Nobiletin

Details

• Internal ID: 66cfd0b8-9d54-4761-b342-3bc2df543dcd
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 8-O-methylated flavonoids
• IUPAC Name: 2-(3,4-dimethoxyphenyl)-5,6,7,8-tetramethoxychromen-4-one
• SMILES (Canonical): COC1=C(C=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C(=C3OC)OC)OC)OC)OC
• SMILES (Isomeric): COC1=C(C=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C(=C3OC)OC)OC)OC)OC
• InChI: 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
• InChI Key: MRIAQLRQZPPODS-UHFFFAOYSA-N
• Popularity: 1,120 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₈
• Molecular Weight: 402.40 g/mol
• Exact Mass: 402.13146766 g/mol
• Topological Polar Surface Area (TPSA): 81.70 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 3.51
• H-Bond Acceptor: 8
• H-Bond Donor: 0
• Rotatable Bonds: 7

Synonyms

• 478-01-3
• Hexamethoxyflavone
• 3',4',5,6,7,8-Hexamethoxyflavone
• 5,6,7,8,3',4'-Hexamethoxyflavone
• 2-(3,4-Dimethoxyphenyl)-5,6,7,8-tetramethoxy-4H-1-benzopyran-4-one
• 2-(3,4-dimethoxyphenyl)-5,6,7,8-tetramethoxychromen-4-one
• NSC-76751
• CCRIS 9012
• UNII-D65ILJ7WLY
• D65ILJ7WLY
• C21H22O8
• NSC 76751
• CHEBI:7602
• 2-(3,4-dimethoxyphenyl)-5,6,7,8-tetramethoxy-4H-chromen-4-one
• 4H-1-Benzopyran-4-one, 2-(3,4-dimethoxyphenyl)-5,6,7,8-tetramethoxy-
• NSC-618903
• CHEMBL76447
• Nobiletin (Hexamethoxyflavone)
• DTXSID30197275
• NSC76751
• Flavone, 5,6,7,8,3',4'-hexamethoxy
• NOBILETIN (USP-RS)
• NOBILETIN [USP-RS]
• FLAVONE, 3',4',5,6,7,8-HEXAMETHOXY-
• SMR000156231
• MFCD03273560
• CPD000156231
• Nobiletin, >=97%
• NOBILETIN [INCI]
• Spectrum2_001697
• Spectrum3_000921
• Spectrum4_001020
• KBioGR_001519
• MLS000574877
• MLS000759462
• MLS000877030
• MLS001424129
• Nobiletin, analytical standard
• SCHEMBL244029
• SPECTRUM1505268
• SPBio_001654
• MEGxp0_000930
• ACon1_000921
• GTPL12446
• KBio3_001922
• DTXCID40119766
• 2-(3,4-dimethoxyphenyl)-5,6,7,8-tetramethoxy-chromen-4-one
• HMS2051D09
• HMS2234A09
• HMS3373C14
• HMS3393D09
• HMS3651G20
• HEXAMETHOXYFLAVONE [WHO-DD]
• HY-N0155
• 3'4'5,6,7,8-Hexamethoxyflavone
• BDBM50338976
• CCG-38781
• LMPK12111468
• NSC618903
• STL565829
• AKOS015965334
• NOBILETIN, 20% (Technical Grade)
• AC-1023
• CS-5518
• NC00186
• SDCCGMLS-0066776.P001
• NCGC00095703-01
• NCGC00095703-02
• NCGC00095703-06
• NCGC00169228-01
• 5,6,7,8,3'',4''-hexamethoxyflavone
• AS-17452
• LS-39643
• NCI60_041691
• FT-0686667
• N0871
• S2333
• SW197566-2
• A827343
• SR-01000712262
• Q-100511
• Q2402963
• SR-01000712262-5
• BRD-K06753942-001-02-0
• 2-(3,4-Dimethoxy-phenyl)-5,6,7,8-tetramethoxy-chromen-4-one
• 4,5,6,7,8,9,10,11,12,13-decahydrocyclododeca[d]oxazole
• 4H-1-Benzopyran-4-one,4-dimethoxyphenyl)-5,6,7,8-tetramethoxy-
• 2-(3,4-dimethoxyphenyl)-5,6,7,8-tetramethoxy-4H- 1-benzopyran-4-one
• 2-(3,4-Dimethoxyphenyl)-5,6,7,8-tetramethoxy-4H-1-benzopyran-4-one, 9CI
• 3 inverted exclamation mark ,4 inverted exclamation mark ,5,6,7,8-HEXAMETHOXYFLAVONE

