NAV

1-(5-Carboxypentyl)-5-[(2,6-Dichlorobenzyl)Oxy]-1 H-Indole-2-Carboxylic Acid

Identification

Generic Name
1-(5-Carboxypentyl)-5-[(2,6-Dichlorobenzyl)Oxy]-1 H-Indole-2-Carboxylic Acid
DrugBank Accession Number
DB02316
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 450.312
Monoisotopic: 449.079678201
Chemical Formula
C22H21Cl2NO5
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
U3-oxoacyl-[acyl-carrier-protein] synthase 3Not AvailableEscherichia coli (strain K12)
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 indolecarboxylic acids and derivatives. These are compounds containing a carboxylic acid group (or a derivative thereof) linked to an indole.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Indolecarboxylic acids and derivatives
Direct Parent
Indolecarboxylic acids and derivatives
Alternative Parents
N-alkylindoles / Indoles / Pyrrole 2-carboxylic acids / Medium-chain fatty acids / Dichlorobenzenes / Alkyl aryl ethers / Heterocyclic fatty acids / Halogenated fatty acids / Substituted pyrroles / Aryl chlorides
show 10 more
Substituents
1,3-dichlorobenzene / Alkyl aryl ether / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzenoid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative
show 27 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
JTGPYFFQVOIJKR-UHFFFAOYSA-N
InChI
InChI=1S/C22H21Cl2NO5/c23-17-5-4-6-18(24)16(17)13-30-15-8-9-19-14(11-15)12-20(22(28)29)25(19)10-3-1-2-7-21(26)27/h4-6,8-9,11-12H,1-3,7,10,13H2,(H,26,27)(H,28,29)
IUPAC Name
1-(5-carboxypentyl)-5-[(2,6-dichlorophenyl)methoxy]-1H-indole-2-carboxylic acid
SMILES
OC(=O)CCCCCN1C(=CC2=C1C=CC(OCC1=C(Cl)C=CC=C1Cl)=C2)C(O)=O

References

General References
Not Available
PubChem Compound
11113761
PubChem Substance
46506154
ChemSpider
9288894
ChEMBL
CHEMBL165315
ZINC
ZINC000012341129
PDBe Ligand
669
PDB Entries
1mzs

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 Solubility0.000823 mg/mLALOGPS
logP4.51ALOGPS
logP5.54Chemaxon
logS-5.7ALOGPS
pKa (Strongest Acidic)3.3Chemaxon
pKa (Strongest Basic)-4.9Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area88.76 Å2Chemaxon
Rotatable Bond Count10Chemaxon
Refractivity114.6 m3·mol-1Chemaxon
Polarizability46.03 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9313
Blood Brain Barrier+0.5213
Caco-2 permeable-0.6884
P-glycoprotein substrateSubstrate0.6656
P-glycoprotein inhibitor INon-inhibitor0.6791
P-glycoprotein inhibitor IIInhibitor0.7598
Renal organic cation transporterInhibitor0.5486
CYP450 2C9 substrateNon-substrate0.7908
CYP450 2D6 substrateNon-substrate0.7491
CYP450 3A4 substrateSubstrate0.5426
CYP450 1A2 substrateInhibitor0.6452
CYP450 2C9 inhibitorNon-inhibitor0.8128
CYP450 2D6 inhibitorNon-inhibitor0.7885
CYP450 2C19 inhibitorNon-inhibitor0.7261
CYP450 3A4 inhibitorNon-inhibitor0.5916
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7443
Ames testNon AMES toxic0.7528
CarcinogenicityNon-carcinogens0.9512
BiodegradationNot ready biodegradable0.9821
Rat acute toxicity2.3459 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.68
hERG inhibition (predictor II)Inhibitor0.6113
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/MSsplash10-001j-4000900000-49c2f7789196704e64a4
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fr2-0007900000-dd54a7b270726f3bab0f
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0gc1-9002700000-31d497f6db33ae93956a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-05al-4439100000-4c4132f1deae01b2aea3
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-9101100000-59552ce0442c069aaaf3
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-053r-5229200000-31ed3e7573df58f11589
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]-197.70735
predicted
DeepCCS 1.0 (2019)
[M+H]+200.10985
predicted
DeepCCS 1.0 (2019)
[M+Na]+208.37712
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. 3-oxoacyl-[acyl-carrier-protein] synthase 3
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Beta-ketoacyl-acyl-carrier-protein synthase iii activity
Specific Function
Catalyzes the condensation reaction of fatty acid synthesis by the addition to an acyl acceptor of two carbons from malonyl-ACP. Catalyzes the first condensation reaction which initiates fatty acid...
Gene Name
fabH
Uniprot ID
P0A6R0
Uniprot Name
3-oxoacyl-[acyl-carrier-protein] synthase 3
Molecular Weight
33514.78 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. 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 June 13, 2005 13:24 / Updated at July 02, 2020 13:14