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Record Information
Version1.0
Creation Date2016-07-13 19:41:58 UTC
Update Date2016-09-23 18:44:38 UTC
LmdbLMDB00082
Secondary Accession NumbersNone
Metabolite Identification
Common NameAlpha-Lactose
Descriptionalpha-Lactose is the major sugar present in milk and the main source of energy supplied to the newborn mammalian in its mother's milk. Lactose is also an important osmotic regulator of lactation. It is digested by the intestinal lactase (EC 3.2.1.108), an enzyme expressed in newborns. Its activity declines following weaning. As a result, adult mammals are normally lactose-intolerant and more than 75% of the animal adult population suffers from lactase deficiency. Lactase deficiency is present in up to 80 percent of blacks and Latinos, and up to 100 percent of American Indians and Asians. Persons with lactose intolerance are unable to digest significant amounts of lactose. Common symptoms include abdominal pain and bloating, excessive flatus, and watery stool following the ingestion of foods containing lactose. A sizable number of adults believe they are lactose intolerant but do not actually have impaired lactose digestion, and some persons with lactase deficiency can tolerate moderate amounts of ingested lactose. A diagnosis of lactose intolerance can usually be made with a careful history supported by dietary manipulation. If necessary, diagnosis can be confirmed by using a breath hydrogen or lactose tolerance test. These mostly uncomfortable symptoms of lactose maldigestion are blamed for a variably dairy consumption. There is, however, emerging evidence that certain lactic acid-producing bacteria, which selectively consume prebiotics, may be beneficial against some lower intestinal diseases. Lactose maldigestion and lactose should perhaps be re-evaluated as a potential provider of such a prebiotic. Treatment consists primarily of avoiding lactose-containing foods. Lactase enzyme supplements may be helpful. The degree of lactose malabsorption varies greatly among patients with lactose intolerance, but most of them can ingest up to 350 mL of milk daily without symptoms. Lactose-intolerant patients must ensure adequate calcium intake. (PMID: 13130292 , 12216958 , 12197838 , 12018807 ).
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
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)splash10-0uxs-0972000000-af8ca1bf1faa3d01a08dSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS; 1 MEOX)splash10-00di-9741000000-a61bf0223a1683f0402eSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS; 1 MEOX)splash10-00di-9641000000-12611bfab50cb066e8afSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03e9-4897000000-332d470623cd7f1e1cedSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-014i-3513539000-d702fa4adb45f44530b6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_3_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_3_16) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_4_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_4_10) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_4_11) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_4_12) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_4_20) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_4_32) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_4_33) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("Alpha-Lactose,3TBDMS,#3" TMS) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0901000000-bcb7aaa42261d980d488Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000f-9300000000-1bc18b05388cd2213573Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-01p9-9000000000-4483af567feecb34a651Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03gl-0907000000-a1de7813fbe8b5258c10Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-0900000000-79cc5059a3f338e8c1ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-3900000000-851d0bc84d91b6e09579Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002f-0749000000-af1d18f2bc3ab8e02883Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0200-2902000000-67218697344afb9e70faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01td-4900000000-40aa2d8125769803cfbbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000x-1069000000-9cd867711bca0eecf935Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9365000000-65403961bfb5e35eaa0dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000l-9200000000-0de9785c1c5df1430dd2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0109000000-9d0f9a68a67bafd734abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01rw-3898000000-7f495a1bcfdbed6466c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ti-9210000000-b8a83657f0266d372beeSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Colostrum
