MiMeDB: Showing metabocard for Lactulose (MMDBc0053407)

Microbial

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-05-16 21:23:28 UTC

Update Date

2023-12-14 16:53:23 UTC

Metabolite ID

MMDBc0053407

Metabolite Identification

Common Name

Lactulose

Description

Lactulose, also known as lactulosum or cephulac, 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. Lactulose, with regard to humans, has been linked to the inborn metabolic disorder celiac disease. Based on a literature review a significant number of articles have been published on Lactulose.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4-O-beta-D-Galactopyranosyl-D-fructofuranose	ChEBI
4-O-beta-D-Galactopyranosyl-D-fructose	ChEBI
D-Lactulose	ChEBI
Lactulosa	ChEBI
Lactulosum	ChEBI
Cephulac	Kegg
Chronulac	Kegg
4-O-b-D-Galactopyranosyl-D-fructofuranose	Generator
4-O-Β-D-galactopyranosyl-D-fructofuranose	Generator
4-O-b-D-Galactopyranosyl-D-fructose	Generator
4-O-Β-D-galactopyranosyl-D-fructose	Generator
(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	HMDB
4-O-beta-delta-Galactopyranosyl-delta-fructofuranose	HMDB
4-O-beta-delta-Galactopyranosyl-delta-fructose	HMDB
Bifiteral	HMDB
delta-Lactulose	HMDB
Normase	HMDB
Amivalex	HMDB
Duphalac	HMDB

Molecular Formula

C₁₂H₂₂O₁₁

Average Mass

342.2965

Monoisotopic Mass

342.116211546

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

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 Key

JCQLYHFGKNRPGE-FCVZTGTOSA-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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

O-glycosyl compound
Disaccharide
C-glycosyl compound
Oxane
Tetrahydrofuran
Secondary alcohol
Hemiacetal
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

glycosylfructose (CHEBI:6359 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Intestine
Spleen

Tissue Locations

Intestine
Spleen

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Celiac disease	Increased	Association	Human Blood	HMDB	10063930

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Actinobacteria	44	Human	Microbial culture
Bacteria	Actinobacteria	39	Human	Microbial culture
Bacteria/Eubacteria	Bacteroidetes	1	Human ; Goat digesta; Sheep digesta; Human feces; Human sputum; Human supragingival plaque; Human saliva; Human urine; Human subgingival plaque; Human mucosa; Human vaginal fluid	Microbial culture
Bacteria	Proteobacteria	1		Microbial culture

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Blood	Detected and Quantified	0.46	0.26	0.79	uM	Adult (>18 years old)	Both	Celiac disease	HMDB	10063930
Human Blood	Detected and Quantified	0.12	0.12	0.13	uM	Adult (>18 years old)	Both	Normal	HMDB	10063930
Human Intestine	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Spleen	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0000740

DrugBank ID

DB00581

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lactulose

METLIN ID

916

PubChem Compound

11333

PDB ID

Not Available

ChEBI ID

6359

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Mortensen PB: The effect of oral-administered lactulose on colonic nitrogen metabolism and excretion. Hepatology. 1992 Dec;16(6):1350-6. doi: 10.1002/hep.1840160608. [PubMed:1446891 ]
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. doi: 10.1016/0016-5085(90)90825-l. [PubMed:2295390 ]
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. doi: 10.1136/gut.28.6.675. [PubMed:3623215 ]
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. doi: 10.1042/cs0720217. [PubMed:3816078 ]
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. doi: 10.1136/gut.24.10.893. [PubMed:6618268 ]
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. doi: 10.1016/0140-6736(93)90939-e. [PubMed:8098788 ]
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. doi: 10.1016/0016-5085(94)90588-6. [PubMed:8299899 ]
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. doi: 10.1023/a:1026679123148. [PubMed:10063930 ]
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. doi: 10.1097/00005176-199903000-00013. [PubMed:10067729 ]
Szilagyi A, Rivard J, Fokeeff K: Improved parameters of lactose maldigestion using lactulose. Dig Dis Sci. 2001 Jul;46(7):1509-19. doi: 10.1023/a:1010652223705. [PubMed:11478504 ]
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. [PubMed:12073265 ]
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. [PubMed:14560443 ]
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. doi: 10.1097/01.sla.0000118594.23874.89. [PubMed:15024312 ]
Mayo Medical Laboratories 2005 Test Catalog [Link]

Showing metabocard for Lactulose (MMDBc0053407)

MOL for #<Metabolite:0x00007f9aa5d0ea48>

3D MOL for #<Metabolite:0x00007f9aa5d0ea48>

3D SDF for #<Metabolite:0x00007f9aa5d0ea48>

3D-SDF for #<Metabolite:0x00007f9aa5d0ea48>

PDB for #<Metabolite:0x00007f9aa5d0ea48>

3D PDB for #<Metabolite:0x00007f9aa5d0ea48>

SMILES for #<Metabolite:0x00007f9aa5d0ea48>

INCHI for #<Metabolite:0x00007f9aa5d0ea48>

Structure for #<Metabolite:0x00007f9aa5d0ea48>

3D Structure for #<Metabolite:0x00007f9aa5d0ea48>