Inulin - DrugBank

ID Pharmacology Interactions References Trials Economics Properties Spectra Taxonomy

Targets (1)

Identification

Name

Inulin

Accession Number

DB00638 (APRD01034)

Type

Small Molecule

Groups

Approved, Nutraceutical

Description

A starch found in the tubers and roots of many plants. Since it is hydrolyzable to fructose, it is classified as a fructosan. It has been used in physiologic investigation for determination of the rate of glomerular function. [PubChem]

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

External IDs

Not Available

Product Ingredients

Not Available

Approved Prescription Products

Not Available

Approved Generic Prescription Products

Not Available

Approved Over the Counter Products

Not Available

Unapproved/Other Products

Not Available

International Brands

Name	Company
Inulin from Jerusalem artichokes	Not Available
Inulin USP 27	Not Available

Brand mixtures

Not Available

Categories

UNII

JOS53KRJ01

CAS number

9005-80-5

Weight

Average: 6179.3581
Monoisotopic: 6176.017855026

Chemical Formula

C₂₂₈H₃₈₂O₁₉₁

InChI Key

JYJIGFIDKWBXDU-MNNPPOADSA-N

InChI

InChI=1S/C228H382O191/c229-1-76-114(268)152(306)153(307)191(381-76)419-228(190(344)151(305)113(38-266)418-228)75-380-227(189(343)150(304)112(37-265)417-227)74-379-226(188(342)149(303)111(36-264)416-226)73-378-225(187(341)148(302)110(35-263)415-225)72-377-224(186(340)147(301)109(34-262)414-224)71-376-223(185(339)146(300)108(33-261)413-223)70-375-222(184(338)145(299)107(32-260)412-222)69-374-221(183(337)144(298)106(31-259)411-221)68-373-220(182(336)143(297)105(30-258)410-220)67-372-219(181(335)142(296)104(29-257)409-219)66-371-218(180(334)141(295)103(28-256)408-218)65-370-217(179(333)140(294)102(27-255)407-217)64-369-216(178(332)139(293)101(26-254)406-216)63-368-215(177(331)138(292)100(25-253)405-215)62-367-214(176(330)137(291)99(24-252)404-214)61-366-213(175(329)136(290)98(23-251)403-213)60-365-212(174(328)135(289)97(22-250)402-212)59-364-211(173(327)134(288)96(21-249)401-211)58-363-210(172(326)133(287)95(20-248)400-210)57-362-209(171(325)132(286)94(19-247)399-209)56-361-208(170(324)131(285)93(18-246)398-208)55-360-207(169(323)130(284)92(17-245)397-207)54-359-206(168(322)129(283)91(16-244)396-206)53-358-205(167(321)128(282)90(15-243)395-205)52-357-204(166(320)127(281)89(14-242)394-204)51-356-203(165(319)126(280)88(13-241)393-203)50-355-202(164(318)125(279)87(12-240)392-202)49-354-201(163(317)124(278)86(11-239)391-201)48-353-200(162(316)123(277)85(10-238)390-200)47-352-199(161(315)122(276)84(9-237)389-199)46-351-198(160(314)121(275)83(8-236)388-198)45-350-197(159(313)120(274)82(7-235)387-197)44-349-196(158(312)119(273)81(6-234)386-196)43-348-195(157(311)118(272)80(5-233)385-195)42-347-194(156(310)117(271)79(4-232)384-194)41-346-193(155(309)116(270)78(3-231)383-193)40-345-192(39-267)154(308)115(269)77(2-230)382-192/h76-191,229-344H,1-75H2/t76-,77-,78-,79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,111-,112-,113-,114-,115-,116-,117-,118-,119-,120-,121-,122-,123-,124-,125-,126-,127-,128-,129-,130-,131-,132-,133-,134-,135-,136-,137-,138-,139-,140-,141-,142-,143-,144-,145-,146-,147-,148-,149-,150-,151-,152+,153-,154+,155+,156+,157+,158+,159+,160+,161+,162+,163+,164+,165+,166+,167+,168+,169+,170+,171+,172+,173+,174+,175+,176+,177+,178+,179+,180+,181+,182+,183+,184+,185+,186+,187+,188+,189+,190+,191-,192-,193-,194-,195-,196-,197-,198-,199-,200-,201-,202-,203-,204-,205-,206-,207-,208-,209-,210-,211-,212-,213-,214-,215-,216-,217-,218-,219-,220-,221-,222-,223-,224-,225-,226-,227-,228+/m1/s1

