DrugBank: Inulin (DB00638)

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

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

Not Available

Salts

Not Available

Brand names

Name	Company
Inulin from Jerusalem artichokes
Inulin USP 27

Brand mixtures

Not Available

Categories

Diagnostic Agents
Hypoglycemic Agents

CAS number

9005-80-5

Weight

Average: 6179.3581
Monoisotopic: 6176.017855026

Chemical Formula

C₂₂₈H₃₈₂O₁₉₁

InChI Key

InChIKey=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

Plain Text

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

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Organic

Classes

Carbohydrates

Substructures

Carbohydrates
Glycerol and Derivatives
Hydroxy Compounds
Pyrans
Acetals and Derivatives
Ethers
Alcohols and Polyols
Heterocyclic compounds
Furans

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.

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.

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

Important The metabolism module of DrugBank is currently in beta. Questions or suggestions? Please contact us.

Substrate	Enzymes	Product
Inulin		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

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	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	ChemAxon
rotatable bond count	149	ChemAxon
refractivity	1251.4	ChemAxon

References

Synthesis Reference

Not Available

General Reference

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
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
Coussement PA: Inulin and oligofructose: safe intakes and legal status. J Nutr. 1999 Jul;129(7 Suppl):1412S-7S. Pubmed
Roberfroid MB: Introducing inulin-type fructans. Br J Nutr. 2005 Apr;93 Suppl 1:S13-25. Pubmed

External Links

Resource	Link
KEGG Drug	D00171
KEGG Compound	C03323
PubChem Compound	24763
PubChem Substance	46508287
ChemSpider	23149
ChEBI	15443
ChEMBL	15443
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	http://en.wikipedia.org/wiki/Inulin

ATC Codes

V04CH01

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

show (71.2 KB)

Interactions

Drug Interactions

Not Available

Food Interactions

Not Available

Targets
1. Cycloinulo-oligosaccharide fructanotransferase Pharmacological action: no Actions: binder Organism class: bacterial UniProt ID: Q9F0I5 Gene: cft Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report 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 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 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 Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

Targets

1. Cycloinulo-oligosaccharide fructanotransferase

Pharmacological action: no
Actions: binder
Organism class: bacterial
UniProt ID: Q9F0I5 Link_out

Gene: cft
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
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
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
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

Comments

Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19