8-Hydroxy-2-oxa-bicyclo[3.3.1]non-6-ene-3,5-dicarboxylic acid
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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
Target Actions Organism UP-protein Not Available Escherichia coli (strain K12) UChorismate mutase AroH Not Available Bacillus subtilis (strain 168) USecreted chorismate mutase Not Available Mycobacterium 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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
- External Links
- 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 … show 1 more
Clinical Trials
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
Property Value Source Water Solubility 78.1 mg/mL ALOGPS logP -0.14 ALOGPS logP -0.36 Chemaxon logS -0.47 ALOGPS pKa (Strongest Acidic) 3.31 Chemaxon pKa (Strongest Basic) -3.3 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 104.06 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 51.19 m3·mol-1 Chemaxon Polarizability 20.3 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-06tf-6920000000-b83f29a9c38e3f2252c6 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-02t9-0940000000-60c29093c6d1151711a8 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-0190000000-ef8987666fa994b7bbb0 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0kg9-1920000000-ff70461655195fbb1835 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-000i-0930000000-a42c0e96f3825c70c2ab Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-000i-0900000000-268cab7db542b1f913af Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-000i-0900000000-8c233159af009e501e8a Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 147.19972 predictedDeepCCS 1.0 (2019) [M+H]+ 149.59563 predictedDeepCCS 1.0 (2019) [M+Na]+ 155.8095 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsP-protein
- 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
- 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]
2. DetailsChorismate mutase AroH
- 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
- 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]
3. DetailsSecreted chorismate mutase
- 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
- 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