IMPPAT Phytochemical information: 
Dehydro-4-methoxycyclobrassinin

Dehydro-4-methoxycyclobrassinin
Summary

SMILES: COc1cccc2c1c1-c(n2)sc(nc1)SC
InChI: InChI=1S/C12H10N2OS2/c1-15-9-5-3-4-8-10(9)7-6-13-12(16-2)17-11(7)14-8/h3-6H,1-2H3
InChIKey: JDYSKRAQSOYTDY-UHFFFAOYSA-N
DeepSMILES: COcccccc6c-cn5)scnc6))SC
Scaffold Graph/Node/Bond level: c1ccc2c3cncsc-3nc2c1
Scaffold Graph/Node level: C1CCC2C(C1)NC1SCNCC12
Scaffold Graph level: C1CCC2C(C1)CC1CCCCC12
Functional groups: cOC; cnc; csc; cSC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
ClassyFire Subclass: Indoles
NP Classifier Biosynthetic pathway: Alkaloids
Synonymous chemical names:
5-methoxy-2-(methylthio)-1,3-thiazino[6,5-b]indole,9cis
External chemical identifiers:
CID:CID_10332932; ChEBI:CHEBI:169362; ZINC:ZINC000014589709
Chemical structure download


Dehydro-4-methoxycyclobrassinin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 262.36
Log P RDKit 3.53
Topological polar surface area (Å2) RDKit 35.01
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 12
Number of heavy atoms RDKit 17
Number of heteroatoms RDKit 5
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 2
Shape complexity RDKit 0.17
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
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


Dehydro-4-methoxycyclobrassinin
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 0.66


Dehydro-4-methoxycyclobrassinin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.43
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes