5,7-Dihydroxy-3',4',5'-trimethoxyflavone

Details

• Internal ID: 57f6848d-c9b0-41a6-904e-a2ecbc187813
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 4-O-methylated flavonoids
• IUPAC Name: 5,7-dihydroxy-2-(3,4,5-trimethoxyphenyl)chromen-4-one
• SMILES (Canonical): COC1=CC(=CC(=C1OC)OC)C2=CC(=O)C3=C(C=C(C=C3O2)O)O
• SMILES (Isomeric): COC1=CC(=CC(=C1OC)OC)C2=CC(=O)C3=C(C=C(C=C3O2)O)O
• InChI: InChI=1S/C18H16O7/c1-22-15-4-9(5-16(23-2)18(15)24-3)13-8-12(21)17-11(20)6-10(19)7-14(17)25-13/h4-8,19-20H,1-3H3
• InChI Key: CPCPHNWWTJLXKQ-UHFFFAOYSA-N
• Popularity: 17 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₆O₇
• Molecular Weight: 344.30 g/mol
• Exact Mass: 344.08960285 g/mol
• Topological Polar Surface Area (TPSA): 94.40 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.90
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• 18103-42-9
• tricetin 3',4',5'-trimethyl ether
• 3',4',5'-O-trimethyltricetin
• 5,7-dihydroxy-2-(3,4,5-trimethoxyphenyl)chromen-4-one
• Tricin 4'-Methyl Ether
• 5,7-Dihydroxy-2-(3,4,5-trimethoxyphenyl)-4-benzopyrone
• Flavone, 5,7-dihydroxy-3',4',5'-trimethoxy-
• NSC-123410
• 4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-(3,4,5-trimethoxyphenyl)-
• MLS002707300
• 2J9JJ5N2H7
• 5,7-Dihydroxy-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one
• CHEBI:543745
• EINECS 242-001-0
• NSC123410
• NSC 123410
• 5, 7-Dihydroxy-3',4',5'-trimethoxyflavone
• 5,7-Dihydroxy-3',4',5'-trimethoxy flavone
• 5,7-dihydroxy-2-(3,4,5-trimethoxyphenyl)-4H-1-benzopyran-4-one
• 5-7-dihydroxy-3-4-5-trimethoxyflavone
• 5,7-Dihydroxy-3',4',5'-trimethoxyflavon
• UNII-2J9JJ5N2H7
• 5,4',5'-trimethoxyflavone
• 5,4',5'-trimethoxy flavone
• 3',4',5'-Trimethoxytricetin
• CHEMBL486590
• SCHEMBL4918477
• DTXSID70171059
• CPCPHNWWTJLXKQ-UHFFFAOYSA-N
• LMPK12110880
• MFCD00016924
• AKOS025287600
• SMR001574694
• XD161933
• 3',4',5'-TRI-O-METHYL-TRICETIN
• 5,7-Dihydroxy-3?,4?,5?-Trimethoxyflavone
• Flavone,7-dihydroxy-3',4',5'-trimethoxy-
• FT-0756628
• 5,7-Dihydroxy-3',4',5'-trimethoxy-Flavone
• C19807
• 5,7-Dihydroxy-3/',4/',5/'-trimethoxyflavone
• Q27105170
• Flavone, 5,7-dihydroxy-3',4',5'-trimethoxy- (8CI)
• 4H-1-Benzopyran-4-one,7-dihydroxy-2-(3,4,5-trimethoxyphenyl)-
• 5,7-Dihydroxy-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one #

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9417	94.17%
Caco-2	+	0.8985	89.85%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6343	63.43%
OATP2B1 inhibitior	-	0.7127	71.27%
OATP1B1 inhibitior	+	0.9528	95.28%
OATP1B3 inhibitior	+	0.8767	87.67%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.7632	76.32%
P-glycoprotein inhibitior	+	0.8343	83.43%
P-glycoprotein substrate	-	0.8621	86.21%
CYP3A4 substrate	+	0.5282	52.82%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8296	82.96%
CYP3A4 inhibition	+	0.6154	61.54%
CYP2C9 inhibition	-	0.7484	74.84%
CYP2C19 inhibition	+	0.5640	56.40%
CYP2D6 inhibition	-	0.7310	73.10%
CYP1A2 inhibition	+	0.8610	86.10%
CYP2C8 inhibition	+	0.7754	77.54%
CYP inhibitory promiscuity	+	0.8068	80.68%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6142	61.42%
Eye corrosion	-	0.9818	98.18%
Eye irritation	+	0.6219	62.19%
Skin irritation	-	0.7187	71.87%
Skin corrosion	-	0.9573	95.73%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5335	53.35%
Micronuclear	+	0.8700	87.00%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.9352	93.52%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.6522	65.22%
Acute Oral Toxicity (c)	III	0.5210	52.10%
Estrogen receptor binding	+	0.9492	94.92%
Androgen receptor binding	+	0.7121	71.21%
Thyroid receptor binding	+	0.7304	73.04%
Glucocorticoid receptor binding	+	0.8488	84.88%
Aromatase binding	+	0.7437	74.37%
PPAR gamma	+	0.8074	80.74%
Honey bee toxicity	-	0.7648	76.48%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6249	62.49%
Fish aquatic toxicity	+	0.8724	87.24%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.92%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.55%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.85%	89.00%
CHEMBL3194	P02766	Transthyretin	93.55%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.57%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.06%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.03%	86.33%
CHEMBL3192	Q9BY41	Histone deacetylase 8	86.35%	93.99%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.06%	99.15%
CHEMBL2581	P07339	Cathepsin D	85.25%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.22%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.29%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	80.40%	94.73%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.06%	90.71%

Plants that contains it

• Adenia globosa
• Aglaia grandis
• Anaphalis busua
• Bhesa nitidissima
• Bridelia ferruginea
• Calycanthus floridus
• Catunaregam tomentosa
• Chiliadenus candicans
• Chrysanthemum × morifolium
• Chrysanthemum morifolium
• Crassothonna sedifolia
• Cyrtocymura scorpioides
• Episcia cupreata
• Haplopteris anguste-elongata
• Impatiens edgeworthii
• Liriodendron tulipifera
• Lycopodium japonicum
• Pterocarpus officinalis
• Ranzania japonica
• Ridsdalea wittii
• Seriphidium kurramense
• Tetrapanax papyrifer
• Teucrium heterophyllum
• Zanthoxylum myriacanthum

Cross-Links

• PubChem: 5379265
• NPASS: NPC62536
• LOTUS: LTS0024244
• wikiData: Q27105170