Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C28H34O9 |
Molecular Weight | 514.5642 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 9 / 9 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12O[C@@]13[C@@](C)(CC[C@]4([H])[C@@]5(C)[C@H](CC(=O)OC(C)(C)[C@]5([H])CC(=O)[C@@]34C)OC(C)=O)[C@@H](OC2=O)C6=COC=C6
InChI
InChIKey=KPDOJFFZKAUIOE-WNGDLQANSA-N
InChI=1S/C28H34O9/c1-14(29)34-19-12-20(31)36-24(2,3)17-11-18(30)27(6)16(26(17,19)5)7-9-25(4)21(15-8-10-33-13-15)35-23(32)22-28(25,27)37-22/h8,10,13,16-17,19,21-22H,7,9,11-12H2,1-6H3/t16-,17+,19+,21+,22-,25+,26-,27+,28-/m1/s1
Molecular Formula | C28H34O9 |
Molecular Weight | 514.5642 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 9 / 9 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Nomilin is a limonoid/triterpenoid found in citrus fruits that exhibits anti-parasitic, antiviral, anticancer, anti-metastatic, anti-angiogenic, anti-inflammatory, immunomodulatory, anti-obesity, anti-diabetic, and antiviral activities. Nomilin prevents growth of Aedes and suppresses replication of HIV-1 by inhibiting HIV-1 protease. In animal models, nomilin induces phase II enzymes by increasing expression of glutathione-S-transferase and NADPH:Quinone reductase. In animals fed high fat diets, nomilin activates GR5, increases glucose tolerance, and decreases body weight, glucose levels, and insulin levels. In vivo, nomilin increases white blood cell counts and antibody titers but suppresses delayed-type hypersensitivity reactions. In vitro, this compound inhibits cell proliferation, migration, invasion, and capillary tube formation and decreases levels of IL-1β, IL-6, TNF-α, VEGF, NO, and GM-CSF. Additionally, nomilin also inhibits aromatase and cellular proliferation in breast cancer cells. Nomilin also inhibits osteoclastogenesis in vitro by suppression of NFATc1 and MAPK signaling pathways. Nomilin inhibits tumor-specific angiogenesis by downregulating VEGF, NO and proinflammatory cytokine profile and also by inhibiting the activation of MMP-2 and MMP-9.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: map04210 |
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Target ID: CHEMBL613551 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21334901 |
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Target ID: CHEMBL247 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21334901 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. | 1991 Jan-Feb |
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Effects of environmentally encountered epoxides on mouse liver epoxide-metabolizing enzymes. | 1991 Jun 1 |
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Effect of limonin and nomilin on HIV-1 replication on infected human mononuclear cells. | 2003 Oct |
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Antiviral activity of seed extract from Citrus bergamia towards human retroviruses. | 2011 Mar 15 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21839074
Mice were treated with 5
consecutive doses of nomilin (6 mg/kg body weight of animal/day, i.p.)
starting simultaneously with the tumor challenge
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21334901
Curator's Comment: To provide semi-quantitative information of the HTLV-1 RT inhibitory
effect, the assay was performed at a low number of
amplification cycles (20 cycles), in the presence or in the absence
of 10, 8, 6, 4, 2, 1 ng/ml for BSext or nomilin.
Nomilin completely inhibited HTLV-1 tax/rex expression at 10 ug/ml.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 18:05:43 GMT 2023
by
admin
on
Fri Dec 15 18:05:43 GMT 2023
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Record UNII |
DRM0753K4T
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Record Status |
Validated (UNII)
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Record Version |
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