IMPPAT Phytochemical information: 
Cadabicine methyl ether

Cadabicine methyl ether
Summary

SMILES: COc1ccc2cc1Oc1ccc(cc1)/C=C\C(=O)NCCCNCCCCNC(=O)C=C2
InChI: InChI=1S/C26H31N3O4/c1-32-23-12-7-21-9-14-26(31)28-17-3-2-15-27-16-4-18-29-25(30)13-8-20-5-10-22(11-6-20)33-24(23)19-21/h5-14,19,27H,2-4,15-18H2,1H3,(H,28,31)(H,29,30)/b13-8-,14-9?
InChIKey: IXYCICGPUOJVOW-IWFLNBKMSA-N
DeepSMILES: COcccccc6Occcccc6))/C=C\C=O)NCCCNCCCCNC=O)C=C%24
Scaffold Graph/Node/Bond level: O=C1C=Cc2cccc(c2)Oc2ccc(cc2)C=CC(=O)NCCCNCCCCN1
Scaffold Graph/Node level: OC1CCC2CCC(CC2)OC2CCCC(CCC(O)NCCCCNCCCN1)C2
Scaffold Graph level: CC1CCCCCCCCCCC(C)CCC2CCCC(C2)CC2CCC(CC1)CC2
Functional groups: cC=CC(=O)NC; cOC; cOc; c/C=C\C(=O)NC; CNC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Macrolactams
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Ornithine alkaloids
NP Classifier Class: Polyamines
Synonymous chemical names:
cadabicine methyl ether
External chemical identifiers:
CID:CID_131752733; ChEBI:CHEBI:168569
Chemical structure download


Cadabicine methyl ether
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 449.55
Log P RDKit 3.52
Topological polar surface area (Å2) RDKit 88.69
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 26
Number of heavy atoms RDKit 33
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 3
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 18
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.31
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
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


Cadabicine methyl ether
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 1
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.62


Cadabicine methyl ether
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.64
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 Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes