Identification

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Name
BIA
Accession Number
DB03336  (EXPT00705)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
X6H65DT067
CAS number
Not Available
Weight
Average: 439.3851
Monoisotopic: 439.13550538
Chemical Formula
C20H20F3N3O5
InChI Key
KVIVJQWOYSWCCZ-UHFFFAOYSA-N
InChI
InChI=1S/C20H20F3N3O5/c21-20(22,23)14-2-1-3-15(12-14)25-8-6-24(7-9-25)5-4-17(27)13-10-16(26(30)31)19(29)18(28)11-13/h1-3,10-12,28-29H,4-9H2
IUPAC Name
1-(3,4-dihydroxy-5-nitrophenyl)-3-{4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}propan-1-one
SMILES
OC1=CC(=CC(=C1O)[N+]([O-])=O)C(=O)CCN1CCN(CC1)C1=CC(=CC=C1)C(F)(F)F

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCatechol O-methyltransferaseNot AvailableHumans
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
4369285
PubChem Substance
46506639
ChemSpider
3571909
ChEMBL
CHEMBL387347
HET
BIA
Wikipedia
BIA
PDB Entries
1h1d

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 Solubility0.0434 mg/mLALOGPS
logP3.7ALOGPS
logP2.46ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)4.92ChemAxon
pKa (Strongest Basic)7.04ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area109.83 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity108.4 m3·mol-1ChemAxon
Polarizability41.6 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8946
Blood Brain Barrier-0.66
Caco-2 permeable-0.5905
P-glycoprotein substrateSubstrate0.8062
P-glycoprotein inhibitor IInhibitor0.5111
P-glycoprotein inhibitor IINon-inhibitor0.6593
Renal organic cation transporterNon-inhibitor0.8121
CYP450 2C9 substrateNon-substrate0.8921
CYP450 2D6 substrateNon-substrate0.8224
CYP450 3A4 substrateNon-substrate0.5218
CYP450 1A2 substrateNon-inhibitor0.7297
CYP450 2C9 inhibitorInhibitor0.5
CYP450 2D6 inhibitorNon-inhibitor0.8364
CYP450 2C19 inhibitorInhibitor0.6883
CYP450 3A4 inhibitorNon-inhibitor0.5684
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5506
Ames testAMES toxic0.5838
CarcinogenicityNon-carcinogens0.7686
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6501 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.5458
hERG inhibition (predictor II)Inhibitor0.7111
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 alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbonyl compounds
Direct Parent
Alkyl-phenylketones
Alternative Parents
N-arylpiperazines / Phenylpiperazines / Trifluoromethylbenzenes / Nitrophenols / Nitrobenzenes / Aniline and substituted anilines / Aryl alkyl ketones / Benzoyl derivatives / Catechols / Dialkylarylamines
show 15 more
Substituents
Alkyl-phenylketone / Phenylpiperazine / N-arylpiperazine / Nitrophenol / Trifluoromethylbenzene / Nitrobenzene / Benzoyl / Catechol / Nitroaromatic compound / Tertiary aliphatic/aromatic amine
show 34 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
C-nitro compound, organofluorine compound, N-arylpiperazine, N-alkylpiperazine (CHEBI:41173)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
O-methyltransferase activity
Specific Function
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOP...
Gene Name
COMT
Uniprot ID
P21964
Uniprot Name
Catechol O-methyltransferase
Molecular Weight
30036.77 Da
References
  1. 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 August 02, 2019 07:16