MeFSAT | MeFSAT: Medicinal Fungi Secondary metabolites And Therapeutics

Secondary metabolite: (2S)-1-[2-(furan-2-yl)-2-oxoethyl]-5-oxopyrrolidine-2-carboxylic acid

Summary

Molecular formula: C11H11NO5
SMILES: OC(=O)[C@@H]1CCC(=O)N1CC(=O)c1ccco1
InChI: InChI=1S/C11H11NO5/c13-8(9-2-1-5-17-9)6-12-7(11(15)16)3-4-10(12)14/h1-2,5,7H,3-4,6H2,(H,15,16)/t7-/m0/s1
InChIKey: IOAYUDNRXFKAMK-ZETCQYMHSA-N

Chemical classification

Kingdom: Organic compounds
Super class: Organic acids and derivatives
Class: Carboxylic acids and derivatives
Sub class: Amino acids, peptides, and analogues

Synonymous chemical names:
(2s)-1-[2-(furan-2-yl)-2-oxoethyl]-5-oxopyrrolidine-2-carboxylic acid

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	237.21
Log P	RDKit	0.54
Topological polar surface area (Å²)	RDKit	87.82
Number of hydrogen bond acceptors	RDKit	4
Number of hydrogen bond donors	RDKit	1
Number of carbon atoms	RDKit	11
Number of heavy atoms	RDKit	17
Number of heteroatoms	RDKit	6
Number of nitrogen atoms	RDKit	1
Number of sulfur atoms	RDKit	0
Number of chiral carbon atoms	RDKit	1
Stereochemical complexity	RDKit	0.09
Number of sp hybridized carbon atoms	RDKit	0
Number of sp² hybridized carbon atoms	RDKit	7
Number of sp³ hybridized carbon atoms	RDKit	4
Fraction of sp³ hybridized carbon atoms (Fsp³)	RDKit	0.36
Shape complexity	RDKit	0.36
Number of rotatable bonds	SwissADME	4
Number of aliphatic carbocycles	RDKit	0
Number of aliphatic heterocycles	RDKit	1
Number of aliphatic rings	RDKit	1
Number of aromatic carbocycles	RDKit	0
Number of aromatic heterocycles	RDKit	1
Number of aromatic rings	RDKit	1
Total number of rings	RDKit	2
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	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
Pfizer’s 3/75 filter	RDKit	Good
GSK 4/400 filter	RDKit	Good
Number of Leadlikeness violations	SwissADME	1
Weighted quantitative estimate of drug-likeness (QEDw) score	RDKit	0.77

ADMET properties

Property name	Tool	Property value
Bioavailability score	SwissADME	0.56
Solubility class [ESOL]	SwissADME	Very soluble
Solubility class [Silicos-IT]	SwissADME	Soluble
Blood Brain Barrier permeation	SwissADME	No
Gastrointestinal absorption	SwissADME	High
Log K_p (Skin permeation, cm/s)	SwissADME	-7.58
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	No
CYP2D6 inhibitor	SwissADME	No
CYP3A4 inhibitor	SwissADME	No
P-glycoprotein substrate	SwissADME	No