ID: ALA83159

Max Phase: Preclinical

Molecular Formula: C10H10O2

Molecular Weight: 162.19

Molecule Type: Small molecule

Representations

Synonyms (3): 2-Methoxy Cinnamaldehyde | 2-Methoxycinnamaldehyde | Ortho-Methoxycinnamaldehyde
Synonyms from Alternative Forms(3):

Canonical SMILES:  COc1ccccc1/C=C/C=O

Standard InChI:  InChI=1S/C10H10O2/c1-12-10-7-3-2-5-9(10)6-4-8-11/h2-8H,1H3/b6-4+

Standard InChI Key:  KKVZAVRSVHUSPL-GQCTYLIASA-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: 162.19

Molecular Weight (Monoisotopic): 162.0681

AlogP: 1.91

#Rotatable Bonds: 3

Polar Surface Area: 26.30

Molecular Species: NEUTRAL

HBA: 2

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 2

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 1.82

CX LogD: 1.82

Aromatic Rings: 1

Heavy Atoms: 12

QED Weighted: 0.50

Np Likeness Score: 0.40

References

1. Kwon B, Lee S, Cho Y, Bok S, So S, Youn M, Chang S.  (1997)  Synthesis and biological activity of cinnamaldehydes as angiogenesis inhibitors,  7  (19): [10.1016/S0960-894X(97)10008-7]

2. Wolf RB.  (1986)  Effects of p-Methoxycinnamaldehyde from Star Anise and Related Cinnamic Acid Derivatives on Velvetleaf Germination,  49  (1): [10.1021/np50043a024]

3. Tsuji-Naito K..  (2008)  Aldehydic components of cinnamon bark extract suppresses RANKL-induced osteoclastogenesis through NFATc1 downregulation.,  16  (20): [PMID:18823786] [10.1016/j.bmc.2008.09.036]

4. Ngoc TM, Lee I, Ha do T, Kim H, Min B, Bae K..  (2009)  Tyrosinase-inhibitory constituents from the twigs of Cinnamomum cassia.,  72  (6): [PMID:19555125] [10.1021/np900031q]

5. Ngoc TM, Khoi NM, Ha do T, Nhiem NX, Tai BH, Don DV, Luong HV, Son DC, Bae K..  (2012)  Xanthine oxidase inhibitory activity of constituents of Cinnamomum cassia twigs.,  22  (14): [PMID:22677314] [10.1016/j.bmcl.2012.05.051]

6. Lee MA, Park HJ, Chung HJ, Kim WK, Lee SK..  (2013)  Antitumor activity of 2-hydroxycinnamaldehyde for human colon cancer cells through suppression of β-catenin signaling.,  76  (7): [PMID:23855266] [10.1021/np400216m]

7. PubChem BioAssay data set, 

8. PubChem BioAssay data set, 

9. Chen J, Lu Y, Ye X, Emam M, Zhang H, Wang H..  (2020)  Current advances in Vibrio harveyi quorum sensing as drug discovery targets.,  207  [PMID:32871343] [10.1016/j.ejmech.2020.112741]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays