IMPPAT Phytochemical information: 
Orthonitrophenyl-beta-D-fucopyranoside

Orthonitrophenyl-beta-D-fucopyranoside
Summary

SMILES: O[C@H]1[C@@H](O[C@@H]([C@@H]([C@@H]1O)O)C)Oc1ccccc1[N+](=O)[O-]
InChI: InChI=1S/C12H15NO7/c1-6-9(14)10(15)11(16)12(19-6)20-8-5-3-2-4-7(8)13(17)18/h2-6,9-12,14-16H,1H3/t6-,9+,10+,11-,12+/m1/s1
InChIKey: SWRPIVXPHLYETN-BVWHHUJWSA-N
DeepSMILES: O[C@H][C@@H]O[C@@H][C@@H][C@@H]6O))O))C)))Occcccc6[N+]=O)[O-]
Scaffold Graph/Node/Bond level: c1ccc(OC2CCCCO2)cc1
Scaffold Graph/Node level: C1CCC(OC2CCCCO2)CC1
Scaffold Graph level: C1CCC(CC2CCCCC2)CC1
Functional groups: CO; cO[C@@H](C)OC; c[N+](=O)[O-]
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbohydrates and carbohydrate conjugates
Synonymous chemical names:
npf
External chemical identifiers:
CID:CID_150889; ChEBI:CHEBI:44419; ZINC:ZINC000006031723; SureChEMBL:SCHEMBL2544558; MolPort-023-222-018
Chemical structure download


Orthonitrophenyl-beta-D-fucopyranoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 285.25
Log P RDKit -0.2
Topological polar surface area (Å2) RDKit 122.29
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 12
Number of heavy atoms RDKit 20
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.42
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 3
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 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2


Orthonitrophenyl-beta-D-fucopyranoside
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 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.52


Orthonitrophenyl-beta-D-fucopyranoside
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 -8.24
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
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