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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:17 UTC
HMDB IDHMDB00740
Secondary Accession Numbers
  • HMDB14719
Metabolite Identification
Common NameLactulose
DescriptionLactulose is a synthetic disaccharide used in the treatment of constipation and hepatic encephalopathy. It has also been used in the diagnosis of gastrointestinal disorders. (From Martindale, The Extra Pharmacopoeia, 30th ed, p887).
Structure
Thumb
Synonyms
ValueSource
4-O-beta-D-Galactopyranosyl-D-fructofuranoseChEBI
4-O-beta-D-Galactopyranosyl-D-fructoseChEBI
LactulosaChEBI
LactulosumChEBI
4-O-b-D-Galactopyranosyl-D-fructofuranoseGenerator
4-O-β-D-galactopyranosyl-D-fructofuranoseGenerator
4-O-b-D-Galactopyranosyl-D-fructoseGenerator
4-O-β-D-galactopyranosyl-D-fructoseGenerator
(2S,3R,4S,5R,6R)-2-[(2R,3S,4S,5R)-4,5-Dihydroxy-2,5-bis(hydroxymethyl)oxolan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triolHMDB
4-O-beta-delta-Galactopyranosyl-delta-fructofuranoseHMDB
4-O-beta-delta-Galactopyranosyl-delta-fructoseHMDB
BifiteralHMDB
CephulacHMDB
D-LactuloseHMDB
delta-LactuloseHMDB
Chemical FormulaC12H22O11
Average Molecular Weight342.2965
Monoisotopic Molecular Weight342.116211546
IUPAC Name(2S,3R,4S,5R,6R)-2-{[(2R,3S,4S,5R)-4,5-dihydroxy-2,5-bis(hydroxymethyl)oxolan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
Traditional Namelactulose
CAS Registry Number4618-18-2
SMILES
OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O
InChI Identifier
InChI=1S/C12H22O11/c13-1-4-6(16)7(17)8(18)11(21-4)22-9-5(2-14)23-12(20,3-15)10(9)19/h4-11,13-20H,1-3H2/t4-,5-,6+,7+,8-,9-,10+,11+,12-/m1/s1
InChI KeyInChIKey=JCQLYHFGKNRPGE-FCVZTGTOSA-N
Chemical Taxonomy
DescriptionThis compound 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 ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassGlycosyl compounds
Direct ParentO-glycosyl compounds
Alternative Parents
Substituents
  • O-glycosyl compound
  • Disaccharide
  • C-glycosyl compound
  • Oxane
  • Oxolane
  • Secondary alcohol
  • Polyol
  • Hemiacetal
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Drug
Biofunction
  • Gastrointestinal Agents
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point169 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility764.0 mg/mLNot Available
LogP-4.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility792.0 mg/mLALOGPS
logP-3.3ALOGPS
logP-4.5ChemAxon
logS0.36ALOGPS
pKa (Strongest Acidic)10.28ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area189.53 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity68.77 m3·mol-1ChemAxon
Polarizability31.49 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • Caecum
  • Intestine
  • Spleen
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.12 (0.12-0.13) uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.46 (0.26-0.79) uMAdult (>18 years old)BothCeliac disease details
Associated Disorders and Diseases
Disease References
Celiac disease
  1. Cox MA, Lewis KO, Cooper BT: Measurement of small intestinal permeability markers, lactulose, and mannitol in serum: results in celiac disease. Dig Dis Sci. 1999 Feb;44(2):402-6. [10063930 ]
Associated OMIM IDs
DrugBank IDDB00581
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022215
KNApSAcK IDNot Available
Chemspider ID10856
KEGG Compound IDC07064
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLactulose
NuGOwiki LinkHMDB00740
Metagene LinkHMDB00740
METLIN ID916
PubChem Compound11333
PDB IDNot Available
ChEBI ID6359
References
Synthesis ReferenceDalev, P.; Tsoneva, P. Method for preparation of lactulose from lactose. Trudove na Nauchnoizsledovatelskiya Khimikofarmatsevtichen Institut (1982), 12 95-102.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Spiller RC, Frost PF, Stewart JS, Bloom SR, Silk DB: Delayed postprandial plasma bile acid response in coeliac patients with slow mouth-caecum transit. Clin Sci (Lond). 1987 Feb;72(2):217-23. [3816078 ]
  2. Ohri SK, Somasundaram S, Koak Y, Macpherson A, Keogh BE, Taylor KM, Menzies IS, Bjarnason I: The effect of intestinal hypoperfusion on intestinal absorption and permeability during cardiopulmonary bypass. Gastroenterology. 1994 Feb;106(2):318-23. [8299899 ]
  3. Cox MA, Lewis KO, Cooper BT: Measurement of small intestinal permeability markers, lactulose, and mannitol in serum: results in celiac disease. Dig Dis Sci. 1999 Feb;44(2):402-6. [10063930 ]
  4. Mortensen PB, Holtug K, Bonnen H, Clausen MR: The degradation of amino acids, proteins, and blood to short-chain fatty acids in colon is prevented by lactulose. Gastroenterology. 1990 Feb;98(2):353-60. [2295390 ]
  5. Goto K, Chew F, Torun B, Peerson JM, Brown KH: Epidemiology of altered intestinal permeability to lactulose and mannitol in Guatemalan infants. J Pediatr Gastroenterol Nutr. 1999 Mar;28(3):282-90. [10067729 ]
  6. La Brooy SJ, Male PJ, Beavis AK, Misiewicz JJ: Assessment of the reproducibility of the lactulose H2 breath test as a measure of mouth to caecum transit time. Gut. 1983 Oct;24(10):893-6. [6618268 ]
  7. Kamphues J, Tabeling R, Stuke O: [Possible interesting dietetic effects of lactulose as a feed additive in pig feed] Dtsch Tierarztl Wochenschr. 2003 Sep;110(9):365-8. [14560443 ]
  8. Mortensen PB: The effect of oral-administered lactulose on colonic nitrogen metabolism and excretion. Hepatology. 1992 Dec;16(6):1350-6. [1446891 ]
  9. Szilagyi A, Rivard J, Fokeeff K: Improved parameters of lactose maldigestion using lactulose. Dig Dis Sci. 2001 Jul;46(7):1509-19. [11478504 ]
  10. van der Hulst RR, van Kreel BK, von Meyenfeldt MF, Brummer RJ, Arends JW, Deutz NE, Soeters PB: Glutamine and the preservation of gut integrity. Lancet. 1993 May 29;341(8857):1363-5. [8098788 ]
  11. van Berge Henegouwen GP, van der Werf SD, Ruben AT: Effect of long term lactulose ingestion on secondary bile salt metabolism in man: potential protective effect of lactulose in colonic carcinogenesis. Gut. 1987 Jun;28(6):675-80. [3623215 ]
  12. Neiko IeM, Mytnyk ZM, Holovach IIu: [Different therapeutic approaches for chronic diffuse liver lesions using ornicetil, lactulose, etimizol and corinfar] Lik Sprava. 2002;(2):64-8. [12073265 ]
  13. Kamiya S, Nagino M, Kanazawa H, Komatsu S, Mayumi T, Takagi K, Asahara T, Nomoto K, Tanaka R, Nimura Y: The value of bile replacement during external biliary drainage: an analysis of intestinal permeability, integrity, and microflora. Ann Surg. 2004 Apr;239(4):510-7. [15024312 ]
  14. Mayo Medical Laboratories 2005 Test Catalog