2-[3-({Methyl[1-(2-Naphthoyl)Piperidin-4-Yl]Amino}Carbonyl)-2-Naphthyl]-1-(1-Naphthyl)-2-Oxoethylphosphonic Acid

Identification

Name
2-[3-({Methyl[1-(2-Naphthoyl)Piperidin-4-Yl]Amino}Carbonyl)-2-Naphthyl]-1-(1-Naphthyl)-2-Oxoethylphosphonic Acid
Accession Number
DB04016  (EXPT02424)
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: 670.6895
Monoisotopic: 670.223273374
Chemical Formula
C40H35N2O6P
InChI Key
XUJQPDQURBZEGJ-KXQOOQHDSA-N
InChI
InChI=1S/C40H35N2O6P/c1-41(32-19-21-42(22-20-32)39(44)31-18-17-26-9-2-3-11-28(26)23-31)40(45)36-25-30-13-5-4-12-29(30)24-35(36)37(43)38(49(46,47)48)34-16-8-14-27-10-6-7-15-33(27)34/h2-18,23-25,32,38H,19-22H2,1H3,(H2,46,47,48)/t38-/m1/s1
IUPAC Name
[(1R)-2-(3-{methyl[1-(naphthalene-2-carbonyl)piperidin-4-yl]carbamoyl}naphthalen-2-yl)-1-(naphthalen-1-yl)-2-oxoethyl]phosphonic acid
SMILES
CN(C1CCN(CC1)C(=O)C1=CC2=CC=CC=C2C=C1)C(=O)C1=CC2=CC=CC=C2C=C1C(=O)[[email protected]@H](C1=CC=CC2=CC=CC=C12)P(O)(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCathepsin GNot AvailableHuman
UChymaseNot 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
656932
PubChem Substance
46507882
ChemSpider
571178
HET
OHH
PDB Entries
1t31 / 1t32

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 Solubility0.000133 mg/mLALOGPS
logP4.49ALOGPS
logP5.08ChemAxon
logS-6.7ALOGPS
pKa (Strongest Acidic)1.56ChemAxon
pKa (Strongest Basic)0.22ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area115.22 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity190.42 m3·mol-1ChemAxon
Polarizability70.01 Å3ChemAxon
Number of Rings7ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8453
Blood Brain Barrier+0.8402
Caco-2 permeable-0.5829
P-glycoprotein substrateSubstrate0.7788
P-glycoprotein inhibitor INon-inhibitor0.6481
P-glycoprotein inhibitor IINon-inhibitor0.8335
Renal organic cation transporterNon-inhibitor0.6348
CYP450 2C9 substrateNon-substrate0.7144
CYP450 2D6 substrateNon-substrate0.77
CYP450 3A4 substrateSubstrate0.5829
CYP450 1A2 substrateNon-inhibitor0.8415
CYP450 2C9 inhibitorNon-inhibitor0.814
CYP450 2D6 inhibitorNon-inhibitor0.9
CYP450 2C19 inhibitorNon-inhibitor0.7823
CYP450 3A4 inhibitorNon-inhibitor0.5785
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8687
Ames testNon AMES toxic0.5493
CarcinogenicityNon-carcinogens0.8724
BiodegradationReady biodegradable0.5626
Rat acute toxicity2.7880 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8342
hERG inhibition (predictor II)Inhibitor0.6125
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 stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Stilbenes
Sub Class
Not Available
Direct Parent
Stilbenes
Alternative Parents
N-benzoylpiperidines / Naphthalenecarboxamides / Aryl alkyl ketones / Tertiary carboxylic acid amides / Organic phosphonic acids / Azacyclic compounds / Organopnictogen compounds / Organophosphorus compounds / Organonitrogen compounds / Organic oxides
show 1 more
Substituents
N-benzoylpiperidine / Stilbene / 2-naphthalenecarboxamide / 2-naphthalenecarboxylic acid or derivatives / Naphthalene / N-acyl-piperidine / Aryl ketone / Aryl alkyl ketone / Benzenoid / Piperidine
show 17 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
N-acylpiperidine, naphthalenes, amidopiperidine (CHEBI:44489)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Serine-type endopeptidase activity
Specific Function
Serine protease with trypsin- and chymotrypsin-like specificity. Cleaves complement C3. Has antibacterial activity against the Gram-negative bacterium P.aeruginosa, antibacterial activity is inhibi...
Gene Name
CTSG
Uniprot ID
P08311
Uniprot Name
Cathepsin G
Molecular Weight
28836.99 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Serine-type peptidase activity
Specific Function
Major secreted protease of mast cells with suspected roles in vasoactive peptide generation, extracellular matrix degradation, and regulation of gland secretion.
Gene Name
CMA1
Uniprot ID
P23946
Uniprot Name
Chymase
Molecular Weight
27324.56 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]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 15:22