IMPPAT Phytochemical information: 
(4S,5R)-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one

(4S,5R)-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one
Summary

SMILES: OC[C@H]1OC(=O)C[C@@H]1O
InChI: InChI=1S/C5H8O4/c6-2-4-3(7)1-5(8)9-4/h3-4,6-7H,1-2H2/t3-,4+/m0/s1
InChIKey: YIXDEYPPAGPYDP-IUYQGCFVSA-N
DeepSMILES: OC[C@H]OC=O)C[C@@H]5O
Scaffold Graph/Node/Bond level: O=C1CCCO1
Scaffold Graph/Node level: OC1CCCO1
Scaffold Graph level: CC1CCCC1
Functional groups: CO; CC(=O)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Lactones
ClassyFire Subclass: Gamma butyrolactones
Synonymous chemical names:
2-deoxy-d-ribono-1,4-lactone, 2-deoxy-d-lyxono-1,4-lactone
External chemical identifiers:
CID:CID_161815; ChEMBL:CHEMBL98888; ChEBI:CHEBI:17281; ZINC:ZINC000004095906; SureChEMBL:SCHEMBL3394583; MolPort-028-959-565
Chemical structure download


(4S,5R)-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 132.12
Log P RDKit -1.34
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 5
Number of heavy atoms RDKit 9
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.4
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 1
Number of sp3 hybridized carbon atoms RDKit 4
Shape complexity RDKit 0.8
Number of rotatable bonds RDKit 1
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 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 1
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 1


(4S,5R)-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one
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 4
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Bad
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.43


(4S,5R)-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one
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 -7.72
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