IMPPAT Phytochemical information: 
18-Beta-hydroxy-3-epi-alpha-yohimbine
18-Beta-hydroxy-3-epi-alpha-yohimbine
Summary

SMILES: COC(=O)[C@H]1[C@H]2C[C@H]3N(C[C@H]2C[C@H]([C@@H]1O)O)CCc1c3[nH]c2c1cccc2
InChI: InChI=1S/C21H26N2O4/c1-27-21(26)18-14-9-16-19-13(12-4-2-3-5-15(12)22-19)6-7-23(16)10-11(14)8-17(24)20(18)25/h2-5,11,14,16-18,20,22,24-25H,6-10H2,1H3/t11-,14+,16-,17-,18+,20+/m1/s1
InChIKey: MMVZFQGCDSDHSV-DOGZXOHNSA-N
DeepSMILES: COC=O)[C@H][C@H]C[C@H]NC[C@H]6C[C@H][C@@H]%10O))O)))))CCcc6[nH]cc5cccc6
Scaffold Graph/Node/Bond level: c1ccc2c3c([nH]c2c1)C1CC2CCCCC2CN1CC3
Scaffold Graph/Node level: C1CCC2CN3CCC4C5CCCCC5NC4C3CC2C1
Scaffold Graph level: C1CCC2CC3C(CCC4C5CCCCC5CC34)CC2C1
Functional groups: COC(C)=O; CN(C)C; CO; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Yohimbine alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Yohimbine-like alkaloids
Synonymous chemical names:
18-hydroxyepialloyohimbine, 18beta-hydroxy-3-epi-alpha-yohimbine, 18-beta-hydroxy-3-epi-alpha-yohimbine
External chemical identifiers:
CID:CID_102004710; MolPort-044-754-106
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
18-Beta-hydroxy-3-epi-alpha-yohimbine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 370.45
Log P RDKit 1.62
Topological polar surface area (Å2) RDKit 85.79
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.29
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.57
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
18-Beta-hydroxy-3-epi-alpha-yohimbine
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 Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.664408
18-Beta-hydroxy-3-epi-alpha-yohimbine
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 -7.17
Number of PAINS structural alerts SwissADME 1
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