R/S goniothalamin

ID: ALA1170485

Chembl Id: CHEMBL1170485

PubChem CID: 5317826

Max Phase: Preclinical

Molecular Formula: C13H12O2

Molecular Weight: 200.24

Molecule Type: Small molecule

Names and Identifiers

Synonyms: (R,S)-Goniothalamin | Rac-Goniothalamin | MLS000574880|SMR000156256|NSC104956|Rac-Goniothalamin|(R,S)-Goniothalamin|2-[(E)-2-phenylethenyl]-2,3-dihydropyran-6-one|MEGxp0_002057|CHEMBL1170485|ACon0_001424|BDBM47423|cid_5317826|HMS2212H06|NCGC00247605-01|2-[(E)-styryl]-2,3-dihydropyran-6-one

Canonical SMILES:  O=C1C=CCC(/C=C/c2ccccc2)O1

Standard InChI:  InChI=1S/C13H12O2/c14-13-8-4-7-12(15-13)10-9-11-5-2-1-3-6-11/h1-6,8-10,12H,7H2/b10-9+

Standard InChI Key:  RLGHFVLWYYVMQZ-MDZDMXLPSA-N

Alternative Forms

1. Parent:

   

   ALA1170485

   2-[(E)-2-phenylethenyl]-2,3-dihydropyran-6-one

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 200.24

Molecular Weight (Monoisotopic): 200.0837

AlogP: 2.57

#Rotatable Bonds: 2

Polar Surface Area: 26.30

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.22

CX LogD: 3.22

Aromatic Rings: 1

Heavy Atoms: 15

QED Weighted: 0.69

Np Likeness Score: 2.29

References

1. Dumitrescu L, Mai Huong DT, Van Hung N, Crousse B, Bonnet-Delpon D..  (2010)  Synthesis and cytotoxic activity of fluorinated analogues of Goniothalamus lactones. Impact of fluorine on oxidative processes.,  45  (7): [PMID:20392543] [10.1016/j.ejmech.2010.03.032]

2. Vendramini-Costa DB, de Castro IB, Ruiz AL, Marquissolo C, Pilli RA, de Carvalho JE..  (2010)  Effect of goniothalamin on the development of Ehrlich solid tumor in mice.,  18  (18): [PMID:20729093] [10.1016/j.bmc.2010.07.053]

3. PubChem BioAssay data set, 

4. Lee SM, Lee WG, Kim YC, Ko H..  (2011)  Synthesis and biological evaluation of α,β-unsaturated lactones as potent immunosuppressive agents.,  21  (19): [PMID:21873054] [10.1016/j.bmcl.2011.08.020]

5. Weber A, Döhl K, Sachs J, Nordschild ACM, Schröder D, Kulik A, Fischer T, Schmitt L, Teusch N, Pietruszka J..  (2017)  Synthesis and cytotoxic activities of goniothalamins and derivatives.,  25  (22): [PMID:28214230] [10.1016/j.bmc.2017.02.004]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays