IMPPAT Phytochemical information: 
Cordifolide A
Cordifolide A
Summary

SMILES: OC[C@H]1O[C@@H](OCCS[C@H]2CC[C@@H]3[C@@]4([C@@]2(O)C(=O)O[C@H]4C[C@@H]2[C@@]3(C)C[C@H](OC2=O)c2cocc2)C)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C28H38O12S/c1-26-10-15(13-5-6-36-12-13)38-23(33)14(26)9-18-27(2)17(26)3-4-19(28(27,35)25(34)40-18)41-8-7-37-24-22(32)21(31)20(30)16(11-29)39-24/h5-6,12,14-22,24,29-32,35H,3-4,7-11H2,1-2H3/t14-,15-,16+,17-,18-,19-,20+,21-,22+,24+,26+,27-,28-/m0/s1
InChIKey: VLSGMHUNRVEKPV-YLFXFDEASA-N
DeepSMILES: OC[C@H]O[C@@H]OCCS[C@H]CC[C@@H][C@@][C@@]6O)C=O)O[C@H]5C[C@@H][C@@]9C)C[C@H]OC6=O)))ccocc5))))))))))))))C))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C1OC(c2ccoc2)CC2C1CC1OC(=O)C3C(SCCOC4CCCCO4)CCC2C13
Scaffold Graph/Node level: OC1OC(C2CCOC2)CC2C1CC1OC(O)C3C(SCCOC4CCCCO4)CCC2C13
Scaffold Graph level: CC1CC(C2CCCC2)CC2C1CC1CC(C)C3C(CCCCC4CCCCC4)CCC2C13
Functional groups: CO; CO[C@@H](C)OC; CSC; COC(=O)C; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Naphthopyrans
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Diterpenoids
NP Classifier Class: Colensane and Clerodane diterpenoids
Synonymous chemical names:
cordifolide
External chemical identifiers:
CID:CID_102451916; ZINC:ZINC000169663472
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Cordifolide A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 598.67
Log P RDKit 0.28
Topological polar surface area (Å2) RDKit 185.35
Number of hydrogen bond acceptors RDKit 13
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 28
Number of heavy atoms RDKit 41
Number of heteroatoms RDKit 13
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 1
Number of chiral carbon atoms RDKit 13
Stereochemical complexity RDKit 0.46
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 22
Shape complexity RDKit 0.79
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 3
Number of saturated rings RDKit 5
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
Cordifolide A
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 3
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.21
Cordifolide A
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -9.70
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
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