IMPPAT Phytochemical information: 
Prostephanaberrine
Prostephanaberrine
Summary

SMILES: COC1=CC[C@@]23[C@](C1=O)(C[C@@H](c1c3cc3OCOc3c1)O)N(C)CC2
InChI: InChI=1S/C19H21NO5/c1-20-6-5-18-4-3-14(23-2)17(22)19(18,20)9-13(21)11-7-15-16(8-12(11)18)25-10-24-15/h3,7-8,13,21H,4-6,9-10H2,1-2H3/t13-,18+,19+/m0/s1
InChIKey: AFTBFIOTWHPFTG-MJXNMMHHSA-N
DeepSMILES: COC=CC[C@][C@]C6=O))C[C@@H]cc6ccOCOc5c9)))))))))O)))NC)CC5
Scaffold Graph/Node/Bond level: O=C1C=CCC23CCNC12CCc1cc2c(cc13)OCO2
Scaffold Graph/Node level: OC1CCCC23CCNC12CCC1CC2OCOC2CC13
Scaffold Graph level: CC1CCCC23CCCC12CCC1CC2CCCC2CC13
Functional groups: CC=C(OC)C(=O)C; c1cOCO1; CO; CN(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Phenanthrenes and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Hasubanan alkaloids
Synonymous chemical names:
prostephanaberrine, Prostephanaberrine
External chemical identifiers:
CID:CID_184517; ZINC:ZINC000085809713; MolPort-039-338-276
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Prostephanaberrine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 343.38
Log P RDKit 1.67
Topological polar surface area (Å2) RDKit 68.23
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.16
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.53
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 2
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 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Prostephanaberrine
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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.836562
Prostephanaberrine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.19
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 Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes