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Details

Stereochemistry ACHIRAL
Molecular Formula C21H22O8
Molecular Weight 402.3946
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NOBILETIN

SMILES

COC1=CC=C(C=C1OC)C2=CC(=O)C3=C(O2)C(OC)=C(OC)C(OC)=C3OC

InChI

InChIKey=MRIAQLRQZPPODS-UHFFFAOYSA-N
InChI=1S/C21H22O8/c1-23-13-8-7-11(9-15(13)24-2)14-10-12(22)16-17(25-3)19(26-4)21(28-6)20(27-5)18(16)29-14/h7-10H,1-6H3

HIDE SMILES / InChI

Molecular Formula C21H22O8
Molecular Weight 402.3946
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Nobiletin is a flavanoid isolatable from citrus peels. It has demonstrated anti-cancer properties in several in vitro cell models and garnered interest as a potential treatment for the motor and cognitive symptoms of Parkinson's disease. However, investigation of this compound has not moved beyond animal studies.

CNS Activity

Curator's Comment: referenced study was conducted in mice.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P21439
Gene ID: 5244.0
Gene Symbol: ABCB4
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
The citrus flavonoid, nobiletin, inhibits peritoneal dissemination of human gastric carcinoma in SCID mice.
2001 Dec
Quantitative distinctions of active site molecular recognition by P-glycoprotein and cytochrome P450 3A4.
2001 Dec
Evaluation of the effects of swainsonine, captopril, tangeretin and nobiletin on the biological behaviour of brain tumour cells in vitro.
2001 Feb
Cancer chemopreventive activity of 3,5,6,7,8,3',4'-heptamethoxyflavone from the peel of citrus plants.
2001 Feb 10
In vitro absorption and metabolism of nobiletin, a chemopreventive polymethoxyflavonoid in citrus fruits.
2001 Jan
Dietary administration of citrus nobiletin inhibits azoxymethane-induced colonic aberrant crypt foci in rats.
2001 Jul 13
Immunotoxicity of a standardized citrus polymethoxylated flavone extract.
2001 Nov
Wogonin and fisetin induce apoptosis in human promyeloleukemic cells, accompanied by a decrease of reactive oxygen species, and activation of caspase 3 and Ca(2+)-dependent endonuclease.
2002 Jan 15
Nobiletin as a tyrosinase inhibitor from the peel of Citrus fruit.
2002 Jun
Increasing resistance against Phytophthora citrophthora in tangelo Nova fruits by modulating polymethoxyflavones levels.
2002 May 8
Further investigation of the modifying effect of various chemopreventive agents on apoptosis and cell proliferation in human colon cancer cells.
2002 Oct
Urinary metabolites of nobiletin orally administered to rats.
2003 Dec
Effect of extraction method on the concentrations of selected bioactive compounds in mandarin juice.
2003 Dec 3
Novel anti-inflammatory actions of nobiletin, a citrus polymethoxy flavonoid, on human synovial fibroblasts and mouse macrophages.
2003 Jun 15
Effects of selected food factors with chemopreventive properties on combined lipopolysaccharide- and interferon-gamma-induced IkappaB degradation in RAW264.7 macrophages.
2003 May 30
Citrus nobiletin inhibits azoxymethane-induced large bowel carcinogenesis in rats.
2004
Cancer prevention by antioxidants.
2004
Prevention of UVB-induced photoinflammation and photoaging by a polymethoxy flavonoid, nobiletin, in human keratinocytes in vivo and in vitro.
2004 Aug 1
Rapid analysis of gene expression changes caused by liver carcinogens and chemopreventive agents using a newly developed three-dimensional microarray system.
2004 Feb
Nobiletin and its related flavonoids with CRE-dependent transcription-stimulating and neuritegenic activities.
2005 Dec 2
Nobiletin, a citrus flavonoid, down-regulates matrix metalloproteinase-7 (matrilysin) expression in HT-29 human colorectal cancer cells.
2005 Feb
Mechanism of neurotrophic action of nobiletin in PC12D cells.
2005 Oct 25
Nobiletin restoring beta-amyloid-impaired CREB phosphorylation rescues memory deterioration in Alzheimer's disease model rats.
2006 Jun 12
Suppressive effects of demethylated metabolites of nobiletin on phorbol ester-induced expression of scavenger receptor genes in THP-1 human monocytic cells.
2007
Citrus nobiletin suppresses bone loss in ovariectomized ddY mice and collagen-induced arthritis in DBA/1J mice: possible involvement of receptor activator of NF-kappaB ligand (RANKL)-induced osteoclastogenesis regulation.
2007
Protective effects of citrus nobiletin and auraptene in transgenic rats developing adenocarcinoma of the prostate (TRAP) and human prostate carcinoma cells.
2007 Apr
Comparative study on nobiletin metabolism with liver microsomes from rats, Guinea pigs and hamsters and rat cytochrome p450.
2007 Dec
Efficient and scalable method in isolation of polymethoxyflavones from orange peel extract by supercritical fluid chromatography.
2007 Feb 1
Determination of polymethoxylated flavones in peels of selected Jamaican and Mexican citrus (Citrus spp.) cultivars by high-performance liquid chromatography.
2007 Jan
Effects of TNF-alpha on leukocyte adhesion molecule expressions in cultured human lymphatic endothelium.
2007 Jul
[Characteristics of nobiletin-loaded nanoemulsion and its in vivo distribution in mice].
2007 Jun
Nobiletin, a citrus flavonoid, reverses learning impairment associated with N-methyl-D-aspartate receptor antagonism by activation of extracellular signal-regulated kinase signaling.
2007 May
Identification of polymethoxylated flavones from green tangerine peel (Pericarpium Citri Reticulatae Viride) by chromatographic and spectroscopic techniques.
2007 May 9
Preparation of nobiletin in self-microemulsifying systems and its intestinal permeability in rats.
2008
Inhibition of oral carcinogenesis by citrus flavonoids.
2008
Sp1 is an essential transcription factor for LPS-induced tissue factor expression in THP-1 monocytic cells, and nobiletin represses the expression through inhibition of NF-kappaB, AP-1, and Sp1 activation.
2008 Apr 1
Nobiletin, a citrus polymethoxy flavonoid, suppresses gene expression and production of aggrecanases-1 and -2 in collagen-induced arthritic mice.
2008 Aug 22
A citrus polymethoxyflavonoid, nobiletin, is a novel MEK inhibitor that exhibits antitumor metastasis in human fibrosarcoma HT-1080 cells.
2008 Feb 1
Minerals, phenolic compounds, and antioxidant capacity of citrus peel extract by hot water.
2008 Jan
Validated reversed phase LC method for quantitative analysis of polymethoxyflavones in citrus peel extracts.
2008 Jan
Nobiletin, a citrus flavonoid with neurotrophic action, augments protein kinase A-mediated phosphorylation of the AMPA receptor subunit, GluR1, and the postsynaptic receptor response to glutamate in murine hippocampus.
2008 Jan 14
Apoptotic effect of citrus fruit extract nobiletin on lung cancer cell line A549 in vitro and in vivo.
2008 Jun
Interactive effects of polymethoxy flavones from Citrus on cell growth inhibition in human neuroblastoma SH-SY5Y cells.
2008 Mar 15
Suppressive effects of nobiletin on hyperleptinemia and colitis-related colon carcinogenesis in male ICR mice.
2008 May
Anti-inflammatory effects of Radix Gentianae Macrophyllae (Qinjiao), Rhizoma Coptidis (Huanglian) and Citri Unshiu Pericarpium (Wenzhou migan) in animal models.
2008 Sep 2
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: referenced study was conducted in mice
In a mouse model of Parkinson's disease mice were induced to motor and cognitive deficits by dosing with 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP). Intraperitoneal administration of 50 mg/kg of Nobiletin for 2 consecutive weeks improved motor and cognitive deficits and continued to improve for 2 weeks after withdrawal. However, nobiletin did not block loss of dopaminergic neurons seen in the MPTP-treated mouse midbrain, nor did it rescue decreased tyrosine hydroxylase (TH) protein levels seen in the striatum or hippocampal CA1 region of these mice.
Route of Administration: Intraperitoneal
Human leukemia HL-60 cells were maintained in RPMI-1640 medium supplemented with 10% fetal bovine serum, 2 mM glutamine and 1% penicillin/streptomycin. Cell line was maintained at 37 deg-C and 5% CO2 atmosphere. HL60 cells were placed into 12-well plates at a density of 2 x 10^5 cells per well. Cultures were incubated overnight and then treated with different concentrations of nobiletin for 24 hours. At the end of incubation, cells were harvested and counted in a hemocytometer. Nobiletin was found to have an IC50 of 41.5 micro-M and AC50 above 100 micro-M.
Substance Class Chemical
Created
by admin
on Sat Dec 16 19:04:07 GMT 2023
Edited
by admin
on Sat Dec 16 19:04:07 GMT 2023
Record UNII
D65ILJ7WLY
Record Status Validated (UNII)
Record Version
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Name Type Language
NOBILETIN
INCI  
Official Name English
NSC-618903
Code English
4H-1-BENZOPYRAN-4-ONE, 2-(3,4-DIMETHOXYPHENYL)-5,6,7,8-TETRAMETHOXY-
Systematic Name English
FLAVONE, 3',4',5,6,7,8-HEXAMETHOXY-
Systematic Name English
NOBILETIN [USP-RS]
Common Name English
3',4',5,6,7,8-HEXAMETHOXYFLAVONE
Systematic Name English
NSC-76751
Code English
2-(3,4-DIMETHOXYPHENYL)-5,6,7,8-TETRAMETHOXY-4H-1-BENZOPYRAN-4-ONE
Systematic Name English
HEXAMETHOXYFLAVONE
WHO-DD  
Systematic Name English
NOBILETIN [INCI]
Common Name English
5,6,7,8,3',4'-HEXAMETHOXYFLAVONE
Systematic Name English
Hexamethoxyflavone [WHO-DD]
Common Name English
Classification Tree Code System Code
DSLD 4008 (Number of products:1)
Created by admin on Sat Dec 16 19:04:07 GMT 2023 , Edited by admin on Sat Dec 16 19:04:07 GMT 2023
Code System Code Type Description
WIKIPEDIA
NOBILETIN
Created by admin on Sat Dec 16 19:04:07 GMT 2023 , Edited by admin on Sat Dec 16 19:04:07 GMT 2023
PRIMARY
EPA CompTox
DTXSID30197275
Created by admin on Sat Dec 16 19:04:07 GMT 2023 , Edited by admin on Sat Dec 16 19:04:07 GMT 2023
PRIMARY
CHEBI
7602
Created by admin on Sat Dec 16 19:04:07 GMT 2023 , Edited by admin on Sat Dec 16 19:04:07 GMT 2023
PRIMARY
NSC
618903
Created by admin on Sat Dec 16 19:04:07 GMT 2023 , Edited by admin on Sat Dec 16 19:04:07 GMT 2023
PRIMARY
RS_ITEM_NUM
1467848
Created by admin on Sat Dec 16 19:04:07 GMT 2023 , Edited by admin on Sat Dec 16 19:04:07 GMT 2023
PRIMARY
FDA UNII
D65ILJ7WLY
Created by admin on Sat Dec 16 19:04:07 GMT 2023 , Edited by admin on Sat Dec 16 19:04:07 GMT 2023
PRIMARY
PUBCHEM
72344
Created by admin on Sat Dec 16 19:04:07 GMT 2023 , Edited by admin on Sat Dec 16 19:04:07 GMT 2023
PRIMARY
NSC
76751
Created by admin on Sat Dec 16 19:04:07 GMT 2023 , Edited by admin on Sat Dec 16 19:04:07 GMT 2023
PRIMARY
CAS
478-01-3
Created by admin on Sat Dec 16 19:04:07 GMT 2023 , Edited by admin on Sat Dec 16 19:04:07 GMT 2023
PRIMARY
SMS_ID
300000032958
Created by admin on Sat Dec 16 19:04:07 GMT 2023 , Edited by admin on Sat Dec 16 19:04:07 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
44% Cell growth rate of mouse myeloid leukemia M1 cells at 50 uM of compound vs control
PARENT -> CONSTITUENT ALWAYS PRESENT
48% Cell growth rate of human acute promyelocytic leukemia HL-60 cells at 50 uM of compound vs control
TRANSPORTER -> INHIBITOR
Decreased the IC50 value of paclitaxel by 15.92-fold. Restored the sensitivity of paclitaxel, doxorubicin, docetaxel, and daunorubicin in ABCB1, overexpressing A2780/T and A549/T cells.
IC50