5-[[(2R)-2-cyclopropyl-7,8-dimethoxy-2H-chromen-5-yl]methyl]pyrimidine-2,4-diamine

Identification

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Name
5-[[(2R)-2-cyclopropyl-7,8-dimethoxy-2H-chromen-5-yl]methyl]pyrimidine-2,4-diamine
Accession Number
DB08741
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: 354.403
Monoisotopic: 354.16919059
Chemical Formula
C19H22N4O3
InChI Key
HWJPWWYTGBZDEG-AWEZNQCLSA-N
InChI
InChI=1S/C19H22N4O3/c1-24-15-8-11(7-12-9-22-19(21)23-18(12)20)13-5-6-14(10-3-4-10)26-16(13)17(15)25-2/h5-6,8-10,14H,3-4,7H2,1-2H3,(H4,20,21,22,23)/t14-/m0/s1
IUPAC Name
5-{[(2R)-2-cyclopropyl-7,8-dimethoxy-2H-chromen-5-yl]methyl}pyrimidine-2,4-diamine
SMILES
[H][C@@]1(OC2=C(OC)C(OC)=CC(CC3=C(N)N=C(N)N=C3)=C2C=C1)C1CC1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
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
10247560
PubChem Substance
99445212
ChemSpider
8423047
BindingDB
50336513
ChEBI
131752
ChEMBL
CHEMBL1236788
HET
XCF
PDB Entries
3frf / 3fy8 / 3fy9 / 3fyv / 3fyw

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 Solubility0.142 mg/mLALOGPS
logP2.35ALOGPS
logP2.49ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)17.32ChemAxon
pKa (Strongest Basic)7.15ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area105.51 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity101.99 m3·mol-1ChemAxon
Polarizability37.51 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.8834
Caco-2 permeable+0.6531
P-glycoprotein substrateSubstrate0.5424
P-glycoprotein inhibitor INon-inhibitor0.7191
P-glycoprotein inhibitor IINon-inhibitor0.582
Renal organic cation transporterNon-inhibitor0.8809
CYP450 2C9 substrateNon-substrate0.8649
CYP450 2D6 substrateNon-substrate0.8579
CYP450 3A4 substrateNon-substrate0.5331
CYP450 1A2 substrateNon-inhibitor0.5366
CYP450 2C9 inhibitorNon-inhibitor0.5475
CYP450 2D6 inhibitorNon-inhibitor0.7058
CYP450 2C19 inhibitorNon-inhibitor0.5
CYP450 3A4 inhibitorNon-inhibitor0.608
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8307
Ames testNon AMES toxic0.5137
CarcinogenicityNon-carcinogens0.9371
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.2832 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9377
hERG inhibition (predictor II)Non-inhibitor0.8162
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 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzopyrans
Sub Class
1-benzopyrans
Direct Parent
1-benzopyrans
Alternative Parents
Anisoles / Aminopyrimidines and derivatives / Alkyl aryl ethers / Imidolactams / Heteroaromatic compounds / Oxacyclic compounds / Azacyclic compounds / Primary amines / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
1-benzopyran / Anisole / Alkyl aryl ether / Aminopyrimidine / Pyrimidine / Benzenoid / Imidolactam / Heteroaromatic compound / Oxacycle / Ether
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Details
1. Dihydrofolate reductase
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 15:34 / Updated on June 04, 2019 07:02