Structure Database (LMSD)
Common Name
Morusin
Systematic Name
Synonyms
- Mulberrochromene
3D model of Morusin
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Morusin is a prenylated flavonoid that has been found in M. alba and has diverse biological activities, including enzyme inhibitory, anti-inflammatory, and antiproliferative properties.1,2,3,4 It inhibits the UDP-glucuronosyltransferase (UGT) isoforms UGT1A6, UGT1A7, and UGT1A8 (IC50s = 4.23, 0.98, and 3 μM, respectively) and the cytochrome P450 (CYP) isoforms CYP3A4, CYP1A2, CYP2C9, and CYP2E1 (IC50s = 2.13, 1.27, 3.18, and 9.28 μM, respectively).1 Morusin (4 μM) inhibits histamine and leukotriene C4 (LTC4) production induced by A23187 (Item No. 11016) and phorbol 12-myristate 13-acetate (PMA; Item No. 10008014) in mouse MC/9 mast cells.2 It also inhibits the growth of MCF-7, MDA‑MB‑231, and MDA‑MB‑453 breast cancer cells (IC50s = 13.53, 10.84, and 11.99 μM, respectively).3 Morusin (12.5 mg/kg per day) decreases colonic tissue damage, TGF-β1 levels, and matrix metalloproteinase-2 (MMP-2) and MMP-9 activity in a rat model of TNBS-induced ulcerative colitis.4
This information has been provided by Cayman Chemical
References
1. Kang, S., Kim, E.O., Kim, S.H., et al. Morusin induces apoptosis by regulating expression of bax and survivin in human breast cancer cells. Oncol. Lett. 13(6), 4558-4562 (2017).
2. Jin, S.E., Ha, H., Shin, H.K., et al. Anti-allergic and anti-inflammatory effects of kuwanon G and morusin on MC/9 mast cells and HaCaT keratinocytes. Molecules 24(2), E265 (2019).
3. Shi, X., Yang, S., Zhang, G., et al. The different metabolism of morusin in various species and its potent inhibition against UDP-glucuronosyltransferase (UGT) and cytochrome p450 (CYP450) enzymes. Xenobiotica 46(5), 467-476 (2016).
4. Nagle, A., Wu, T., Kuhen, K., et al. Imidazolopiperazines: Lead optimization of the second-generation antimalarial agents. J. Med. Chem. 55(9), 4244-4273 (2012).
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Viridiplantae
(#33090)
Flavonoid imported from http://metabolomics.jp/
String Representations
InChiKey (Click to copy)
XFFOMNJIDRDDLQ-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C25H24O6/c1-13(2)5-7-17-22(29)21-19(28)12-20-16(9-10-25(3,4)31-20)24(21)30-23(17)15-8-6-14(26)11-18(15)27/h5-6,8-12,26-28H,7H2,1-4H3
SMILES (Click to copy)
C12OC(C)(C)C=CC=1C1OC(C3C=CC(O)=CC=3O)=C(C/C=C(\C)/C)C(=O)C=1C(O)=C2
Other Databases
KEGG ID
HMDB ID
CHEBI ID
METABOLOMICS ID
PubChem CID
Cayman ID
Calculated Physicochemical Properties
Heavy Atoms
31
Rings
4
Aromatic Rings
3
Rotatable Bonds
3
Van der Waals Molecular Volume
385.26
Topological Polar Surface Area
102.20
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
6
logP
6.46
Molar Refractivity
120.41
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