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Identification
NameD-Sorbitol
Accession NumberDB01638  (EXPT02939)
TypeSmall Molecule
GroupsExperimental
Description

A polyhydric alcohol with about half the sweetness of sucrose. Sorbitol occurs naturally and is also produced synthetically from glucose. It was formerly used as a diuretic and may still be used as a laxative and in irrigating solutions for some surgical procedures. It is also used in many manufacturing processes, as a pharmaceutical aid, and in several research applications. [PubChem]

Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixtures
Brand NameIngredients
Sorbitol-MannitolMannitol + D-Sorbitol
CategoriesNot Available
CAS number50-70-4
WeightAverage: 182.1718
Monoisotopic: 182.07903818
Chemical FormulaC6H14O6
InChI KeyFBPFZTCFMRRESA-JGWLITMVSA-N
InChI
InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5-,6-/m1/s1
IUPAC Name
(2R,3R,4R,5S)-hexane-1,2,3,4,5,6-hexol
SMILES
OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganooxygen Compounds
ClassCarbohydrates and Carbohydrate Conjugates
SubclassSugar Alcohols
Direct parentSugar Alcohols
Alternative parentsSecondary Alcohols; 1,2-Diols; Polyamines; Primary Alcohols
Substituents1,2-diol; secondary alcohol; polyol; polyamine; primary alcohol; alcohol
Classification descriptionThis compound belongs to the sugar alcohols. These are hydrogenated forms of carbohydrate, whose carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationSorbitol will either be excreted in the urine by the kidneys, or metabolized to carbon dioxide and dextrose.
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.6525
Blood Brain Barrier - 0.5997
Caco-2 permeable - 0.8958
P-glycoprotein substrate Non-substrate 0.662
P-glycoprotein inhibitor I Non-inhibitor 0.9535
P-glycoprotein inhibitor II Non-inhibitor 0.9551
Renal organic cation transporter Non-inhibitor 0.9252
CYP450 2C9 substrate Non-substrate 0.8706
CYP450 2D6 substrate Non-substrate 0.878
CYP450 3A4 substrate Non-substrate 0.7431
CYP450 1A2 substrate Non-inhibitor 0.824
CYP450 2C9 substrate Non-inhibitor 0.9419
CYP450 2D6 substrate Non-inhibitor 0.9412
CYP450 2C19 substrate Non-inhibitor 0.9232
CYP450 3A4 substrate Non-inhibitor 0.9402
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.958
Ames test Non AMES toxic 0.9132
Carcinogenicity Non-carcinogens 0.7823
Biodegradation Ready biodegradable 0.8595
Rat acute toxicity 1.1260 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9709
hERG inhibition (predictor II) Non-inhibitor 0.9329
Pharmacoeconomics
Manufacturers
  • Baxter healthcare corp
  • B braun medical inc
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point111http://pubchem.ncbi.nlm.nih.gov/compound/5780?from=summary
water solubility2.75E+006 mg/L (at 30 °C)MULLIN,JW (1972)
logP-2.20SANGSTER (1994)
logS1.09ADME Research, USCD
pKa13.6BENSON,FR (1978)
Predicted Properties
PropertyValueSource
Water Solubility229.0ALOGPS
logP-2.7ALOGPS
logP-3.7ChemAxon
logS0.1ALOGPS
pKa (Strongest Acidic)12.59ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area121.38 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity38.4 m3·mol-1ChemAxon
Polarizability17.12 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraGC-MSMS/MS1D NMR2D NMR
References
Synthesis Reference

Gerhard Darsow, “Process for the preparation of epimer-free sugar alcohols from the group consisting of xylitol, sorbitol (D-glucitol), 4-O-.beta.-D-galactopyranosyl-D-glucitol and 4-O-.alpha.-D-glucopyranosyl-D-sorbitol.” U.S. Patent US5162517, issued August, 1985.

US5162517
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD00096
KEGG CompoundC00794
PubChem Compound5780
PubChem Substance46507030
ChemSpider440
ChEBI17924
ChEMBL
PharmGKBPA451455
HETSOR
WikipediaSorbitol
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Xylose isomerase

Kind: protein

Organism: Streptomyces rubiginosus

Pharmacological action: unknown

Components

Name UniProt ID Details
Xylose isomerase P24300 Details

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
  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

2. Xylose isomerase

Kind: protein

Organism: Actinoplanes missouriensis (strain ATCC 14538 / DSM 43046 / CBS 188.64 / JCM 3121 / NCIMB 12654 / NBRC 102363 / 431)

Pharmacological action: unknown

Components

Name UniProt ID Details
Xylose isomerase P12851 Details

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
  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

3. Xylose isomerase

Kind: protein

Organism: Arthrobacter sp. (strain NRRL B3728)

Pharmacological action: unknown

Components

Name UniProt ID Details
Xylose isomerase P12070 Details

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
  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

4. Malate synthase G

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: unknown

Components

Name UniProt ID Details
Malate synthase G P37330 Details

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
  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

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Drug created on June 13, 2005 07:24 / Updated on December 01, 2014 10:38