NAV

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

Identification

Generic Name
(2R)-3-{[(4Z)-5,6-DIPHENYL-6,7-DIHYDRO-4H-PYRROLO[2,3-D]PYRIMIDIN-4-YLIDENE]AMINO}PROPANE-1,2-DIOL
DrugBank Accession Number
DB07648
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 360.4091
Monoisotopic: 360.158625904
Chemical Formula
C21H20N4O2
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
USerine/threonine-protein kinase Chk1Not AvailableHumans
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 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
1,2-diol / 2-phenylpyrrole / 3-phenylpyrrole / Alcohol / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Heteroaromatic compound
show 15 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
pyrrolopyrimidine (CHEBI:41839)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
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][C@](O)(CO)CNC1=C2C(NC(=C2C2=CC=CC=C2)C2=CC=CC=C2)=NC=N1

References

General References
Not Available
PubChem Compound
4369435
PubChem Substance
99444119
ChemSpider
3571997
ZINC
ZINC000006475920
PDBe Ligand
DF2
PDB Entries
2bro

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 Solubility0.0275 mg/mLALOGPS
logP2.58ALOGPS
logP2.48Chemaxon
logS-4.1ALOGPS
pKa (Strongest Acidic)12.27Chemaxon
pKa (Strongest Basic)6.31Chemaxon
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/MSsplash10-03di-0009000000-f7aef4bb04f61af268e8
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0019000000-50dc7482cf867c63bdf4
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0009000000-7adf8aefa6e97524de09
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0092000000-cfa961926ecd97d49d3c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0w2a-0069000000-f4edb288b76e697a1ac3
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-05fs-0094000000-671315c122b513e651c3
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]-174.97755
predicted
DeepCCS 1.0 (2019)
[M+H]+177.33557
predicted
DeepCCS 1.0 (2019)
[M+Na]+183.9594
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Serine/threonine-protein kinase Chk1
Kind
Protein
Organism
Humans
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. [Article]

Drug created at September 15, 2010 21:24 / Updated at June 12, 2020 16:52