IMPPAT Phytochemical information: 
Gravacridonediol
Gravacridonediol
Summary

SMILES: OCC(C1Oc2c(C1)c1c(c(c2)O)c(=O)c2c(n1C)cccc2)(O)C
InChI: InChI=1S/C19H19NO5/c1-19(24,9-21)15-7-11-14(25-15)8-13(22)16-17(11)20(2)12-6-4-3-5-10(12)18(16)23/h3-6,8,15,21-22,24H,7,9H2,1-2H3
InChIKey: RQAGSTDFTGSIGB-UHFFFAOYSA-N
DeepSMILES: OCCCOccC5)cccc6)O))c=O)ccn6C))cccc6)))))))))))))O)C
Scaffold Graph/Node/Bond level: O=c1c2ccccc2[nH]c2c3c(ccc12)OCC3
Scaffold Graph/Node level: OC1C2CCCCC2NC2C3CCOC3CCC12
Scaffold Graph level: CC1C2CCCCC2CC2C3CCCC3CCC12
Functional groups: CO; cOC; cO; c=O; cn(C)c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Quinolines and derivatives
ClassyFire Subclass: Benzoquinolines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Anthranilic acid alkaloids
NP Classifier Class: Acridone alkaloids
Synonymous chemical names:
Gravacridonediol, gravacridonediol, gravacridondiol
External chemical identifiers:
CID:CID_5317836; ChEMBL:CHEMBL562500
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Gravacridonediol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 341.36
Log P RDKit 1.44
Topological polar surface area (Å2) RDKit 91.92
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.11
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.32
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 4
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 4
Gravacridonediol
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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.61
Gravacridonediol
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.77
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No