3'-Demethylnobiletin

Details

• Internal ID: ab321c75-cd11-4a6d-a303-349b7c372e12
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 8-O-methylated flavonoids
• IUPAC Name: 2-(3-hydroxy-4-methoxyphenyl)-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)O
• SMILES (Isomeric): COC1=C(C=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C(=C3OC)OC)OC)OC)O
• InChI: InChI=1S/C20H20O8/c1-23-13-7-6-10(8-11(13)21)14-9-12(22)15-16(24-2)18(25-3)20(27-5)19(26-4)17(15)28-14/h6-9,21H,1-5H3
• InChI Key: XFYYZBJXMSDKCV-UHFFFAOYSA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₀O₈
• Molecular Weight: 388.40 g/mol
• Exact Mass: 388.11581759 g/mol
• Topological Polar Surface Area (TPSA): 92.70 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 3.21
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

• 112448-39-2
• 2-(3-hydroxy-4-methoxyphenyl)-5,6,7,8-tetramethoxychromen-4-one
• 3'-hydroxy-5,6,7,8,4'-pentamethoxyflavone
• 96E9T839AP
• 3'-Hydroxy-4',5,6,7,8-pentamethoxyflavone
• 4H-1-Benzopyran-4-one, 2-(3-hydroxy-4-methoxyphenyl)-5,6,7,8-tetramethoxy-
• 2-(3-HYDROXY-4-METHOXYPHENYL)-5,6,7,8-TETRAMETHOXY-4H-1-BENZOPYRAN-4-ONE
• UNII-96E9T839AP
• CHEMBL225704
• SCHEMBL1764091
• DTXSID80150057
• CHEBI:175928
• HY-N4127
• LMPK12111478
• AKOS030530144
• PD125556
• CS-0032152
• FT-0775330
• F21505

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9823	98.23%
Caco-2	+	0.8770	87.70%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7745	77.45%
OATP2B1 inhibitior	-	0.8656	86.56%
OATP1B1 inhibitior	+	0.9473	94.73%
OATP1B3 inhibitior	+	0.9817	98.17%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.7043	70.43%
P-glycoprotein inhibitior	+	0.8568	85.68%
P-glycoprotein substrate	-	0.8651	86.51%
CYP3A4 substrate	-	0.5132	51.32%
CYP2C9 substrate	-	0.8382	83.82%
CYP2D6 substrate	-	0.7720	77.20%
CYP3A4 inhibition	-	0.5748	57.48%
CYP2C9 inhibition	-	0.8861	88.61%
CYP2C19 inhibition	+	0.5778	57.78%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	+	0.8530	85.30%
CYP2C8 inhibition	+	0.6904	69.04%
CYP inhibitory promiscuity	+	0.6103	61.03%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5716	57.16%
Eye corrosion	-	0.9793	97.93%
Eye irritation	-	0.6958	69.58%
Skin irritation	-	0.7150	71.50%
Skin corrosion	-	0.9836	98.36%
Ames mutagenesis	-	0.5564	55.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.4380	43.80%
Micronuclear	+	0.8359	83.59%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.9504	95.04%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.7129	71.29%
Acute Oral Toxicity (c)	II	0.4982	49.82%
Estrogen receptor binding	+	0.8423	84.23%
Androgen receptor binding	+	0.8148	81.48%
Thyroid receptor binding	+	0.6820	68.20%
Glucocorticoid receptor binding	+	0.6221	62.21%
Aromatase binding	+	0.5419	54.19%
PPAR gamma	+	0.7960	79.60%
Honey bee toxicity	-	0.8293	82.93%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6249	62.49%
Fish aquatic toxicity	+	0.8902	89.02%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.84%	94.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.41%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.85%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.15%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.24%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.11%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.95%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.89%	99.15%
CHEMBL3194	P02766	Transthyretin	85.93%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.52%	94.45%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	84.88%	98.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.18%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	82.03%	94.73%
CHEMBL1937	Q92769	Histone deacetylase 2	81.81%	94.75%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.73%	86.92%

Plants that contains it

• Agnorhiza bolanderi
• Anaxagorea crassipetala
• Araujia sericifera
• Arnica nevadensis
• Artemisia gmelinii
• Beyeria sulcata var. brevipes
• Bursaria spinosa
• Chloranthus tianmushanensis
• Chromolaena odorata
• Chromolaena pulchella
• Citrus × aurantium
• Citrus japonica
• Craibia grandiflora
• Dendrosenecio kilimanjari
• Dipterocarpus alatus
• Drosera peltata
• Echinops amplexicaulis
• Ficus formosana
• Gardenia fosbergii
• Ilex affinis
• Isodon umbrosus
• Kaempferia pulchra
• Litogyne gariepina
• Odixia angusta
• Prosopis glandulosa
• Prunus laurocerasus
• Pteris plumieri
• Quercus cerris
• Salvia officinalis
• Senecio squalidus
• Seriphidium cinum
• Sesbania punicea
• Simira eliezeriana
• Sorbus pallescens
• Stenostomum lucidum
• Tanacetum artemisioides
• Taxodium huegelii
• Vitex madiensis

Cross-Links

• PubChem: 183466
• NPASS: NPC50715
• ChEMBL: CHEMBL225704
• LOTUS: LTS0187030
• wikiData: Q83015982