5-[(3R)-3-(5-methoxy-4'-methylbiphenyl-3-yl)but-1-yn-1-yl]-6-methylpyrimidine-2,4-diamine

Identification

Name
5-[(3R)-3-(5-methoxy-4'-methylbiphenyl-3-yl)but-1-yn-1-yl]-6-methylpyrimidine-2,4-diamine
Accession Number
DB07141
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: 372.4629
Monoisotopic: 372.19501141
Chemical Formula
C23H24N4O
InChI Key
QVXYJVHNRPNRJL-HNNXBMFYSA-N
InChI
InChI=1S/C23H24N4O/c1-14-5-8-17(9-6-14)19-11-18(12-20(13-19)28-4)15(2)7-10-21-16(3)26-23(25)27-22(21)24/h5-6,8-9,11-13,15H,1-4H3,(H4,24,25,26,27)/t15-/m0/s1
IUPAC Name
5-[(3R)-3-[3-methoxy-5-(4-methylphenyl)phenyl]but-1-yn-1-yl]-6-methylpyrimidine-2,4-diamine
SMILES
[H][[email protected]](C)(C#CC1=C(C)N=C(N)N=C1N)C1=CC(OC)=CC(=C1)C1=CC=C(C)C=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UDihydrofolate reductaseNot 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
44144378
PubChem Substance
99443612
ChemSpider
24636429
BindingDB
50298814
ChEMBL
CHEMBL575218
HET
53S
PDB Entries
3eek / 4h97

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 Solubility0.00269 mg/mLALOGPS
logP4.22ALOGPS
logP4.65ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)17.61ChemAxon
pKa (Strongest Basic)7.29ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area87.05 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity113.53 m3·mol-1ChemAxon
Polarizability43.06 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9924
Blood Brain Barrier+0.8939
Caco-2 permeable+0.7274
P-glycoprotein substrateNon-substrate0.6681
P-glycoprotein inhibitor INon-inhibitor0.8522
P-glycoprotein inhibitor IINon-inhibitor0.7762
Renal organic cation transporterNon-inhibitor0.8683
CYP450 2C9 substrateNon-substrate0.8363
CYP450 2D6 substrateNon-substrate0.843
CYP450 3A4 substrateNon-substrate0.5353
CYP450 1A2 substrateInhibitor0.7223
CYP450 2C9 inhibitorNon-inhibitor0.5784
CYP450 2D6 inhibitorNon-inhibitor0.9141
CYP450 2C19 inhibitorNon-inhibitor0.657
CYP450 3A4 inhibitorInhibitor0.5207
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6191
Ames testAMES toxic0.5087
CarcinogenicityNon-carcinogens0.9109
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.2837 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9316
hERG inhibition (predictor II)Non-inhibitor0.6779
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 biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Biphenyls and derivatives
Direct Parent
Biphenyls and derivatives
Alternative Parents
Phenoxy compounds / Methoxybenzenes / Anisoles / Toluenes / Aminopyrimidines and derivatives / Alkyl aryl ethers / Imidolactams / Heteroaromatic compounds / Azacyclic compounds / Primary amines
show 2 more
Substituents
Biphenyl / Phenoxy compound / Anisole / Phenol ether / Methoxybenzene / Alkyl aryl ether / Aminopyrimidine / Toluene / Pyrimidine / Imidolactam
show 13 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

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]

Drug created on September 15, 2010 15:19 / Updated on December 01, 2017 15:46