IMPPAT Phytochemical information: 
Vicolide C
Vicolide C
Summary

SMILES: CC[C@@H](C(=O)O[C@H]1[C@H](OC(=O)C)[C@H](C)C[C@@H](O)[C@@H]2[C@@]([C@@H]([C@@H]3[C@@H]1C(=C)C(=O)O3)O)(C)O2)C
InChI: InChI=1S/C22H32O9/c1-7-9(2)20(26)29-16-14-11(4)21(27)30-17(14)18(25)22(6)19(31-22)13(24)8-10(3)15(16)28-12(5)23/h9-10,13-19,24-25H,4,7-8H2,1-3,5-6H3/t9-,10+,13+,14+,15+,16+,17-,18+,19+,22-/m0/s1
InChIKey: JBZUUXNUAXEKGK-AZOCKGJASA-N
DeepSMILES: CC[C@@H]C=O)O[C@H][C@H]OC=O)C)))[C@H]C)C[C@@H]O)[C@@H][C@@][C@@H][C@@H][C@@H]%10C=C)C=O)O5)))))O))C)O3))))))))))C
Scaffold Graph/Node/Bond level: C=C1C(=O)OC2CC3OC3CCCCCC12
Scaffold Graph/Node level: CC1C(O)OC2CC3OC3CCCCCC21
Scaffold Graph level: CC1CC2CC3CC3CCCCCC2C1C
Functional groups: COC(C)=O; CC(=O)OC; CO; C[C@@]1(C)O[C@@H]1C; C=C1CCOC1=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic acids and derivatives
ClassyFire Class: Carboxylic acids and derivatives
ClassyFire Subclass: Tricarboxylic acids and derivatives
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Sesquiterpenoids
NP Classifier Class: Germacrane sesquiterpenoids
Synonymous chemical names:
vicolide c, Vicolide C
External chemical identifiers:
CID:CID_76312409; ChEMBL:CHEMBL2269924; ZINC:ZINC000038656835
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Vicolide C
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 440.49
Log P RDKit 0.89
Topological polar surface area (Å2) RDKit 131.89
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 31
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 10
Stereochemical complexity RDKit 0.45
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 17
Shape complexity RDKit 0.77
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3
Vicolide C
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 Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.283041
Vicolide C
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 -7.89
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 3
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes