IMPPAT Phytochemical information: 
Caccigenin lactone
Caccigenin lactone
Summary

SMILES: OC[C@]1(C)[C@@H](O)[C@H](O)C[C@]2([C@H]1CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@]13[C@H]2CC([C@H](C1)OC3=O)(C)C)C)C
InChI: InChI=1S/C30H46O5/c1-25(2)13-18-17-7-8-21-26(3)14-19(32)23(33)27(4,16-31)20(26)9-10-29(21,6)28(17,5)11-12-30(18)15-22(25)35-24(30)34/h7,18-23,31-33H,8-16H2,1-6H3/t18-,19+,20+,21+,22-,23-,26-,27-,28+,29+,30+/m0/s1
InChIKey: VTORIUYQHNEHNN-MUGVOSBHSA-N
DeepSMILES: OC[C@]C)[C@@H]O)[C@H]O)C[C@][C@H]6CC[C@@][C@@H]6CC=C[C@@]6C)CC[C@][C@H]6CC[C@H]C6)OC7=O))))C)C))))))))))))C)))))C
Scaffold Graph/Node/Bond level: O=C1OC2CCC3C4=CCC5C6CCCCC6CCC5C4CCC13C2
Scaffold Graph/Node level: OC1OC2CCC3C4CCC5C6CCCCC6CCC5C4CCC13C2
Scaffold Graph level: CC1CC2CCC3C4CCC5C6CCCCC6CCC5C4CCC13C2
Functional groups: CO; CC=C(C)C; COC(=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Triterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Oleanane triterpenoids
Synonymous chemical names:
caccigenin lactone
External chemical identifiers:
CID:CID_21594251; ZINC:ZINC000138708264
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Caccigenin lactone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 486.69
Log P RDKit 4.63
Topological polar surface area (Å2) RDKit 86.99
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 30
Number of heavy atoms RDKit 35
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 11
Stereochemical complexity RDKit 0.37
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 27
Shape complexity RDKit 0.9
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 5
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 6
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 4
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 5
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
Caccigenin lactone
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 3
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.37
Caccigenin lactone
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.52
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