Record Information
Version1.0
Creation Date2016-09-30 22:20:38 UTC
Update Date2020-06-04 22:55:40 UTC
MCDB ID BMDB0000186
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 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 Nameα-lactose
CAS Registry Number63-42-3
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 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
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 Properties
PropertyValueSource
logP-3ALOGPS
logP-4.7ChemAxon
logS0.23ALOGPS
pKa (Strongest Acidic)11.25ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area189.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity68.34 m³·mol⁻¹ChemAxon
Polarizability30.92 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)splash10-0uxs-0972000000-af8ca1bf1faa3d01a08d2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS; 1 MEOX)splash10-00di-9741000000-a61bf0223a1683f0402e2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS; 1 MEOX)splash10-00di-9641000000-12611bfab50cb066e8af2014-06-16View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03e9-4897000000-332d470623cd7f1e1ced2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-014i-3513539000-d702fa4adb45f44530b62017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_3_3) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_3_16) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_4_2) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_4_10) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_4_11) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_4_12) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_4_20) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_4_32) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_4_33) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("Alpha-Lactose,3TBDMS,#3" TMS) - 70eV, PositiveNot Available2021-10-14View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0901000000-bcb7aaa42261d980d4882012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000f-9300000000-1bc18b05388cd22135732012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-01p9-9000000000-4483af567feecb34a6512012-07-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03gl-0907000000-a1de7813fbe8b5258c102017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-0900000000-79cc5059a3f338e8c1dd2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-3900000000-851d0bc84d91b6e095792017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002f-0749000000-af1d18f2bc3ab8e028832017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0200-2902000000-67218697344afb9e70fa2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01td-4900000000-40aa2d8125769803cfbb2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000x-1069000000-9cd867711bca0eecf9352021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9365000000-65403961bfb5e35eaa0d2021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000l-9200000000-0de9785c1c5df1430dd22021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0109000000-9d0f9a68a67bafd734ab2021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01rw-3898000000-7f495a1bcfdbed6466c42021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ti-9210000000-b8a83657f0266d372bee2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Not Available2021-10-10View Spectrum
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 Available2012-12-04View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 400 MHz, H2O, experimental)Not Available2012-12-05View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified124636 - 150268 uM details
Detected and Quantified134970 +/- 6719 uM
  • Carbohydrate Poly...
details
Detected and Quantified116857 - 146072 uM
  • International Dai...
details
Detected and Quantified131172 uM details
Detected and Quantified135554 uM details
Detected and Quantified138768 uM details
Detected and Quantified139645 uM details
Detected and Quantified140522 uM details
Detected and Quantified142858 uM details
Detected and Quantified143151 uM details
Detected and Quantified143735 uM details
Detected and Quantified144027 uM details
Detected and Quantified144319 uM details
Detected and Quantified145780 uM details
Detected and Quantified134970 +/- 1169 uM details
Detected and Quantified137600 +/- 2045 uM details
Detected and Quantified138768 +/- 1169 uM details
Detected and Quantified139645 +/- 876 uM details
Detected but not QuantifiedNot Applicable details
Detected and Quantified19 uM details
Detected and Quantified134386 uM details
Detected and Quantified124736 - 153216 uM details
Detected and Quantified45792 - 61243 uM details
Detected and Quantified137892 uM details
Detected and Quantified137892 uM details
Detected and Quantified139060 uM details
Detected and Quantified138768 uM details
Detected and Quantified139060 uM details
Detected and Quantified134678 uM details
Detected and Quantified134970 uM details
Detected and Quantified134970 uM details
Detected and Quantified117931 +/- 5096 uM details
Detected and Quantified120445 +/- 4407 uM details
Detected and Quantified113883 +/- 3432 uM details
Detected and Quantified122036 +/- 8571 uM details
Detected and Quantified109180 +/- 4189 uM details
Detected and Quantified103625 +/- 5268 uM details
Detected and Quantified109682 +/- 4836 uM details
Detected and Quantified145196 +/- 3214 uM
  • RAJAN SHARMA YUDH...
details
Detected and Quantified119779 +/- 2921 uM
  • Tommaso R.I. Cata...
details
HMDB IDHMDB0000186
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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)Download (PDF)
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]