IMPPAT Phytochemical information: 
Azuleno(4,5-b)furan-2(3H)-one, decahydro-4,8-dihydroxy-3,6,9-tris(methylene)-, (3aR-(3aalpha,4alpha,6aalpha,8beta,9aalpha,9bbeta))-

Azuleno(4,5-b)furan-2(3H)-one, decahydro-4,8-dihydroxy-3,6,9-tris(methylene)-, (3aR-(3aalpha,4alpha,6aalpha,8beta,9aalpha,9bbeta))-
Summary

SMILES: O[C@H]1C[C@@H]2[C@H](C1=C)C1OC(=O)C(=C)[C@@H]1[C@H](CC2=C)O
InChI: InChI=1S/C15H18O4/c1-6-4-11(17)13-8(3)15(18)19-14(13)12-7(2)10(16)5-9(6)12/h9-14,16-17H,1-5H2/t9-,10-,11-,12-,13+,14?/m0/s1
InChIKey: VPRPYNVJJXOFKZ-RTHOXKBDSA-N
DeepSMILES: O[C@H]C[C@@H][C@H]C5=C))COC=O)C=C)[C@@H]5[C@H]CC%10=C)))O
Scaffold Graph/Node/Bond level: C=C1C(=O)OC2C1CCC(=C)C1CCC(=C)C12
Scaffold Graph/Node level: CC1CCC2C(C)C(O)OC2C2C(C)CCC12
Scaffold Graph level: CC1CC2C(CCC(C)C3CCC(C)C32)C1C
Functional groups: CO; C=C(C)C; C=C1CCOC1=O
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
NP Classifier Class: Guaiane sesquiterpenoids
Synonymous chemical names:
deacylcynaropicrin
External chemical identifiers:
CID:CID_71586749
Chemical structure download


Azuleno(4,5-b)furan-2(3H)-one, decahydro-4,8-dihydroxy-3,6,9-tris(methylene)-, (3aR-(3aalpha,4alpha,6aalpha,8beta,9aalpha,9bbeta))-
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 262.31
Log P RDKit 0.96
Topological polar surface area (Å2) RDKit 66.76
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 19
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.4
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.53
Number of rotatable bonds RDKit 0
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 2
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


Azuleno(4,5-b)furan-2(3H)-one, decahydro-4,8-dihydroxy-3,6,9-tris(methylene)-, (3aR-(3aalpha,4alpha,6aalpha,8beta,9aalpha,9bbeta))-
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 0.39


Azuleno(4,5-b)furan-2(3H)-one, decahydro-4,8-dihydroxy-3,6,9-tris(methylene)-, (3aR-(3aalpha,4alpha,6aalpha,8beta,9aalpha,9bbeta))-
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.65
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
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