IUPAC Name

(2R,3R,4S,5S,6R)-2-{[(2S,3S,4S,5R)-2-({[(2R,3S,4S,5R)-2-({[(2R,3S,4S,5R)-2-({[(2R,3S,4S,5R)-2-({[(2R,3S,4S,5R)-2-({[(2R,3S,4S,5R)-2-({[(2R,3S,4S,5R)-2-({[(2R,3S,4S,5R)-2-({[(2R,3S,4S,5R)-2-({[(2R,3S,4S,5R)-2-({[(2R,3S,4S,5R)-2-({[(2R,3S,4S,5R)-2-({[(2R,3S,4S,5R)-2-({[(2R,3S,4S,5R)-2-({[(2R,3S,4S,5R)-2-({[(2R,3S,4S,5R)-2-({[(2R,3S,4S,5R)-2-({[(2R,3S,4S,5R)-2-({[(2R,3S,4S,5R)-2-({[(2R,3S,4S,5R)-2-({[(2R,3S,4S,5R)-2-({[(2R,3S,4S,5R)-2-({[(2R,3S,4S,5R)-2-({[(2R,3S,4S,5R)-2-({[(2R,3S,4S,5R)-2-({[(2R,3S,4S,5R)-2-({[(2R,3S,4S,5R)-2-({[(2R,3S,4S,5R)-2-({[(2R,3S,4S,5R)-2-({[(2R,3S,4S,5R)-2-({[(2R,3S,4S,5R)-2-({[(2R,3S,4S,5R)-2-({[(2R,3S,4S,5R)-2-({[(2R,3S,4S,5R)-2-({[(2R,3S,4S,5R)-2-({[(2R,3S,4S,5R)-2-({[(2R,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

SMILES

OC[[email protected]]1O[C@@](CO)(OC[C@@]2(OC[C@@]3(OC[C@@]4(OC[C@@]5(OC[C@@]6(OC[C@@]7(OC[C@@]8(OC[C@@]9(OC[C@@]%10(OC[C@@]%11(OC[C@@]%12(OC[C@@]%13(OC[C@@]%14(OC[C@@]%15(OC[C@@]%16(OC[C@@]%17(OC[C@@]%18(OC[C@@]%19(OC[C@@]%20(OC[C@@]%21(OC[C@@]%22(OC[C@@]%23(OC[C@@]%24(OC[C@@]%25(OC[C@@]%26(OC[C@@]%27(OC[C@@]%28(OC[C@@]%29(OC[C@@]%30(OC[C@@]%31(OC[C@@]%32(OC[C@@]%33(OC[C@@]%34(OC[C@@]%35(OC[C@@]%36(OC[C@@]%37(O[[email protected]]%38O[[email protected]](CO)[C@@H](O)[[email protected]](O)[[email protected]]%38O)O[[email protected]](CO)[C@@H](O)[C@@H]%37O)O[[email protected]](CO)[C@@H](O)[C@@H]%36O)O[[email protected]](CO)[C@@H](O)[C@@H]%35O)O[[email protected]](CO)[C@@H](O)[C@@H]%34O)O[[email protected]](CO)[C@@H](O)[C@@H]%33O)O[[email protected]](CO)[C@@H](O)[C@@H]%32O)O[[email protected]](CO)[C@@H](O)[C@@H]%31O)O[[email protected]](CO)[C@@H](O)[C@@H]%30O)O[[email protected]](CO)[C@@H](O)[C@@H]%29O)O[[email protected]](CO)[C@@H](O)[C@@H]%28O)O[[email protected]](CO)[C@@H](O)[C@@H]%27O)O[[email protected]](CO)[C@@H](O)[C@@H]%26O)O[[email protected]](CO)[C@@H](O)[C@@H]%25O)O[[email protected]](CO)[C@@H](O)[C@@H]%24O)O[[email protected]](CO)[C@@H](O)[C@@H]%23O)O[[email protected]](CO)[C@@H](O)[C@@H]%22O)O[[email protected]](CO)[C@@H](O)[C@@H]%21O)O[[email protected]](CO)[C@@H](O)[C@@H]%20O)O[[email protected]](CO)[C@@H](O)[C@@H]%19O)O[[email protected]](CO)[C@@H](O)[C@@H]%18O)O[[email protected]](CO)[C@@H](O)[C@@H]%17O)O[[email protected]](CO)[C@@H](O)[C@@H]%16O)O[[email protected]](CO)[C@@H](O)[C@@H]%15O)O[[email protected]](CO)[C@@H](O)[C@@H]%14O)O[[email protected]](CO)[C@@H](O)[C@@H]%13O)O[[email protected]](CO)[C@@H](O)[C@@H]%12O)O[[email protected]](CO)[C@@H](O)[C@@H]%11O)O[[email protected]](CO)[C@@H](O)[C@@H]%10O)O[[email protected]](CO)[C@@H](O)[C@@H]9O)O[[email protected]](CO)[C@@H](O)[C@@H]8O)O[[email protected]](CO)[C@@H](O)[C@@H]7O)O[[email protected]](CO)[C@@H](O)[C@@H]6O)O[[email protected]](CO)[C@@H](O)[C@@H]5O)O[[email protected]](CO)[C@@H](O)[C@@H]4O)O[[email protected]](CO)[C@@H](O)[C@@H]3O)O[[email protected]](CO)[C@@H](O)[C@@H]2O)[C@@H](O)[C@@H]1O

