7,8-Dihydro-5,6-dehydrokavain

  • GreenMolBD CID : 4594
  • Molecular Formula : C14H14O3
  • Molecular Weight : 230.263
  • Exact Molecular Mass : 230.094
  • IUPAC Name : 4-methoxy-6-(2-phenylethyl)pyran-2-one
  • InChI : InChI=1S/C14H14O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-6,9-10H,7-8H2,1H3
  • InChI Key : OVXOWIKMOIVICB-UHFFFAOYSA-N
  • Canonical SMILES : COC1=CC(=O)OC(=C1)CCC2=CC=CC=C2
  • Isomeric SMILES : COc1cc(oc(=O)c1)CCc2ccccc2
  • Cross Reference  Pubchem

1. Classification

1.1. Description

This compound belongs to the class of organic compounds known as kavalactones. These are lactones, which is structurally characterized by a benzene ring and a pyranone moiety, linked to each other to form a 4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one skeleton.

1.2. Taxonomy Tree

1.3. Alternative Parent

Pyranones and derivatives; Alkyl aryl ethers; Benzene and substituted derivatives; Vinylogous esters; Heteroaromatic compounds; Lactones; Oxacyclic compounds; Organic oxides; Hydrocarbon derivatives;

1.4. Molecular Framework

Aromatic heteromonocyclic compounds

1.5. Substituents

Kavalactone; Alkyl aryl ether; Pyranone; Monocyclic benzene moiety; Pyran; Benzenoid; Vinylogous ester; Heteroaromatic compound; Lactone; Ether; Organoheterocyclic compound; Oxacycle; Organic oxygen compound; Hydrocarbon derivative; Organooxygen compound; Organic oxide; Aromatic heteromonocyclic compound

2. Physical Properties

SlogP TPSA HBD HBA nHA nRB nAA nAB SMR vdw_vol vdw_area Density
2.59017 35.53 0 3 17 4 6 6 6.403 321.106 240.309 0.717095

3. Quantum Information

Heat of Formation Dipole Moment Electronegativity Homo Lumo Hardness
-83.259407 3.88 -4.942 -9.38197 -0.50179 4.44

4. Compound Reactivity

DLP nRFG nLMR
0 1 3

5. Topkat Properties

WOE Prediction Ames Prediction DTP Prediction Rat Oral LD50 (g/kg body weight) Rat Inhalational LC50 (mg/m3/h) Chronic LOAEL (g/kg body weight) Skin Irritancy Skin Sensitization Ocular Irritancy Aerobic Biodegradability Prediction Fathead Minnow LC50 (g/l) Daphnia EC50 (mg/l)
Non-Carcinogen Non-Mutagen Toxic 0.833283 6473.82 0.0147388 Mild Strong Mild Degradable 0.00152618 4.04813

6. Drug-Likeliness Test

Lipinski's rule of five Jorgensen's rule of three Goshe filter Veber filter PAINS1 PAINS2 PAINS3
Yes Yes Yes Yes Yes Yes Yes

7. Synonyms

Name
Dihydro-5,6-dehydrokawain
7,8-Dihydro-5,6-dehydrokawain
2H-Pyran-2-one, 4-methoxy-6-(2-phenylethyl)-
3155-51-9
4-Methoxy-6-(2-phenylethyl)-2H-pyran-2-one
4-Methoxy-6-phenethyl-2H-pyran-2-one
5,6-Ddk
AC1L4O1I
AC1Q69KC
CHEMBL1946699
5,6-Dehydro-7,8-dihydrokavain
CTK4G7340
DTXSID10185453
OVXOWIKMOIVICB-UHFFFAOYSA-N
4-methoxy-6-phenethylpyran-2-one
5,6-Didehydro-7,8-dihydrokawain
4-methoxy-6-phenethyl-pyran-2-one
Kawain, 5,6-dehydro-7,8-dihydro-
AKOS030537312
HE049663
HE334488
2H-Pyran-2-one, 4-methoxy-6-phenethyl-
2H-Pyran-2-one,4-methoxy-6-(2-phenylethyl)-
2,4-Heptadienoic acid, 5-hydroxy-3-methoxy-7-phenyl-, .delta.-lactone
7,8-Dihydro-5,6-dehydrokavain

8. Compound in Different Plants

Compound Name Plant Name Compound in Plant Parts Ref
7,8-Dihydro-5,6-dehydrokavain
Echinochloa cruss-galli Root 4

9. Targets

ID Target Name Gene Symbol Organism Protein Crystal Complex Activity Values Reference
Potency (nM) Ki (nM) IC50 (nM) Kd (nM) EC50 (nM) kon (M-1-s-1) koff (s-1) Biological Assay DOI Article PMID PubChem AID

10. Chemical Vendors

SID Source Name Source URL Source Detail Registry ID Source Record URL
337553202AKos Consulting & SolutionsSource URLSource DetailAKOS030537312Source Record URL
347231651LabNetwork, a WuXi AppTec CompanySource URLSource DetailLN01288753Source Record URL
103118994AAA ChemistrySource URLSource DetailAR-1E2129Source Record URL
103118995AAA ChemistrySource URLSource DetailAR-1E2130Source Record URL
355124253MuseChemSource URLSource DetailR040802Source Record URL
347731393Yuhao ChemicalSource URLSource DetailRT9746Source Record URL
113445255ABI ChemSource URLSource DetailAC1L4O1ISource Record URL
117584813ABI ChemSource URLSource DetailAC1Q69KCSource Record URL
348968790Chemieliva Pharmaceutical Co., LtdSource URLSource DetailPBCM0486941Source Record URL
162835657ChemTikSource URLSource DetailCTK4G7340Source Record URL
57349216NovoSeekSource URLSource Detail160673Source Record URL
3606901581717 CheMall CorporationSource URLSource DetailBG07502825Source Record URL