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Details

Stereochemistry ACHIRAL
Molecular Formula C5H12O5
Molecular Weight 152.1458
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ADONITOL

SMILES

OC[C@H](O)[C@H](O)[C@H](O)CO

InChI

InChIKey=HEBKCHPVOIAQTA-ZXFHETKHSA-N
InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5-

HIDE SMILES / InChI
Adonitol, also known as ribitol, is the reduced alcohol form of ribose. This compound was first described in 1892 Merck annual report as a crystalline pentahydric alcohol obtained from Adonis vernalis. It is a component of teichoic acids found in the cell walls of Gram positive bacteria. Adonitol is a substrate of the enzyme, called ribitol dehydrogenase, which can be used for direct production of allitol from d-fructose without any by-product formation and this may have potential use as an industrial enzyme. Adonitol is also a moiety present in riboflavin (vitamin B2).

Originator

Sources: Journal - Chemical Society, London, Volume 64, Part 1
Curator's Comment: # Merck

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: ribitol dehydrogenase from Providencia alcalifaciens RIMD 1656011
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
A rapid, automated enzymatic fluorometric assay for determination of D-arabinitol in serum.
2000 Apr
Application of Saccharomyces cerevisiae and Pichia stipitis karyoductants to the production of ethanol from xylose.
2001
Quantitative determination of C-polysaccharide in Streptococcus pneumoniae capsular polysaccharides by use of high-performance anion-exchange chromatography with pulsed amperometric detection.
2001 Apr 6
[Effect of sodium fluoride mouth rinses containing xylitol and sorbitol on the number of Streptococcus mutans from human saliva].
2001 Jan
Xylitol production by recombinant Saccharomyces cerevisiae expressing the Pichia stipitis and Candida shehatae XYL1 genes.
2001 Jan
Chemostat study of xylitol production by Candida guilliermondii.
2001 Jan
Acceptance of the xylitol chewing gum regimen by preschool children and teachers in a Head Start program: a pilot study.
2001 Jan-Feb
Does chewing explain the caries-preventive results with xylitol?
2001 Jul
Expression of bifunctional enzymes with xylose reductase and xylitol dehydrogenase activity in Saccharomyces cerevisiae alters product formation during xylose fermentation.
2001 Jul
[Solutions for the hyperalimentation].
2001 May
Influence of maternal xylitol consumption on mother-child transmission of mutans streptococci: 6-year follow-up.
2001 May-Jun
Influence of temperature and pH on xylitol production from xylose by Debaryomyces hansenii.
2001 Oct 5
Extraction by reversed micelles of the intracellular enzyme xylose reductase.
2001 Spring
Activity of xylose reductase from Candida mogii grown in media containing different concentrations of rice straw hydrolysate.
2001 Spring
A six-week clinical study to compare the stain removal efficacy of three dentifrices.
2002
A clinical study to compare the anticalculus efficacy of three dentifrice formulations.
2002
Furfural, 5-hydroxymethyl furfural, and acetoin act as external electron acceptors during anaerobic fermentation of xylose in recombinant Saccharomyces cerevisiae.
2002 Apr 20
Population analysis of a binary bacterial culture by multi-parametric flow cytometry.
2002 Aug 7
Improved bone biomechanical properties in xylitol-fed aged rats.
2002 Jan
Effect of a triclosan-containing toothpaste supplemented with 10% xylitol on mutans streptococci in saliva and dental plaque. A 6-month clinical study.
2002 Jan-Feb
Metabolic behavior of immobilized Candida guilliermondii cells during batch xylitol production from sugarcane bagasse acid hydrolyzate.
2002 Jul 20
Metal trifluoromethanesulfonate-catalyzed regioselective borane-reductive ring opening of benzylidene acetals: a concise synthesis of 1,4-dideoxy-1,4-imino-L-xylitol.
2002 Mar 7
Influence of oxygen availability on cell growth and xylitol production by Candida guilliermondii.
2002 Spring
Xylose reductase and xylitol dehydrogenase activities of Candida guilliermondii as a function of different treatments of sugarcane bagasse hemicellulosic hydrolysate employing experimental design.
2002 Spring
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Ribitol kinase was assayed by measuring the residual ribitol after incubation by the colorimetric method, after the removal of proteins and phosphorylated compounds from the incubation mixture. The standard assay mixture contained ATP, 20 umol; ribitol, 25 umol; ennzyme solution containing 200-500 ug of protein.
Name Type Language
ADONITOL
MI  
Common Name English
MESO-RIBITOL
Common Name English
ADONIT
Common Name English
RIBO-PENTITOL
Common Name English
1,2,3,4,5-PENTANEPENTOL
Systematic Name English
ADONITOL [MI]
Common Name English
RIBITOL
Common Name English
NSC-16868
Code English
PENTITOL
Common Name English
ADONITE
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 666518
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LOINC 47884-2
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Code System Code Type Description
MERCK INDEX
m1427
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PRIMARY Merck Index
CHEBI
25899
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PRIMARY
CAS
488-81-3
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PRIMARY
EPA CompTox
DTXSID601032335
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PRIMARY
SMS_ID
300000017833
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DRUG BANK
DB14704
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WIKIPEDIA
RIBITOL
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PRIMARY
ECHA (EC/EINECS)
207-685-7
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PRIMARY
CHEBI
15963
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PRIMARY
FDA UNII
353ZQ9TVDA
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PRIMARY
NSC
16868
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PRIMARY