2-{4-[2-(2-AMINO-4-OXO-4,7-DIHYDRO-3H-PYRROLO[2,3-D]PYRIMIDIN-5-YL)-ETHYL]-BENZOYLAMINO}-3-METHYL-BUTYRIC ACID

Identification

Name
2-{4-[2-(2-AMINO-4-OXO-4,7-DIHYDRO-3H-PYRROLO[2,3-D]PYRIMIDIN-5-YL)-ETHYL]-BENZOYLAMINO}-3-METHYL-BUTYRIC ACID
Accession Number
DB08131
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: 397.4277
Monoisotopic: 397.175004249
Chemical Formula
C20H23N5O4
InChI Key
MYENGRJSPURSQB-HNNXBMFYSA-N
InChI
InChI=1S/C20H23N5O4/c1-10(2)15(19(28)29)23-17(26)12-6-3-11(4-7-12)5-8-13-9-22-16-14(13)18(27)25-20(21)24-16/h3-4,6-7,9-10,15H,5,8H2,1-2H3,(H,23,26)(H,28,29)(H4,21,22,24,25,27)/t15-/m0/s1
IUPAC Name
(2S)-2-{[4-(2-{2-amino-4-oxo-3H,4H,7H-pyrrolo[2,3-d]pyrimidin-5-yl}ethyl)phenyl]formamido}-3-methylbutanoic acid
SMILES
[H][[email protected]](NC(=O)C1=CC=C(CCC2=CNC3=C2C(=O)NC(N)=N3)C=C1)(C(C)C)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UThymidylate synthaseNot AvailableEscherichia coli (strain K12)
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
446560
PubChem Substance
99444602
ChemSpider
393882
HET
LYD
PDB Entries
1jut

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 Solubility0.0321 mg/mLALOGPS
logP1.69ALOGPS
logP1.43ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)3.4ChemAxon
pKa (Strongest Basic)4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area149.67 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity108.09 m3·mol-1ChemAxon
Polarizability42.11 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.791
Blood Brain Barrier+0.5262
Caco-2 permeable-0.7863
P-glycoprotein substrateSubstrate0.5201
P-glycoprotein inhibitor INon-inhibitor0.9614
P-glycoprotein inhibitor IINon-inhibitor0.9489
Renal organic cation transporterNon-inhibitor0.9277
CYP450 2C9 substrateNon-substrate0.7178
CYP450 2D6 substrateNon-substrate0.8194
CYP450 3A4 substrateNon-substrate0.5706
CYP450 1A2 substrateNon-inhibitor0.8549
CYP450 2C9 inhibitorNon-inhibitor0.8273
CYP450 2D6 inhibitorNon-inhibitor0.9001
CYP450 2C19 inhibitorNon-inhibitor0.8296
CYP450 3A4 inhibitorNon-inhibitor0.8673
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9277
Ames testNon AMES toxic0.7832
CarcinogenicityNon-carcinogens0.9615
BiodegradationNot ready biodegradable0.9607
Rat acute toxicity2.4980 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9813
hERG inhibition (predictor II)Non-inhibitor0.8414
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 hippuric acids. These are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
Hippuric acids
Alternative Parents
Valine and derivatives / N-acyl-alpha amino acids / Pyrrolo[2,3-d]pyrimidines / Benzoyl derivatives / Aminopyrimidines and derivatives / Pyrimidones / Substituted pyrroles / Heteroaromatic compounds / Vinylogous amides / Amino acids
show 9 more
Substituents
N-acyl-alpha amino acid or derivatives / N-acyl-alpha-amino acid / Hippuric acid / Valine or derivatives / Alpha-amino acid or derivatives / Pyrrolopyrimidine / Pyrrolo[2,3-d]pyrimidine / Benzoyl / Pyrimidone / Aminopyrimidine
show 25 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
pyrrolopyrimidine, valine derivative (CHEBI:43833)

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Thymidylate synthase activity
Specific Function
Provides the sole de novo source of dTMP for DNA biosynthesis. This protein also binds to its mRNA thus repressing its own translation.
Gene Name
thyA
Uniprot ID
P0A884
Uniprot Name
Thymidylate synthase
Molecular Weight
30479.475 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 15:28 / Updated on November 09, 2017 04:26