IMPPAT Phytochemical information: 
19-(R)-Acetyldihydrogelsevirine
19-(R)-Acetyldihydrogelsevirine
Summary

SMILES: CON1c2ccccc2[C@]2(C1=O)[C@@H]1OC[C@@H]3[C@@H]4[C@H]2[C@]([C@@H]3C1)(CN4C)C(OC(=O)C)C
InChI: InChI=1S/C23H28N2O5/c1-12(30-13(2)26)22-11-24(3)19-14-10-29-18(9-16(14)22)23(20(19)22)15-7-5-6-8-17(15)25(28-4)21(23)27/h5-8,12,14,16,18-20H,9-11H2,1-4H3/t12?,14-,16+,18+,19+,20-,22+,23-/m0/s1
InChIKey: BTZWFBFZHHQPCI-HVEPCGSVSA-N
DeepSMILES: CONcccccc6[C@]C9=O))[C@@H]OC[C@@H][C@@H][C@H]7[C@][C@@H]5C9))CN5C)))COC=O)C)))C
Scaffold Graph/Node/Bond level: O=C1Nc2ccccc2C12C1CC3C(CO1)C1NCC3C12
Scaffold Graph/Node level: OC1NC2CCCCC2C12C1CC3C(CO1)C1NCC3C12
Scaffold Graph level: CC1CC2CCCCC2C12C1CCC3C(C1)C1CCC3C12
Functional groups: cN(OC)C(=O)C; COC; CN(C)C; COC(C)=O
Chemical classification

NP Classifier Biosynthetic pathway: Alkaloids
Synonymous chemical names:
19-(r)-acetyldihydrogelsevirine, 19-(R)-Acetyldihydrogelsevirine
External chemical identifiers:
CID:CID_177462919
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
19-(R)-Acetyldihydrogelsevirine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 412.49
Log P RDKit 1.75
Topological polar surface area (Å2) RDKit 68.31
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 30
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 8
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 15
Shape complexity RDKit 0.65
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
19-(R)-Acetyldihydrogelsevirine
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 Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.7
19-(R)-Acetyldihydrogelsevirine
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 -7.72
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 Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No