8-Hydroxy-2-oxa-bicyclo[3.3.1]non-6-ene-3,5-dicarboxylic acid

Identification

Generic Name
8-Hydroxy-2-oxa-bicyclo[3.3.1]non-6-ene-3,5-dicarboxylic acid
DrugBank Accession Number
DB08648
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 228.1987
Monoisotopic: 228.063388116
Chemical Formula
C10H12O6
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UP-proteinNot AvailableEscherichia coli (strain K12)
UChorismate mutase AroHNot AvailableBacillus subtilis (strain 168)
USecreted chorismate mutaseNot AvailableMycobacterium tuberculosis
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

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as pyrans. These are compounds containing a pyran ring, which is a six-member heterocyclic, non-aromatic ring with five carbon atoms, one oxygen atom and two ring double bonds.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyrans
Sub Class
Not Available
Direct Parent
Pyrans
Alternative Parents
Oxanes / Dicarboxylic acids and derivatives / Secondary alcohols / Oxacyclic compounds / Dialkyl ethers / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Alcohol / Aliphatic heteropolycyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Dialkyl ether / Dicarboxylic acid or derivatives / Ether / Hydrocarbon derivative / Organic oxide
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
KRZHNRULRHECRF-JQCUSGDOSA-N
InChI
InChI=1S/C10H12O6/c11-5-1-2-10(9(14)15)3-6(5)16-7(4-10)8(12)13/h1-2,5-7,11H,3-4H2,(H,12,13)(H,14,15)/t5-,6-,7+,10+/m1/s1
IUPAC Name
(1R,3S,5S,8R)-8-hydroxy-2-oxabicyclo[3.3.1]non-6-ene-3,5-dicarboxylic acid
SMILES
[H][C@]12C[C@](C[C@H](O1)C(O)=O)(C=C[C@H]2O)C(O)=O

References

General References
Not Available
PubChem Compound
445314
PubChem Substance
99445119
ChemSpider
392988
BindingDB
50173884
ChEMBL
CHEMBL197577
ZINC
ZINC000005851130
PDBe Ligand
TSA
PDB Entries
1ecm / 1fig / 2cht / 2fp2 / 2gtv / 2w1a / 3csm / 3zp4 / 4csm / 5ckx
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Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

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

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility78.1 mg/mLALOGPS
logP-0.14ALOGPS
logP-0.36ChemAxon
logS-0.47ALOGPS
pKa (Strongest Acidic)3.31ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area104.06 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity51.19 m3·mol-1ChemAxon
Polarizability20.3 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

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Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Prephenate dehydratase activity
Specific Function
Catalyzes the Claisen rearrangement of chorismate to prephenate and the decarboxylation/dehydration of prephenate to phenylpyruvate.
Gene Name
pheA
Uniprot ID
P0A9J8
Uniprot Name
P-protein
Molecular Weight
43110.945 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Kind
Protein
Organism
Bacillus subtilis (strain 168)
Pharmacological action
Unknown
General Function
Chorismate mutase activity
Specific Function
Catalyzes the Claisen rearrangement of chorismate to prephenate. Probably involved in the aromatic amino acid biosynthesis.
Gene Name
aroH
Uniprot ID
P19080
Uniprot Name
Chorismate mutase AroH
Molecular Weight
14516.91 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Unknown
General Function
Catalyzes the Claisen rearrangement of chorismate to prephenate. May play some role in the pathogenicity.
Specific Function
Chorismate mutase activity
Gene Name
Not Available
Uniprot ID
P9WIB9
Uniprot Name
Secreted chorismate mutase
Molecular Weight
21944.46 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at September 15, 2010 21:33 / Updated at June 16, 2021 12:31