Survey with prize
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Bovine Metabolome Database.
Record Information
Version1.0
Creation Date2016-09-30 22:20:38 UTC
Update Date2020-06-04 22:55:40 UTC
BMDB IDBMDB0000186
Secondary Accession Numbers
  • BMDB00186
Metabolite Identification
Common NameAlpha-Lactose
DescriptionAlpha-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
Thumb
Synonyms
ValueSource
1-beta-D-Galactopyranosyl-4-alpha-D-glucopyranoseChEBI
4-O-beta-D-Galactopyranosyl-alpha-D-glucopyranoseChEBI
Anhydrous lactoseChEBI
beta-D-Galp-(1->4)-alpha-D-GLCPChEBI
LactoseChEBI
Milk sugarChEBI
1-b-D-Galactopyranosyl-4-a-D-glucopyranoseGenerator
1-Β-D-galactopyranosyl-4-α-D-glucopyranoseGenerator
4-O-b-D-Galactopyranosyl-a-D-glucopyranoseGenerator
4-O-Β-D-galactopyranosyl-α-D-glucopyranoseGenerator
b-D-Galp-(1->4)-a-D-GLCPGenerator
Β-D-galp-(1->4)-α-D-GLCPGenerator
a-LactoseGenerator
Α-lactoseGenerator
(+)-LactoseHMDB
1-beta-delta-Galactopyranosyl-4-alpha-delta-glucopyranoseHMDB
4-O-HexopyranosylhexoseHMDB
AletobioseHMDB
DilactoseHMDB
Fast-flo lactoseHMDB
Flowlac 100HMDB
GalactinumHMDB
GLC-(4-1)GalHMDB
Granulac 140mHMDB
LactinHMDB
Lactin (carbohydrate)HMDB
LactobioseHMDB
Lactohale 300HMDB
Lactose anhydrideHMDB
Lactose fast-floHMDB
OsmolactanHMDB
Pharmatosa DCL 21HMDB
Pharmatose 21HMDB
Pharmatose 325mHMDB
Pharmatose DCL 15HMDB
PrismalacHMDB
Respitose ML 003HMDB
Respitose SV 003HMDB
Saccharum lactinHMDB
SachelacHMDB
Sorbalac 400HMDB
Sorbolac 400HMDB
SpherolacHMDB
Super-tabHMDB
TablettoseHMDB
Tablettose 70HMDB
Tablettose 80HMDB
Zeparox epHMDB
Lactose, anhydrousHMDB
Chemical FormulaC12H22O11
Average Molecular Weight342.2965
Monoisotopic Molecular Weight342.116211546
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number63-42-3
SMILESNot Available
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 KeyGUBGYTABKSRVRQ-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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentO-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 FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Golgi
  • Lysosome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point201 - 202 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility195 mg/mL at 20 °CNot Available
LogPNot AvailableNot Available
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Cytoplasm
  • Golgi
  • Lysosome
Biospecimen Locations
  • Bladder
  • Colostrum
  • Epidermis
  • Intestine
  • Liver
  • Mammary Gland
  • Milk
  • Platelet
  • Ruminal Fluid
  • Skeletal Muscle
  • Spleen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BladderExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
ColostrumDetected and Quantified116857.753-146072.192 uMNot SpecifiedNot SpecifiedNormal details
ColostrumDetected and Quantified78878.984-134386.416 uMNot SpecifiedNot SpecifiedNormal details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified109682.11 +/- 4835.98 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified131172.828 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified18.989 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified134386.416 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified135554.994 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified124736 - 153216 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified138768.582 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified45792 - 61243 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified139645.0154 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified140521.449 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified142858.604 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified143150.748 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified143735.0367 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified144027.181 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified144319.325 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified145780.0474 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified134970.705 +/- 1168.578 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified137600.00467 +/- 2045.0107 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified138768.582 +/- 1168.578 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified139645.0154 +/- 876.433 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified124636 - 150268 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified116857.583 - 146071.978 uMNot SpecifiedNot SpecifiedNormal
    • International Dai...
details
MilkDetected and Quantified134970.508 +/- 6719.311 uMNot SpecifiedNot SpecifiedNormal
    • Carbohydrate Poly...
