METHYL 3-CHLORO-2-{3-[(2,5-DIHYDROXY-4-METHOXYPHENYL)AMINO]-3-OXOPROPYL}-4,6-DIHYDROXYBENZOATE
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Overview
- DrugBank ID
- DB08464
- Type
- Small Molecule
- Clinical Trials
- Phase 0
- 0
- Phase 1
- 0
- Phase 2
- 0
- Phase 3
- 0
- Phase 4
- 0
Identification
- Generic Name
- METHYL 3-CHLORO-2-{3-[(2,5-DIHYDROXY-4-METHOXYPHENYL)AMINO]-3-OXOPROPYL}-4,6-DIHYDROXYBENZOATE
- DrugBank Accession Number
- DB08464
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 411.79
Monoisotopic: 411.072094264 - Chemical Formula
- C18H18ClNO8
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UHeat shock protein HSP 90-beta Not Available Humans UEndoplasmin 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 p-hydroxybenzoic acid alkyl esters. These are aromatic compounds containing a benzoic acid, which is esterified with an alkyl group and para-substituted with a hydroxyl group.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Benzoic acids and derivatives
- Direct Parent
- p-Hydroxybenzoic acid alkyl esters
- Alternative Parents
- o-Hydroxybenzoic acid esters / Salicylic acid and derivatives / Methoxyphenols / 3-halobenzoic acids and derivatives / Anilides / Methoxyanilines / Benzoyl derivatives / Anisoles / Hydroquinones / Methoxybenzenes show 19 more
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / 2-chlorophenol / 2-halophenol / 3-halobenzoic acid or derivatives / 4-chlorophenol / 4-halophenol / Alkyl aryl ether / Anilide / Anisole / Aromatic homomonocyclic compound show 39 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- GUVWEHNRWHNDRF-UHFFFAOYSA-N
- InChI
- InChI=1S/C18H18ClNO8/c1-27-14-7-10(21)9(5-11(14)22)20-15(25)4-3-8-16(18(26)28-2)12(23)6-13(24)17(8)19/h5-7,21-24H,3-4H2,1-2H3,(H,20,25)
- IUPAC Name
- methyl 3-chloro-2-{2-[(2,5-dihydroxy-4-methoxyphenyl)carbamoyl]ethyl}-4,6-dihydroxybenzoate
- SMILES
- COC(=O)C1=C(CCC(=O)NC2=C(O)C=C(OC)C(O)=C2)C(Cl)=C(O)C=C1O
References
- General References
- Not Available
- External Links
- PubChem Compound
- 11373270
- PubChem Substance
- 99444935
- ChemSpider
- 9548187
- ZINC
- ZINC000024798681
- PDBe Ligand
- RDA
- PDB Entries
- 2fxs / 2gfd
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 0.0399 mg/mL ALOGPS logP 2.53 ALOGPS logP 3.38 Chemaxon logS -4 ALOGPS pKa (Strongest Acidic) 7.04 Chemaxon pKa (Strongest Basic) -4.1 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 5 Chemaxon Polar Surface Area 145.55 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 101.46 m3·mol-1 Chemaxon Polarizability 39.28 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 - 0.844 Blood Brain Barrier - 0.7534 Caco-2 permeable - 0.6833 P-glycoprotein substrate Substrate 0.5107 P-glycoprotein inhibitor I Non-inhibitor 0.8439 P-glycoprotein inhibitor II Non-inhibitor 0.752 Renal organic cation transporter Non-inhibitor 0.9281 CYP450 2C9 substrate Non-substrate 0.6973 CYP450 2D6 substrate Non-substrate 0.8542 CYP450 3A4 substrate Substrate 0.6508 CYP450 1A2 substrate Non-inhibitor 0.7207 CYP450 2C9 inhibitor Non-inhibitor 0.6886 CYP450 2D6 inhibitor Non-inhibitor 0.9194 CYP450 2C19 inhibitor Non-inhibitor 0.6256 CYP450 3A4 inhibitor Non-inhibitor 0.8387 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5291 Ames test Non AMES toxic 0.875 Carcinogenicity Non-carcinogens 0.9325 Biodegradation Not ready biodegradable 0.9693 Rat acute toxicity 2.5249 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9663 hERG inhibition (predictor II) Non-inhibitor 0.7265
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-003r-0059200000-aa6c4969036d7689863a Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0m90-0946300000-13875027c6f93ddf72c4 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0gx0-0119000000-139377b68ac5ce5d5c75 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0f79-2901000000-313afcaccb395f6c4466 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-002e-0968000000-e2e6703bc9a3176db1f3 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-9110000000-c87275acebfb6d3b237e 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]- 183.3719 predictedDeepCCS 1.0 (2019) [M+H]+ 185.7299 predictedDeepCCS 1.0 (2019) [M+Na]+ 192.39377 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsHeat shock protein HSP 90-beta
