| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:20:38 UTC |
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| Update Date | 2020-06-04 22:55:40 UTC |
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| BMDB ID | BMDB0000186 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Alpha-Lactose |
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| 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. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 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 |
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| Chemical Formula | C12H22O11 |
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| Average Molecular Weight | 342.2965 |
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| Monoisotopic Molecular Weight | 342.116211546 |
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| 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 |
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| Traditional Name | α-lactose |
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| CAS Registry Number | 63-42-3 |
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| 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 |
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| 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 |
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| InChI Key | GUBGYTABKSRVRQ-XLOQQCSPSA-N |
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| Chemical Taxonomy |
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| 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. |
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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 | O-glycosyl compounds |
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| Alternative Parents | |
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| Substituents | - O-glycosyl compound
- Disaccharide
- Oxane
- Secondary alcohol
- Hemiacetal
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Acetal
- Hydrocarbon derivative
- Primary alcohol
- Alcohol
- Aliphatic heteromonocyclic compound
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| Molecular Framework | Aliphatic heteromonocyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Status | Detected and Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | |
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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 | 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 |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | |
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| GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS) | splash10-0uxs-0972000000-af8ca1bf1faa3d01a08d | View in MoNA |
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| GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS; 1 MEOX) | splash10-00di-9741000000-a61bf0223a1683f0402e | View in MoNA |
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| GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS; 1 MEOX) | splash10-00di-9641000000-12611bfab50cb066e8af | View in MoNA |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-03e9-4897000000-332d470623cd7f1e1ced | View in MoNA |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive | splash10-014i-3513539000-d702fa4adb45f44530b6 | View in MoNA |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_3_3) - 70eV, Positive | Not Available | View in JSpectraViewer |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_3_16) - 70eV, Positive | Not Available | View in JSpectraViewer |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_4_2) - 70eV, Positive | Not Available | View in JSpectraViewer |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_4_10) - 70eV, Positive | Not Available | View in JSpectraViewer |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_4_11) - 70eV, Positive | Not Available | View in JSpectraViewer |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_4_12) - 70eV, Positive | Not Available | View in JSpectraViewer |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_4_20) - 70eV, Positive | Not Available | View in JSpectraViewer |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_4_32) - 70eV, Positive | Not Available | View in JSpectraViewer |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_4_33) - 70eV, Positive | Not Available | View in JSpectraViewer |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS ("Alpha-Lactose,3TBDMS,#3" TMS) - 70eV, Positive | Not Available | View in JSpectraViewer |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive | Not Available | View in JSpectraViewer |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive | Not Available | View in JSpectraViewer |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive | Not Available | View in JSpectraViewer |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive | Not Available | View in JSpectraViewer |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive | Not Available | View in JSpectraViewer |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive | Not Available | View in JSpectraViewer |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive | Not Available | View in JSpectraViewer |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, Positive | Not Available | View in JSpectraViewer |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive | Not Available | View in JSpectraViewer |
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| LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-03di-0901000000-bcb7aaa42261d980d488 | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-000f-9300000000-1bc18b05388cd2213573 | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-01p9-9000000000-4483af567feecb34a651 | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03gl-0907000000-a1de7813fbe8b5258c10 | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03e9-0900000000-79cc5059a3f338e8c1dd | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03di-3900000000-851d0bc84d91b6e09579 | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-002f-0749000000-af1d18f2bc3ab8e02883 | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0200-2902000000-67218697344afb9e70fa | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-01td-4900000000-40aa2d8125769803cfbb | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000x-1069000000-9cd867711bca0eecf935 | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-9365000000-65403961bfb5e35eaa0d | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-000l-9200000000-0de9785c1c5df1430dd2 | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0006-0109000000-9d0f9a68a67bafd734ab | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01rw-3898000000-7f495a1bcfdbed6466c4 | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-01ti-9210000000-b8a83657f0266d372bee | View in MoNA |
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| 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | Not Available | View in JSpectraViewer |
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| 1D NMR | 13C NMR Spectrum (1D, 125 MHz, H2O, experimental) | Not Available | View in JSpectraViewer |
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| 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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| 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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| 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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| 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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| 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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| 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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| 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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| 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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| 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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| 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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| 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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| 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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| 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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| 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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| 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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| 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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| 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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| 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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| 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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| 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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| 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, experimental) | Not Available | View in JSpectraViewer |
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| 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) | Not Available | View in JSpectraViewer |
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| 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 400 MHz, H2O, experimental) | Not Available | View in JSpectraViewer |
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| 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]
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