IMPPAT Phytochemical information: 
Methoxybrassenin B

Methoxybrassenin B
Summary

SMILES: CSC(=NC(=O)c1cn(c2c1cccc2)OC)SC
InChI: InChI=1S/C13H14N2O2S2/c1-17-15-8-10(9-6-4-5-7-11(9)15)12(16)14-13(18-2)19-3/h4-8H,1-3H3
InChIKey: NFGCTENDKLNJTI-UHFFFAOYSA-N
DeepSMILES: CSC=NC=O)ccncc5cccc6))))))OC)))))))SC
Scaffold Graph/Node/Bond level: c1ccc2[nH]ccc2c1
Scaffold Graph/Node level: C1CCC2NCCC2C1
Scaffold Graph level: C1CCC2CCCC2C1
Functional groups: cC(=O)N=C(SC)SC; cn(OC)c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
ClassyFire Subclass: Indolecarboxylic acids and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
Synonymous chemical names:
methoxybrassenin b
External chemical identifiers:
CID:CID_15145690; ChEBI:CHEBI:174782; ZINC:ZINC000014589433
Chemical structure download


Methoxybrassenin B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 294.4
Log P RDKit 2.92
Topological polar surface area (Å2) RDKit 43.59
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 13
Number of heavy atoms RDKit 19
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 2
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 10
Number of sp3 hybridized carbon atoms RDKit 3
Shape complexity RDKit 0.23
Number of rotatable bonds RDKit 4
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


Methoxybrassenin B
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 0.630786


Methoxybrassenin B
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.06
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No