Furo[2,3d]Pyrimidine Antifolate

Identification

Generic Name
Furo[2,3d]Pyrimidine Antifolate
DrugBank Accession Number
DB02026
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 442.4253
Monoisotopic: 442.160082466
Chemical Formula
C20H22N6O6
Synonyms
Not Available

Pharmacology

Indication

Not Available

Reduce drug development failure rates
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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

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 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
Amine / Amino acid / Aminobenzamide / Aminobenzoic acid or derivatives / Aminopyrimidine / Aniline or substituted anilines / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzamide
show 32 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
furopyrimidine, N-acyl-L-glutamic acid (CHEBI:44035)
Affected organisms
Not Available

Chemical Identifiers

UNII
VBP3BN3U2V
CAS number
Not Available
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

References

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

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 Solubility0.425 mg/mLALOGPS
logP0.37ALOGPS
logP-1.1Chemaxon
logS-3ALOGPS
pKa (Strongest Acidic)2.47Chemaxon
pKa (Strongest Basic)5.21Chemaxon
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/MSsplash10-0002-0090100000-e661bd8054ad0702012c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0f6x-0406900000-7bc1c76720923bd0a201
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0uk9-1908400000-ccbf715af52e852eb2d8
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0090000000-0d7ccb263336067ad92e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0950000000-ae39b1dba55b9c12a4fa
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0f96-3900100000-9651683f8992fb829469
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]-224.9278073
predicted
DarkChem Lite v0.1.0
[M-H]-194.83904
predicted
DeepCCS 1.0 (2019)
[M+H]+223.6370073
predicted
DarkChem Lite v0.1.0
[M+H]+197.2346
predicted
DeepCCS 1.0 (2019)
[M+Na]+224.8571073
predicted
DarkChem Lite v0.1.0
[M+Na]+203.14713
predicted
DeepCCS 1.0 (2019)

Targets

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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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52