IMPPAT Phytochemical information: 
Dehydrodiscretamine
Dehydrodiscretamine
Summary

SMILES: COC1=CC2=C3C=c4ccc(c(c4=C[NH+]3CCC2=CC1=O)OC)O
InChI: InChI=1S/C19H17NO4/c1-23-18-9-13-12(8-17(18)22)5-6-20-10-14-11(7-15(13)20)3-4-16(21)19(14)24-2/h3-4,7-10,21H,5-6H2,1-2H3/p+1
InChIKey: XXLNLCVMHJBPLJ-UHFFFAOYSA-O
DeepSMILES: COC=CC=CC=cccccc6=C[NH+]%10CCC%14=CC%18=O)))))))))OC)))O
Scaffold Graph/Node/Bond level: O=C1C=CC2=C3C=c4ccccc4=C[NH+]3CCC2=C1
Scaffold Graph/Node level: OC1CCC2C(CCN3CC4CCCCC4CC23)C1
Scaffold Graph level: CC1CCC2C(CCC3CC4CCCCC4CC32)C1
Functional groups: CC1=C2C=C(OC)C(=O)C=C2CC[NH+]1C; cOC; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Protoberberine alkaloids and derivatives
Synonymous chemical names:
dehydrodiscretamine, Dehydrodiscretamine
External chemical identifiers:
CID:CID_102316663; ZINC:ZINC000005999210
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Dehydrodiscretamine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 324.36
Log P RDKit -0.49
Topological polar surface area (Å2) RDKit 60.2
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 24
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 15
Number of sp3 hybridized carbon atoms RDKit 4
Shape complexity RDKit 0.21
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 4
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 4
Dehydrodiscretamine
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 1
Ghose filter RDKit Failed
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 0.771146
Dehydrodiscretamine
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 No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.48
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No