IMPPAT Phytochemical information: 
Hecubine
Hecubine
Summary

SMILES: CC[C@]12CCc3c(CCN(C1)C[C@@H]1[C@H]2O1)c1c(n3C)cccc1
InChI: InChI=1S/C20H26N2O/c1-3-20-10-8-17-15(14-6-4-5-7-16(14)21(17)2)9-11-22(13-20)12-18-19(20)23-18/h4-7,18-19H,3,8-13H2,1-2H3/t18-,19-,20+/m1/s1
InChIKey: XUDAGNVXWJRKJD-AQNXPRMDSA-N
DeepSMILES: CC[C@]CCccCCNC9)C[C@@H][C@H]%11O3)))))))ccn5C))cccc6
Scaffold Graph/Node/Bond level: c1ccc2c3c([nH]c2c1)CCC1CN(CC3)CC2OC12
Scaffold Graph/Node level: C1CCC2C(C1)NC1CCC3CN(CCC12)CC1OC31
Scaffold Graph level: C1CCC2C(C1)CC1CCC3CC(CCC12)CC1CC31
Functional groups: CN(C)C; C[C@H]1O[C@H]1C; cn(C)c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Quebrachamine alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Carboline alkaloids
Synonymous chemical names:
hecubine, Hecubine, n-methyl-voaphylline (hecubine)
External chemical identifiers:
CID:CID_11438319; ZINC:ZINC000139159090
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Hecubine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 310.44
Log P RDKit 3.15
Topological polar surface area (Å2) RDKit 20.7
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.15
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.6
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Hecubine
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 0.75
Hecubine
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.87
Number of PAINS structural alerts SwissADME 1
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 No
P-glycoprotein substrate SwissADME No