Pharmacology

Indication

Historically used in an important medical test of renal function, specifically a measure of glomerular filtration rate. Sometimes used to help relieve symptoms of diabetes mellitus - a condition characterised by hyperglycemia and/or hyperinsulinemia.

Structured Indications

Not Available

Pharmacodynamics

The inulin test is a procedure by which the filtering capacity of the glomeruli (the main filtering structures of the kidney) is determined by measuring the rate at which inulin, the test substance, is cleared from blood plasma. Inulin is one of the more suitable and accurate substance to measure because it is a small, inert polysaccharide molecule that readily passes through the glomeruli. The inulin clearance test is performed by injecting inulin, waiting for it to be distributed, and then measuring plasma and urine inulin concentrations by various assays. As nutraceutical agents inulins may have antitumor, antimicrobial, hypolipidemic and hypoglycemic actions. They may also help to improve mineral absorption and balance and may have antiosteoporotic activity.

Mechanism of action

As a diagnostic agent, inulin is readily soluble and essentially indigestible. It readily passes through the blood and into the urine. It is neither secreted nor resorbed by the kidney making it an excellent indicator for renal clearance rates. The inulin clearance test has largely been succeeded by the creatinine clearance test as a measure of glomerular filtration rate. As a hypoglycemic agent, inulin is not digestible by human enzymes ptyalin and amylase, which are designed to digest starch. As a result, inulin passes through much of the digestive system intact. It is only in the colon that bacteria metabolise inulin, with the release of significant quantities of carbon dioxide and/or methane. Because inulin is not broken down into simple sugars (monosaccharides) by normal digestion, it does not elevate blood sugar levels, hence, helping diabetics regulate blood sugar levels.

Target	Kind	Pharmacological action	Actions	Organism	UniProt ID
Cycloinulo-oligosaccharide fructanotransferase	Protein	no	binder	Paenibacillus macerans	Q9F0I5	details

Absorption

Poorly absorbed, passes through to urine unmetabolized

Volume of distribution

Not Available

Protein binding

None

Metabolism

Metabolized into carbon dioxide and methane by colonic bacteria

Substrate	Enzymes	Product
Inulin	Not Available	Methane	Details

Route of elimination

Not Available

Half life

2-4 hours

Clearance

Not Available

Toxicity

Not Available

Affected organisms

Humans and other mammals

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

Not Available

Food Interactions

Not Available

References

Synthesis Reference

Ernst Hoehn, Curtis J. McKay, E. Donald Murray, "Production of high fructose syrup from inulin involving ultrafiltration." U.S. Patent US4421852, issued July, 1981.

US4421852

General References

Abrams SA, Griffin IJ, Hawthorne KM, Liang L, Gunn SK, Darlington G, Ellis KJ: A combination of prebiotic short- and long-chain inulin-type fructans enhances calcium absorption and bone mineralization in young adolescents. Am J Clin Nutr. 2005 Aug;82(2):471-6. [PubMed:16087995 ]
Coudray C, Demigne C, Rayssiguier Y: Effects of dietary fibers on magnesium absorption in animals and humans. J Nutr. 2003 Jan;133(1):1-4. [PubMed:12514257 ]
Coussement PA: Inulin and oligofructose: safe intakes and legal status. J Nutr. 1999 Jul;129(7 Suppl):1412S-7S. [PubMed:10395609 ]
Roberfroid MB: Introducing inulin-type fructans. Br J Nutr. 2005 Apr;93 Suppl 1:S13-25. [PubMed:15877886 ]

External Links

Resource	Link
KEGG Drug	D00171
KEGG Compound	C03323
PubChem Compound	24763
PubChem Substance	46508287
ChemSpider	23149
ChEBI	15443
ChEMBL	CHEMBL1201646
Therapeutic Targets Database	DAP001304
PharmGKB	PA450043
Drugs.com	http://www.drugs.com/cons/inulin-intravenous.html
PDRhealth	http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/inu_0299.shtml
Wikipedia	Inulin

ATC Codes

V04CH01 — Inulin and other polyfructosans

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

Download (71.2 KB)

Clinical Trials

Phase	Status	Purpose	Conditions	Count
1, 2	Active Not Recruiting	Basic Science	Critically Ill / Premature Birth of Newborn	1
2	Completed	Treatment	Breath odour / Tongue Diseases	1
2	Completed	Treatment	Premature Neonates	1
2	Unknown Status	Prevention	Adenomatous Polyposis Coli	1
Not Available	Completed	Treatment	Fatty Acids, Nonesterified / Glomerular Filtration Rate (GFR) / Renal Circulation / Renal Plasma Flow	1
Not Available	Withdrawn	Not Available	Chronic Kidney Disease (CKD)	1

Pharmacoeconomics

Manufacturers

Iso tex diagnostics inc

Packagers

Dosage forms

Not Available

Prices

Not Available

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	178 °C	Not Available
water solubility	280 mg/mL (at 80 °C), insoluble at room temperature	Not Available

Predicted Properties

Property	Value	Source
logP	-62	ChemAxon
pKa (Strongest Acidic)	11.27	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	191	ChemAxon
Hydrogen Donor Count	116	ChemAxon
Polar Surface Area	3038.93 Å²	ChemAxon
Rotatable Bond Count	149	ChemAxon
Refractivity	1251.4 m³·mol^-1	ChemAxon
Number of Rings	38	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted ADMET features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Not Available

Taxonomy

Description

This compound belongs to the class of chemical entities known as polysaccharides. These are compounds containing more than ten saccharide units.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

O-glycosyl compounds / C-glycosyl compounds / Ketals / Oxanes / Oxolanes / Secondary alcohols / Polyols / Oxacyclic compounds / Primary alcohols / Hydrocarbon derivatives

Substituents

Polysaccharide / C-glycosyl compound / Glycosyl compound / O-glycosyl compound / Ketal / Oxane / Oxolane / Secondary alcohol / Acetal / Oxacycle

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Targets

Details

1. Cycloinulo-oligosaccharide fructanotransferase

Kind: Protein
Organism: Paenibacillus macerans
Pharmacological action: no
Actions: binder

General Function:: Transferase activity
Specific Function:: Not Available
Gene Name:: cft
Uniprot ID:: Q9F0I5
Uniprot Name:: Cycloinulo-oligosaccharide fructanotransferase
Molecular Weight:: 149562.53 Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kawamura M, Uchiyama T, Kuramoto T, Tamura Y, Mizutani K: Formation of a cycloinulo-oligosaccharide from inulin by an extracellular enzyme of Bacillus circulans OKUMZ 31B. Carbohydr Res. 1989 Oct 23;192:83-90. [PubMed:2611778 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Drug created on June 13, 2005 07:24 / Updated on July 18, 2017 16:51

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Structure for DB00638 (Inulin)

Targets

References