  • Milk
  • Ruminal Fluid
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
ColostrumDetected and Quantified116857.753-146072.192 uMNot AvailableBovine details
ColostrumDetected and Quantified27-46 uMNot AvailableBovine details
ColostrumDetected and Quantified78878.984-134386.416 uMNot AvailableBovine details
MilkDetected and Quantified134386.416 uMNot AvailableBovine details
MilkDetected and Quantified46200+/-400 mg/kgNot AvailableBovine details
MilkDetected and Quantified46200+/-400 mg/kgNot AvailableBovine details
MilkDetected and Quantified47100+/-700 mg/kgNot AvailableBovine details
MilkDetected and Quantified47500+/-400 mg/kgNot AvailableBovine details
MilkDetected and Quantified47800+/-300 mg/kgNot AvailableBovine details
MilkDetected and Quantified45600 mg/kgNot AvailableOvine details
MilkDetected and Quantified46000 mg/kgNot AvailableOvine details
MilkDetected and Quantified47100 mg/kgNot AvailableOvine details
MilkDetected and Quantified47300 mg/kgNot AvailableOvine details
MilkDetected and Quantified48300 mg/kgNot AvailableOvine details
MilkDetected and Quantified49100 mg/kgNot AvailableOvine details
MilkDetected and Quantified43200-43300 mg/kgNot AvailableCaprine details
MilkDetected and Quantified43100 mg/kgNot AvailableCaprine details
MilkDetected and Quantified42400-44100 mg/kgNot AvailableCaprine details
MilkDetected and Quantified41500-44100 mg/kgNot AvailableCaprine details
MilkDetected and Quantified45792 - 61243 uMNot AvailableBovine details
MilkDetected and Quantified18.989 uMNot AvailableBovine details
MilkDetected and Quantified124736-153216 uMNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableOvine details
MilkDetected and Quantified44900 mg/kgNot AvailableBovine details
MilkDetected and Quantified44900 mg/kgNot AvailableBovine details
MilkDetected and Quantified46400 mg/kgNot AvailableBovine details
MilkDetected and Quantified47500 mg/kgNot AvailableBovine details
MilkDetected and Quantified47500 mg/kgNot AvailableBovine details
MilkDetected and Quantified47800 mg/kgNot AvailableBovine details
MilkDetected and Quantified48100 mg/kgNot AvailableBovine details
MilkDetected and Quantified48100 mg/kgNot AvailableBovine details
MilkDetected and Quantified48900 mg/kgNot AvailableBovine details
MilkDetected and Quantified49000 mg/kgNot AvailableBovine details
MilkDetected and Quantified49200 mg/kgNot AvailableBovine details
MilkDetected and Quantified72-116 g/dNot AvailableCaprine
    • Park, Y. W; Juáre...
details
MilkDetected and Quantified49200 mg/kgNot AvailableBovine details
MilkDetected and Quantified52-84 g/dNot AvailableCaprine
    • Park, Y. W; Juáre...
details
MilkDetected and Quantified49300 mg/kgNot AvailableBovine details
MilkDetected and Quantified64-120 g/dNot AvailableCaprine
    • Park, Y. W; Juáre...
details
MilkDetected and Quantified49400 mg/kgNot AvailableBovine details
MilkDetected and Quantified43-104 g/dNot AvailableCaprine
    • Park, Y. W; Juáre...
details
MilkDetected and Quantified49900 mg/kgNot AvailableBovine details
MilkDetected and Quantified43800-44100 mg/kgNot AvailableCaprine
    • Park, Y. W; Juáre...
details
MilkDetected and Quantified42400-42800 mg/kgNot AvailableCaprine
    • Park, Y. W; Juáre...
details
MilkDetected and Quantified41500-42900 mg/kgNot AvailableCaprine
    • Park, Y. W; Juáre...
details
MilkDetected and Quantified41600-44100 mg/kgNot AvailableCaprine
    • Park, Y. W; Juáre...
details
Ruminal FluidDetected but not QuantifiedNot ApplicableNot AvailableBovine details
DrugBank IDNot Available
HMDB IDHMDB0000186
FooDB IDFDB021789
Phenol Explorer IDNot Available
KNApSAcK IDC00001136
BiGG ID34366
BioCyc IDLACTOSE
METLIN ID267
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID76293
ChEBI ID36219
PubChem Compound ID84571
Kegg Compound IDC00243
YMDB IDNot Available
ECMDB IDECMDB00186
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Delaveau P: [Milk lactose. Hypothesis on its biological importance]. Ann Pharm Fr. 2003;61(5):340-2. [13130292 ]
  2. Vilotte JL: Lowering the milk lactose content in vivo: potential interests, strategies and physiological consequences. Reprod Nutr Dev. 2002 Mar-Apr;42(2):127-32. [12216958 ]
  3. Szilagyi A: Review article: lactose--a potential prebiotic. Aliment Pharmacol Ther. 2002 Sep;16(9):1591-602. [12197838 ]
  4. Swagerty DL Jr, Walling AD, Klein RM: Lactose intolerance. Am Fam Physician. 2002 May 1;65(9):1845-50. [12018807 ]