Coumarin 120
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Identification
- Generic Name
- Coumarin 120
- DrugBank Accession Number
- DB08168
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 175.184
Monoisotopic: 175.063328537 - Chemical Formula
- C10H9NO2
- Synonyms
- 7-Amino-4-methylcoumarin
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism APeptidyl-prolyl cis-trans isomerase A inhibitorHumans UPeptidyl-prolyl cis-trans isomerase A Not Available Escherichia coli (strain K12) UPeptidyl-prolyl cis-trans isomerase F, mitochondrial Not Available Humans UHistone deacetylase 8 Not Available Humans - 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
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).
- Kingdom
- Organic compounds
- Super Class
- Phenylpropanoids and polyketides
- Class
- Coumarins and derivatives
- Sub Class
- Not Available
- Direct Parent
- Coumarins and derivatives
- Alternative Parents
- 1-benzopyrans / Pyranones and derivatives / Benzenoids / Heteroaromatic compounds / Lactones / Oxacyclic compounds / Primary amines / Organopnictogen compounds / Organooxygen compounds / Organic oxides show 1 more
- Substituents
- 1-benzopyran / Amine / Aromatic heteropolycyclic compound / Benzenoid / Benzopyran / Coumarin / Heteroaromatic compound / Hydrocarbon derivative / Lactone / Organic nitrogen compound show 10 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- 7-aminocoumarins (CHEBI:51771)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- OCY3JCT44X
- CAS number
- 26093-31-2
- InChI Key
- GLNDAGDHSLMOKX-UHFFFAOYSA-N
- InChI
- InChI=1S/C10H9NO2/c1-6-4-10(12)13-9-5-7(11)2-3-8(6)9/h2-5H,11H2,1H3
- IUPAC Name
- 7-amino-4-methyl-2H-chromen-2-one
- SMILES
- CC1=CC(=O)OC2=C1C=CC(N)=C2
References
- General References
- Not Available
- External Links
- KEGG Compound
- C01386
- PubChem Compound
- 92249
- PubChem Substance
- 99444639
- ChemSpider
- 83285
- BindingDB
- 71742
- ChEBI
- 51771
- ChEMBL
- CHEMBL270672
- ZINC
- ZINC000000057949
- PDBe Ligand
- MCM
- PDB Entries
- 1vai / 1vdn / 2v5w / 3ewf / 4fz3 / 4qa5 / 4qa6 / 4qa7 / 5bwl / 5d1c … show 11 more
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 1.3 mg/mL ALOGPS logP 1.59 ALOGPS logP 1.25 Chemaxon logS -2.1 ALOGPS pKa (Strongest Basic) 3.37 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 52.32 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 50.53 m3·mol-1 Chemaxon Polarizability 17.93 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 + 0.986 Blood Brain Barrier + 0.875 Caco-2 permeable + 0.6716 P-glycoprotein substrate Non-substrate 0.7337 P-glycoprotein inhibitor I Non-inhibitor 0.8339 P-glycoprotein inhibitor II Non-inhibitor 0.9153 Renal organic cation transporter Non-inhibitor 0.8632 CYP450 2C9 substrate Non-substrate 0.7603 CYP450 2D6 substrate Non-substrate 0.7489 CYP450 3A4 substrate Non-substrate 0.6194 CYP450 1A2 substrate Inhibitor 0.9003 CYP450 2C9 inhibitor Non-inhibitor 0.8614 CYP450 2D6 inhibitor Non-inhibitor 0.8836 CYP450 2C19 inhibitor Non-inhibitor 0.7249 CYP450 3A4 inhibitor Non-inhibitor 0.5351 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7116 Ames test Non AMES toxic 0.9133 Carcinogenicity Non-carcinogens 0.888 Biodegradation Not ready biodegradable 0.78 Rat acute toxicity 1.9424 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8733 hERG inhibition (predictor II) Non-inhibitor 0.9058
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 136.71779 predictedDeepCCS 1.0 (2019) [M+H]+ 139.27449 predictedDeepCCS 1.0 (2019) [M+Na]+ 147.39201 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsPeptidyl-prolyl cis-trans isomerase A
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Catalyzes the cis-trans isomerization of proline imidic peptide bonds in oligopeptides (PubMed:2001362, PubMed:20676357, PubMed:21245143, PubMed:21593166, PubMed:25678563). Exerts a strong chemotactic effect on leukocytes partly through activation of one of its membrane receptors BSG/CD147, initiating a signaling cascade that culminates in MAPK/ERK activation (PubMed:11943775, PubMed:21245143). Activates endothelial cells (ECs) in a pro-inflammatory manner by stimulating activation of NF-kappa-B and ERK, JNK and p38 MAP-kinases and by inducing expression of adhesion molecules including SELE and VCAM1 (PubMed:15130913). Induces apoptosis in ECs by promoting the FOXO1-dependent expression of CCL2 and BCL2L11 which are involved in EC chemotaxis and apoptosis (PubMed:31063815). In response to oxidative stress, initiates proapoptotic and antiapoptotic signaling