| Record Information |
|---|
| Version | 1.0 |
|---|
| Creation Date | 2016-09-30 22:20:38 UTC |
|---|
| Update Date | 2020-06-04 22:55:40 UTC |
|---|
| BMDB ID | BMDB0000186 |
|---|
| Secondary Accession Numbers | |
|---|
| Metabolite Identification |
|---|
| Common Name | Alpha-Lactose |
|---|
| Description | Alpha-Lactose, also known as anhydrous lactose or tablettose, belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. Alpha-Lactose exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Alpha-Lactose exists in all living organisms, ranging from bacteria to humans. Alpha-Lactose participates in a number of enzymatic reactions, within cattle. In particular, Alpha-Lactose can be converted into melibiose and D-galactose through the action of the enzyme Alpha-galactosidase a. In addition, Alpha-Lactose can be converted into D-galactose through the action of the enzyme Beta-galactosidase. In cattle, Alpha-lactose is involved in the metabolic pathway called the galactose metabolism pathway. Alpha-Lactose is a potentially toxic compound. |
|---|
| Structure | |
|---|
| Synonyms | | Value | Source |
|---|
| 1-beta-D-Galactopyranosyl-4-alpha-D-glucopyranose | ChEBI | | 4-O-beta-D-Galactopyranosyl-alpha-D-glucopyranose | ChEBI | | Anhydrous lactose | ChEBI | | beta-D-Galp-(1->4)-alpha-D-GLCP | ChEBI | | Lactose | ChEBI | | Milk sugar | ChEBI | | 1-b-D-Galactopyranosyl-4-a-D-glucopyranose | Generator | | 1-Β-D-galactopyranosyl-4-α-D-glucopyranose | Generator | | 4-O-b-D-Galactopyranosyl-a-D-glucopyranose | Generator | | 4-O-Β-D-galactopyranosyl-α-D-glucopyranose | Generator | | b-D-Galp-(1->4)-a-D-GLCP | Generator | | Β-D-galp-(1->4)-α-D-GLCP | Generator | | a-Lactose | Generator | | Α-lactose | Generator | | (+)-Lactose | HMDB | | 1-beta-delta-Galactopyranosyl-4-alpha-delta-glucopyranose | HMDB | | 4-O-Hexopyranosylhexose | HMDB | | Aletobiose | HMDB | | Dilactose | HMDB | | Fast-flo lactose | HMDB | | Flowlac 100 | HMDB | | Galactinum | HMDB | | GLC-(4-1)Gal | HMDB | | Granulac 140m | HMDB | | Lactin | HMDB | | Lactin (carbohydrate) | HMDB | | Lactobiose | HMDB | | Lactohale 300 | HMDB | | Lactose anhydride | HMDB | | Lactose fast-flo | HMDB | | Osmolactan | HMDB | | Pharmatosa DCL 21 | HMDB | | Pharmatose 21 | HMDB | | Pharmatose 325m | HMDB | | Pharmatose DCL 15 | HMDB | | Prismalac | HMDB | | Respitose ML 003 | HMDB | | Respitose SV 003 | HMDB | | Saccharum lactin | HMDB | | Sachelac | HMDB | | Sorbalac 400 | HMDB | | Sorbolac 400 | HMDB | | Spherolac | HMDB | | Super-tab | HMDB | | Tablettose | HMDB | | Tablettose 70 | HMDB | | Tablettose 80 | HMDB | | Zeparox ep | HMDB | | Lactose, anhydrous | HMDB |
|
|---|
| Chemical Formula | C12H22O11 |
|---|
| Average Molecular Weight | 342.2965 |
|---|
| Monoisotopic Molecular Weight | 342.116211546 |
|---|
| IUPAC Name | (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxane-3,4,5-triol |
|---|
| Traditional Name | α-lactose |
|---|
| CAS Registry Number | 63-42-3 |
|---|
| SMILES | OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O |
|---|
| InChI Identifier | InChI=1S/C12H22O11/c13-1-3-5(15)6(16)9(19)12(22-3)23-10-4(2-14)21-11(20)8(18)7(10)17/h3-20H,1-2H2/t3-,4-,5+,6+,7-,8-,9-,10-,11+,12+/m1/s1 |
|---|
| InChI Key | GUBGYTABKSRVRQ-XLOQQCSPSA-N |
|---|
| Chemical Taxonomy |
|---|
| Description | belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. |
|---|
| Kingdom | Organic compounds |
|---|
| Super Class | Organic oxygen compounds |
|---|
| Class | Organooxygen compounds |
|---|
| Sub Class | Carbohydrates and carbohydrate conjugates |
|---|
| Direct Parent | O-glycosyl compounds |
|---|
| Alternative Parents | |
|---|
| Substituents | - O-glycosyl compound
- Disaccharide
- Oxane
- Secondary alcohol
- Hemiacetal
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Acetal
- Hydrocarbon derivative
- Primary alcohol
- Alcohol
- Aliphatic heteromonocyclic compound
|
|---|
| Molecular Framework | Aliphatic heteromonocyclic compounds |
|---|
| External Descriptors | |
|---|
| Ontology |
|---|
| Status | Detected and Quantified |
|---|
| Origin | |
|---|
| Biofunction | Not Available |
|---|
| Application | Not Available |
|---|
| Cellular locations | |
|---|
| Physical Properties |
|---|
| State | Solid |
|---|
| Experimental Properties | | Property | Value | Reference |
|---|
| Melting Point | 201 - 202 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 195 mg/mL at 20 °C | Not Available | | LogP | Not Available | Not Available |
|
|---|
| Predicted Properties | |
|---|
| Spectra |
|---|
| Spectra | |
|---|
| Biological Properties |
|---|
| Cellular Locations | |
|---|
| Biospecimen Locations | - Bladder
- Colostrum
- Epidermis
- Intestine
- Liver
- Mammary Gland
- Milk
- Platelet
- Ruminal Fluid
- Skeletal Muscle
- Spleen
|
|---|
| Pathways | |
|---|
| Normal Concentrations |
|---|
| |
