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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2020-11-24 22:14:40 UTC
NP-MRD IDNP0000332
Secondary Accession NumbersNone
Natural Product 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 human 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 ). Lactose in the urine is a biomarker for the consumption of milk.
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
WURCS=2.0/2,2,1/[a2122h-1a_1-5][a2112h-1b_1-5]/1-2/a4-b1ChEBI
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 Mass342.2965 Da
Monoisotopic Mass342.11621 Da
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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 400 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)V.dorna832021-08-08View Spectrum
Species
Species of Origin
  • Animalia
  • Eubacteria
  • 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
    Water Solubility586 g/LALOGPS
    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
    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
    Good Scents IDNot Available
    References
    General References
    1. Jung SK, Fujimoto D: A novel beta-galactoside-binding lectin in adult rat kidney. J Biochem. 1994 Sep;116(3):547-53. [PubMed:7852273 ]
    2. Oozeer R, Furet JP, Goupil-Feuillerat N, Anba J, Mengaud J, Corthier G: Differential activities of four Lactobacillus casei promoters during bacterial transit through the gastrointestinal tracts of human-microbiota-associated mice. Appl Environ Microbiol. 2005 Mar;71(3):1356-63. [PubMed:15746338 ]
    3. Dimopoulos MA, Anagnostopoulos A: Thalidomide in relapsed/refractory multiple myeloma: pivotal trials conducted outside the United States. Semin Hematol. 2003 Oct;40(4 Suppl 4):8-16. [PubMed:15015891 ]
    4. Muthusamy A, Erickson DR, Sheykhnazari M, Bhavanandan VP: Enhanced binding of modified pentosan polysulfate and heparin to bladder--a strategy for improved treatment of interstitial cystitis. Urology. 2006 Jan;67(1):209-13. [PubMed:16413377 ]
    5. Johnson JD, Simoons FJ, Hurwitz R, Grange A, Mitchell CH, Sinatra FR, Sunshine P, Robertson WV, Bennett PH, Kretchmer N: Lactose malabsorption among the Pima indians of Arizona. Gastroenterology. 1977 Dec;73(6):1299-304. [PubMed:578795 ]
    6. Lustenberger RW: [A 23-year old patient with chronic diarrhea. Celiac disease and lactose intolerance]. Praxis (Bern 1994). 2005 Feb 2;94(5):163-4. [PubMed:15745382 ]
    7. Sharma A, DiCioccio RA, Allen HJ: Identification and synthesis of a novel 15 kDa beta-galactoside-binding lectin in human leukocytes. Glycobiology. 1992 Aug;2(4):285-92. [PubMed:1421750 ]
    8. Rana SV, Bhasin DK, Vinayak VK: Lactose hydrogen breath test in Giardia lamblia-positive patients. Dig Dis Sci. 2005 Feb;50(2):259-61. [PubMed:15745082 ]
    9. Mitchell JD, Brand J, Halbisch J: Weight-gain inhibition by lactose in Australian Aboriginal children. A controlled trial of normal and lactose hydrolysed milk. Lancet. 1977 Mar 5;1(8010):500-2. [PubMed:65606 ]
    10. Soupene E, van Heeswijk WC, Plumbridge J, Stewart V, Bertenthal D, Lee H, Prasad G, Paliy O, Charernnoppakul P, Kustu S: Physiological studies of Escherichia coli strain MG1655: growth defects and apparent cross-regulation of gene expression. J Bacteriol. 2003 Sep;185(18):5611-26. [PubMed:12949114 ]
    11. Yeoh E, Horowitz M, Russo A, Muecke T, Robb T, Chatterton B: The effects of abdominal irradiation for seminoma of the testis on gastrointestinal function. J Gastroenterol Hepatol. 1995 Mar-Apr;10(2):125-30. [PubMed:7787155 ]
    12. Bondesson E, Bengtsson T, Borgstrom L, Nilsson LE, Norrgren K, Olsson B, Svensson M, Wollmer P: Dose delivery late in the breath can increase dry powder aerosol penetration into the lungs. J Aerosol Med. 2005 Spring;18(1):23-33. [PubMed:15741771 ]
    13. Roberson CM: Lactose intolerance. Ala Nurse. 2004 Dec-2005 Feb;31(4):23-4; quiz 24. [PubMed:15662762 ]
    14. Kim KI, Lee WS, Benevenga NJ: Feeding diets containing high levels of milk products or cellulose decrease urease activity and ammonia production in rat intestine. J Nutr. 1998 Jul;128(7):1186-91. [PubMed:9649604 ]
    15. Gunther S, Patterson RE, Kristal AR, Stratton KL, White E: Demographic and health-related correlates of herbal and specialty supplement use. J Am Diet Assoc. 2004 Jan;104(1):27-34. [PubMed:14702580 ]
    16. Delaveau P: [Milk lactose. Hypothesis on its biological importance]. Ann Pharm Fr. 2003;61(5):340-2. [PubMed:13130292 ]
    17. 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. [PubMed:12216958 ]
    18. Szilagyi A: Review article: lactose--a potential prebiotic. Aliment Pharmacol Ther. 2002 Sep;16(9):1591-602. [PubMed:12197838 ]
    19. Swagerty DL Jr, Walling AD, Klein RM: Lactose intolerance. Am Fam Physician. 2002 May 1;65(9):1845-50. [PubMed:12018807 ]