IMPPAT Phytochemical information: 
Celacinnine

Celacinnine
Summary

SMILES: O=C1NCCCN(CCCCN[C@@H](C1)c1ccccc1)C(=O)/C=C/c1ccccc1
InChI: InChI=1S/C25H31N3O2/c29-24-20-23(22-12-5-2-6-13-22)26-16-7-8-18-28(19-9-17-27-24)25(30)15-14-21-10-3-1-4-11-21/h1-6,10-15,23,26H,7-9,16-20H2,(H,27,29)/b15-14+/t23-/m0/s1
InChIKey: OROFOUPCOTVAJQ-NSFRLNINSA-N
DeepSMILES: O=CNCCCNCCCCN[C@@H]C%13)cccccc6))))))))))))C=O)/C=C/cccccc6
Scaffold Graph/Node/Bond level: O=C1CC(c2ccccc2)NCCCCN(C(=O)C=Cc2ccccc2)CCCN1
Scaffold Graph/Node level: OC1CC(C2CCCCC2)NCCCCN(C(O)CCC2CCCCC2)CCCN1
Scaffold Graph level: CC1CCCCC(C(C)CCC2CCCCC2)CCCCCC(C2CCCCC2)C1
Functional groups: CNC(=O)C; c/C=C/C(=O)N(C)C; 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:
celacinnine
External chemical identifiers:
CID:CID_6452921; ChEBI:CHEBI:132186; ZINC:ZINC000014652469
Chemical structure download


Celacinnine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 405.54
Log P RDKit 3.55
Topological polar surface area (Å2) RDKit 61.44
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 25
Number of heavy atoms RDKit 30
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 3
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.04
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 16
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.36
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


Celacinnine
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 Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.77


Celacinnine
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 Yes
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 1
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