IMPPAT Phytochemical information: 
Ephedradine B
Ephedradine B
Summary

SMILES: COc1cc(ccc1O)[C@@H]1Oc2c3[C@H]1C(=O)N1CCCCNCCCN[C@H](c(c3)cc2)CC(=O)NCCC1
InChI: InChI=1S/C29H38N4O5/c1-37-25-17-20(6-8-23(25)34)28-27-21-16-19(7-9-24(21)38-28)22-18-26(35)32-13-5-15-33(29(27)36)14-3-2-10-30-11-4-12-31-22/h6-9,16-17,22,27-28,30-31,34H,2-5,10-15,18H2,1H3,(H,32,35)/t22-,27+,28-/m0/s1
InChIKey: OZQWWKNRYQISEO-ZGOJTZKKSA-N
DeepSMILES: COcccccc6O))))[C@@H]Occ[C@H]5C=O)NCCCCNCCCN[C@H]cc%16)cc%18)))CC=O)NCCC%17
Scaffold Graph/Node/Bond level: O=C1CC2NCCCNCCCCN(CCCN1)C(=O)C1c3cc2ccc3OC1c1ccccc1
Scaffold Graph/Node level: OC1CC2NCCCNCCCCN(CCCN1)C(O)C1C3CC2CCC3OC1C1CCCCC1
Scaffold Graph level: CC1CCCCC2CCCCCCCCCC(C1)C1CCC3CC(C4CCCCC4)C(C2C)C3C1
Functional groups: CNC(=O)C; cOC; cO; CN(C)C(=O)C; CNC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: 2-arylbenzofuran flavonoids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Ornithine alkaloids
NP Classifier Class: Polyamines
Synonymous chemical names:
ephedradine-b
External chemical identifiers:
CID:CID_156055; ZINC:ZINC000085504886
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Ephedradine B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 522.65
Log P RDKit 2.76
Topological polar surface area (Å2) RDKit 112.16
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 29
Number of heavy atoms RDKit 38
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 4
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.1
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 14
Number of sp3 hybridized carbon atoms RDKit 15
Shape complexity RDKit 0.52
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
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
Ephedradine B
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
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 0.48
Ephedradine B
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 -8.47
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