IMPPAT Phytochemical information: 
Deoxyaconine

Deoxyaconine
Summary

SMILES: COCC12CN(CC)C3C4([C@@H]2C(OC)C3[C@@]2([C@@H]3C4C[C@@](C3O)([C@H](C2)OC)O)O)C(CC1O)OC
InChI: InChI=1S/C25H41NO8/c1-6-26-10-22(11-31-2)13(27)7-14(32-3)25-12-8-23(29)15(33-4)9-24(30,16(12)21(23)28)17(20(25)26)18(34-5)19(22)25/h12-21,27-30H,6-11H2,1-5H3/t12?,13?,14?,15-,16+,17?,18?,19+,20?,21?,22?,23-,24+,25?/m0/s1
InChIKey: WZGCQIYOKDLWMF-MNDTZMJDSA-N
DeepSMILES: COCCCNCC))CC[C@@H]6COC))C5[C@@][C@@H]C7C[C@@]C5O))[C@H]C7)OC)))O)))))O)))))CCC8O)))OC
Scaffold Graph/Node/Bond level: C1CC2CNC3C4CC2C3(C1)C1CC2CCC4C1C2
Scaffold Graph/Node level: C1CC2CNC3C4CC2C3(C1)C1CC2CCC4C1C2
Scaffold Graph level: C1CC2CCC3C4CC2C3(C1)C1CC2CCC4C1C2
Functional groups: COC; CN(C)C; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Diterpenoids
NP Classifier Biosynthetic pathway: Alkaloids|Terpenoids
NP Classifier Superclass: Pseudoalkaloids
NP Classifier Class: Terpenoid alkaloids
Synonymous chemical names:
pseudaconine
External chemical identifiers:
CID:CID_78358520
Chemical structure download


Deoxyaconine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 483.6
Log P RDKit -0.76
Topological polar surface area (Å2) RDKit 121.08
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 25
Number of heavy atoms RDKit 34
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 14
Stereochemical complexity RDKit 0.56
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 0
Number of sp3 hybridized carbon atoms RDKit 25
Shape complexity RDKit 1
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 5
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 6
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 5
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 6
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6


Deoxyaconine
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 3
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.39


Deoxyaconine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -10.36
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 No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes