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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
Structure of NOMILIN

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

HIDE SMILES / InChI

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

TargetsConditions
PubMed

PubMed

TitleDatePubMed
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.
1991 Jan-Feb
Effects of environmentally encountered epoxides on mouse liver epoxide-metabolizing enzymes.
1991 Jun 1
Effect of limonin and nomilin on HIV-1 replication on infected human mononuclear cells.
2003 Oct
Antiviral activity of seed extract from Citrus bergamia towards human retroviruses.
2011 Mar 15
Patents

Sample Use Guides

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
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 Fri Dec 15 18:05:43 GMT 2023
Edited
by admin
on Fri Dec 15 18:05:43 GMT 2023
Record UNII
DRM0753K4T
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NOMILIN
MI  
Common Name English
1-(ACETYLOXY)-1,2-DIHYDROOBACUNOIC ACID .EPSILON.-LACTONE
Common Name English
NOMILIN [MI]
Common Name English
NSC-297134
Code English
(1S,3AS,4AR,4BR,6AR,11S,11AR,11BR,13AS)-11-(ACETYLOXY)-1-(3-FURANYL)DECAHYDRO-4B,7,7,11A,13A-PENTAMETHYLOXIRENO(4,4A)-2-BENZOPYRAN(6,5-G)(2)BENZOXEPIN-3,5,9(3AH,4BH,6H)-TRIONE
Common Name English
Code System Code Type Description
MESH
C059405
Created by admin on Fri Dec 15 18:05:43 GMT 2023 , Edited by admin on Fri Dec 15 18:05:43 GMT 2023
PRIMARY
NSC
297134
Created by admin on Fri Dec 15 18:05:43 GMT 2023 , Edited by admin on Fri Dec 15 18:05:43 GMT 2023
PRIMARY
CAS
1063-77-0
Created by admin on Fri Dec 15 18:05:43 GMT 2023 , Edited by admin on Fri Dec 15 18:05:43 GMT 2023
PRIMARY
EPA CompTox
DTXSID50909978
Created by admin on Fri Dec 15 18:05:43 GMT 2023 , Edited by admin on Fri Dec 15 18:05:43 GMT 2023
PRIMARY
MERCK INDEX
m8031
Created by admin on Fri Dec 15 18:05:43 GMT 2023 , Edited by admin on Fri Dec 15 18:05:43 GMT 2023
PRIMARY Merck Index
PUBCHEM
72320
Created by admin on Fri Dec 15 18:05:43 GMT 2023 , Edited by admin on Fri Dec 15 18:05:43 GMT 2023
PRIMARY
FDA UNII
DRM0753K4T
Created by admin on Fri Dec 15 18:05:43 GMT 2023 , Edited by admin on Fri Dec 15 18:05:43 GMT 2023
PRIMARY