IMPPAT Phytochemical information: 
Darienine

Darienine
Summary

SMILES: COc1c(OC)c(O)cc2c1-c1nccc(c1C2=O)C
InChI: InChI=1S/C15H13NO4/c1-7-4-5-16-12-10(7)13(18)8-6-9(17)14(19-2)15(20-3)11(8)12/h4-6,17H,1-3H3
InChIKey: BZDOUYRDEWHTCN-UHFFFAOYSA-N
DeepSMILES: COccOC))cO)ccc6-cncccc6C9=O)))C
Scaffold Graph/Node/Bond level: O=C1c2ccccc2-c2ncccc21
Scaffold Graph/Node level: OC1C2CCCCC2C2NCCCC12
Scaffold Graph level: CC1C2CCCCC2C2CCCCC12
Functional groups: cOC; cO; cnc; cC(=O)c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Phenol ethers
ClassyFire Subclass: Anisoles
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Nicotinic acid alkaloids
NP Classifier Class: Pyridine alkaloids
Synonymous chemical names:
darienine(tetrahydroproteoberberine alkaloids), darienine, Darienine
External chemical identifiers:
CID:CID_130672; ChEMBL:CHEMBL449820; ZINC:ZINC000006071993; FDASRS:F33SQ49WKW
Chemical structure download


Darienine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 271.27
Log P RDKit 2.32
Topological polar surface area (Å2) RDKit 68.65
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 20
Number of heteroatoms RDKit 5
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 12
Number of sp3 hybridized carbon atoms RDKit 3
Shape complexity RDKit 0.2
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
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


Darienine
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 0.77


Darienine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.55
Number of PAINS structural alerts SwissADME 1
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 Yes
P-glycoprotein substrate SwissADME Yes