5-[3-(2,5-dimethoxyphenyl)prop-1-yn-1-yl]-6-ethylpyrimidine-2,4-diamine

Identification

Name
5-[3-(2,5-dimethoxyphenyl)prop-1-yn-1-yl]-6-ethylpyrimidine-2,4-diamine
Accession Number
DB08234
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: 312.3663
Monoisotopic: 312.158625904
Chemical Formula
C17H20N4O2
InChI Key
NNFDQABYXZBKRK-UHFFFAOYSA-N
InChI
InChI=1S/C17H20N4O2/c1-4-14-13(16(18)21-17(19)20-14)7-5-6-11-10-12(22-2)8-9-15(11)23-3/h8-10H,4,6H2,1-3H3,(H4,18,19,20,21)
IUPAC Name
5-[3-(2,5-dimethoxyphenyl)prop-1-yn-1-yl]-6-ethylpyrimidine-2,4-diamine
SMILES
CCC1=NC(N)=NC(N)=C1C#CCC1=CC(OC)=CC=C1OC

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UDihydrofolate reductaseNot AvailableBacillus anthracis
UDihydrofolate reductaseNot AvailableHuman
UDihydrofolate reductase (dfrB)Not AvailableStaphylococcus aureus (strain bovine RF122 / ET3-1)
UDihydrofolate reductaseNot AvailableStaphylococcus aureus
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
25058133
PubChem Substance
99444705
ChemSpider
24702741
BindingDB
26519
ChEMBL
CHEMBL485961
HET
N22
PDB Entries
2kgk / 3cse / 3e0b / 3fq0 / 3fqo / 3i8a / 3qlw

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 Solubility0.018 mg/mLALOGPS
logP2.6ALOGPS
logP2.75ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)17.6ChemAxon
pKa (Strongest Basic)7.12ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area96.28 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity89.9 m3·mol-1ChemAxon
Polarizability33.83 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9756
Blood Brain Barrier+0.9266
Caco-2 permeable+0.6538
P-glycoprotein substrateNon-substrate0.5343
P-glycoprotein inhibitor INon-inhibitor0.7668
P-glycoprotein inhibitor IINon-inhibitor0.8306
Renal organic cation transporterNon-inhibitor0.771
CYP450 2C9 substrateNon-substrate0.8397
CYP450 2D6 substrateNon-substrate0.8258
CYP450 3A4 substrateSubstrate0.5155
CYP450 1A2 substrateNon-inhibitor0.5177
CYP450 2C9 inhibitorNon-inhibitor0.6469
CYP450 2D6 inhibitorNon-inhibitor0.8039
CYP450 2C19 inhibitorNon-inhibitor0.6907
CYP450 3A4 inhibitorInhibitor0.6015
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7889
Ames testNon AMES toxic0.5398
CarcinogenicityNon-carcinogens0.8928
BiodegradationNot ready biodegradable0.9966
Rat acute toxicity2.4417 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8502
hERG inhibition (predictor II)Non-inhibitor0.6865
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 dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Methoxybenzenes
Direct Parent
Dimethoxybenzenes
Alternative Parents
Phenoxy compounds / Anisoles / Aminopyrimidines and derivatives / Alkyl aryl ethers / Imidolactams / Heteroaromatic compounds / Azacyclic compounds / Primary amines / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
P-dimethoxybenzene / Dimethoxybenzene / Phenoxy compound / Anisole / Phenol ether / Alkyl aryl ether / Aminopyrimidine / Pyrimidine / Imidolactam / Heteroaromatic compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Bacillus anthracis
Pharmacological action
Unknown
General Function
Nadp binding
Specific Function
Key enzyme in folate metabolism. Catalyzes an essential reaction for de novo glycine and purine synthesis, and for DNA precursor synthesis.
Gene Name
dfrA
Uniprot ID
Q81R22
Uniprot Name
Dihydrofolate reductase
Molecular Weight
19124.795 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]
Details
2. Dihydrofolate reductase
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Nadph binding
Specific Function
Key enzyme in folate metabolism. Contributes to the de novo mitochondrial thymidylate biosynthesis pathway. Catalyzes an essential reaction for de novo glycine and purine synthesis, and for DNA pre...
Gene Name
DHFR
Uniprot ID
P00374
Uniprot Name
Dihydrofolate reductase
Molecular Weight
21452.61 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]
Kind
Protein
Organism
Staphylococcus aureus (strain bovine RF122 / ET3-1)
Pharmacological action
Unknown
General Function
Key enzyme in folate metabolism. Catalyzes an essential reaction for de novo glycine and purine synthesis, and for DNA precursor synthesis.
Specific Function
Dihydrofolate reductase activity
Gene Name
dfrB
Uniprot ID
A0A0M3KKX1
Uniprot Name
Dihydrofolate reductase
Molecular Weight
17991.48 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]
Kind
Protein
Organism
Staphylococcus aureus
Pharmacological action
Unknown
General Function
Nadp binding
Specific Function
Key enzyme in folate metabolism. Catalyzes an essential reaction for de novo glycine and purine synthesis, and for DNA precursor synthesis.
Gene Name
folA
Uniprot ID
P0A017
Uniprot Name
Dihydrofolate reductase
Molecular Weight
18250.85 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 September 15, 2010 15:30 / Updated on December 01, 2017 16:02