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Molecular chaperone that promotes the maturation, structural maintenance and proper regulation of specific target proteins involved for instance in cell cycle control and signal transduction. Undergoes a functional cycle linked to its ATPase activity. This cycle probably induces conformational changes in the client proteins, thereby causing their activation. Interacts dynamically with various co-chaperones that modulate its substrate recognition, ATPase cycle and chaperone function (PubMed:16478993, PubMed:19696785). Engages with a range of client protein classes via its interaction with various co-chaperone proteins or complexes, that act as adapters, simultaneously able to interact with the specific client and the central chaperone itself. Recruitment of ATP and co-chaperone followed by client protein forms a functional chaperone. After the completion of the chaperoning process, properly folded client protein and co-chaperone leave HSP90 in an ADP-bound partially open conformation and finally, ADP is released from HSP90 which acquires an open conformation for the next cycle (PubMed:26991466, PubMed:27295069). Apart from its chaperone activity, it also plays a role in the regulation of the transcription machinery. HSP90 and its co-chaperones modulate transcription at least at three different levels. They first alter the steady-state levels of certain transcription factors in response to various physiological cues. Second, they modulate the activity of certain epigenetic modifiers, such as histone deacetylases or DNA methyl transferases, and thereby respond to the change in the environment. Third, they participate in the eviction of histones from the promoter region of certain genes and thereby turn on gene expression (PubMed:25973397). Antagonizes STUB1-mediated inhibition of TGF-beta signaling via inhibition of STUB1-mediated SMAD3 ubiquitination and degradation (PubMed:24613385). Promotes cell differentiation by chaperoning BIRC2 and thereby protecting from auto-ubiquitination and degradation by the proteasomal machinery (PubMed:18239673). Main chaperone involved in the phosphorylation/activation of the STAT1 by chaperoning both JAK2 and PRKCE under heat shock and in turn, activates its own transcription (PubMed:20353823). Involved in the translocation into ERGIC (endoplasmic reticulum-Golgi intermediate compartment) of leaderless cargos (lacking the secretion signal sequence) such as the interleukin 1/IL-1; the translocation process is mediated by the cargo receptor TMED10 (PubMed:32272059)
- Specific Function
- ATP binding
- Gene Name
- HSP90AB1
- Uniprot ID
- P08238
- Uniprot Name
- Heat shock protein HSP 90-beta
- Molecular Weight
- 83263.475 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. DetailsEndoplasmin
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Molecular chaperone that functions in the processing and transport of secreted proteins (By similarity). When associated with CNPY3, required for proper folding of Toll-like receptors (By similarity). Functions in endoplasmic reticulum associated degradation (ERAD) (PubMed:18264092). Has ATPase activity (By similarity). May participate in the unfolding of cytosolic leaderless cargos (lacking the secretion signal sequence) such as the interleukin 1/IL-1 to facilitate their translocation into the ERGIC (endoplasmic reticulum-Golgi intermediate compartment) and secretion; the translocation process is mediated by the cargo receptor TMED10 (PubMed:32272059)
- Specific Function
- ATP binding
- Gene Name
- HSP90B1
- Uniprot ID
- P14625
- Uniprot Name
- Endoplasmin
- Molecular Weight
- 92468.06 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