[4-({5-(AMINOCARBONYL)-4-[(3-METHYLPHENYL)AMINO]PYRIMIDIN-2-YL}AMINO)PHENYL]ACETIC ACID
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Identification
- Generic Name
- [4-({5-(AMINOCARBONYL)-4-[(3-METHYLPHENYL)AMINO]PYRIMIDIN-2-YL}AMINO)PHENYL]ACETIC ACID
- DrugBank Accession Number
- DB08513
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 377.3966
Monoisotopic: 377.148789499 - Chemical Formula
- C20H19N5O3
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UMitogen-activated protein kinase 1 Not Available Humans UInsulin receptor Not Available Humans UInsulin receptor substrate 1 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
- Not Available
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as pyrimidinecarboxylic acids and derivatives. These are compounds containing a pyrimidine ring which bears a carboxylic acid group (or a derivative thereof).
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Diazines
- Sub Class
- Pyrimidines and pyrimidine derivatives
- Direct Parent
- Pyrimidinecarboxylic acids and derivatives
- Alternative Parents
- Aniline and substituted anilines / Toluenes / Aminopyrimidines and derivatives / Imidolactams / Vinylogous amides / Heteroaromatic compounds / Amino acids / Primary carboxylic acid amides / Carboxylic acids / Azacyclic compounds show 6 more
- Substituents
- Amine / Amino acid / Amino acid or derivatives / Aminopyrimidine / Aniline or substituted anilines / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxamide group show 18 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
- PAIQRYUOBBCBSE-UHFFFAOYSA-N
- InChI
- InChI=1S/C20H19N5O3/c1-12-3-2-4-15(9-12)23-19-16(18(21)28)11-22-20(25-19)24-14-7-5-13(6-8-14)10-17(26)27/h2-9,11H,10H2,1H3,(H2,21,28)(H,26,27)(H2,22,23,24,25)
- IUPAC Name
- 2-[4-({5-carbamoyl-4-[(3-methylphenyl)amino]pyrimidin-2-yl}amino)phenyl]acetic acid
- SMILES
- CC1=CC(NC2=NC(NC3=CC=C(CC(O)=O)C=C3)=NC=C2C(N)=O)=CC=C1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 24871491
- PubChem Substance
- 99444984
- ChemSpider
- 25058535
- ZINC
- ZINC000039018730
- PDBe Ligand
- S91
- PDB Entries
- 2z7l / 2z8c
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 0.0219 mg/mL ALOGPS logP 3.15 ALOGPS logP 3.71 Chemaxon logS -4.2 ALOGPS pKa (Strongest Acidic) 2.34 Chemaxon pKa (Strongest Basic) 4.16 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 130.23 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 105.38 m3·mol-1 Chemaxon Polarizability 39.47 Å3 Chemaxon Number of Rings 3 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 + 0.9254 Blood Brain Barrier + 0.8202 Caco-2 permeable - 0.6224 P-glycoprotein substrate Non-substrate 0.7051 P-glycoprotein inhibitor I Non-inhibitor 0.8618 P-glycoprotein inhibitor II Non-inhibitor 0.9721 Renal organic cation transporter Non-inhibitor 0.9515 CYP450 2C9 substrate Non-substrate 0.7832 CYP450 2D6 substrate Non-substrate 0.8817 CYP450 3A4 substrate Non-substrate 0.7451 CYP450 1A2 substrate Non-inhibitor 0.6078 CYP450 2C9 inhibitor Non-inhibitor 0.9468 CYP450 2D6 inhibitor Non-inhibitor 0.9489 CYP450 2C19 inhibitor Non-inhibitor 0.9519 CYP450 3A4 inhibitor Non-inhibitor 0.9343 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.963 Ames test Non AMES toxic 0.78 Carcinogenicity Non-carcinogens 0.8616 Biodegradation Not ready biodegradable 0.9029 Rat acute toxicity 2.3969 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9892 hERG inhibition (predictor II) Non-inhibitor 0.9003
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-0009000000-c740a1938b2d7c8f744c Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-003r-0129000000-e1d5eea8739762a525a0 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-03fr-0009000000-ab427375b2fab45a35ec Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-00o9-0049000000-3a86d29559e3a53c4ddd Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-03yr-0169000000-84f70505556c7715ba1c Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-000i-1394000000-6089db355502bd709a17 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]- 186.9819 predictedDeepCCS 1.0 (2019) [M+H]+ 189.33992 predictedDeepCCS 1.0 (2019) [M+Na]+ 196.05312 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsMitogen-activated protein kinase 1
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Serine/threonine kinase which acts as an essential component of the MAP kinase signal transduction pathway. MAPK1/ERK2 and MAPK3/ERK1 are the 2 MAPKs which play an important role in the MAPK/ERK cascade. They participate also in a signaling cascade initiated by activated KIT and KITLG/SCF. Depending on the cellular context, the MAPK/ERK cascade mediates diverse biological functions such as cell growth, adhesion, survival and differentiation through the regulation of transcription, translation, cytoskeletal rearrangements. The MAPK/ERK cascade also plays a role in initiation and regulation of meiosis, mitosis, and postmitotic functions in differentiated cells by phosphorylating a number of transcription factors. About 160 substrates have already been discovered for ERKs. Many of these substrates are localized in the nucleus, and seem to participate in the regulation of transcription upon stimulation. However, other substrates are found in the cytosol as well as in other cellular organelles, and those are responsible for processes such as translation, mitosis and apoptosis. Moreover, the MAPK/ERK cascade