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:
dehydroascorbic acid, gamma lactone, dehydroascorbic-acid, dehydroascorbate
External chemical identifiers:
CID:CID_440667; ChEBI: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 174.11
Log P RDKit -2.6
Topological polar surface area (Å2) RDKit 100.9
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 6
Number of heavy atoms RDKit 12
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.33
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 3
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 2
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


Dehydroascorbic acid
Drug-likeness
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 0.351454


Dehydroascorbic acid
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 Low
Log Kp (Skin permeation, cm/s) SwissADME -8.09
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 1
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