IMPPAT Phytochemical information: 
Nodosin
Nodosin
Summary

SMILES: C=C1[C@@H]2C[C@H]([C@@H]3[C@](C1=O)(C2)C(=O)O[C@@H]1[C@]23CO[C@H]([C@@H]2C(CC1)(C)C)O)O
InChI: InChI=1S/C20H26O6/c1-9-10-6-11(21)13-19(7-10,15(9)22)17(24)26-12-4-5-18(2,3)14-16(23)25-8-20(12,13)14/h10-14,16,21,23H,1,4-8H2,2-3H3/t10-,11-,12+,13-,14-,16-,19+,20+/m1/s1
InChIKey: WZYJEEIAFBHYJS-SONIPUFESA-N
DeepSMILES: C=C[C@@H]C[C@H][C@@H][C@]C7=O))C6)C=O)O[C@@H][C@@]6CO[C@H][C@@H]5CCC9))C)C)))O))))))))))O
Scaffold Graph/Node/Bond level: C=C1C(=O)C23CC1CCC2C12COCC1CCCC2OC3=O
Scaffold Graph/Node level: CC1C2CCC3C45COCC4CCCC5OC(O)C3(C2)C1O
Scaffold Graph level: CC1C2CCC3C45CCCC4CCCC5CC(C)C3(C2)C1C
Functional groups: C=C(C)C(=O)C; COC(=O)C; CO[C@@H](O)C; CO
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: Diterpenoids
NP Classifier Class: Secokaurane diterpenoids
Synonymous chemical names:
nodosin, Nodosin
External chemical identifiers:
CID:CID_10248089; ChEMBL:CHEMBL510160; ChEBI:CHEBI:70379; ZINC:ZINC000038423106; MolPort-035-705-900
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Nodosin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 362.42
Log P RDKit 1.2
Topological polar surface area (Å2) RDKit 93.06
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 2
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 8
Stereochemical complexity RDKit 0.4
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 16
Shape complexity RDKit 0.8
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 3
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 5
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Nodosin
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 0.382057
Nodosin
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 -7.47
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 Yes