IMPPAT Phytochemical information: 
Levoglucosan
Levoglucosan
Summary

SMILES: O[C@H]1[C@H](O)[C@H]2CO[C@@H]([C@@H]1O)O2
InChI: InChI=1S/C6H10O5/c7-3-2-1-10-6(11-2)5(9)4(3)8/h2-9H,1H2/t2-,3-,4+,5-,6-/m1/s1
InChIKey: TWNIBLMWSKIRAT-VFUOTHLCSA-N
DeepSMILES: O[C@H][C@H]O)[C@H]CO[C@@H][C@@H]7O))O5
Scaffold Graph/Node/Bond level: C1CC2COC(C1)O2
Scaffold Graph/Node level: C1CC2COC(C1)O2
Scaffold Graph level: C1CC2CCC(C1)C2
Functional groups: CO; C[C@@H]1OCCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Oxepanes
NP Classifier Biosynthetic pathway: Carbohydrates
NP Classifier Superclass: Saccharides
NP Classifier Class: Monosaccharides
Synonymous chemical names:
glucosan
External chemical identifiers:
CID:CID_2724705; ChEMBL:CHEMBL3138649; ChEBI:CHEBI:30997; ZINC:ZINC000003881595; FDASRS:5132N17FSD; SureChEMBL:SCHEMBL195289; MolPort-002-507-094
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Levoglucosan
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 162.14
Log P RDKit -2.18
Topological polar surface area (Å2) RDKit 79.15
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 6
Number of heavy atoms RDKit 11
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.83
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 0
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 1
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2
Levoglucosan
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 2
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.377329
Levoglucosan
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Highly soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -8.82
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 Yes