IMPPAT Phytochemical information: 
(3S)-3-hydroxy-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one
(3S)-3-hydroxy-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one
Summary

SMILES: O[C@H]1CCn2c1nc1ccccc1c2=O
InChI: InChI=1S/C11H10N2O2/c14-9-5-6-13-10(9)12-8-4-2-1-3-7(8)11(13)15/h1-4,9,14H,5-6H2/t9-/m0/s1
InChIKey: SDIVYZXRQHWCKF-VIFPVBQESA-N
DeepSMILES: O[C@H]CCnc5ncccccc6c%10=O
Scaffold Graph/Node/Bond level: O=c1c2ccccc2nc2n1CCC2
Scaffold Graph/Node level: OC1C2CCCCC2NC2CCCN21
Scaffold Graph level: CC1C2CCCCC2CC2CCCC21
Functional groups: CO; cn(c)C; cnc; c=O
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:
vasicinone
External chemical identifiers:
CID:CID_442935; ChEMBL:CHEMBL3120244; ChEBI:CHEBI:9936; ZINC:ZINC000100064968; FDASRS:G6T5819NXM; MolPort-039-338-135
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(3S)-3-hydroxy-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 202.21
Log P RDKit 0.83
Topological polar surface area (Å2) RDKit 55.12
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 11
Number of heavy atoms RDKit 15
Number of heteroatoms RDKit 4
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
(3S)-3-hydroxy-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.69
(3S)-3-hydroxy-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one
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 -7.16
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