T: [New radioisotope method of quantitative determination of galactose-1-phosphate in red blood cells in galactosemia]. Pol Tyg Lek. 1975 Dec 22;30(51):2123-6. [PubMed:1197109 ]
- Wharton CH, Berry HK, Bofinger MK: Galactose-1-phosphate accumulation by a Duarte-transferase deficiency double heterozygote. Clin Genet. 1978 Feb;13(2):171-5. [PubMed:627109 ]
- Gitzelmann R, Steinmann B, Mitchell B, Haigis E: Uridine diphosphate galactose 4'-epimerase deficiency. IV. Report of eight cases in three families. Helv Paediatr Acta. 1977 Apr;31(6):441-52. [PubMed:404274 ]
- Barbouth D, Slepak T, Klapper H, Lai K, Elsas LJ: Prevention of a molecular misdiagnosis in galactosemia. Genet Med. 2006 Mar;8(3):178-82. [PubMed:16540753 ]
- Mankowski T, Radomyska B, Zbieg-Sendecka E: Preliminary results of UDP galactose pyrophosphorylase in the erythrocytes of healthy persons and in patients with galactosaemia. Mater Med Pol. 1990 Jul-Sep;22(3):191-3. [PubMed:2132425 ]
- Moller HE, Ullrich K, Vermathen P, Schuierer G, Koch HG: In vivo study of brain metabolism in galactosemia by 1H and 31P magnetic resonance spectroscopy. Eur J Pediatr. 1995;154(7 Suppl 2):S8-13. [PubMed:7671972 ]
- Barth CA, Kopra N: Oral intake of glucose plus galactose and erythrocyte galactose-1-phosphate. A nutritional evaluation of hydrolyzed lactose. Z Ernahrungswiss. 1986 Sep;25(3):171-9. [PubMed:3776241 ]
- Pesce MA, Bodourian SH: Clinical significance of plasma galactose and erythrocyte galactose-1-phosphate measurements in transferase-deficient galactosemia and in individuals with below-normal transferase activity. Clin Chem. 1982 Feb;28(2):301-5. [PubMed:6276048 ]
- Schadewaldt P, Kamalanathan L, Hammen HW, Wendel U: Age dependence of endogenous galactose formation in Q188R homozygous galactosemic patients. Mol Genet Metab. 2004 Jan;81(1):31-44. [PubMed:14728989 ]
- Pesce MA, Bodourian SH, Nicholson JF: A new microfluorometric method for the measurement of galactose-1-phosphate in erythrocytes. Clin Chim Acta. 1982 Feb 5;118(2-3):177-89. [PubMed:7055979 ]
- Gitzelmann R: Galactose-1-phosphate in the pathophysiology of galactosemia. Eur J Pediatr. 1995;154(7 Suppl 2):S45-9. doi: 10.1007/BF02143803. [PubMed:7671964 ]
- McCorvie TJ, Gleason TJ, Fridovich-Keil JL, Timson DJ: Misfolding of galactose 1-phosphate uridylyltransferase can result in type I galactosemia. Biochim Biophys Acta. 2013 Aug;1832(8):1279-93. doi: 10.1016/j.bbadis.2013.04.004. Epub 2013 Apr 11. [PubMed:23583749 ]
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