IMPPAT Phytochemical information: 
Curcumanolide B
Curcumanolide B
Summary

SMILES: CC(=C1C[C@@]2(OC1=O)[C@@H](C)CC[C@@H]2C(=C)C)C
InChI: InChI=1S/C15H22O2/c1-9(2)12-8-15(17-14(12)16)11(5)6-7-13(15)10(3)4/h11,13H,3,6-8H2,1-2,4-5H3/t11-,13+,15+/m0/s1
InChIKey: KHOTZHZBHNDKOB-NJZAAPMLSA-N
DeepSMILES: CC=CC[C@@]OC5=O)))[C@@H]C)CC[C@@H]5C=C)C)))))))))C
Scaffold Graph/Node/Bond level: C=C1CC2(CCCC2)OC1=O
Scaffold Graph/Node level: CC1CC2(CCCC2)OC1O
Scaffold Graph level: CC1CC2(CCCC2)CC1C
Functional groups: CC(C)=C1CCOC1=O; C=C(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: Sesquiterpenoids
Synonymous chemical names:
curcumanolide-b, curcumanolide b, curcumanolide B, curcumariolide b
External chemical identifiers:
CID:CID_14191394; ChEMBL:CHEMBL2332434; ZINC:ZINC000013412544
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Curcumanolide B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 234.34
Log P RDKit 3.63
Topological polar surface area (Å2) RDKit 26.3
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 17
Number of heteroatoms RDKit 2
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.2
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.67
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2
Curcumanolide B
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 Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.393233
Curcumanolide B
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -4.68
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No