ID: ALA428441

Max Phase: Preclinical

Molecular Formula: C29H26O8

Molecular Weight: 502.52

Molecule Type: Small molecule

Representations

Synonyms (1): 4-(4-hydroxy-3-methoxybenzylidene) curcumin
Synonyms from Alternative Forms(1):

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

Standard InChI:  InChI=1S/C29H26O8/c1-35-27-15-18(6-11-24(27)32)4-9-22(30)21(14-20-8-13-26(34)29(17-20)37-3)23(31)10-5-19-7-12-25(33)28(16-19)36-2/h4-17,32-34H,1-3H3/b9-4+,10-5+

Standard InChI Key:  UBAXBJGMRVTJRB-LUZURFALSA-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: 502.52

Molecular Weight (Monoisotopic): 502.1628

AlogP: 4.78

#Rotatable Bonds: 10

Polar Surface Area: 122.52

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.58

CX Basic pKa:

CX LogP: 5.72

CX LogD: 5.69

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.21

Np Likeness Score: 0.24

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. Yuan M, Luo M, Song Y, Xu Q, Wang X, Cao Y, Bu X, Ren Y, Hu X..  (2011)  Identification of curcumin derivatives as human glyoxalase I inhibitors: A combination of biological evaluation, molecular docking, 3D-QSAR and molecular dynamics simulation studies.,  19  (3): [PMID:21237663] [10.1016/j.bmc.2010.12.039]

3. Qiu X, Du Y, Lou B, Zuo Y, Shao W, Huo Y, Huang J, Yu Y, Zhou B, Du J, Fu H, Bu X..  (2010)  Synthesis and identification of new 4-arylidene curcumin analogues as potential anticancer agents targeting nuclear factor-κB signaling pathway.,  53  (23): [PMID:21070043] [10.1021/jm1004545]

4. Chakraborti S, Das L, Kapoor N, Das A, Dwivedi V, Poddar A, Chakraborti G, Janik M, Basu G, Panda D, Chakrabarti P, Surolia A, Bhattacharyya B..  (2011)  Curcumin recognizes a unique binding site of tubulin.,  54  (18): [PMID:21830815] [10.1021/jm2004046]

5. 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]

6. 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]

7. 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]

8. Rodrigues FC, Anil Kumar NV, Thakur G..  (2019)  Developments in the anticancer activity of structurally modified curcumin: An up-to-date review.,  177  [PMID:31129455] [10.1016/j.ejmech.2019.04.058]

Source

Source(1):

• Scientific Literature