NAV

METHYL 3-CHLORO-2-{3-[(2,5-DIHYDROXY-4-METHOXYPHENYL)AMINO]-3-OXOPROPYL}-4,6-DIHYDROXYBENZOATE

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
3D
Similar Structures
Weight
Average: 411.79
Monoisotopic: 411.072094264
Chemical Formula
C18H18ClNO8
Synonyms
Not Available
Poor quality drug data slowing you down?
Unlock 38% more drug discovery time and eliminate decision-making doubts with this one-stop guide to quality drug data.
Download eBook
Poor quality drug data slowing you down?
Download eBook

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UHeat shock protein HSP 90-betaNot AvailableHumans
UEndoplasminNot AvailableHumans
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 outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
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
PubChem Compound
11373270
PubChem Substance
99444935
ChemSpider
9548187
ZINC
ZINC000024798681
PDBe Ligand
RDA
PDB Entries
2fxs / 2gfd

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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
PropertyValueSource
Water Solubility0.0399 mg/mLALOGPS
logP2.53ALOGPS
logP3.38Chemaxon
logS-4ALOGPS
pKa (Strongest Acidic)7.04Chemaxon
pKa (Strongest Basic)-4.1Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area145.55 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity101.46 m3·mol-1Chemaxon
Polarizability39.28 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.844
Blood Brain Barrier-0.7534
Caco-2 permeable-0.6833
P-glycoprotein substrateSubstrate0.5107
P-glycoprotein inhibitor INon-inhibitor0.8439
P-glycoprotein inhibitor IINon-inhibitor0.752
Renal organic cation transporterNon-inhibitor0.9281
CYP450 2C9 substrateNon-substrate0.6973
CYP450 2D6 substrateNon-substrate0.8542
CYP450 3A4 substrateSubstrate0.6508
CYP450 1A2 substrateNon-inhibitor0.7207
CYP450 2C9 inhibitorNon-inhibitor0.6886
CYP450 2D6 inhibitorNon-inhibitor0.9194
CYP450 2C19 inhibitorNon-inhibitor0.6256
CYP450 3A4 inhibitorNon-inhibitor0.8387
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5291
Ames testNon AMES toxic0.875
CarcinogenicityNon-carcinogens0.9325
BiodegradationNot ready biodegradable0.9693
Rat acute toxicity2.5249 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9663
hERG inhibition (predictor II)Non-inhibitor0.7265
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-003r-0059200000-aa6c4969036d7689863a
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0m90-0946300000-13875027c6f93ddf72c4
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0gx0-0119000000-139377b68ac5ce5d5c75
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0f79-2901000000-313afcaccb395f6c4466
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-002e-0968000000-e2e6703bc9a3176db1f3
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9110000000-c87275acebfb6d3b237e
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-183.3719
predicted
DeepCCS 1.0 (2019)
[M+H]+185.7299
predicted
DeepCCS 1.0 (2019)
[M+Na]+192.39377
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Details1. Heat shock protein HSP 90-beta
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Utp binding
Specific 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. Under...
Gene Name
HSP90AB1
Uniprot ID
P08238
Uniprot Name
Heat shock protein HSP 90-beta
Molecular Weight
83263.475 Da
References
  1. 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]
Details2. Endoplasmin
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Virion binding
Specific Function
Molecular chaperone that functions in the processing and transport of secreted proteins. When associated with CNPY3, required for proper folding of Toll-like receptors (By similarity). Functions in...
Gene Name
HSP90B1
Uniprot ID
P14625
Uniprot Name
Endoplasmin
Molecular Weight
92468.06 Da
References
  1. 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