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Structure Database (LMSD)

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Common Name

Tricin

Systematic Name

5,7,4'-Trihydroxy-3',5'-dimethoxyflavone

Synonyms

LM ID

LMPK12110873

Formula

C₁₇H₁₄O₇

Exact Mass

Calculate m/z

330.073955

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

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View studies deposited in Metabolomics Workbench in which this molecule has been identified

Classification

Category

Main Class

Sub Class

Polyketides [PK]

Flavonoids [PK12]

Flavones and Flavonols [PK1211]

Biological Context

Tricin is a flavone that has been found in O. sativa and has diverse biological activities.^1,2,3,4 It scavenges ABTS radicals in a cell-free assay (IC50 = 0.312 mg/ml).¹ Tricin (0.1-10 µM) reduces virus titer and expression of the human cytomegalovirus (HCMV) genes IE1 and UL54 in HCMV-infected human embryonic lung fibroblast (HEL) cells, an effect that can be reversed by overexpression of chemokine (C-C motif) ligand 2 (CCL2).² It inhibits IgE-induced degranulation of RBL-2H3 cells (IC50 = 4.83 µM).³ In vivo, tricin (37.5 mg/kg per day) reduces tumor growth and the number of lung metastases in a CT26 murine colon carcinoma model.⁴

This information has been provided by Cayman Chemical

References

1. Akai, Y., Sadanari, H., Takemoto, M., et al. Inhibition of human cytomegalovirus replication by tricin is associated with depressed CCL2 expression. Antiviral Res. 148, 15-19 (2017).

2. Kuwabara, H., Mouri, K., Otsuka, H., et al. Tricin from a malagasy connaraceous plant with potent antihistaminic activity. J. Nat. Prod. 66(9), 1273-1275 (2003).

3. Quan, N.V., Thien, D.D., Khanh, T.D., et al. Momilactones A, B, and tricin in rice grain and by-products are potential skin aging inhibitors. Foods 8(12), 602 (2019).

4. Yue, G.G.-L., Gao, S., Lee, J.K.-M., et al. A natural flavone tricin from grains can alleviate tumor growth and lung metastasis in colorectal tumor mice. Molecules 25(16), 3730 (2020).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Viridiplantae (#33090)

Flavonoid imported from http://metabolomics.jp/

String Representations

InChiKey (Click to copy)

HRGUSFBJBOKSML-UHFFFAOYSA-N

InChi (Click to copy)

InChI=1S/C17H14O7/c1-22-14-3-8(4-15(23-2)17(14)21)12-7-11(20)16-10(19)5-9(18)6-13(16)24-12/h3-7,18-19,21H,1-2H3

SMILES (Click to copy)

C12C(=O)C=C(C3C=C(OC)C(O)=C(OC)C=3)OC=1C=C(O)C=C2O

Other Databases

Wikipedia

KEGG ID

HMDB ID

CHEBI ID

METABOLOMICS ID

PubChem CID

Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 24

Rings 3

Aromatic Rings 3

Rotatable Bonds 3

Van der Waals Molecular Volume 273.29

Topological Polar Surface Area 109.36

Hydrogen Bond Donors 3

Hydrogen Bond Acceptors 7

logP 3.49

Molar Refractivity 86.13

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