IMPPAT Phytochemical information: 
Spicatanol methyl ether

Spicatanol methyl ether
Summary

SMILES: CO[C@@H]1OC(=O)C=C1/C=C/[C@H]1C(=CC(=O)[C@@H]2[C@]1(C)CCCC2(C)C)C
InChI: InChI=1S/C21H28O4/c1-13-11-16(22)18-20(2,3)9-6-10-21(18,4)15(13)8-7-14-12-17(23)25-19(14)24-5/h7-8,11-12,15,18-19H,6,9-10H2,1-5H3/b8-7+/t15-,18-,19+,21+/m0/s1
InChIKey: ILKIVDALMQTOOO-XYSGFGBLSA-N
DeepSMILES: CO[C@@H]OC=O)C=C5/C=C/[C@H]C=CC=O)[C@@H][C@]6C)CCCC6C)C)))))))))C
Scaffold Graph/Node/Bond level: O=C1C=C(C=CC2C=CC(=O)C3CCCCC23)CO1
Scaffold Graph/Node level: OC1CC(CCC2CCC(O)C3CCCCC23)CO1
Scaffold Graph level: CC1CCC(CCC2CCC(C)C3CCCCC23)C1
Functional groups: CO[C@@H]1OC(=O)C=C1/C=C/C; CC(=CC(=O)C)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
Synonymous chemical names:
spicatanol methyl ether
External chemical identifiers:
CID:CID_44574437; ChEMBL:CHEMBL467052; ZINC:ZINC000040878699
Chemical structure download


Spicatanol methyl ether
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 344.45
Log P RDKit 3.98
Topological polar surface area (Å2) RDKit 52.6
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.19
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.62
Number of rotatable bonds RDKit 3
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


Spicatanol methyl ether
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 Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.73


Spicatanol methyl ether
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
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 -5.80
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No