in ECs via activation of NF-kappa-B and AKT1 and up-regulation of antiapoptotic protein BCL2 (PubMed:23180369). Negatively regulates MAP3K5/ASK1 kinase activity, autophosphorylation and oxidative stress-induced apoptosis mediated by MAP3K5/ASK1 (PubMed:26095851). Necessary for the assembly of TARDBP in heterogeneous nuclear ribonucleoprotein (hnRNP) complexes and regulates TARDBP binding to RNA UG repeats and TARDBP-dependent expression of HDAC6, ATG7 and VCP which are involved in clearance of protein aggregates (PubMed:25678563). Plays an important role in platelet activation and aggregation (By similarity). Regulates calcium mobilization and integrin ITGA2B:ITGB3 bidirectional signaling via increased ROS production as well as by facilitating the interaction between integrin and the cell cytoskeleton (By similarity). Binds heparan sulfate glycosaminoglycans (PubMed:11943775). Inhibits replication of influenza A virus (IAV) (PubMed:19207730). Inhibits ITCH/AIP4-mediated ubiquitination of matrix protein 1 (M1) of IAV by impairing the interaction of ITCH/AIP4 with M1, followed by the suppression of the nuclear export of M1, and finally reduction of the replication of IAV (PubMed:22347431, PubMed:30328013)
- Specific Function
- cyclosporin A binding
- Gene Name
- PPIA
- Uniprot ID
- P62937
- Uniprot Name
- Peptidyl-prolyl cis-trans isomerase A
- Molecular Weight
- 18012.42 Da
References
- 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]
2. DetailsPeptidyl-prolyl cis-trans isomerase A
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- PPIases accelerate the folding of proteins (Probable). It catalyzes the cis-trans isomerization of proline imidic peptide bonds in oligopeptides (PubMed:2190212).
- Specific Function
- peptidyl-prolyl cis-trans isomerase activity
- Gene Name
- ppiA
- Uniprot ID
- P0AFL3
- Uniprot Name
- Peptidyl-prolyl cis-trans isomerase A
- Molecular Weight
- 20431.205 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- PPIase that catalyzes the cis-trans isomerization of proline imidic peptide bonds in oligopeptides and may therefore assist protein folding (PubMed:20676357). Involved in regulation of the mitochondrial permeability transition pore (mPTP) (PubMed:26387735). It is proposed that its association with the mPTP is masking a binding site for inhibiting inorganic phosphate (Pi) and promotes the open probability of the mPTP leading to apoptosis or necrosis; the requirement of the PPIase activity for this function is debated (PubMed:26387735). In cooperation with mitochondrial p53/TP53 is involved in activating oxidative stress-induced necrosis (PubMed:22726440). Involved in modulation of mitochondrial membrane F(1)F(0) ATP synthase activity and regulation of mitochondrial matrix adenine nucleotide levels (By similarity). Has anti-apoptotic activity independently of mPTP and in cooperation with BCL2 inhibits cytochrome c-dependent apoptosis (PubMed:19228691)
- Specific Function
- cyclosporin A binding
- Gene Name
- PPIF
- Uniprot ID
- P30405
- Uniprot Name
- Peptidyl-prolyl cis-trans isomerase F, mitochondrial
- Molecular Weight
- 22040.09 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]
4. DetailsHistone deacetylase 8
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Histone deacetylase that catalyzes the deacetylation of lysine residues on the N-terminal part of the core histones (H2A, H2B, H3 and H4) (PubMed:10748112, PubMed:10922473, PubMed:10926844, PubMed:14701748, PubMed:28497810). Histone deacetylation gives a tag for epigenetic repression and plays an important role in transcriptional regulation, cell cycle progression and developmental events (PubMed:10748112, PubMed:10922473, PubMed:10926844, PubMed:14701748). Histone deacetylases act via the formation of large multiprotein complexes (PubMed:10748112, PubMed:10922473, PubMed:10926844, PubMed:14701748). Also involved in the deacetylation of cohesin complex protein SMC3 regulating release of cohesin complexes from chromatin (PubMed:22885700). May play a role in smooth muscle cell contractility (PubMed:15772115). In addition to protein deacetylase activity, also has protein-lysine deacylase activity: acts as a protein decrotonylase by mediating decrotonylation ((2E)-butenoyl) of histones (PubMed:28497810)
- Specific Function
- DNA-binding transcription factor binding
- Gene Name
- HDAC8
- Uniprot ID
- Q9BY41
- Uniprot Name
- Histone deacetylase 8
- Molecular Weight
- 41757.29 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 21:29 / Updated at August 26, 2024 19:22