| Bladder | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Colostrum | Detected and Quantified | 116857.753-146072.192 uM | Not Specified | Not Specified | Normal | | details | | Colostrum | Detected and Quantified | 78878.984-134386.416 uM | Not Specified | Not Specified | Normal | | details | | Epidermis | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Intestine | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 109682.11 +/- 4835.98 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 131172.828 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 18.989 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 134386.416 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 135554.994 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 124736 - 153216 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 138768.582 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 45792 - 61243 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 139645.0154 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 140521.449 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 142858.604 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 143150.748 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 143735.0367 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 144027.181 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 144319.325 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 145780.0474 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 134970.705 +/- 1168.578 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 137600.00467 +/- 2045.0107 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 138768.582 +/- 1168.578 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 139645.0154 +/- 876.433 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 124636 - 150268 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 116857.583 - 146071.978 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 134970.508 +/- 6719.311 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 109179.54 +/- 4189.15 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 145195.759 +/- 3213.588 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 119779.197 +/- 2921.444 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 137892.149 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 137892.149 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 117931 +/- 5096 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 120445 +/- 4407 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 139060.727 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 113883 +/- 3432 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 138768.582 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 122036 +/- 8571 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 139060.727 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 134678.561 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 103625.15 +/- 5267.57 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 134970.705 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 134970.705 uM | Not Specified | Not Specified | Normal | | details | | Platelet | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Skeletal Muscle | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Spleen | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details |
|
|---|
| Abnormal Concentrations |
|---|
| Not Available |
|---|
| External Links |
|---|
| HMDB ID | HMDB0000186 |
|---|
| DrugBank ID | Not Available |
|---|
| Phenol Explorer Compound ID | Not Available |
|---|
| FooDB ID | FDB021789 |
|---|
| KNApSAcK ID | C00001136 |
|---|
| Chemspider ID | 76293 |
|---|
| KEGG Compound ID | C00243 |
|---|
| BioCyc ID | LACTOSE |
|---|
| BiGG ID | 34366 |
|---|
| Wikipedia Link | Not Available |
|---|
| METLIN ID | 267 |
|---|
| PubChem Compound | 84571 |
|---|
| PDB ID | Not Available |
|---|
| ChEBI ID | 36219 |
|---|
| References |
|---|
| Synthesis Reference | Ruffing, Anne; Mao, Zichao; Ruizhen Chen, Rachel. Metabolic engineering of Agrobacterium sp. for UDP-galactose regeneration and oligosaccharide synthesis. Metabolic Engineering (2006), 8(5), 465-473. |
|---|
| Material Safety Data Sheet (MSDS) | Not Available |
|---|
| General References | - Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. [PubMed:20338431 ]
- 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 ]
- Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3. [PubMed:23040012 ]
- Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11. [PubMed:9718493 ]
- Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22. [PubMed:23182357 ]
- 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 ]
- Gopal PK, Gill HS: Oligosaccharides and glycoconjugates in bovine milk and colostrum. Br J Nutr. 2000 Nov;84 Suppl 1:S69-74. [PubMed:11242449 ]
- O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
- I.M.P.L.V.O Ferreira, A.M.P Gomes, M.A Ferreira (1998). Carbohydrate Polymers 37 (1998) 225-229. Carbohydrate Polymers.
- R. Mehra, P. Kelly (2006). International Dairy Journal 16 (2006) 1334-1340. International Dairy Journal.
- A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
- Fooddata+, The Technical University of Denmark (DTU) [Link]
|
|---|