IMPPAT Phytochemical information: 
Ascorbigen

Ascorbigen
Summary

SMILES: O[C@H]1CO[C@]2([C@@H]1OC(=O)C2(O)Cc1c[nH]c2c1cccc2)O
InChI: InChI=1S/C15H15NO6/c17-11-7-21-15(20)12(11)22-13(18)14(15,19)5-8-6-16-10-4-2-1-3-9(8)10/h1-4,6,11-12,16-17,19-20H,5,7H2/t11-,12+,14?,15-/m0/s1
InChIKey: OMSJCIOTCFHSIT-KNUOEEMSSA-N
DeepSMILES: O[C@H]CO[C@][C@@H]5OC=O)C5O)Ccc[nH]cc5cccc6))))))))))))))O
Scaffold Graph/Node/Bond level: O=C1OC2CCOC2C1Cc1c[nH]c2ccccc12
Scaffold Graph/Node level: OC1OC2CCOC2C1CC1CNC2CCCCC12
Scaffold Graph level: CC1CC2CCCC2C1CC1CCC2CCCCC21
Functional groups: CO; CO[C@](O)(C)C; CC(=O)OC; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Furofurans
ClassyFire Subclass: Isosorbides
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Simple indole alkaloids
Synonymous chemical names:
ascorbigen
External chemical identifiers:
CID:CID_3081416; ChEBI:CHEBI:64944; SureChEMBL:SCHEMBL14163965
Chemical structure download


Ascorbigen
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 305.29
Log P RDKit -0.55
Topological polar surface area (Å2) RDKit 112.01
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 22
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.27
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.4
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 4
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 4


Ascorbigen
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 1
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 0.553778


Ascorbigen
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 -8.48
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