IMPPAT Phytochemical information: 
Cunninghamic acid A
Cunninghamic acid A
Summary

SMILES: C=CC1(CCC=C(C1)/C=C/C1C(=C)CCC2C1(C)CCCC2(C)C(=O)O)/C=C/C1C(=C)CCC2C1(C)CCCC2(C)C(=O)O
InChI: InChI=1S/C40H56O4/c1-8-40(25-19-31-28(3)14-18-33-37(31,5)21-11-23-39(33,7)35(43)44)24-9-12-29(26-40)15-16-30-27(2)13-17-32-36(30,4)20-10-22-38(32,6)34(41)42/h8,12,15-16,19,25,30-33H,1-3,9-11,13-14,17-18,20-24,26H2,4-7H3,(H,41,42)(H,43,44)/b16-15+,25-19+
InChIKey: YYXHOWXUYGQYQE-OSTGZTDHSA-N
DeepSMILES: C=CCCCC=CC6)/C=C/CC=C)CCCC6C)CCCC6C)C=O)O))))))))))))))))))/C=C/CC=C)CCCC6C)CCCC6C)C=O)O
Scaffold Graph/Node/Bond level: C=C1CCC2CCCCC2C1C=CC1=CCCC(C=CC2C(=C)CCC3CCCCC32)C1
Scaffold Graph/Node level: CC1CCC2CCCCC2C1CCC1CCCC(CCC2C(C)CCC3CCCCC32)C1
Scaffold Graph level: CC1CCC2CCCCC2C1CCC1CCCC(CCC2C(C)CCC3CCCCC32)C1
Functional groups: C=CC; CC=C(/C=C/C)C; CC(=O)O; C=C(C)C; C/C=C/C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Diterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Diterpenoids
NP Classifier Class: Labdane diterpenoids
Synonymous chemical names:
Cunninghamic acid A, cunninghamic acid a
External chemical identifiers:
CID:CID_102146779
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Cunninghamic acid A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 600.88
Log P RDKit 10.11
Topological polar surface area (Å2) RDKit 74.6
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 40
Number of heavy atoms RDKit 44
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.23
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 14
Number of sp3 hybridized carbon atoms RDKit 26
Shape complexity RDKit 0.65
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 5
Number of aliphatic heterocycles RDKit 0
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 4
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Cunninghamic acid 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 4
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.29
Cunninghamic acid A
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.85
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -2.96
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 Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes