IMPPAT Phytochemical information: 
Vicolide B
Vicolide B
Summary

SMILES: C/C=C(/C(=O)O[C@@H]1[C@H](C)CC(=O)/C=C(\C[C@@H]2[C@@H]([C@H]1O)C(=C)C(=O)O2)/C)\C
InChI: InChI=1S/C20H26O6/c1-6-11(3)19(23)26-18-12(4)9-14(21)7-10(2)8-15-16(17(18)22)13(5)20(24)25-15/h6-7,12,15-18,22H,5,8-9H2,1-4H3/b10-7-,11-6+/t12-,15-,16+,17-,18-/m1/s1
InChIKey: ZQOKMZFGSMWPTI-LXTYMCCDSA-N
DeepSMILES: C/C=C/C=O)O[C@@H][C@H]C)CC=O)/C=C\C[C@@H][C@@H][C@H]%10O))C=C)C=O)O5))))))/C)))))))))\C
Scaffold Graph/Node/Bond level: C=C1C(=O)OC2CC=CC(=O)CCCCC12
Scaffold Graph/Node level: CC1C(O)OC2CCCC(O)CCCCC21
Scaffold Graph level: CC1CCCCC2C(CCC1)CC(C)C2C
Functional groups: C/C=C(\C)C(=O)OC; CC(=O)/C=C(/C)C; CO; C=C1CCOC1=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Terpene lactones
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Sesquiterpenoids
NP Classifier Class: Germacrane sesquiterpenoids
Synonymous chemical names:
Vicolide B, vicolide b
External chemical identifiers:
CID:CID_6445538
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Vicolide B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 362.42
Log P RDKit 2.27
Topological polar surface area (Å2) RDKit 89.9
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.25
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.55
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2
Vicolide B
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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.598616
Vicolide B
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 -7.24
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No