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Identification
NameInulin
Accession NumberDB00638  (APRD01034)
TypeSmall Molecule
GroupsApproved, Nutraceutical
DescriptionA 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
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
Inulin from Jerusalem artichokesNot Available
Inulin USP 27Not Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIJOS53KRJ01
CAS number9005-80-5
WeightAverage: 6179.3581
Monoisotopic: 6176.017855026
Chemical FormulaC228H382O191
InChI KeyJYJIGFIDKWBXDU-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
IndicationHistorically 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
PharmacodynamicsThe 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 actionAs 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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Cycloinulo-oligosaccharide fructanotransferaseProteinno
binder
Paenibacillus maceransQ9F0I5 details
Related Articles
AbsorptionPoorly absorbed, passes through to urine unmetabolized
Volume of distributionNot Available
Protein bindingNone
Metabolism

Metabolized into carbon dioxide and methane by colonic bacteria

SubstrateEnzymesProduct
Inulin
Not Available
MethaneDetails
Route of eliminationNot Available
Half life2-4 hours
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot 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
  1. 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 ]
  2. 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 ]
  3. Coussement PA: Inulin and oligofructose: safe intakes and legal status. J Nutr. 1999 Jul;129(7 Suppl):1412S-7S. [PubMed:10395609 ]
  4. Roberfroid MB: Introducing inulin-type fructans. Br J Nutr. 2005 Apr;93 Suppl 1:S13-25. [PubMed:15877886 ]
External Links
ATC CodesV04CH01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (71.2 KB)
ADMET
Predicted ADMET featuresNot Available
Pharmacoeconomics
Manufacturers
  • Iso tex diagnostics inc
Packagers
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point178 °CNot Available
water solubility280 mg/mL (at 80 °C), insoluble at room temperatureNot Available
Predicted Properties
PropertyValueSource
logP-62ChemAxon
pKa (Strongest Acidic)11.27ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count191ChemAxon
Hydrogen Donor Count116ChemAxon
Polar Surface Area3038.93 Å2ChemAxon
Rotatable Bond Count149ChemAxon
Refractivity1251.4 m3·mol-1ChemAxon
Number of Rings38ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
ClassificationNot classified

Targets

Kind
Protein
Organism
Paenibacillus macerans
Pharmacological action
no
Actions
binder
General Function:
Transferase activity
Specific Function:
Not Available
Gene Name:
cft
Uniprot ID:
Q9F0I5
Molecular Weight:
149562.53 Da
References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23