IMPPAT Phytochemical information: 
(-)-Dioxibrassinin

(-)-Dioxibrassinin
Summary

SMILES: CSC(=S)NCC1(O)C(=O)Nc2c1cccc2
InChI: InChI=1S/C11H12N2O2S2/c1-17-10(16)12-6-11(15)7-4-2-3-5-8(7)13-9(11)14/h2-5,15H,6H2,1H3,(H,12,16)(H,13,14)
InChIKey: DXLDPLVGKCAHPY-UHFFFAOYSA-N
DeepSMILES: CSC=S)NCCO)C=O)Ncc5cccc6
Scaffold Graph/Node/Bond level: O=C1Cc2ccccc2N1
Scaffold Graph/Node level: OC1CC2CCCCC2N1
Scaffold Graph level: CC1CC2CCCCC2C1
Functional groups: CNC(=S)SC; CO; cNC(=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic acids and derivatives
ClassyFire Class: Carboxylic acids and derivatives
ClassyFire Subclass: Amino acids, peptides, and analogues
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Simple oxindole alkaloids
Synonymous chemical names:
(-)-dioxibrassinin, dioxibrassinin
External chemical identifiers:
CID:CID_11807698; ChEBI:CHEBI:173897; SureChEMBL:SCHEMBL16377153
Chemical structure download


(-)-Dioxibrassinin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 268.36
Log P RDKit 1.06
Topological polar surface area (Å2) RDKit 61.36
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 11
Number of heavy atoms RDKit 17
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 2
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 3
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 0
Number of aromatic rings RDKit 1
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


(-)-Dioxibrassinin
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 0.700296


(-)-Dioxibrassinin
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 -6.91
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No