MeFSAT | MeFSAT: Medicinal Fungi Secondary metabolites And Therapeutics

Secondary metabolite: 3-Isobutyl-4-[4-(3-methyl-2-butenyloxy)phenyl]-1h-pyrrol-1-ol-2,5-dione

Summary

Molecular formula: C19H23NO4
SMILES: CC(=CCOc1ccc(cc1)C1=C(CC(C)C)C(=O)N(C1=O)O)C
InChI: InChI=1S/C19H23NO4/c1-12(2)9-10-24-15-7-5-14(6-8-15)17-16(11-13(3)4)18(21)20(23)19(17)22/h5-9,13,23H,10-11H2,1-4H3
InChIKey: OJSZXJGYUVZRNU-UHFFFAOYSA-N

Chemical classification

Kingdom: Organic compounds
Super class: Benzenoids
Class: Phenol ethers

Synonymous chemical names:
3-isobutyl-4-[4-(3-methyl-2-butenyloxy)phenyl]-1h-pyrrol-1-ol-2,5-dione, antrodin c

Chemical structure download

2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT

Physicochemical properties

Property name	Tool	Property value
Molecular weight (g/mol)	RDKit	329.4
Log P	RDKit	3.59
Topological polar surface area (Å²)	RDKit	66.84
Number of hydrogen bond acceptors	RDKit	4
Number of hydrogen bond donors	RDKit	1
Number of carbon atoms	RDKit	19
Number of heavy atoms	RDKit	24
Number of heteroatoms	RDKit	5
Number of nitrogen atoms	RDKit	1
Number of sulfur atoms	RDKit	0
Number of chiral carbon atoms	RDKit	0
Stereochemical complexity	RDKit	0
Number of sp hybridized carbon atoms	RDKit	0
Number of sp² hybridized carbon atoms	RDKit	12
Number of sp³ hybridized carbon atoms	RDKit	7
Fraction of sp³ hybridized carbon atoms (Fsp³)	RDKit	0.37
Shape complexity	RDKit	0.37
Number of rotatable bonds	SwissADME	6
Number of aliphatic carbocycles	RDKit	0
Number of aliphatic heterocycles	RDKit	1
Number of aliphatic rings	RDKit	1
Number of aromatic carbocycles	RDKit	1
Number of aromatic heterocycles	RDKit	0
Number of aromatic rings	RDKit	1
Total number of rings	RDKit	2
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	2

Drug-likeness properties

Property name	Tool	Property 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
Egan filter	RDKit	Good
Pfizer’s 3/75 filter	RDKit	Bad
GSK 4/400 filter	RDKit	Good
Number of Leadlikeness violations	SwissADME	1
Weighted quantitative estimate of drug-likeness (QEDw) score	RDKit	0.49

ADMET properties

Property name	Tool	Property value
Bioavailability score	SwissADME	0.55
Solubility class [ESOL]	SwissADME	Moderately soluble
Solubility class [Silicos-IT]	SwissADME	Moderately soluble
Blood Brain Barrier permeation	SwissADME	Yes
Gastrointestinal absorption	SwissADME	High
Log K_p (Skin permeation, cm/s)	SwissADME	-5.68
Number of PAINS structural alerts	SwissADME	0
Number of Brenk structural alerts	SwissADME	3
CYP1A2 inhibitor	SwissADME	Yes
CYP2C19 inhibitor	SwissADME	Yes
CYP2C9 inhibitor	SwissADME	Yes
CYP2D6 inhibitor	SwissADME	No
CYP3A4 inhibitor	SwissADME	No
P-glycoprotein substrate	SwissADME	No