IMPPAT Phytochemical information: 
Asparagusic acid

Asparagusic acid
Summary

SMILES: OC(=O)C1CSSC1
InChI: InChI=1S/C4H6O2S2/c5-4(6)3-1-7-8-2-3/h3H,1-2H2,(H,5,6)
InChIKey: AYGMEFRECNWRJC-UHFFFAOYSA-N
DeepSMILES: OC=O)CCSSC5
Scaffold Graph/Node/Bond level: C1CSSC1
Scaffold Graph/Node level: C1CSSC1
Scaffold Graph level: C1CCCC1
Functional groups: CC(=O)O; CSSC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Dithiolanes
ClassyFire Subclass: Dithiolanecarboxylic acids
NP Classifier Biosynthetic pathway: Amino acids and Peptides
Synonymous chemical names:
asparagusic-acid, asparagusic acid
External chemical identifiers:
CID:CID_16682; ChEMBL:CHEMBL3581910; ChEBI:CHEBI:18091; ZINC:ZINC000000901181; FDASRS:VAD3XV509R; SureChEMBL:SCHEMBL2796676; MolPort-022-879-154
Chemical structure download


Asparagusic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 150.22
Log P RDKit 1.08
Topological polar surface area (Å2) RDKit 37.3
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 4
Number of heavy atoms RDKit 8
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 2
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 1
Number of sp3 hybridized carbon atoms RDKit 3
Shape complexity RDKit 0.75
Number of rotatable bonds RDKit 1
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


Asparagusic acid
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 3
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.57


Asparagusic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
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 -7.06
Number of PAINS structural alerts SwissADME 0
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