IMPPAT Phytochemical information: 
12-Bromo-19,20-dihydroakuammicine
12-Bromo-19,20-dihydroakuammicine
Summary

SMILES: CC[C@@H]1CN2CCC34[C@@H]2C[C@@H]1C(=C3Nc1c4cccc1Br)C(=O)OC
InChI: InChI=1S/C20H23BrN2O2/c1-3-11-10-23-8-7-20-13-5-4-6-14(21)17(13)22-18(20)16(19(24)25-2)12(11)9-15(20)23/h4-6,11-12,15,22H,3,7-10H2,1-2H3/t11-,12+,15+,20?/m1/s1
InChIKey: BEXFFFOCSSEUMG-SDPVTAKPSA-N
DeepSMILES: CC[C@@H]CNCCC[C@@H]5C[C@@H]9C=C6Ncc9cccc6Br)))))))))C=O)OC
Scaffold Graph/Node/Bond level: C1=C2Nc3ccccc3C23CCN2CCC1CC23
Scaffold Graph/Node level: C1CCC2C(C1)NC1CC3CCN4CCC12C4C3
Scaffold Graph level: C1CCC2C(C1)CC1CC3CCC4CCC12C4C3
Functional groups: CN(C)C; cNC(=C(C(=O)OC)C)C; cBr
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Strychnos alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Corynanthe type|Strychnos type
Synonymous chemical names:
12-bromo-19,20-dihydroakuammicine
External chemical identifiers:
CID:CID_102494047
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
12-Bromo-19,20-dihydroakuammicine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 403.32
Log P RDKit 3.67
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 20
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.2
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.55
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
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
12-Bromo-19,20-dihydroakuammicine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
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 0.76562
12-Bromo-19,20-dihydroakuammicine
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 -6.10
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No