IMPPAT Phytochemical information: 
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Summary

SMILES: COc1cc2-c3cc(/C=C\C(=O)O[C@@H]4C[C@@H](c2cc1OC)N1CCCC[C@@H]1C4)ccc3O
InChI: InChI=1S/C26H29NO5/c1-30-24-14-19-20(15-25(24)31-2)22-13-18(12-17-5-3-4-10-27(17)22)32-26(29)9-7-16-6-8-23(28)21(19)11-16/h6-9,11,14-15,17-18,22,28H,3-5,10,12-13H2,1-2H3/b9-7-/t17-,18+,22+/m1/s1
InChIKey: WCZWUYYJZVBKDZ-VMSBZHFZSA-N
DeepSMILES: COccc-ccc/C=C\C=O)O[C@@H]C[C@@H]c%12cc%16OC)))))NCCCC[C@@H]6C%10))))))))))))))ccc6O
Scaffold Graph/Node/Bond level: O=C1C=Cc2cccc(c2)-c2ccccc2C2CC(CC3CCCCN32)O1
Scaffold Graph/Node level: OC1CCC2CCCC(C2)C2CCCCC2C2CC(CC3CCCCN32)O1
Scaffold Graph level: CC1CCC2CCCC(C2)C2CCCCC2C2CC(C1)CC1CCCCC12
Functional groups: cOC; c/C=C\C(=O)OC; CN(C)C; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Quinolizidines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Lysine alkaloids
NP Classifier Class: Quinolizidine alkaloids
Synonymous chemical names:
vertine
External chemical identifiers:
CID:CID_5315204; ChEMBL:CHEMBL1173218; ChEBI:CHEBI:3929; ZINC:ZINC000005371559; FDASRS:OR77C8W8TA; SureChEMBL:SCHEMBL1119034; MolPort-046-856-592
Chemical structure download


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Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 435.52
Log P RDKit 4.7
Topological polar surface area (Å2) RDKit 68.23
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 26
Number of heavy atoms RDKit 32
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.12
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.42
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
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


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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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.689695


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ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.69
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