ID: ALA440408

Max Phase: Preclinical

Molecular Formula: C28H24O6

Molecular Weight: 456.49

Molecule Type: Small molecule

Representations

Synonyms (1): 4-benzylidene curcumin
Synonyms from Alternative Forms(1):

Canonical SMILES:  COc1cc(/C=C/C(=O)C(=Cc2ccccc2)C(=O)/C=C/c2ccc(O)c(OC)c2)ccc1O

Standard InChI:  InChI=1S/C28H24O6/c1-33-27-17-20(10-14-25(27)31)8-12-23(29)22(16-19-6-4-3-5-7-19)24(30)13-9-21-11-15-26(32)28(18-21)34-2/h3-18,31-32H,1-2H3/b12-8+,13-9+

Standard InChI Key:  MHUKQIHYJHGFKT-QHKWOANTSA-N

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

Properties

Molecular Weight: 456.49

Molecular Weight (Monoisotopic): 456.1573

AlogP: 5.06

#Rotatable Bonds: 9

Polar Surface Area: 93.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.80

CX Basic pKa:

CX LogP: 6.18

CX LogD: 6.16

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.27

Np Likeness Score: 0.21

References

1. Mishra S, Karmodiya K, Surolia N, Surolia A..  (2008)  Synthesis and exploration of novel curcumin analogues as anti-malarial agents.,  16  (6): [PMID:18194869] [10.1016/j.bmc.2007.12.054]

2. Sahu PK, Sahu PK, Gupta SK, Thavaselvam D, Agarwal DD..  (2012)  Synthesis and evaluation of antimicrobial activity of 4H-pyrimido[2,1-b]benzothiazole, pyrazole and benzylidene derivatives of curcumin.,  54  [PMID:22683240] [10.1016/j.ejmech.2012.05.020]

3. Sahu PK, Sahu PK, Sahu PL, Agarwal DD..  (2016)  Structure activity relationship, cytotoxicity and evaluation of antioxidant activity of curcumin derivatives.,  26  (4): [PMID:26810315] [10.1016/j.bmcl.2015.12.013]

4. Rišiaňová L, Fischer-Fodor E, Valentová J, Tatomir C, Corina Decea N, Virag P, Pechová I, Devínsky F, Miklášová N..  (2017)  Synthesis, structural characterization and biological activity of novel Knoevenagel condensates on DLD-1 human colon carcinoma.,  27  (11): [PMID:28438541] [10.1016/j.bmcl.2017.04.031]

Source

Source(1):

• Scientific Literature