IMPPAT Phytochemical information: 
(2S)-4-hydroxy-5-oxo-4-(2,3,4-trihydroxyoxolan-2-yl)pyrrolidine-2-carboxylic acid
(2S)-4-hydroxy-5-oxo-4-(2,3,4-trihydroxyoxolan-2-yl)pyrrolidine-2-carboxylic acid
Summary

SMILES: OC1COC(C1O)(O)C1(O)C[C@H](NC1=O)C(=O)O
InChI: InChI=1S/C9H13NO8/c11-4-2-18-9(17,5(4)12)8(16)1-3(6(13)14)10-7(8)15/h3-5,11-12,16-17H,1-2H2,(H,10,15)(H,13,14)/t3-,4?,5?,8?,9?/m0/s1
InChIKey: FLVJBXHFHKVHJN-NRVMPZMMSA-N
DeepSMILES: OCCOCC5O))O)CO)C[C@H]NC5=O)))C=O)O
Scaffold Graph/Node/Bond level: O=C1NCCC1C1CCCO1
Scaffold Graph/Node level: OC1NCCC1C1CCCO1
Scaffold Graph level: CC1CCCC1C1CCCC1
Functional groups: CO; COC(C)(O)C; CC(=O)NC; CC(=O)O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic acids and derivatives
ClassyFire Class: Carboxylic acids and derivatives
ClassyFire Subclass: Amino acids, peptides, and analogues
NP Classifier Biosynthetic pathway: Amino acids and Peptides
Synonymous chemical names:
ascorbalamic acid
External chemical identifiers:
CID:CID_90472498
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(2S)-4-hydroxy-5-oxo-4-(2,3,4-trihydroxyoxolan-2-yl)pyrrolidine-2-carboxylic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 263.2
Log P RDKit -3.87
Topological polar surface area (Å2) RDKit 156.55
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 9
Number of heavy atoms RDKit 18
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.56
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 2
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.78
Number of rotatable bonds RDKit 1
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
(2S)-4-hydroxy-5-oxo-4-(2,3,4-trihydroxyoxolan-2-yl)pyrrolidine-2-carboxylic acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 1
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.295254
(2S)-4-hydroxy-5-oxo-4-(2,3,4-trihydroxyoxolan-2-yl)pyrrolidine-2-carboxylic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
Solubility class [ESOL] SwissADME Highly soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -10.61
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