N-[(E)-3-[(2R,3S,4R,5R)-5-(6-Aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]prop-2-enyl]-2,3-dihydroxy-5-nitrobenzamide

Identification

Name
N-[(E)-3-[(2R,3S,4R,5R)-5-(6-Aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]prop-2-enyl]-2,3-dihydroxy-5-nitrobenzamide
Accession Number
DB03907
Description
Not Available
Type
Small Molecule
Groups
Experimental
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Structure
Thumb
Weight
Average: 473.3963
Monoisotopic: 473.129510619
Chemical Formula
C19H19N7O8
Synonyms
Not Available

Pharmacology

Indication
Not Available
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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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
Adverse Effects
Learn about our commercial Adverse Effects data.
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Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 5'-deoxyribonucleosides. These are nucleosides in which the oxygen atom at the 5'position of the ribose moiety has been replaced by another atom. The nucleobases here are limited to purine, pyrimidine, and pyridine derivatives.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
5'-deoxyribonucleosides
Sub Class
Not Available
Direct Parent
5'-deoxyribonucleosides
Alternative Parents
Glycosylamines / 6-aminopurines / Salicylamides / Nitrophenols / Benzamides / Nitrobenzenes / Benzoyl derivatives / Catechols / Nitroaromatic compounds / Aminopyrimidines and derivatives
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Substituents
1,2-diol / 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / 5'-deoxyribonucleoside / 6-aminopurine / Alcohol / Allyl-type 1,3-dipolar organic compound / Amine / Amino acid or derivatives / Aminopyrimidine
show 46 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
C-nitro compound, benzamides, adenosines (CHEBI:41491)

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
UHHBFOLQOQSPLU-WGRQDFERSA-N
InChI
InChI=1S/C19H19N7O8/c20-16-12-17(23-6-22-16)25(7-24-12)19-15(30)14(29)11(34-19)2-1-3-21-18(31)9-4-8(26(32)33)5-10(27)13(9)28/h1-2,4-7,11,14-15,19,27-30H,3H2,(H,21,31)(H2,20,22,23)/b2-1+/t11-,14-,15-,19-/m1/s1
IUPAC Name
N-[(2E)-3-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]prop-2-en-1-yl]-2,3-dihydroxy-5-nitrobenzamide
SMILES
[H]N([H])C1=C2N=CN([[email protected]@H]3O[[email protected]](\C=C\CN([H])C(=O)C4=C(O)C(O)=CC(=C4)[N+]([O-])=O)[[email protected]@H](O)[[email protected]]3O)C2=NC=N1

References

General References
Not Available
PubChem Compound
4369234
PubChem Substance
46504513
ChemSpider
3571884
BindingDB
84475
ZINC
ZINC000034828673
PDBe Ligand
CL4
PDB Entries
1jr4

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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
logP-0.015ChemAxon
pKa (Strongest Acidic)6.1ChemAxon
pKa (Strongest Basic)3.94ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area232.01 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity115.57 m3·mol-1ChemAxon
Polarizability44.54 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9961
Blood Brain Barrier+0.7558
Caco-2 permeable-0.6505
P-glycoprotein substrateSubstrate0.5
P-glycoprotein inhibitor INon-inhibitor0.8823
P-glycoprotein inhibitor IINon-inhibitor0.7675
Renal organic cation transporterNon-inhibitor0.9359
CYP450 2C9 substrateNon-substrate0.8334
CYP450 2D6 substrateNon-substrate0.837
CYP450 3A4 substrateNon-substrate0.5282
CYP450 1A2 substrateNon-inhibitor0.6208
CYP450 2C9 inhibitorNon-inhibitor0.7174
CYP450 2D6 inhibitorNon-inhibitor0.8642
CYP450 2C19 inhibitorNon-inhibitor0.6114
CYP450 3A4 inhibitorInhibitor0.598
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5701
Ames testAMES toxic0.7822
CarcinogenicityNon-carcinogens0.6597
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.4610 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9295
hERG inhibition (predictor II)Non-inhibitor0.6878
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

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. 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 June 12, 2020 10:52

Pm 3