is also involved in the regulation of the endosomal dynamics, including lysosome processing and endosome cycling through the perinuclear recycling compartment (PNRC); as well as in the fragmentation of the Golgi apparatus during mitosis. The substrates include transcription factors (such as ATF2, BCL6, ELK1, ERF, FOS, HSF4 or SPZ1), cytoskeletal elements (such as CANX, CTTN, GJA1, MAP2, MAPT, PXN, SORBS3 or STMN1), regulators of apoptosis (such as BAD, BTG2, CASP9, DAPK1, IER3, MCL1 or PPARG), regulators of translation (such as EIF4EBP1 and FXR1) and a variety of other signaling-related molecules (like ARHGEF2, DCC, FRS2 or GRB10). Protein kinases (such as RAF1, RPS6KA1/RSK1, RPS6KA3/RSK2, RPS6KA2/RSK3, RPS6KA6/RSK4, SYK, MKNK1/MNK1, MKNK2/MNK2, RPS6KA5/MSK1, RPS6KA4/MSK2, MAPKAPK3 or MAPKAPK5) and phosphatases (such as DUSP1, DUSP4, DUSP6 or DUSP16) are other substrates which enable the propagation the MAPK/ERK signal to additional cytosolic and nuclear targets, thereby extending the specificity of the cascade. Mediates phosphorylation of TPR in response to EGF stimulation. May play a role in the spindle assembly checkpoint. Phosphorylates PML and promotes its interaction with PIN1, leading to PML degradation. Phosphorylates CDK2AP2 (By similarity)
- Specific Function
- ATP binding
- Gene Name
- MAPK1
- Uniprot ID
- P28482
- Uniprot Name
- Mitogen-activated protein kinase 1
- Molecular Weight
- 41389.265 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. DetailsInsulin receptor
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Receptor tyrosine kinase which mediates the pleiotropic actions of insulin. Binding of insulin leads to phosphorylation of several intracellular substrates, including, insulin receptor substrates (IRS1, 2, 3, 4), SHC, GAB1, CBL and other signaling intermediates. Each of these phosphorylated proteins serve as docking proteins for other signaling proteins that contain Src-homology-2 domains (SH2 domain) that specifically recognize different phosphotyrosine residues, including the p85 regulatory subunit of PI3K and SHP2. Phosphorylation of IRSs proteins lead to the activation of two main signaling pathways: the PI3K-AKT/PKB pathway, which is responsible for most of the metabolic actions of insulin, and the Ras-MAPK pathway, which regulates expression of some genes and cooperates with the PI3K pathway to control cell growth and differentiation. Binding of the SH2 domains of PI3K to phosphotyrosines on IRS1 leads to the activation of PI3K and the generation of phosphatidylinositol-(3, 4, 5)-triphosphate (PIP3), a lipid second messenger, which activates several PIP3-dependent serine/threonine kinases, such as PDPK1 and subsequently AKT/PKB. The net effect of this pathway is to produce a translocation of the glucose transporter SLC2A4/GLUT4 from cytoplasmic vesicles to the cell membrane to facilitate glucose transport. Moreover, upon insulin stimulation, activated AKT/PKB is responsible for: anti-apoptotic effect of insulin by inducing phosphorylation of BAD; regulates the expression of gluconeogenic and lipogenic enzymes by controlling the activity of the winged helix or forkhead (FOX) class of transcription factors. Another pathway regulated by PI3K-AKT/PKB activation is mTORC1 signaling pathway which regulates cell growth and metabolism and integrates signals from insulin. AKT mediates insulin-stimulated protein synthesis by phosphorylating TSC2 thereby activating mTORC1 pathway. The Ras/RAF/MAP2K/MAPK pathway is mainly involved in mediating cell growth, survival and cellular differentiation of insulin. Phosphorylated IRS1 recruits GRB2/SOS complex, which triggers the activation of the Ras/RAF/MAP2K/MAPK pathway. In addition to binding insulin, the insulin receptor can bind insulin-like growth factors (IGFI and IGFII). Isoform Short has a higher affinity for IGFII binding. When present in a hybrid receptor with IGF1R, binds IGF1. PubMed:12138094 shows that hybrid receptors composed of IGF1R and INSR isoform Long are activated with a high affinity by IGF1, with low affinity by IGF2 and not significantly activated by insulin, and that hybrid receptors composed of IGF1R and INSR isoform Short are activated by IGF1, IGF2 and insulin. In contrast, PubMed:16831875 shows that hybrid receptors composed of IGF1R and INSR isoform Long and hybrid receptors composed of IGF1R and INSR isoform Short have similar binding characteristics, both bind IGF1 and have a low affinity for insulin. In adipocytes, inhibits lipolysis (By similarity)
- Specific Function
- amyloid-beta binding
- Gene Name
- INSR
- Uniprot ID
- P06213
- Uniprot Name
- Insulin receptor
- Molecular Weight
- 156331.465 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. DetailsInsulin receptor substrate 1
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- May mediate the control of various cellular processes by insulin. When phosphorylated by the insulin receptor binds specifically to various cellular proteins containing SH2 domains such as phosphatidylinositol 3-kinase p85 subunit or GRB2. Activates phosphatidylinositol 3-kinase when bound to the regulatory p85 subunit (By similarity)
- Specific Function
- insulin receptor binding
- Gene Name
- IRS1
- Uniprot ID
- P35568
- Uniprot Name
- Insulin receptor substrate 1
- Molecular Weight
- 131589.815 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 21:32 / Updated at June 12, 2020 16:52