IMPPAT Phytochemical information: 
Dehydroascorbic acid

Dehydroascorbic acid
Summary

SMILES: OC[C@@H]([C@H]1OC(=O)C(=O)C1=O)O
InChI: InChI=1S/C6H6O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-8H,1H2/t2-,5+/m0/s1
InChIKey: SBJKKFFYIZUCET-JLAZNSOCSA-N
DeepSMILES: OC[C@@H][C@H]OC=O)C=O)C5=O))))))O
Scaffold Graph/Node/Bond level: O=C1COC(=O)C1=O
Scaffold Graph/Node level: OC1COC(O)C1O
Scaffold Graph level: CC1CCC(C)C1C
Functional groups: CO; O=C1COC(=O)C1=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Lactones
ClassyFire Subclass: Gamma butyrolactones
NP Classifier Biosynthetic pathway: Polyketides
Synonymous chemical names:
dehydroascorbate, dehydroascorbic acid, dehydroascorbic-acid, gamma lactone
External chemical identifiers:
CID:440667; ChEBI:27956; ZINC:ZINC000001532648; FDASRS:Y2Z3ZTP9UM; SureChEMBL:SCHEMBL66326; MolPort-001-792-396
Chemical structure download


Dehydroascorbic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 0
Log P RDKit 0
Topological polar surface area (Å2) RDKit
Number of hydrogen bond acceptors RDKit
Number of hydrogen bond donors RDKit
Number of carbon atoms RDKit
Number of heavy atoms RDKit
Number of heteroatoms RDKit
Number of nitrogen atoms RDKit
Number of sulfur atoms RDKit
Number of chiral carbon atoms RDKit
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit
Number of sp2 hybridized carbon atoms RDKit
Number of sp3 hybridized carbon atoms RDKit
Shape complexity RDKit
Number of rotatable bonds RDKit
Number of aliphatic carbocycles RDKit
Number of aliphatic heterocycles RDKit
Number of aliphatic rings RDKit
Number of aromatic carbocycles RDKit
Number of aromatic heterocycles RDKit
Number of aromatic rings RDKit
Total number of rings RDKit
Number of saturated carbocycles RDKit
Number of saturated heterocycles RDKit
Number of saturated rings RDKit
Number of Smallest Set of Smallest Rings (SSSR) RDKit


Dehydroascorbic acid
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 3
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 0.3515


Dehydroascorbic acid
ADMET 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 Low
Log Kp (Skin permeation, cm/s) SwissADME -8.09
Number of PAINS structural alerts SwissADME 1.0
Number of Brenk structural alerts SwissADME 1.0
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


Dehydroascorbic acid
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000216797NFKBIA800
ENSP00000237858GLRX942
ENSP00000253303RGN800
ENSP00000302851SLC23A1793
ENSP00000306100PAM900
ENSP00000344322SLC23A2739
ENSP00000358727GSTO1925
ENSP00000376776DBH919
ENSP00000416293SLC2A1910
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.