details
MilkDetected and Quantified109179.54 +/- 4189.15 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified145195.759 +/- 3213.588 uMNot SpecifiedNot Specified
Normal
    • RAJAN SHARMA YUDH...
details
MilkDetected and Quantified119779.197 +/- 2921.444 uMNot SpecifiedNot Specified
Normal
    • Tommaso R.I. Cata...
details
MilkDetected and Quantified137892.149 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified137892.149 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified117931 +/- 5096 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified120445 +/- 4407 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified139060.727 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified113883 +/- 3432 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified138768.582 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified122036 +/- 8571 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified139060.727 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified134678.561 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified103625.15 +/- 5267.57 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified134970.705 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified134970.705 uMNot SpecifiedNot Specified
Normal
details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Ruminal FluidDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Skeletal MuscleExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
SpleenExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000186
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021789
KNApSAcK IDC00001136
Chemspider ID76293
KEGG Compound IDC00243
BioCyc IDLACTOSE
BiGG ID34366
Wikipedia LinkNot Available
METLIN ID267
PubChem Compound84571
PDB IDNot Available
ChEBI ID36219
References
Synthesis ReferenceRuffing, 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
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. Gopal PK, Gill HS: Oligosaccharides and glycoconjugates in bovine milk and colostrum. Br J Nutr. 2000 Nov;84 Suppl 1:S69-74. [PubMed:11242449 ]
  8. 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 ]
  9. I.M.P.L.V.O Ferreira, A.M.P Gomes, M.A Ferreira (1998). Carbohydrate Polymers 37 (1998) 225-229. Carbohydrate Polymers.
  10. R. Mehra, P. Kelly (2006). International Dairy Journal 16 (2006) 1334-1340. International Dairy Journal.
  11. 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.
  12. Fooddata+, The Technical University of Denmark (DTU) [Link]

Enzymes

General function:
Involved in alpha-tubulin binding
Specific function:
The Golgi complex form catalyzes the production of lactose in the lactating mammary gland and could also be responsible for the synthesis of complex-type N-linked oligosaccharides in many glycoproteins as well as the carbohydrate moieties of glycolipids.
Gene Name:
B4GALT1
Uniprot ID:
P08037
Molecular weight:
44843.0
Reactions
Uridine diphosphategalactose + D-Glucose → Uridine 5'-diphosphate + Alpha-Lactosedetails
D-Glucose + Uridine diphosphategalactose → Uridine 5'-diphosphate + Alpha-Lactosedetails
General function:
Involved in calcium ion binding
Specific function:
Regulatory subunit of lactose synthase, changes the substrate specificity of galactosyltransferase in the mammary gland making glucose a good acceptor substrate for this enzyme. This enables LS to synthesize lactose, the major carbohydrate component of milk. In other tissues, galactosyltransferase transfers galactose onto the N-acetylglucosamine of the oligosaccharide chains in glycoproteins.
Gene Name:
LALBA
Uniprot ID:
P00711
Molecular weight:
16247.0
Reactions
D-Glucose + Uridine diphosphategalactose → Uridine 5'-diphosphate + Alpha-Lactosedetails
General function:
Carbohydrate transport and metabolism
Specific function:
Lectin that binds to various sugars: mannose = ManNAc > fucose > GlcNAc > glucose = maltose > galactose > lactose > GalNAc. Could play a role in immune defense.
Gene Name:
CL43
Uniprot ID:
P42916
Molecular weight:
33616.0
General function:
Involved in sugar binding
Specific function:
Galectin that binds lactose and a related range of sugars. May be involved in the assembly of adherens junctions (By similarity).
Gene Name:
LGALS4
Uniprot ID:
Q3T0D6
Molecular weight:
37171.0
General function:
Not Available
Specific function:
Removes terminal alpha-N-acetylgalactosamine residues from glycolipids and glycopeptides. Required for the breakdown of glycolipids (By similarity).
Gene Name:
NAGA
Uniprot ID:
Q58DH9
Molecular weight:
46533.0
Reactions
Alpha-Lactose → Melibiose + D-Galactosedetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
LCT
Uniprot ID:
E1BK89
Molecular weight:
219131.0
Reactions
Alpha-D-Glucose + D-Galactose → Alpha-Lactose + Waterdetails
Alpha-Lactose + Water → D-Glucose + D-Galactosedetails