(2R)-3-{[(4Z)-5,6-DIPHENYL-6,7-DIHYDRO-4H-PYRROLO[2,3-D]PYRIMIDIN-4-YLIDENE]AMINO}PROPANE-1,2-DIOL

Identification

Name
(2R)-3-{[(4Z)-5,6-DIPHENYL-6,7-DIHYDRO-4H-PYRROLO[2,3-D]PYRIMIDIN-4-YLIDENE]AMINO}PROPANE-1,2-DIOL
Accession Number
DB07648
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: 360.4091
Monoisotopic: 360.158625904
Chemical Formula
C21H20N4O2
InChI Key
TWEONIHFGKSPLC-MRXNPFEDSA-N
InChI
InChI=1S/C21H20N4O2/c26-12-16(27)11-22-20-18-17(14-7-3-1-4-8-14)19(15-9-5-2-6-10-15)25-21(18)24-13-23-20/h1-10,13,16,26-27H,11-12H2,(H2,22,23,24,25)/t16-/m1/s1
IUPAC Name
(2R)-3-({5,6-diphenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)propane-1,2-diol
SMILES
[H][[email protected]](O)(CO)CNC1=C2C(NC(=C2C2=CC=CC=C2)C2=CC=CC=C2)=NC=N1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
USerine/threonine-protein kinase Chk1Not AvailableHuman
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
4369435
PubChem Substance
99444119
ChemSpider
3571997
HET
DF2
PDB Entries
2bro

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 Solubility0.0275 mg/mLALOGPS
logP2.58ALOGPS
logP2.48ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)12.27ChemAxon
pKa (Strongest Basic)7.07ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area94.06 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity106.67 m3·mol-1ChemAxon
Polarizability38.77 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9902
Blood Brain Barrier+0.871
Caco-2 permeable-0.5937
P-glycoprotein substrateNon-substrate0.5639
P-glycoprotein inhibitor INon-inhibitor0.7941
P-glycoprotein inhibitor IINon-inhibitor0.5406
Renal organic cation transporterNon-inhibitor0.8582
CYP450 2C9 substrateNon-substrate0.8155
CYP450 2D6 substrateNon-substrate0.7522
CYP450 3A4 substrateNon-substrate0.7002
CYP450 1A2 substrateNon-inhibitor0.7163
CYP450 2C9 inhibitorNon-inhibitor0.767
CYP450 2D6 inhibitorNon-inhibitor0.7785
CYP450 2C19 inhibitorNon-inhibitor0.6536
CYP450 3A4 inhibitorNon-inhibitor0.6889
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5265
Ames testNon AMES toxic0.6437
CarcinogenicityNon-carcinogens0.871
BiodegradationNot ready biodegradable0.9717
Rat acute toxicity2.5901 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9449
hERG inhibition (predictor II)Inhibitor0.5831
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 phenylpyrroles. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrole ring through a CC or CN bond.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyrroles
Sub Class
Substituted pyrroles
Direct Parent
Phenylpyrroles
Alternative Parents
Pyrrolo[2,3-d]pyrimidines / Secondary alkylarylamines / Aminopyrimidines and derivatives / Imidolactams / Benzene and substituted derivatives / Heteroaromatic compounds / Secondary alcohols / 1,2-diols / Azacyclic compounds / Primary alcohols
show 2 more
Substituents
2-phenylpyrrole / 3-phenylpyrrole / Pyrrolo[2,3-d]pyrimidine / Pyrrolopyrimidine / Aminopyrimidine / Secondary aliphatic/aromatic amine / Monocyclic benzene moiety / Imidolactam / Benzenoid / Pyrimidine
show 15 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
pyrrolopyrimidine (CHEBI:41839)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Protein serine/threonine kinase activity
Specific Function
Serine/threonine-protein kinase which is required for checkpoint-mediated cell cycle arrest and activation of DNA repair in response to the presence of DNA damage or unreplicated DNA. May also nega...
Gene Name
CHEK1
Uniprot ID
O14757
Uniprot Name
Serine/threonine-protein kinase Chk1
Molecular Weight
54433.115 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 15:24 / Updated on December 01, 2017 15:54