IMPPAT Phytochemical information: 
15,16-Dihydro-15-methoxy-16-oxohardwickiic acid
15,16-Dihydro-15-methoxy-16-oxohardwickiic acid
Summary

SMILES: COC1C=C(C(=O)O1)CC[C@@]1(C)[C@H](C)CC[C@@]2([C@@H]1CCC=C2C(=O)O)C
InChI: InChI=1S/C21H30O5/c1-13-8-10-21(3)15(18(22)23)6-5-7-16(21)20(13,2)11-9-14-12-17(25-4)26-19(14)24/h6,12-13,16-17H,5,7-11H2,1-4H3,(H,22,23)/t13-,16-,17?,20+,21+/m1/s1
InChIKey: LKCDRCCSEGFFNK-CULFUZIZSA-N
DeepSMILES: COCC=CC=O)O5))CC[C@@]C)[C@H]C)CC[C@@][C@@H]6CCC=C6C=O)O)))))))C
Scaffold Graph/Node/Bond level: O=C1OCC=C1CCC1CCCC2C=CCCC21
Scaffold Graph/Node level: OC1OCCC1CCC1CCCC2CCCCC21
Scaffold Graph level: CC1CCCC1CCC1CCCC2CCCCC21
Functional groups: COC1C=C(C)C(=O)O1; CC=C(C(=O)O)C
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: Colensane and Clerodane diterpenoids
Synonymous chemical names:
Hardwickiic acid, 15-methoxy-16-oxo-15,16H-, 15-methoxy-16-oxo-15,16h-hardwickiic acid
External chemical identifiers:
CID:CID_91884914; MolPort-035-705-813
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
15,16-Dihydro-15-methoxy-16-oxohardwickiic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 362.47
Log P RDKit 4.09
Topological polar surface area (Å2) RDKit 72.83
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.24
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 15
Shape complexity RDKit 0.71
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3
15,16-Dihydro-15-methoxy-16-oxohardwickiic acid
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 0
Ghose rule RDKit Passed
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 0.75
15,16-Dihydro-15-methoxy-16-oxohardwickiic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.85
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.07
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No