NAV

beta-D-glucuronic acid

Identification

Generic Name
beta-D-glucuronic acid
DrugBank Accession Number
DB03156
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 194.1394
Monoisotopic: 194.042652674
Chemical Formula
C6H10O7
Synonyms
  • beta-D-Glucopyranuronic acid
  • GlcAb
  • GlcAβ
  • β-D-glucopyranuronic acid
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UHyaluronate lyaseNot AvailableStreptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)
UChondroitinase-ACNot AvailablePedobacter heparinus (strain ATCC 13125 / DSM 2366 / NCIB 9290)
UAlpha-glucuronidaseNot AvailableGeobacillus stearothermophilus
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Hygienium Hand Sanitizer wipesbeta-D-glucuronic acid (0.36 g/100mL) + Ethanol (70 mL/100mL)ClothTopicalGrande Gloria Production S.A.2020-03-30Not applicableUS flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as glucuronic acid derivatives. These are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Glucuronic acid derivatives
Alternative Parents
Beta hydroxy acids and derivatives / Pyrans / Oxanes / Monosaccharides / Secondary alcohols / Hemiacetals / Polyols / Oxacyclic compounds / Monocarboxylic acids and derivatives / Carboxylic acids
show 3 more
Substituents
Alcohol / Aliphatic heteromonocyclic compound / Beta-hydroxy acid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Glucuronic acid or derivatives / Hemiacetal / Hydrocarbon derivative / Hydroxy acid
show 9 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
D-glucopyranuronic acid (CHEBI:28860)
Affected organisms
Not Available

Chemical Identifiers

UNII
00A9JB14O6
CAS number
23018-83-9
InChI Key
AEMOLEFTQBMNLQ-QIUUJYRFSA-N
InChI
InChI=1S/C6H10O7/c7-1-2(8)4(5(10)11)13-6(12)3(1)9/h1-4,6-9,12H,(H,10,11)/t1-,2-,3+,4-,6+/m0/s1
IUPAC Name
(2S,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid
SMILES
O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O

References

Synthesis Reference

Gerhard Weber, Karlheinz Schrader, "D-glucuronic acid-urea condensate preparation for smoothing human skin." U.S. Patent US4703041, issued October 27, 1987.

US4703041
General References
Not Available
KEGG Compound
C08350
PubChem Compound
441478
PubChem Substance
46504768
ChemSpider
390202
ChEBI
28860
ChEMBL
CHEMBL1159524
ZINC
ZINC000004097543
PDBe Ligand
BDP
Wikipedia
Glucuronic_acid
PDB Entries
1cap / 1gqk / 1gql / 1hm3 / 1hmw / 1hua / 1loh / 1lxk / 1lxm / 1n7q …
show 79 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
ClothTopical
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)165 °CPhysProp
water solubility485 mg/mLHMP experimental
logP-2.57HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility295.0 mg/mLALOGPS
logP-2.3ALOGPS
logP-2.6Chemaxon
logS0.18ALOGPS
pKa (Strongest Acidic)3.21Chemaxon
pKa (Strongest Basic)-3.7Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area127.45 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity35.79 m3·mol-1Chemaxon
Polarizability16.37 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.578
Blood Brain Barrier+0.5892
Caco-2 permeable-0.7
P-glycoprotein substrateNon-substrate0.6735
P-glycoprotein inhibitor INon-inhibitor0.9619
P-glycoprotein inhibitor IINon-inhibitor0.9857
Renal organic cation transporterNon-inhibitor0.9366
CYP450 2C9 substrateNon-substrate0.8459
CYP450 2D6 substrateNon-substrate0.9061
CYP450 3A4 substrateNon-substrate0.7387
CYP450 1A2 substrateNon-inhibitor0.9586
CYP450 2C9 inhibitorNon-inhibitor0.977
CYP450 2D6 inhibitorNon-inhibitor0.9713
CYP450 2C19 inhibitorNon-inhibitor0.9793
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.97
Ames testNon AMES toxic0.9426
CarcinogenicityNon-carcinogens0.9428
BiodegradationReady biodegradable0.7998
Rat acute toxicity1.6092 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9828
hERG inhibition (predictor II)Non-inhibitor0.9744
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0fvi-3900000000-623cfb10797e088f31a3
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0900000000-3a39449d2e6aa10234be
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-2900000000-48ed0829b5fce66f8d71
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-005a-2900000000-010a8307eb17a5b4a8cc
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a71-9500000000-c499dd509a03e2597d7a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-9100000000-bcbcf0fb9fe4df88bc0f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0q29-9200000000-d90c328665d0b887bfa1
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-135.085
predicted
DeepCCS 1.0 (2019)
[M+H]+137.24315
predicted
DeepCCS 1.0 (2019)
[M+Na]+144.51854
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Details1. Hyaluronate lyase
Kind
Protein
Organism
Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)
Pharmacological action
Unknown
General Function
Hyaluronate lyase activity
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
Q54873
Uniprot Name
Hyaluronate lyase
Molecular Weight
120770.645 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. [Article]
  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. [Article]
Details2. Chondroitinase-AC
Kind
Protein
Organism
Pedobacter heparinus (strain ATCC 13125 / DSM 2366 / NCIB 9290)
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Not Available
Gene Name
cslA
Uniprot ID
Q59288
Uniprot Name
Chondroitinase-AC
Molecular Weight
79693.285 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. [Article]
  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. [Article]
Details3. Alpha-glucuronidase
Kind
Protein
Organism
Geobacillus stearothermophilus
Pharmacological action
Unknown
General Function
Xylan alpha-1,2-glucuronosidase activity
Specific Function
Not Available
Gene Name
aguA
Uniprot ID
Q8VVD2
Uniprot Name
Xylan alpha-1,2-glucuronidase
Molecular Weight
78485.96 Da

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52