IMPPAT Phytochemical information: 
6Alpha-Hydroxyraumacline
6Alpha-Hydroxyraumacline
Summary

SMILES: CC[C@@H]1CO[C@H]([C@H]2[C@H]1C[C@@H]1N[C@H]2[C@H](c2c1n(C)c1c2cccc1)O)O
InChI: InChI=1S/C20H26N2O3/c1-3-10-9-25-20(24)15-12(10)8-13-18-16(19(23)17(15)21-13)11-6-4-5-7-14(11)22(18)2/h4-7,10,12-13,15,17,19-21,23-24H,3,8-9H2,1-2H3/t10-,12+,13+,15+,17-,19+,20-/m1/s1
InChIKey: MRVRYGOAJGOYRP-FJFWSJDQSA-N
DeepSMILES: CC[C@@H]CO[C@H][C@H][C@H]6C[C@@H]N[C@H]6[C@H]cc6nC)cc5cccc6)))))))))O))))))))O
Scaffold Graph/Node/Bond level: c1ccc2c3c([nH]c2c1)C1CC2CCOCC2C(C3)N1
Scaffold Graph/Node level: C1CCC2C(C1)NC1C3CC4CCOCC4C(CC21)N3
Scaffold Graph level: C1CCC2C(C1)CC1CC2CC2C3CCCCC3CC12
Functional groups: CO[C@@H](O)C; CNC; cn(C)c; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Macroline alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Carboline alkaloids
Synonymous chemical names:
6alpha-Hydroxyraumacline, 6alpha-hydroxyraumacline
External chemical identifiers:
CID:CID_163034550
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
6Alpha-Hydroxyraumacline
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 342.44
Log P RDKit 2.24
Topological polar surface area (Å2) RDKit 66.65
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 3
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 7
Stereochemical complexity RDKit 0.35
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.6
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
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 0
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
6Alpha-Hydroxyraumacline
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 0.743522
6Alpha-Hydroxyraumacline
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.44
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