IMPPAT Phytochemical information: 
protoveratrine A
protoveratrine A
Summary

SMILES: CC[C@H](C(=O)O[C@H]1[C@H](O)[C@H]2[C@H]([C@H]3[C@]1(O)[C@@H]1[C@H](OC(=O)C)[C@H](OC(=O)C)[C@H]4[C@]5([C@]1(C3)O[C@]4(O)[C@H](CC5)OC(=O)[C@](CC)(O)C)C)CN1[C@H]([C@@]2(C)O)CC[C@@H](C1)C)C
InChI: InChI=1S/C41H63NO14/c1-10-20(4)34(46)55-33-28(45)27-23(18-42-17-19(3)12-13-25(42)38(27,9)49)24-16-39-32(40(24,33)50)30(53-22(6)44)29(52-21(5)43)31-36(39,7)15-14-26(41(31,51)56-39)54-35(47)37(8,48)11-2/h19-20,23-33,45,48-51H,10-18H2,1-9H3/t19-,20+,23-,24-,25-,26-,27+,28+,29-,30+,31-,32+,33-,36-,37-,38+,39+,40-,41+/m0/s1
InChIKey: HYTGGNIMZXFORS-MGYKWWNKSA-N
DeepSMILES: CC[C@H]C=O)O[C@H][C@H]O)[C@H][C@H][C@H][C@]6O)[C@@H][C@H]OC=O)C)))[C@H]OC=O)C)))[C@H][C@][C@]6C9)O[C@]5O)[C@H]CC7))OC=O)[C@]CC))O)C))))))))C))))))))CN[C@H][C@@]6C)O))CC[C@@H]C6)C)))))))))))))C
Scaffold Graph/Node/Bond level: C1CCN2CC3C(CCC4C3CC35OC6CCCC3C6CCC45)CC2C1
Scaffold Graph/Node level: C1CCN2CC3C(CCC4C3CC35OC6CCCC3C6CCC45)CC2C1
Scaffold Graph level: C1CCC2CC3C(CCC4C3CC35CC6CCCC3C6CCC45)CC2C1
Functional groups: COC(C)=O; CO; CC(=O)OC; CO[C@@](O)(C)C; CN(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Steroids and steroid derivatives
ClassyFire Subclass: Steroidal alkaloids
NP Classifier Biosynthetic pathway: Alkaloids|Terpenoids
NP Classifier Superclass: Pseudoalkaloids
NP Classifier Class: Steroidal alkaloids
Synonymous chemical names:
protoveratrine a
External chemical identifiers:
CID:CID_8931; ChEMBL:CHEMBL2105769; ChEBI:CHEBI:8594; ZINC:ZINC000085537146; FDASRS:XP343X1HJU
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
protoveratrine A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 793.95
Log P RDKit 1.61
Topological polar surface area (Å2) RDKit 218.82
Number of hydrogen bond acceptors RDKit 15
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 41
Number of heavy atoms RDKit 56
Number of heteroatoms RDKit 15
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 19
Stereochemical complexity RDKit 0.46
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 37
Shape complexity RDKit 0.9
Number of rotatable bonds RDKit 12
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 7
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 7
Number of saturated carbocycles RDKit 4
Number of saturated heterocycles RDKit 3
Number of saturated rings RDKit 7
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7
protoveratrine A
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 3
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.17
protoveratrine A
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -9.62
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
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