[3-(1-Benzyl-3-Carbamoylmethyl-2-Methyl-1h-Indol-5-Yloxy)-Propyl-]-Phosphonic Acid

Identification

Name
[3-(1-Benzyl-3-Carbamoylmethyl-2-Methyl-1h-Indol-5-Yloxy)-Propyl-]-Phosphonic Acid
Accession Number
DB02504  (EXPT00335)
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: 416.4074
Monoisotopic: 416.150108432
Chemical Formula
C21H25N2O5P
InChI Key
AQEYCNKFBRLUOT-UHFFFAOYSA-N
InChI
InChI=1S/C21H25N2O5P/c1-15-18(13-21(22)24)19-12-17(28-10-5-11-29(25,26)27)8-9-20(19)23(15)14-16-6-3-2-4-7-16/h2-4,6-9,12H,5,10-11,13-14H2,1H3,(H2,22,24)(H2,25,26,27)
IUPAC Name
(3-{[1-benzyl-3-(carbamoylmethyl)-2-methyl-1H-indol-5-yl]oxy}propyl)phosphonic acid
SMILES
CC1=C(CC(N)=O)C2=C(C=CC(OCCCP(O)(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
3711
PubChem Substance
46506847
ChemSpider
3580
BindingDB
50055341
ChEMBL
CHEMBL149502
HET
8IN
PDB Entries
1db4

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 Solubility0.0338 mg/mLALOGPS
logP2.07ALOGPS
logP1.58ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)1.81ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area114.78 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity111.59 m3·mol-1ChemAxon
Polarizability43.47 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.6466
Blood Brain Barrier+0.8874
Caco-2 permeable-0.7302
P-glycoprotein substrateSubstrate0.7276
P-glycoprotein inhibitor INon-inhibitor0.8345
P-glycoprotein inhibitor IINon-inhibitor0.9126
Renal organic cation transporterNon-inhibitor0.6563
CYP450 2C9 substrateNon-substrate0.7136
CYP450 2D6 substrateNon-substrate0.762
CYP450 3A4 substrateSubstrate0.6088
CYP450 1A2 substrateNon-inhibitor0.7996
CYP450 2C9 inhibitorNon-inhibitor0.7226
CYP450 2D6 inhibitorNon-inhibitor0.884
CYP450 2C19 inhibitorNon-inhibitor0.6493
CYP450 3A4 inhibitorInhibitor0.5616
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5
Ames testNon AMES toxic0.6357
CarcinogenicityNon-carcinogens0.8847
BiodegradationNot ready biodegradable0.8944
Rat acute toxicity2.5251 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9125
hERG inhibition (predictor II)Inhibitor0.6295
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 / Organic phosphonic acids / Heteroaromatic compounds / Primary carboxylic acid amides / Azacyclic compounds / Organopnictogen compounds / Organophosphorus compounds
show 4 more
Substituents
N-alkylindole / 3-alkylindole / Indole / Alkyl aryl ether / Monocyclic benzene moiety / Benzenoid / Substituted pyrrole / Organophosphonic acid / Organophosphonic acid derivative / Heteroaromatic compound
show 16 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 05:18