(3E,5E)-3,5-Bis(3,4,5-trimethoxybenzylidene)-1-methylpiperidin-4-one

ID: ALA1224773

Chembl Id: CHEMBL1224773

Cas Number: 1195795-93-7

PubChem CID: 2327500

Max Phase: Preclinical

Molecular Formula: C26H31NO7

Molecular Weight: 469.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C2\CN(C)C/C(=C\c3cc(OC)c(OC)c(OC)c3)C2=O)cc(OC)c1OC

Standard InChI:  InChI=1S/C26H31NO7/c1-27-14-18(8-16-10-20(29-2)25(33-6)21(11-16)30-3)24(28)19(15-27)9-17-12-22(31-4)26(34-7)23(13-17)32-5/h8-13H,14-15H2,1-7H3/b18-8+,19-9+

Standard InChI Key:  OGEWTDITEXRGCF-GCBPPVMSSA-N

Alternative Forms

1. Parent:

   

   ALA1224773

   (3E,5E)-1-methyl-3,5-bis[(3,4,5-trimethoxyphenyl)methylidene]piperidin-4-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: 469.53

Molecular Weight (Monoisotopic): 469.2101

AlogP: 3.72

#Rotatable Bonds: 8

Polar Surface Area: 75.69

Molecular Species: NEUTRAL

HBA: 8

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 4.88

CX LogP: 3.34

CX LogD: 3.33

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.54

Np Likeness Score: -0.03

References

1. Yadav B, Taurin S, Rosengren RJ, Schumacher M, Diederich M, Somers-Edgar TJ, Larsen L..  (2010)  Synthesis and cytotoxic potential of heterocyclic cyclohexanone analogues of curcumin.,  18  (18): [PMID:20728364] [10.1016/j.bmc.2010.07.063]

2. Deck LM, Hunsaker LA, Vander Jagt TA, Whalen LJ, Royer RE, Vander Jagt DL..  (2018)  Activation of anti-oxidant Nrf2 signaling by enone analogues of curcumin.,  143  [PMID:29223100] [10.1016/j.ejmech.2017.11.048]

3. Chen L, Li Q, Weng B, Wang J, Zhou Y, Cheng D, Sirirak T, Qiu P, Wu J..  (2018)  Design, synthesis, anti-lung cancer activity, and chemosensitization of tumor-selective MCACs based on ROS-mediated JNK pathway activation and NF-κB pathway inhibition.,  151  [PMID:29655083] [10.1016/j.ejmech.2018.03.051]

4. Zhang Y, Liu Z, Wu J, Bai B, Chen H, Xiao Z, Chen L, Zhao Y, Lum H, Wang Y, Zhang H, Liang G..  (2018)  New MD2 inhibitors derived from curcumin with improved anti-inflammatory activity.,  148  [PMID:29466778] [10.1016/j.ejmech.2018.02.008]

5. Moreira J, Saraiva L, Pinto MM, Cidade H..  (2020)  Diarylpentanoids with antitumor activity: A critical review of structure-activity relationship studies.,  192  [PMID:32172081] [10.1016/j.ejmech.2020.112177]

Source

Source(1):

• Scientific Literature