2-[(1R)-2-carboxy-1-(naphthalen-1-ylmethyl)ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid
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Identification
- Generic Name
- 2-[(1R)-2-carboxy-1-(naphthalen-1-ylmethyl)ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid
- DrugBank Accession Number
- DB08731
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 403.3842
Monoisotopic: 403.105587281 - Chemical Formula
- C23H17NO6
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UBeta-lactamase Not Available Escherichia coli (strain K12) - 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 phthalimides. These are aromatic heterocyclic compounds containing a 1,3-dioxoisoindoline moiety. They are imide derivatives of phthalic anhydrides.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Isoindoles and derivatives
- Sub Class
- Isoindolines
- Direct Parent
- Phthalimides
- Alternative Parents
- Naphthalenes / Isoindoles / N-substituted carboxylic acid imides / Dicarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives show 1 more
- Substituents
- Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Carboxylic acid imide / Carboxylic acid imide, n-substituted / Dicarboxylic acid or derivatives / Hydrocarbon derivative show 9 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- GPOKTQCDBPECSS-MRXNPFEDSA-N
- InChI
- InChI=1S/C23H17NO6/c25-20(26)12-16(10-14-6-3-5-13-4-1-2-7-17(13)14)24-21(27)18-9-8-15(23(29)30)11-19(18)22(24)28/h1-9,11,16H,10,12H2,(H,25,26)(H,29,30)/t16-/m1/s1
- IUPAC Name
- 2-[(2R)-1-carboxy-3-(naphthalen-1-yl)propan-2-yl]-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid
- SMILES
- [H][C@](CC(O)=O)(CC1=CC=CC2=CC=CC=C12)N1C(=O)C2=CC=C(C=C2C1=O)C(O)=O
References
- General References
- Not Available
- External Links
- PubChem Compound
- 24764434
- PubChem Substance
- 99445202
- ChemSpider
- 25058908
- ZINC
- ZINC000016052515
- PDBe Ligand
- WH6
- PDB Entries
- 2r9x
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 0.00646 mg/mL ALOGPS logP 2.39 ALOGPS logP 3.35 Chemaxon logS -4.8 ALOGPS pKa (Strongest Acidic) 3.33 Chemaxon pKa (Strongest Basic) -6.5 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 111.98 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 107.74 m3·mol-1 Chemaxon Polarizability 40.76 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.8458 Blood Brain Barrier + 0.9248 Caco-2 permeable - 0.5572 P-glycoprotein substrate Non-substrate 0.6462 P-glycoprotein inhibitor I Non-inhibitor 0.9602 P-glycoprotein inhibitor II Non-inhibitor 0.9552 Renal organic cation transporter Non-inhibitor 0.8225 CYP450 2C9 substrate Non-substrate 0.7058 CYP450 2D6 substrate Non-substrate 0.8342 CYP450 3A4 substrate Non-substrate 0.5327 CYP450 1A2 substrate Non-inhibitor 0.8933 CYP450 2C9 inhibitor Non-inhibitor 0.9441 CYP450 2D6 inhibitor Non-inhibitor 0.931 CYP450 2C19 inhibitor Non-inhibitor 0.9591 CYP450 3A4 inhibitor Non-inhibitor 0.9353 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9538 Ames test Non AMES toxic 0.8678 Carcinogenicity Non-carcinogens 0.9078 Biodegradation Not ready biodegradable 0.7411 Rat acute toxicity 2.3849 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9879 hERG inhibition (predictor II) Non-inhibitor 0.9512
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0udr-0116900000-ebff7e205fdd4d824165 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-03dl-0519000000-48c14e3b9add5c5d0748 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0f7c-0709500000-60c57a368e1b909da837 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-014l-1902000000-1e31d8a216b1842f85bf Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0ufv-0900000000-8b412a74582dc34441f0 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0007-5920000000-4444bb6dcdc5dfcf08a6 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]- 194.34775 predictedDeepCCS 1.0 (2019) [M+H]+ 196.7433 predictedDeepCCS 1.0 (2019) [M+Na]+ 202.65584 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsBeta-lactamase
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- Beta-lactamase activity
- Specific Function
- This protein is a serine beta-lactamase with a substrate specificity for cephalosporins.
- Gene Name
- ampC
- Uniprot ID
- P00811
- Uniprot Name
- Beta-lactamase
- Molecular Weight
- 41555.3 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 21:34 / Updated at June 12, 2020 16:52