IMPPAT Phytochemical information: 
8-Angeloylegelolide

8-Angeloylegelolide
Summary

SMILES: C/C=C(/C(=O)OC1CC(C)(O)c2c(C3C1C(C)C(=O)O3)c(oc2)C)\C
InChI: InChI=1S/C19H24O6/c1-6-9(2)17(20)24-13-7-19(5,22)12-8-23-11(4)15(12)16-14(13)10(3)18(21)25-16/h6,8,10,13-14,16,22H,7H2,1-5H3/b9-6+
InChIKey: UUYOHEAYCPQMKY-RMKNXTFCSA-N
DeepSMILES: C/C=C/C=O)OCCCC)O)ccCC7CC)C=O)O5)))))coc5))C)))))))))\C
Scaffold Graph/Node/Bond level: O=C1CC2CCCc3cocc3C2O1
Scaffold Graph/Node level: OC1CC2CCCC3COCC3C2O1
Scaffold Graph level: CC1CC2CCCC3CCCC3C2C1
Functional groups: C/C=C(\C)C(=O)OC; CO; COC(=O)C; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Cycloheptafurans
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Sesquiterpenoids
NP Classifier Class: Germacrane sesquiterpenoids
Synonymous chemical names:
8-angeloyl egelolide
External chemical identifiers:
CID:CID_131752230; ChEBI:CHEBI:175420
Chemical structure download


8-Angeloylegelolide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 348.4
Log P RDKit 2.93
Topological polar surface area (Å2) RDKit 85.97
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 5
Stereochemical complexity RDKit 0.26
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 3
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 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 3
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 3


8-Angeloylegelolide
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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.65


8-Angeloylegelolide
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 -6.81
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