IMPPAT Phytochemical information: 
12alpha-Hydroxy-13,18-dehydroparain
12alpha-Hydroxy-13,18-dehydroparain
Summary

SMILES: COC1=CC(C)C2C(C1=O)(C)C1C(O)C(O)C(=C)C3C1(C(C2)OC(=O)C3)C
InChI: InChI=1S/C21H28O6/c1-9-6-13(26-5)19(25)21(4)11(9)7-14-20(3)12(8-15(22)27-14)10(2)16(23)17(24)18(20)21/h6,9,11-12,14,16-18,23-24H,2,7-8H2,1,3-5H3
InChIKey: CKRHSGZMMGXRKZ-UHFFFAOYSA-N
DeepSMILES: COC=CCC)CCC6=O))C)CCO)CO)C=C)CC6CC%10)OC=O)C6))))C
Scaffold Graph/Node/Bond level: C=C1CCC2C3C(=O)C=CCC3CC3OC(=O)CC1C32
Scaffold Graph/Node level: CC1CCC2C3C(O)CCCC3CC3OC(O)CC1C32
Scaffold Graph level: CC1CC2CC3CCCC(C)C3C3CCC(C)C(C1)C23
Functional groups: CC=C(OC)C(=O)C; CO; C=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: Terpene lactones
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Quassinoids
Synonymous chemical names:
12α-hydroxy-13,18-dehydroparain
External chemical identifiers:
CID:CID_73081379; ChEBI:CHEBI:175842
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
12alpha-Hydroxy-13,18-dehydroparain
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 376.45
Log P RDKit 1.61
Topological polar surface area (Å2) RDKit 93.06
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.43
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 1
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
12alpha-Hydroxy-13,18-dehydroparain
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.533482
12alpha-Hydroxy-13,18-dehydroparain
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.72
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