5,6,8,3',4',5'-Hexamethoxyflavone

Details

• Internal ID: 66252a4b-ceda-485c-9e9e-7c1b1cd6ac5b
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 8-O-methylated flavonoids
• IUPAC Name: 5,6,8-trimethoxy-2-(3,4,5-trimethoxyphenyl)chromen-4-one
• SMILES (Canonical): COC1=CC(=CC(=C1OC)OC)C2=CC(=O)C3=C(O2)C(=CC(=C3OC)OC)OC
• SMILES (Isomeric): COC1=CC(=CC(=C1OC)OC)C2=CC(=O)C3=C(O2)C(=CC(=C3OC)OC)OC
• InChI: InChI=1S/C21H22O8/c1-23-14-7-11(8-15(24-2)19(14)27-5)13-9-12(22)18-20(28-6)16(25-3)10-17(26-4)21(18)29-13/h7-10H,1-6H3
• InChI Key: YSFDTCPVUDPZGB-UHFFFAOYSA-N
• Popularity: 2 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

• 135010-79-6
• DTXSID40658064
• LMPK12110111
• 3',4',5,5',6,8-Hexamethoxyflavone
• 5,6,8-Trimethoxy-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one
• 5,6,8-Trimethoxy-2-(3,4,5-trimethoxyphenyl)-4H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9901	99.01%
Caco-2	+	0.8665	86.65%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7006	70.06%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9469	94.69%
OATP1B3 inhibitior	+	0.9919	99.19%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.8478	84.78%
P-glycoprotein inhibitior	+	0.9363	93.63%
P-glycoprotein substrate	-	0.9019	90.19%
CYP3A4 substrate	-	0.5359	53.59%
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	-	0.5978	59.78%
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	-	0.7133	71.33%
Skin irritation	-	0.7565	75.65%
Skin corrosion	-	0.9845	98.45%
Ames mutagenesis	-	0.5864	58.64%
Human Ether-a-go-go-Related Gene inhibition	+	0.6572	65.72%
Micronuclear	+	0.7759	77.59%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	-	0.9439	94.39%
Respiratory toxicity	-	0.6556	65.56%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.5935	59.35%
Acute Oral Toxicity (c)	II	0.6245	62.45%
Estrogen receptor binding	+	0.9022	90.22%
Androgen receptor binding	+	0.7290	72.90%
Thyroid receptor binding	+	0.7144	71.44%
Glucocorticoid receptor binding	+	0.7182	71.82%
Aromatase binding	+	0.5365	53.65%
PPAR gamma	+	0.6835	68.35%
Honey bee toxicity	-	0.6129	61.29%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9192	91.92%

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	94.60%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.25%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.42%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.47%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.79%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.92%	85.14%
CHEMBL2581	P07339	Cathepsin D	82.51%	98.95%
CHEMBL4302	P08183	P-glycoprotein 1	81.80%	92.98%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	81.79%	94.03%

Plants that contains it

• Ageratum conyzoides
• Murraya paniculata
• Murraya paniculata

Cross-Links

• PubChem: 44257604
• NPASS: NPC38813
• LOTUS: LTS0252568
• wikiData: Q82573785