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Identification
Name2-{4-[2-(2-AMINO-4-OXO-4,7-DIHYDRO-3H-PYRROLO[2,3-D]PYRIMIDIN-5-YL)-ETHYL]-BENZOYLAMINO}-3-METHYL-BUTYRIC ACID
Accession NumberDB08131
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS numberNot Available
WeightAverage: 397.4277
Monoisotopic: 397.175004249
Chemical FormulaC20H23N5O4
InChI KeyMYENGRJSPURSQB-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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzamides
Direct ParentHippuric acids
Alternative Parents
Substituents
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Hippuric acid
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Pyrrolopyrimidine
  • Benzoic acid or derivatives
  • Benzoyl
  • Pyrimidone
  • Amino fatty acid
  • Fatty acyl
  • Substituted pyrrole
  • Pyrimidine
  • Primary aromatic amine
  • Heteroaromatic compound
  • Vinylogous amide
  • Pyrrole
  • Secondary carboxylic acid amide
  • Lactam
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrateNon-inhibitor0.8273
CYP450 2D6 substrateNon-inhibitor0.9001
CYP450 2C19 substrateNon-inhibitor0.8296
CYP450 3A4 substrateNon-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
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Thymidylate synthase

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: unknown

Components

Name UniProt ID Details
Thymidylate synthase P0A884 Details

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

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Drug created on September 15, 2010 15:28 / Updated on September 16, 2013 18:08