IMPPAT Phytochemical information: 
Glycosmicine

Glycosmicine
Summary

SMILES: O=c1[nH]c(=O)n(c2c1cccc2)C
InChI: InChI=1S/C9H8N2O2/c1-11-7-5-3-2-4-6(7)8(12)10-9(11)13/h2-5H,1H3,(H,10,12,13)
InChIKey: RWFOOMQYIRITHL-UHFFFAOYSA-N
DeepSMILES: O=c[nH]c=O)ncc6cccc6))))))C
Scaffold Graph/Node/Bond level: O=c1[nH]c(=O)c2ccccc2[nH]1
Scaffold Graph/Node level: OC1NC(O)C2CCCCC2N1
Scaffold Graph level: CC1CC(C)C2CCCCC2C1
Functional groups: c=O; c[nH]c; cn(C)c
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:
Glycosmicine, 4-methyl-2,4-dioxo-quinazolin(glycosmicine), glycosmicine
External chemical identifiers:
CID:CID_11788; ZINC:ZINC000000175955; SureChEMBL:SCHEMBL5033267; MolPort-006-345-284
Chemical structure download


Glycosmicine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 176.18
Log P RDKit 0.23
Topological polar surface area (Å2) RDKit 54.86
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 9
Number of heavy atoms RDKit 13
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 1
Shape complexity RDKit 0.11
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 2
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 2


Glycosmicine
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 Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.624166


Glycosmicine
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 -7.15
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No