IMPPAT Phytochemical information: 
Vicolide A

Vicolide A
Summary

SMILES: C/C=C(/C(=O)OC1C(O)C2C(C3C(C1C)C(=O)C=C3C)OC(=O)C2=C)\C
InChI: InChI=1S/C20H24O6/c1-6-8(2)19(23)25-17-10(4)14-12(21)7-9(3)13(14)18-15(16(17)22)11(5)20(24)26-18/h6-7,10,13-18,22H,5H2,1-4H3/b8-6+
InChIKey: AECULMKGNBGPKV-SOFGYWHQSA-N
DeepSMILES: C/C=C/C=O)OCCO)CCCCC7C))C=O)C=C5C))))))OC=O)C5=C))))))))))\C
Scaffold Graph/Node/Bond level: C=C1C(=O)OC2C1CCCC1C(=O)C=CC12
Scaffold Graph/Node level: CC1C(O)OC2C1CCCC1C(O)CCC12
Scaffold Graph level: CC1CC2C(CCCC3C(C)CCC32)C1C
Functional groups: C/C=C(\C)C(=O)OC; CO; CC1=CC(=O)CC1; 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: Guaiane sesquiterpenoids
Synonymous chemical names:
vicolide a, Vicolide A
External chemical identifiers:
CID:CID_5477684
Chemical structure download


Vicolide A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 360.41
Log P RDKit 1.73
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 7
Stereochemical complexity RDKit 0.35
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 2
Number of aliphatic heterocycles RDKit 1
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 1
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


Vicolide A
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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.6


Vicolide A
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