NAV

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

Generic 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
DrugBank Accession Number
DB08131
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 397.4277
Monoisotopic: 397.175004249
Chemical Formula
C20H23N5O4
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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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

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 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
Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Benzoyl / Carbonyl group / Carboxamide group
show 25 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
pyrrolopyrimidine, valine derivative (CHEBI:43833)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
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][C@](NC(=O)C1=CC=C(CCC2=CNC3=C2C(=O)NC(N)=N3)C=C1)(C(C)C)C(O)=O

References

General References
Not Available
PubChem Compound
446560
PubChem Substance
99444602
ChemSpider
393882
ZINC
ZINC000005882138
PDBe Ligand
LYD
PDB Entries
1jut

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 Solubility0.0321 mg/mLALOGPS
logP1.69ALOGPS
logP2.21Chemaxon
logS-4.1ALOGPS
pKa (Strongest Acidic)3.8Chemaxon
pKa (Strongest Basic)1.71Chemaxon
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/MSsplash10-001i-0092000000-ae41d8fea21b6268b382
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fr2-0309000000-f1cad45484e37cd8e62b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01b9-9700000000-6e7b25bd195bf46fe16f
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0090000000-e650dc7849188d6adc15
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03yi-3980000000-7b610f2674bd26e35250
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-02dl-8952000000-4895e705192b86c1e596
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]-192.88391
predicted
DeepCCS 1.0 (2019)
[M+H]+195.2419
predicted
DeepCCS 1.0 (2019)
[M+Na]+201.42986
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Thymidylate synthase
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. [Article]

Drug created at September 15, 2010 21:28 / Updated at June 12, 2020 16:52