IMPPAT Phytochemical information: 
Cadamine

Cadamine
Summary

SMILES: OCC1c2cncc(c2CC2N1CCc1c2[nH]c2c1cccc2)C(=O)OC
InChI: InChI=1S/C21H21N3O3/c1-27-21(26)16-10-22-9-15-14(16)8-18-20-13(6-7-24(18)19(15)11-25)12-4-2-3-5-17(12)23-20/h2-5,9-10,18-19,23,25H,6-8,11H2,1H3
InChIKey: SIZFHMVDXZLUER-UHFFFAOYSA-N
DeepSMILES: OCCccnccc6CCN%10CCcc6[nH]cc5cccc6)))))))))))))))C=O)OC
Scaffold Graph/Node/Bond level: c1ccc2c3c([nH]c2c1)C1Cc2ccncc2CN1CC3
Scaffold Graph/Node level: C1CCC2C(C1)NC1C2CCN2CC3CNCCC3CC12
Scaffold Graph level: C1CCC2CC3C(CCC4C5CCCCC5CC34)CC2C1
Functional groups: CN(C)C; CO; cC(=O)OC; c[nH]c; cnc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
ClassyFire Subclass: Pyridoindoles
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Carboline alkaloids
Synonymous chemical names:
cadamine
External chemical identifiers:
CID:73657079
Chemical structure download


Cadamine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 363.42
Log P RDKit 2.54
Topological polar surface area (Å2) RDKit 78.45
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 3
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.1
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 14
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.33
Number of rotatable bonds RDKit 3
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 2
Number of aromatic rings RDKit 3
Total number of rings RDKit 5
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 5


Cadamine
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 Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.6843


Cadamine
ADMET 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 -7.35
Number of PAINS structural alerts SwissADME 1.0
Number of Brenk structural alerts SwissADME 0.0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes