(2E,4E)-5-Benzo[1,3]dioxol-5-yl-penta-2,4-dienoic acid methyl ester

ID: ALA42965

Chembl Id: CHEMBL42965

Cas Number: 6190-46-1

PubChem CID: 9921021

Max Phase: Preclinical

Molecular Formula: C13H12O4

Molecular Weight: 232.24

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Methyl Piperate | Methyl piperate|CHEMBL42965|6190-46-1|(2E,4E)-methyl 5-(benzo[d][1,3]dioxol-5-yl)penta-2,4-dienoate|Piperinic acid methyl ester|Piperinsaure-methylester|Piperic acid methyl ester|SCHEMBL3244271|VOZJBFJHMHRLDN-ZUVMSYQZSA-N|BDBM50305644|HY-N12134|CS-0892113|(2E,4E)-5-Benzo[1,3]dioxol-5-yl-penta-2,4-dienoic acid methyl ester|2,4-Pentadienoic acid, 5-(1,3-benzodioxol-5-yl)-, methyl ester, (E,E)-|2,4-Pentadienoic acid, 5-(1,3-benzodioxol-5-yl)-, methyl ester, (2E,4E)-

Canonical SMILES:  COC(=O)/C=C/C=C/c1ccc2c(c1)OCO2

Standard InChI:  InChI=1S/C13H12O4/c1-15-13(14)5-3-2-4-10-6-7-11-12(8-10)17-9-16-11/h2-8H,9H2,1H3/b4-2+,5-3+

Standard InChI Key:  VOZJBFJHMHRLDN-ZUVMSYQZSA-N

Alternative Forms

1. Parent:

   

   ALA42965

   METHYL PIPERATE

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: 232.24

Molecular Weight (Monoisotopic): 232.0736

AlogP: 2.16

#Rotatable Bonds: 3

Polar Surface Area: 44.76

Molecular Species:

HBA: 4

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 2.67

CX LogD: 2.67

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.45

Np Likeness Score: 0.79

References

1. Raj HG, Gupta S, Prasad AK, Boll PM, Wengel J, Biswas G, Singh SK, Sharma NK, Bisht KS, Parmar VS.  (1995)  Methylenedioxyphenyl substituted compounds from Piper species as inhibitors of liver microsome-mediated aflatoxin B1-DNA binding in vitro,  5  (15): [10.1016/0960-894X(95)00272-U]

2. 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]

3. Zhang H, Matsuda H, Nakamura S, Yoshikawa M..  (2008)  Effects of amide constituents from pepper on adipogenesis in 3T3-L1 cells.,  18  (11): [PMID:18477507] [10.1016/j.bmcl.2008.04.052]

4. Rahman T, Rahmatullah M..  (2010)  Proposed structural basis of interaction of piperine and related compounds with monoamine oxidases.,  20  (2): [PMID:19969454] [10.1016/j.bmcl.2009.11.106]

5. 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]

6. Mu LH, Wang B, Ren HY, Liu P, Guo DH, Wang FM, Bai L, Guo YS..  (2012)  Synthesis and inhibitory effect of piperine derivates on monoamine oxidase.,  22  (9): [PMID:22475561] [10.1016/j.bmcl.2012.02.090]

7. Lee HW, Ryu HW, Kang MG, Park D, Oh SR, Kim H..  (2016)  Potent selective monoamine oxidase B inhibition by maackiain, a pterocarpan from the roots of Sophora flavescens.,  26  (19): [PMID:27575476] [10.1016/j.bmcl.2016.08.044]

Source

Source(1):

• Scientific Literature