IMPPAT Phytochemical information: 
Ajmalan-17-ol, 19,20-didehydro-, (17R,19E)-(9CI)

Ajmalan-17-ol, 19,20-didehydro-, (17R,19E)-(9CI)
Summary

SMILES: C/C=C\1/CN2[C@@H]3[C@@H]4[C@H]1C[C@H]2[C@H]1[C@@]([C@@H]4O)(C3)c2c(N1C)cccc2
InChI: InChI=1S/C20H24N2O/c1-3-11-10-22-15-8-12(11)17-16(22)9-20(19(17)23)13-6-4-5-7-14(13)21(2)18(15)20/h3-7,12,15-19,23H,8-10H2,1-2H3/b11-3-/t12-,15-,16-,17-,18-,19+,20+/m0/s1
InChIKey: VBEQZFNVRMPLSM-MVVFEDHTSA-N
DeepSMILES: C/C=C/CN[C@@H][C@@H][C@H]/6C[C@H]6[C@H][C@@][C@@H]7O))C8)ccN5C))cccc6
Scaffold Graph/Node/Bond level: C=C1CN2C3CC45CC3C1CC2C4Nc1ccccc15
Scaffold Graph/Node level: CC1CN2C3CC45CC3C1CC2C4NC1CCCCC15
Scaffold Graph level: CC1CC2C3CC45CC3C1CC2C4CC1CCCCC15
Functional groups: C/C=C(/C)C; CN(C)C; CO; cN(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Ajmaline-sarpagine alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Corynanthe type
Synonymous chemical names:
tetraphyllicine
External chemical identifiers:
CID:CID_6436266; ZINC:ZINC000033838203
Chemical structure download


Ajmalan-17-ol, 19,20-didehydro-, (17R,19E)-(9CI)
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 308.43
Log P RDKit 2.16
Topological polar surface area (Å2) RDKit 26.71
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 3
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 0
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 5
Number of aliphatic rings RDKit 6
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 7
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 4
Number of saturated rings RDKit 5
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7


Ajmalan-17-ol, 19,20-didehydro-, (17R,19E)-(9CI)
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.74


Ajmalan-17-ol, 19,20-didehydro-, (17R,19E)-(9CI)
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 -7.13
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 Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes