NAV

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

Identification

Generic Name
5-[(3R)-3-(5-methoxy-2',6'-dimethylbiphenyl-3-yl)but-1-yn-1-yl]-6-methylpyrimidine-2,4-diamine
DrugBank Accession Number
DB07144
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 386.4894
Monoisotopic: 386.210661474
Chemical Formula
C24H26N4O
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UDihydrofolate reductaseNot 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
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Toxicity

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 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
m-Xylenes / Phenoxy compounds / Methoxybenzenes / Anisoles / Aminopyrimidines and derivatives / Alkyl aryl ethers / Imidolactams / Heteroaromatic compounds / Azacyclic compounds / Primary amines
show 2 more
Substituents
Alkyl aryl ether / Amine / Aminopyrimidine / Anisole / Aromatic heteromonocyclic compound / Azacycle / Biphenyl / Ether / Heteroaromatic compound / Hydrocarbon derivative
show 14 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
XZXVRKHUCSXVBM-AWEZNQCLSA-N
InChI
InChI=1S/C24H26N4O/c1-14(9-10-21-17(4)27-24(26)28-23(21)25)18-11-19(13-20(12-18)29-5)22-15(2)7-6-8-16(22)3/h6-8,11-14H,1-5H3,(H4,25,26,27,28)/t14-/m0/s1
IUPAC Name
5-[(3R)-3-{5-methoxy-2',6'-dimethyl-[1,1'-biphenyl]-3-yl}but-1-yn-1-yl]-6-methylpyrimidine-2,4-diamine
SMILES
[H][C@](C)(C#CC1=C(N)N=C(N)N=C1C)C1=CC(OC)=CC(=C1)C1=C(C)C=CC=C1C

References

General References
Not Available
PubChem Compound
44144380
PubChem Substance
99443615
ChemSpider
24637592
BindingDB
50298828
ChEMBL
CHEMBL573077
ZINC
ZINC000040860441
PDBe Ligand
53V
PDB Entries
3eem

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
Water Solubility0.00217 mg/mLALOGPS
logP4.58ALOGPS
logP5.17Chemaxon
logS-5.2ALOGPS
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
Refractivity118.57 m3·mol-1Chemaxon
Polarizability44.56 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
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/MSsplash10-000i-0009000000-ee00fc830eae74b0bd56
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0009000000-97707a71d3d5c977796a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-009i-1509000000-fd8bd7a41e90990ffeb7
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0frl-0009000000-545ea740dc859a6faac5
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fdw-1319000000-ece871b54d1193c7a21d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0lkc-2439000000-6aa124c748619fdf4682
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-191.90529
predicted
DeepCCS 1.0 (2019)
[M+H]+194.26329
predicted
DeepCCS 1.0 (2019)
[M+Na]+200.50493
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Dihydrofolate reductase
Kind
Protein
Organism
Humans
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. [Article]

Drug created at September 15, 2010 21:19 / Updated at June 12, 2020 16:52