IMPPAT Phytochemical information: 
Isoapetalic acid

Isoapetalic acid
Summary

SMILES: CCCC(c1c2OC(C)C(C(=O)c2c(c2c1OC(C)(C)C=C2)O)C)CC(=O)O
InChI: InChI=1S/C22H28O6/c1-6-7-13(10-15(23)24)16-20-14(8-9-22(4,5)28-20)19(26)17-18(25)11(2)12(3)27-21(16)17/h8-9,11-13,26H,6-7,10H2,1-5H3,(H,23,24)
InChIKey: JZWLSXINEVHWEP-UHFFFAOYSA-N
DeepSMILES: CCCCccOCC)CC=O)c6ccc%10OCC)C)C=C6))))))O))))C))))))CC=O)O
Scaffold Graph/Node/Bond level: O=C1CCOc2cc3c(cc21)C=CCO3
Scaffold Graph/Node level: OC1CCOC2CC3OCCCC3CC12
Scaffold Graph level: CC1CCCC2CC3CCCCC3CC12
Functional groups: cOC; cC(=O)C; cC=CC; cO; CC(=O)O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Benzopyrans
ClassyFire Subclass: 1-benzopyrans
NP Classifier Biosynthetic pathway: Polyketides
Synonymous chemical names:
apetalic acid
External chemical identifiers:
CID:CID_341189; MolPort-005-944-851
Chemical structure download


Isoapetalic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 388.46
Log P RDKit 4.53
Topological polar surface area (Å2) RDKit 93.06
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.14
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.55
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


Isoapetalic acid
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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.769466


Isoapetalic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.35
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes