4-(1-Benzyl-3-Carbamoylmethyl-2-Methyl-1h-Indol-5-Yloxy)-Butyric Acid

Identification

Name
4-(1-Benzyl-3-Carbamoylmethyl-2-Methyl-1h-Indol-5-Yloxy)-Butyric Acid
Accession Number
DB02936  (EXPT00286)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 380.437
Monoisotopic: 380.173607266
Chemical Formula
C22H24N2O4
InChI Key
STENXUCYNKOBHJ-UHFFFAOYSA-N
InChI
InChI=1S/C22H24N2O4/c1-15-18(13-21(23)25)19-12-17(28-11-5-8-22(26)27)9-10-20(19)24(15)14-16-6-3-2-4-7-16/h2-4,6-7,9-10,12H,5,8,11,13-14H2,1H3,(H2,23,25)(H,26,27)
IUPAC Name
4-{[1-benzyl-3-(carbamoylmethyl)-2-methyl-1H-indol-5-yl]oxy}butanoic acid
SMILES
CC1=C(CC(N)=O)C2=C(C=CC(OCCCC(O)=O)=C2)N1CC1=CC=CC=C1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UPhospholipase A2, membrane associatedNot AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
3710
PubChem Substance
46504907
ChemSpider
3579
BindingDB
50055291
ChEMBL
CHEMBL356752
HET
6IN
PDB Entries
1db5

Clinical Trials

Clinical Trials
Not Available

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 Solubility0.00529 mg/mLALOGPS
logP3.23ALOGPS
logP2.9ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)4.16ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area94.55 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity106.94 m3·mol-1ChemAxon
Polarizability41.7 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9041
Blood Brain Barrier+0.5119
Caco-2 permeable-0.7733
P-glycoprotein substrateSubstrate0.7329
P-glycoprotein inhibitor INon-inhibitor0.8622
P-glycoprotein inhibitor IINon-inhibitor0.7292
Renal organic cation transporterNon-inhibitor0.5606
CYP450 2C9 substrateNon-substrate0.7844
CYP450 2D6 substrateNon-substrate0.7282
CYP450 3A4 substrateSubstrate0.5893
CYP450 1A2 substrateNon-inhibitor0.7967
CYP450 2C9 inhibitorNon-inhibitor0.7294
CYP450 2D6 inhibitorNon-inhibitor0.8651
CYP450 2C19 inhibitorNon-inhibitor0.5062
CYP450 3A4 inhibitorInhibitor0.5729
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.655
Ames testNon AMES toxic0.8478
CarcinogenicityNon-carcinogens0.9424
BiodegradationNot ready biodegradable0.8776
Rat acute toxicity2.1464 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9734
hERG inhibition (predictor II)Inhibitor0.5447
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/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as n-alkylindoles. These are compounds containing an indole moiety that carries an alkyl chain at the 1-position.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
N-alkylindoles
Direct Parent
N-alkylindoles
Alternative Parents
3-alkylindoles / Alkyl aryl ethers / Substituted pyrroles / Benzene and substituted derivatives / Heteroaromatic compounds / Primary carboxylic acid amides / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds
show 4 more
Substituents
N-alkylindole / 3-alkylindole / Indole / Alkyl aryl ether / Monocyclic benzene moiety / Substituted pyrrole / Benzenoid / Pyrrole / Heteroaromatic compound / Carboxamide group
show 15 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Phospholipid binding
Specific Function
Thought to participate in the regulation of the phospholipid metabolism in biomembranes including eicosanoid biosynthesis. Catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-ph...
Gene Name
PLA2G2A
Uniprot ID
P14555
Uniprot Name
Phospholipase A2, membrane associated
Molecular Weight
16082.525 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. [PubMed:17139284]
  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. [PubMed:17016423]
  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. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 05:26