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Identification
NameD-Sorbitol
Accession NumberDB01638  (EXPT02939)
TypeSmall Molecule
GroupsApproved
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.

Structure
Thumb
Synonyms
(−)-sorbitol
D-glucitol
L-Gulitol
External Identifiers Not Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNII506T60A25R
CAS number50-70-4
WeightAverage: 182.1718
Monoisotopic: 182.07903818
Chemical FormulaC6H14O6
InChI KeyInChIKey=FBPFZTCFMRRESA-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[[email protected]](O)[C@@H](O)[[email protected]](O)[[email protected]](O)CO
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassSugar alcohols
Direct ParentSugar alcohols
Alternative Parents
Substituents
  • Sugar alcohol
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Pharmacology
IndicationUsed as a non-stimulant laxative via an oral suspension or enema.
PharmacodynamicsNot Available
Mechanism of actionSorbitol exerts its laxative effect by drawing water into the large intestine, thereby stimulating bowel movements.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
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
ToxicityAcute oral toxicity (LD50): 15900 mg/kg [Rat].
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Fructose intolerance, hereditaryDiseaseSMP00725
GalactosemiaDiseaseSMP00182
FructosuriaDiseaseSMP00561
Galactose MetabolismMetabolicSMP00043
Fructose and Mannose DegradationMetabolicSMP00064
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.6525
Blood Brain Barrier-0.5997
Caco-2 permeable-0.8958
P-glycoprotein substrateNon-substrate0.662
P-glycoprotein inhibitor INon-inhibitor0.9535
P-glycoprotein inhibitor IINon-inhibitor0.9551
Renal organic cation transporterNon-inhibitor0.9252
CYP450 2C9 substrateNon-substrate0.8706
CYP450 2D6 substrateNon-substrate0.878
CYP450 3A4 substrateNon-substrate0.7431
CYP450 1A2 substrateNon-inhibitor0.824
CYP450 2C9 inhibitorNon-inhibitor0.9419
CYP450 2D6 inhibitorNon-inhibitor0.9412
CYP450 2C19 inhibitorNon-inhibitor0.9232
CYP450 3A4 inhibitorNon-inhibitor0.9402
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.958
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.7823
BiodegradationReady biodegradable0.8595
Rat acute toxicity1.1260 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9709
hERG inhibition (predictor II)Non-inhibitor0.9329
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
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 Solubility229.0 mg/mLALOGPS
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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-1zf7000000-19d96a9ba7ba0c482c83View in MoNA
GC-MSGC-MS Spectrum - GC-MS (6 TMS)splash10-3ztf000000-d907b75f68a7927501a7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-xz00000000-700285f86eac0a3501d1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-z000000000-84676b839b145250d67dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-z000000000-dce72cab270c488d65daView in MoNA
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
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 ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSDownload (47.1 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Streptomyces rubiginosus
Pharmacological action
unknown
General Function:
Xylose isomerase activity
Specific Function:
Involved in D-xylose catabolism.
Gene Name:
xylA
Uniprot ID:
P24300
Molecular Weight:
43226.915 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 ]
Kind
Protein
Organism
Actinoplanes missouriensis (strain ATCC 14538 / DSM 43046 / CBS 188.64 / JCM 3121 / NCIMB 12654 / NBRC 102363 / 431)
Pharmacological action
unknown
General Function:
Xylose isomerase activity
Specific Function:
Not Available
Gene Name:
xylA
Uniprot ID:
P12851
Molecular Weight:
43498.425 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 ]
Kind
Protein
Organism
Arthrobacter sp. (strain NRRL B3728)
Pharmacological action
unknown
General Function:
Xylose isomerase activity
Specific Function:
Not Available
Gene Name:
xylA
Uniprot ID:
P12070
Molecular Weight:
43291.15 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 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
unknown
General Function:
Metal ion binding
Specific Function:
Involved in the glycolate utilization. Catalyzes the condensation and subsequent hydrolysis of acetyl-coenzyme A (acetyl-CoA) and glyoxylate to form malate and CoA.
Gene Name:
glcB
Uniprot ID:
P37330
Molecular Weight:
80487.88 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 ]
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Drug created on June 13, 2005 07:24 / Updated on October 27, 2015 20:55