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9901	99.01%
Caco-2	+	0.8660	86.60%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7006	70.06%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9490	94.90%
OATP1B3 inhibitior	+	0.9919	99.19%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.7932	79.32%
P-glycoprotein inhibitior	+	0.9512	95.12%
P-glycoprotein substrate	-	0.8493	84.93%
CYP3A4 substrate	-	0.5212	52.12%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7654	76.54%
CYP3A4 inhibition	+	0.6138	61.38%
CYP2C9 inhibition	-	0.7985	79.85%
CYP2C19 inhibition	+	0.7445	74.45%
CYP2D6 inhibition	-	0.9546	95.46%
CYP1A2 inhibition	+	0.9694	96.94%
CYP2C8 inhibition	+	0.5942	59.42%
CYP inhibitory promiscuity	+	0.8123	81.23%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5636	56.36%
Eye corrosion	-	0.9682	96.82%
Eye irritation	-	0.7022	70.22%
Skin irritation	-	0.7565	75.65%
Skin corrosion	-	0.9845	98.45%
Ames mutagenesis	-	0.5364	53.64%
Human Ether-a-go-go-Related Gene inhibition	+	0.7297	72.97%
Micronuclear	+	0.7759	77.59%
Hepatotoxicity	-	0.8500	85.00%
skin sensitisation	-	0.9439	94.39%
Respiratory toxicity	-	0.7000	70.00%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.6455	64.55%
Acute Oral Toxicity (c)	II	0.6245	62.45%
Estrogen receptor binding	+	0.9009	90.09%
Androgen receptor binding	+	0.8443	84.43%
Thyroid receptor binding	+	0.7042	70.42%
Glucocorticoid receptor binding	+	0.7518	75.18%
Aromatase binding	+	0.6053	60.53%
PPAR gamma	+	0.7071	70.71%
Honey bee toxicity	-	0.7749	77.49%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9192	91.92%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	28183.8 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	28183.8 nM; 28183.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL5393	Q9UNQ0	ATP-binding cassette sub-family G member 2	4900 nM; 4400 nM	IC50; IC50	PMID: 21354800; PMID: 21354800
CHEMBL340	P08684	Cytochrome P450 3A4	25118.9 nM; 25118.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	19952.6 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	31622.8 nM; 22387.2 nM; 25118.9 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	11220.2 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	25118.9 nM	Potency	via CMAUP
CHEMBL4302	P08183	P-glycoprotein 1	11500 nM	IC50	PMID: 11743742

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.93%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.30%	86.33%
CHEMBL2581	P07339	Cathepsin D	91.20%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.13%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.75%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.58%	85.14%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	83.59%	85.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.94%	86.92%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	82.80%	94.03%
CHEMBL3401	O75469	Pregnane X receptor	81.08%	94.73%
CHEMBL5747	Q92793	CREB-binding protein	81.04%	95.12%
CHEMBL5903	Q04771	Activin receptor type-1	81.03%	89.93%
CHEMBL1907	P15144	Aminopeptidase N	80.18%	93.31%

Plants that contains it

• Ageratum conyzoides
• Agnorhiza bolanderi
• Anaxagorea crassipetala
• Araujia sericifera
• Arnica nevadensis
• Artemisia gmelinii
• Beyeria sulcata var. brevipes
• Blumea fistulosa
• Bursaria spinosa
• Chloranthus tianmushanensis
• Chromolaena odorata
• Chromolaena pulchella
• Citrus × aurantium
• Citrus deliciosa
• Citrus japonica
• Citrus maxima
• Citrus medica
• Citrus trifoliata
• Craibia grandiflora
• Dendrosenecio kilimanjari
• Dipterocarpus alatus
• Drosera peltata
• Echinops amplexicaulis
• Eupatorium leucolepis
• Ficus formosana
• Gardenia fosbergii
• Ilex affinis
• Isodon umbrosus
• Juncus effusus
• Kaempferia pulchra
• Litogyne gariepina
• Murraya exotica
• Murraya paniculata
• Odixia angusta
• Oxalis pes-caprae
• Ozothamnus lycopodioides
• Prosopis glandulosa
• Prunus laurocerasus
• Pteris plumieri
• Quercus cerris
• Salvia officinalis
• Senecio squalidus
• Seriphidium cinum
• Sesbania punicea
• Simira eliezeriana
• Sorbus pallescens
• Stenostomum lucidum
• Taxodium huegelii
• Tripterygium wilfordii
• Viburnum tinus
• Vitex madiensis

Cross-Links

• PubChem: 72344
• NPASS: NPC85233
• ChEMBL: CHEMBL76447
• LOTUS: LTS0100173
• wikiData: Q2402963