Synonyms(1): Methyl Piperate Synonyms from Alternative Forms(1):
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
Associated Targets(non-human)
Hepatocyte 1455 Activities
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3T3-L1 3664 Activities
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L929 3802 Activities
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Monoamine oxidase A 498 Activities
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Monoamine oxidase B 346 Activities
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Monoamine oxidase A 2058 Activities
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Monoamine oxidase B 2209 Activities
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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
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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]
