IMPPAT Phytochemical information: 
Hernandaline

Hernandaline
Summary

SMILES: COc1cc2-c3c(OC)c(OC)cc4c3[C@H](Cc2cc1Oc1cc(OC)c(cc1C=O)OC)N(C)CC4
InChI: InChI=1S/C29H31NO7/c1-30-8-7-16-10-26(35-5)29(36-6)28-19-13-23(33-3)25(11-17(19)9-20(30)27(16)28)37-21-14-24(34-4)22(32-2)12-18(21)15-31/h10-15,20H,7-9H2,1-6H3/t20-/m0/s1
InChIKey: HLUNBGMOGGEWFX-FQEVSTJZSA-N
DeepSMILES: COccc-ccOC))cOC))ccc6[C@H]Cc%10cc%14OcccOC))ccc6C=O))))OC)))))))))))NC)CC6
Scaffold Graph/Node/Bond level: c1ccc(Oc2ccc3c(c2)CC2NCCc4cccc-3c42)cc1
Scaffold Graph/Node level: C1CCC(OC2CCC3C(C2)CC2NCCC4CCCC3C42)CC1
Scaffold Graph level: C1CCC(CC2CCC3C(C2)CC2CCCC4CCCC3C42)CC1
Functional groups: cOC; CN(C)C; cOc; cC=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Aporphines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Aporphine alkaloids
Synonymous chemical names:
hernandaline
External chemical identifiers:
CID:CID_12310422; ZINC:ZINC000015273855
Chemical structure download


Hernandaline
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 505.57
Log P RDKit 5.09
Topological polar surface area (Å2) RDKit 75.69
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 29
Number of heavy atoms RDKit 37
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.03
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 19
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.34
Number of rotatable bonds RDKit 8
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 0
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


Hernandaline
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 2
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 0.39


Hernandaline
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 -6.31
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes