(1-Benzyl-5-methoxy-2-methyl-1H-indol-3-yl)acetic acid

Identification

Name
(1-Benzyl-5-methoxy-2-methyl-1H-indol-3-yl)acetic acid
Accession Number
DB03121  (EXPT01810)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
59283-35-1
Weight
Average: 309.3591
Monoisotopic: 309.136493479
Chemical Formula
C19H19NO3
InChI Key
ZEKCBTQHDTUHRJ-UHFFFAOYSA-N
InChI
InChI=1S/C19H19NO3/c1-13-16(11-19(21)22)17-10-15(23-2)8-9-18(17)20(13)12-14-6-4-3-5-7-14/h3-10H,11-12H2,1-2H3,(H,21,22)
IUPAC Name
2-(1-benzyl-5-methoxy-2-methyl-1H-indol-3-yl)acetic acid
SMILES
COC1=CC2=C(C=C1)N(CC1=CC=CC=C1)C(C)=C2CC(O)=O

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
1372
PubChem Substance
46505875
ChemSpider
1331
BindingDB
50055737
ChEMBL
CHEMBL148756
HET
I3N
PDB Entries
1dcy

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 Solubility0.0101 mg/mLALOGPS
logP3.82ALOGPS
logP3.7ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)4.43ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area51.46 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity89.57 m3·mol-1ChemAxon
Polarizability33.54 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9956
Blood Brain Barrier+0.9693
Caco-2 permeable+0.7814
P-glycoprotein substrateNon-substrate0.5087
P-glycoprotein inhibitor INon-inhibitor0.7332
P-glycoprotein inhibitor IINon-inhibitor0.6728
Renal organic cation transporterNon-inhibitor0.5469
CYP450 2C9 substrateNon-substrate0.7492
CYP450 2D6 substrateNon-substrate0.5889
CYP450 3A4 substrateSubstrate0.5764
CYP450 1A2 substrateInhibitor0.8883
CYP450 2C9 inhibitorNon-inhibitor0.5897
CYP450 2D6 inhibitorNon-inhibitor0.8141
CYP450 2C19 inhibitorInhibitor0.7365
CYP450 3A4 inhibitorNon-inhibitor0.5916
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7091
Ames testNon AMES toxic0.6564
CarcinogenicityNon-carcinogens0.9429
BiodegradationNot ready biodegradable0.9521
Rat acute toxicity2.6349 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9359
hERG inhibition (predictor II)Non-inhibitor0.7355
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 indole-3-acetic acid derivatives. These are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Indolyl carboxylic acids and derivatives
Direct Parent
Indole-3-acetic acid derivatives
Alternative Parents
N-alkylindoles / 3-alkylindoles / Anisoles / Alkyl aryl ethers / Substituted pyrroles / Benzene and substituted derivatives / Heteroaromatic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds
show 5 more
Substituents
Indole-3-acetic acid derivative / N-alkylindole / 3-alkylindole / Indole / Anisole / Alkyl aryl ether / Monocyclic benzene moiety / Benzenoid / Substituted pyrrole / Heteroaromatic compound
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 05:29