Furo[2,3d]Pyrimidine Antifolate

Identification

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Name
Furo[2,3d]Pyrimidine Antifolate
Accession Number
DB02026  (EXPT00981)
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: 442.4253
Monoisotopic: 442.160082466
Chemical Formula
C20H22N6O6
InChI Key
WXINNGCGSCFUCR-ZDUSSCGKSA-N
InChI
InChI=1S/C20H22N6O6/c1-26(8-11-9-32-18-15(11)16(21)24-20(22)25-18)12-4-2-10(3-5-12)17(29)23-13(19(30)31)6-7-14(27)28/h2-5,9,13H,6-8H2,1H3,(H,23,29)(H,27,28)(H,30,31)(H4,21,22,24,25)/t13-/m0/s1
IUPAC Name
(2S)-2-({4-[({2,4-diaminofuro[2,3-d]pyrimidin-5-yl}methyl)(methyl)amino]phenyl}formamido)pentanedioic acid
SMILES
[H][C@@](CCC(O)=O)(NC(=O)C1=CC=C(C=C1)N(C)CC1=COC2=NC(N)=NC(N)=C12)C(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UDihydrofolate reductaseNot AvailablePneumocystis carinii
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
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

References

General References
Not Available
External Links
PubChem Compound
158376
PubChem Substance
46506042
ChemSpider
139334
BindingDB
50091145
ChEMBL
CHEMBL104829
HET
MOT
PDB Entries
1daj / 1hfp / 1hfq / 1hfr

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 Solubility0.425 mg/mLALOGPS
logP0.37ALOGPS
logP-0.58ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)3.22ChemAxon
pKa (Strongest Basic)4.48ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area197.9 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity115.56 m3·mol-1ChemAxon
Polarizability44.44 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9109
Blood Brain Barrier-0.9161
Caco-2 permeable-0.7654
P-glycoprotein substrateSubstrate0.6823
P-glycoprotein inhibitor INon-inhibitor0.8032
P-glycoprotein inhibitor IINon-inhibitor0.9434
Renal organic cation transporterNon-inhibitor0.8795
CYP450 2C9 substrateNon-substrate0.8153
CYP450 2D6 substrateNon-substrate0.8082
CYP450 3A4 substrateSubstrate0.5434
CYP450 1A2 substrateNon-inhibitor0.8445
CYP450 2C9 inhibitorNon-inhibitor0.8614
CYP450 2D6 inhibitorNon-inhibitor0.9232
CYP450 2C19 inhibitorNon-inhibitor0.8563
CYP450 3A4 inhibitorNon-inhibitor0.7996
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9644
Ames testNon AMES toxic0.8166
CarcinogenicityNon-carcinogens0.9538
BiodegradationNot ready biodegradable0.9337
Rat acute toxicity3.1217 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9332
hERG inhibition (predictor II)Non-inhibitor0.7217
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 glutamic acid and derivatives. These are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Glutamic acid and derivatives
Alternative Parents
N-acyl-alpha amino acids / Hippuric acids / Aminobenzamides / Furo[2,3-d]pyrimidines / Aniline and substituted anilines / Benzoyl derivatives / Dialkylarylamines / Aminopyrimidines and derivatives / Aralkylamines / Imidolactams
show 13 more
Substituents
Glutamic acid or derivatives / N-acyl-alpha amino acid or derivatives / N-acyl-alpha-amino acid / Hippuric acid / Hippuric acid or derivatives / Aminobenzamide / Aminobenzoic acid or derivatives / Furo[2,3-d]pyrimidine / Benzamide / Benzoic acid or derivatives
show 32 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
furopyrimidine, N-acyl-L-glutamic acid (CHEBI:44035)

Targets

Kind
Protein
Organism
Pneumocystis carinii
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
Not Available
Uniprot ID
P16184
Uniprot Name
Dihydrofolate reductase
Molecular Weight
23883.325 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on January 02, 2020 04:55