IMPPAT Phytochemical information: 
Dicentrinone

Dicentrinone
Summary

SMILES: COc1cc2-c3c4OCOc4cc4c3c(C(=O)c2cc1OC)ncc4
InChI: InChI=1S/C19H13NO5/c1-22-12-6-10-11(7-13(12)23-2)18(21)17-15-9(3-4-20-17)5-14-19(16(10)15)25-8-24-14/h3-7H,8H2,1-2H3
InChIKey: NEQVOBXBOFZEMR-UHFFFAOYSA-N
DeepSMILES: COccc-ccOCOc5ccc9cC=O)c%13cc%17OC))))))ncc6
Scaffold Graph/Node/Bond level: O=C1c2ccccc2-c2c3c(cc4ccnc1c24)OCO3
Scaffold Graph/Node level: OC1C2CCCCC2C2C3OCOC3CC3CCNC1C32
Scaffold Graph level: CC1C2CCCCC2C2C3CCCC3CC3CCCC1C32
Functional groups: cOC; c1cOCO1; cC(=O)c; cnc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Aporphines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Aporphine alkaloids
Synonymous chemical names:
dicentrinone
External chemical identifiers:
CID:CID_177744; ChEMBL:CHEMBL463284; FDASRS:K6CE5RM6EI; SureChEMBL:SCHEMBL6685214
Chemical structure download


Dicentrinone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 335.32
Log P RDKit 3.19
Topological polar surface area (Å2) RDKit 66.88
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 0
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 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 16
Number of sp3 hybridized carbon atoms RDKit 3
Shape complexity RDKit 0.16
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 5
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 5


Dicentrinone
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 0.56


Dicentrinone
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.98
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 Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No