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

Identification

Generic Name
5-[[(2R)-2-cyclopropyl-7,8-dimethoxy-2H-chromen-5-yl]methyl]pyrimidine-2,4-diamine
DrugBank Accession Number
DB08741
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 354.403
Monoisotopic: 354.16919059
Chemical Formula
C19H22N4O3
Synonyms
Not Available

Pharmacology

Indication

Not Available

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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

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 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 / Alkyl aryl ether / Amine / Aminopyrimidine / Anisole / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Ether / Heteroaromatic compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
RG4NWL6NKS
CAS number
Not Available
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

References

General References
Not Available
PubChem Compound
10247560
PubChem Substance
99445212
ChemSpider
8423047
BindingDB
50336513
ChEBI
131752
ChEMBL
CHEMBL1236788
ZINC
ZINC000003612862
PDBe Ligand
XCF
PDB Entries
3frf / 3fy8 / 3fy9 / 3fyv / 3fyw

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 Solubility0.142 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/MSsplash10-0a4i-0009000000-84bd9a5653cca48073ec
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0009000000-3dc59f30dc86ad78addb
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0049000000-e7582a888fb23070072e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0009000000-b9538285b676e7a5f8ca
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-08fr-1179000000-0b7a4266291bd39274ba
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-002b-0091000000-5af35df9f6fa3f23af43
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]-183.62573
predicted
DeepCCS 1.0 (2019)
[M+H]+185.98375
predicted
DeepCCS 1.0 (2019)
[M+Na]+192.41693
predicted
DeepCCS 1.0 (2019)

Targets

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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. [Article]

Drug created at September 15, 2010 21:34 / Updated at June 12, 2020 16:52