IMPPAT Phytochemical information: 
Orobanchol

Orobanchol
Summary

SMILES: O=C1O[C@H]2[C@@H](/C/1=C\O[C@@H]1OC(=O)C(=C1)C)[C@@H](C1=C2C(C)(C)CCC1)O
InChI: InChI=1S/C19H22O6/c1-9-7-12(24-17(9)21)23-8-11-13-15(20)10-5-4-6-19(2,3)14(10)16(13)25-18(11)22/h7-8,12-13,15-16,20H,4-6H2,1-3H3/b11-8+/t12-,13+,15-,16+/m1/s1
InChIKey: CDBBMEYPRMUMTR-RZXXLYMMSA-N
DeepSMILES: O=CO[C@H][C@@H]/C/5=C\O[C@@H]OC=O)C=C5)C))))))))[C@@H]C=C5CC)C)CCC6))))))O
Scaffold Graph/Node/Bond level: O=C1C=CC(OC=C2C(=O)OC3C4=C(CCCC4)CC23)O1
Scaffold Graph/Node level: OC1CCC(OCC2C(O)OC3C4CCCCC4CC23)O1
Scaffold Graph level: CC1CCC(CCC2C(C)CC3C4CCCCC4CC23)C1
Functional groups: CC1=C[C@H](O/C=C2\CCOC2=O)OC1=O; CC(=C(C)C)C; CO
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: Apocarotenoids
NP Classifier Class: Apocarotenoids (β-)
Synonymous chemical names:
orobanchol
External chemical identifiers:
CID:CID_10665247; ChEMBL:CHEMBL2270919; ZINC:ZINC000103279087; SureChEMBL:SCHEMBL13857704
Chemical structure download


Orobanchol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 346.38
Log P RDKit 2.14
Topological polar surface area (Å2) RDKit 82.06
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.21
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.58
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 2
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 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4


Orobanchol
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 0.356994


Orobanchol
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
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 -7.26
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 4
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No