IMPPAT Phytochemical information: 
Holafrine
Holafrine
Summary

SMILES: O=C(O[C@@H]1CC2C(C3[C@@]41CNC([C@H]4CC3)C)CC=C1[C@]2(C)CC[C@@H](C1)N(C)C)CC=C(C)C
InChI: InChI=1S/C29H46N2O2/c1-18(2)7-12-27(32)33-26-16-25-22(24-11-10-23-19(3)30-17-29(23,24)26)9-8-20-15-21(31(5)6)13-14-28(20,25)4/h7-8,19,21-26,30H,9-17H2,1-6H3/t19?,21-,22?,23+,24?,25?,26+,28-,29?/m0/s1
InChIKey: MDIHJZIBYXGUFH-YBVJDGITSA-N
DeepSMILES: O=CO[C@@H]CCCC[C@]6CNC[C@H]5CC8)))C))))))CC=C[C@]6C)CC[C@@H]C6)NC)C))))))))))))))CC=CC)C
Scaffold Graph/Node/Bond level: C1=C2CCCCC2C2CCC34CNCC3CCC4C2C1
Scaffold Graph/Node level: C1CCC2C(C1)CCC1C2CCC23CNCC2CCC13
Scaffold Graph level: C1CCC2C(C1)CCC1C2CCC23CCCC2CCC13
Functional groups: CC(=O)OC; CNC; CC=C(C)C; CN(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Steroids and steroid derivatives
ClassyFire Subclass: Steroid esters
NP Classifier Biosynthetic pathway: Alkaloids|Terpenoids
NP Classifier Superclass: Pseudoalkaloids
NP Classifier Class: Steroidal alkaloids
Synonymous chemical names:
Holafrine, holafrine
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Holafrine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 454.7
Log P RDKit 5.35
Topological polar surface area (Å2) RDKit 41.57
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 29
Number of heavy atoms RDKit 33
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.31
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 24
Shape complexity RDKit 0.83
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 3
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Holafrine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 2
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.459498
Holafrine
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 -5.24
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 No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No