IMPPAT Phytochemical information: 
Calenduloside A
Calenduloside A
Summary

SMILES: OCC1OC(OC2CCC3(C(C2(C)C)CCC2(C3CC=C3C2(C)CCC2(C3CC(C)(C)CC2)C(=O)O)C)C)C(C(C1OC1OC(CO)C(C(C1O)O)O)O)O
InChI: InChI=1S/C42H68O13/c1-37(2)14-16-42(36(50)51)17-15-40(6)21(22(42)18-37)8-9-26-39(5)12-11-27(38(3,4)25(39)10-13-41(26,40)7)54-34-32(49)30(47)33(24(20-44)53-34)55-35-31(48)29(46)28(45)23(19-43)52-35/h8,22-35,43-49H,9-20H2,1-7H3,(H,50,51)
InChIKey: WIGHCPZBXOGLKE-UHFFFAOYSA-N
DeepSMILES: OCCOCOCCCCCC6C)C))CCCC6CC=CC6C)CCCC6CCC)C)CC6)))))C=O)O))))))))))C)))))C))))))CCC6OCOCCO))CCC6O))O))O)))))))O))O
Scaffold Graph/Node/Bond level: C1=C2C3CCCCC3CCC2C2CCC3CC(OC4CCC(OC5CCCCO5)CO4)CCC3C2C1
Scaffold Graph/Node level: C1CCC(OC2CCC(OC3CCC4C(CCC5C4CCC4C6CCCCC6CCC45)C3)OC2)OC1
Scaffold Graph level: C1CCC(CC2CCC(CC3CCC4C(CCC5C4CCC4C6CCCCC6CCC45)C3)CC2)CC1
Functional groups: CO; CC(=O)O; COC(OC)C; COC(C)OC; CC=C(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Terpene glycosides
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Oleanane triterpenoids
Synonymous chemical names:
calenduloside a
External chemical identifiers:
CID:CID_3439408
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Calenduloside A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 780.99
Log P RDKit 2.88
Topological polar surface area (Å2) RDKit 215.83
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 8
Number of carbon atoms RDKit 42
Number of heavy atoms RDKit 55
Number of heteroatoms RDKit 13
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 18
Stereochemical complexity RDKit 0.43
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 39
Shape complexity RDKit 0.93
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 5
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 7
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 7
Number of saturated carbocycles RDKit 4
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 6
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7
Calenduloside A
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 3
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.138054
Calenduloside A
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -8.40
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