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Identification
- Generic Name
- 3-[5-(3-nitrophenyl)thiophen-2-yl]propanoic acid
- DrugBank Accession Number
- DB07139
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for 3-[5-(3-nitrophenyl)thiophen-2-yl]propanoic acid (DB07139)
- Weight
- Average: 277.296
Monoisotopic: 277.040878535 - Chemical Formula
- C13H11NO4S
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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Not Available
- Mechanism of action
Target Actions Organism AAldo-keto reductase family 1 member B1 inhibitorHumans - 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 nitrobenzenes. These are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Nitrobenzenes
- Direct Parent
- Nitrobenzenes
- Alternative Parents
- Nitroaromatic compounds / 2,5-disubstituted thiophenes / Heteroaromatic compounds / Propargyl-type 1,3-dipolar organic compounds / Organic oxoazanium compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organonitrogen compounds / Organic oxides show 2 more
- Substituents
- 2,5-disubstituted thiophene / Allyl-type 1,3-dipolar organic compound / Aromatic heteromonocyclic compound / C-nitro compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Heteroaromatic compound / Hydrocarbon derivative / Monocarboxylic acid or derivatives show 14 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- IHKCOKRMJRDWAL-UHFFFAOYSA-N
- InChI
- InChI=1S/C13H11NO4S/c15-13(16)7-5-11-4-6-12(19-11)9-2-1-3-10(8-9)14(17)18/h1-4,6,8H,5,7H2,(H,15,16)
- IUPAC Name
- 3-[5-(3-nitrophenyl)thiophen-2-yl]propanoic acid
- SMILES
- OC(=O)CCC1=CC=C(S1)C1=CC(=CC=C1)[N+]([O-])=O
References
- General References
- Not Available
- External Links
- PubChem Compound
- 25210476
- PubChem Substance
- 99443610
- ChemSpider
- 25056818
- ZINC
- ZINC000039131891
- PDBe Ligand
- 53N
- PDB Entries
- 3dn5 / 4yu1
Clinical Trials
- Clinical Trials
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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 0.00483 mg/mL ALOGPS logP 3.67 ALOGPS logP 3.55 Chemaxon logS -4.8 ALOGPS pKa (Strongest Acidic) 4.37 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 80.44 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 70.25 m3·mol-1 Chemaxon Polarizability 27.67 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
Property Value Probability Human Intestinal Absorption + 0.9063 Blood Brain Barrier + 0.7933 Caco-2 permeable - 0.5519 P-glycoprotein substrate Non-substrate 0.8194 P-glycoprotein inhibitor I Non-inhibitor 0.9003 P-glycoprotein inhibitor II Non-inhibitor 0.9255 Renal organic cation transporter Non-inhibitor 0.9328 CYP450 2C9 substrate Non-substrate 0.6519 CYP450 2D6 substrate Non-substrate 0.8252 CYP450 3A4 substrate Non-substrate 0.6006 CYP450 1A2 substrate Inhibitor 0.6377 CYP450 2C9 inhibitor Non-inhibitor 0.7377 CYP450 2D6 inhibitor Non-inhibitor 0.8981 CYP450 2C19 inhibitor Non-inhibitor 0.7449 CYP450 3A4 inhibitor Non-inhibitor 0.9615 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7727 Ames test AMES toxic 0.8595 Carcinogenicity Non-carcinogens 0.7637 Biodegradation Not ready biodegradable 0.6324 Rat acute toxicity 2.5952 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9411 hERG inhibition (predictor II) Non-inhibitor 0.9189
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-001i-0190000000-b739583c5269a0787790 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]- 151.40018 predictedDeepCCS 1.0 (2019) [M+H]+ 154.09181 predictedDeepCCS 1.0 (2019) [M+Na]+ 161.94766 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Catalyzes the NADPH-dependent reduction of a wide variety of carbonyl-containing compounds to their corresponding alcohols. Displays enzymatic activity towards endogenous metabolites such as aromatic and aliphatic aldehydes, ketones, monosacharides, bile acids and xenobiotics substrates. Key enzyme in the polyol pathway, catalyzes reduction of glucose to sorbitol during hyperglycemia (PubMed:1936586). Reduces steroids and their derivatives and prostaglandins. Displays low enzymatic activity toward all-trans-retinal, 9-cis-retinal, and 13-cis-retinal (PubMed:12732097, PubMed:19010934, PubMed:8343525). Catalyzes the reduction of diverse phospholipid aldehydes such as 1-palmitoyl-2-(5-oxovaleroyl)-sn -glycero-3-phosphoethanolamin (POVPC) and related phospholipid aldehydes that are generated from the oxydation of phosphotidylcholine and phosphatdyleethanolamides (PubMed:17381426). Plays a role in detoxifying dietary and lipid-derived unsaturated carbonyls, such as crotonaldehyde, 4-hydroxynonenal, trans-2-hexenal, trans-2,4-hexadienal and their glutathione-conjugates carbonyls (GS-carbonyls) (PubMed:21329684)
- Specific Function
- Aldose reductase (nadph) activity
- Gene Name
- AKR1B1
- Uniprot ID
- P15121
- Uniprot Name
- Aldo-keto reductase family 1 member B1
- Molecular Weight
- 35853.125 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]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Drug created at September 15, 2010 21:19 / Updated at August 26, 2024 19:22