ID: ALA271663

Max Phase: Preclinical

Molecular Formula: C8H6O3

Molecular Weight: 150.13

Molecule Type: Small molecule

Representations

Synonyms (2): Benzo[D][1,3]Dioxole-5-Carbaldehyde | Piperonal
Synonyms from Alternative Forms(2):

Canonical SMILES:  O=Cc1ccc2c(c1)OCO2

Standard InChI:  InChI=1S/C8H6O3/c9-4-6-1-2-7-8(3-6)11-5-10-7/h1-4H,5H2

Standard InChI Key:  SATCULPHIDQDRE-UHFFFAOYSA-N

Molecule Features

Natural Product: Yes

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: 150.13

Molecular Weight (Monoisotopic): 150.0317

AlogP: 1.23

#Rotatable Bonds: 1

Polar Surface Area: 35.53

Molecular Species:

HBA: 3

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 3

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 1.31

CX LogD: 1.31

Aromatic Rings: 1

Heavy Atoms: 11

QED Weighted: 0.56

Np Likeness Score: 0.33

References

1. Matsuda H, Ninomiya K, Morikawa T, Yasuda D, Yamaguchi I, Yoshikawa M..  (2008)  Protective effects of amide constituents from the fruit of Piper chaba on D-galactosamine/TNF-alpha-induced cell death in mouse hepatocytes.,  18  (6): [PMID:18289853] [10.1016/j.bmcl.2008.01.101]

2. Matsuda H, Ninomiya K, Morikawa T, Yasuda D, Yamaguchi I, Yoshikawa M..  (2009)  Hepatoprotective amide constituents from the fruit of Piper chaba: Structural requirements, mode of action, and new amides.,  17  (20): [PMID:19775895] [10.1016/j.bmc.2009.08.050]

3. PubChem BioAssay data set, 

4. Tong F, Coats JR..  (2012)  Quantitative structure-activity relationships of monoterpenoid binding activities to the housefly GABA receptor.,  68  (8): [PMID:22461383] [10.1002/ps.3280]

5. Caboni P, Aissani N, Cabras T, Falqui A, Marotta R, Liori B, Ntalli N, Sarais G, Sasanelli N, Tocco G..  (2013)  Potent nematicidal activity of phthalaldehyde, salicylaldehyde, and cinnamic aldehyde against Meloidogyne incognita.,  61  (8): [PMID:23379671] [10.1021/jf305164m]

6. Sharma UK, Sood S, Sharma N, Rahi P, Kumar R, Sinha AK, Gulati A.  (2013)  Synthesis and SAR investigation of natural phenylpropene-derived methoxylated cinnamaldehydes and their novel Schiff bases as potent antimicrobial and antioxidant agents,  22  (11): [10.1007/s00044-013-0484-9]

7. PubChem BioAssay data set, 

8. Das S, Mitra I, Batuta S, Niharul Alam M, Roy K, Begum NA..  (2014)  Design, synthesis and exploring the quantitative structure-activity relationship of some antioxidant flavonoid analogues.,  24  (21): [PMID:25278230] [10.1016/j.bmcl.2014.09.028]

9. Liu S, Wei W, Li Y, Liu X, Cao X, Lei K, Zhou M..  (2015)  Design, synthesis, biological evaluation and molecular docking studies of phenylpropanoid derivatives as potent anti-hepatitis B virus agents.,  95  [PMID:25847765] [10.1016/j.ejmech.2015.03.056]

10. Huber SK, Höfner G, Wanner KT..  (2019)  Application of the concept of oxime library screening by mass spectrometry (MS) binding assays to pyrrolidine-3-carboxylic acid derivatives as potential inhibitors of γ-aminobutyric acid transporter 1 (GAT1).,  27  (13): [PMID:31097402] [10.1016/j.bmc.2019.05.001]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays