IMPPAT Phytochemical information: 
Pyrrolo(2,1-b)quinazolin-9(1H)-one, 2,3-dihydro-3,7-dihydroxy-, (3S)-

Pyrrolo(2,1-b)quinazolin-9(1H)-one, 2,3-dihydro-3,7-dihydroxy-, (3S)-
Summary

SMILES: Oc1ccc2c(c1)c(=O)n1c(n2)[C@H](CC1)O
InChI: InChI=1S/C11H10N2O3/c14-6-1-2-8-7(5-6)11(16)13-4-3-9(15)10(13)12-8/h1-2,5,9,14-15H,3-4H2/t9-/m0/s1
InChIKey: MKNHUAILAQZBTQ-VIFPVBQESA-N
DeepSMILES: Occcccc6)c=O)ncn6)[C@H]CC5))O
Scaffold Graph/Node/Bond level: O=c1c2ccccc2nc2n1CCC2
Scaffold Graph/Node level: OC1C2CCCCC2NC2CCCN21
Scaffold Graph level: CC1C2CCCCC2CC2CCCC21
Functional groups: cO; c=O; cn(c)C; cnc; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Diazanaphthalenes
ClassyFire Subclass: Benzodiazines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Anthranilic acid alkaloids
NP Classifier Class: Quinazoline alkaloids
Synonymous chemical names:
Vasicinolone, vasicinolone
External chemical identifiers:
CID:CID_158720; ChEMBL:CHEMBL4205756; ZINC:ZINC000014827650; MolPort-023-278-984
Chemical structure download


Pyrrolo(2,1-b)quinazolin-9(1H)-one, 2,3-dihydro-3,7-dihydroxy-, (3S)-
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 218.21
Log P RDKit 0.54
Topological polar surface area (Å2) RDKit 75.35
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 11
Number of heavy atoms RDKit 16
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.09
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 3
Shape complexity RDKit 0.27
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


Pyrrolo(2,1-b)quinazolin-9(1H)-one, 2,3-dihydro-3,7-dihydroxy-, (3S)-
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.676305


Pyrrolo(2,1-b)quinazolin-9(1H)-one, 2,3-dihydro-3,7-dihydroxy-, (3S)-
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.61
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No