(2S)-3',4'-Dimethoxy-5,7-dihydroxy-6-[(2E)-3,7-dimethyl-2,6-octadienyl]-2,3-dihydroflavone

Details

• Internal ID: 324140a9-6ef1-4f10-9aa2-47ded47be0e4
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > 6-prenylated flavans > 6-prenylated flavanones
• IUPAC Name: (2S)-2-(3,4-dimethoxyphenyl)-6-[(2E)-3,7-dimethylocta-2,6-dienyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC(=CCCC(=CCC1=C(C2=C(C=C1O)OC(CC2=O)C3=CC(=C(C=C3)OC)OC)O)C)C
• SMILES (Isomeric): CC(=CCC/C(=C/CC1=C(C2=C(C=C1O)O[C@@H](CC2=O)C3=CC(=C(C=C3)OC)OC)O)/C)C
• InChI: InChI=1S/C27H32O6/c1-16(2)7-6-8-17(3)9-11-19-20(28)14-25-26(27(19)30)21(29)15-23(33-25)18-10-12-22(31-4)24(13-18)32-5/h7,9-10,12-14,23,28,30H,6,8,11,15H2,1-5H3/b17-9+/t23-/m0/s1
• InChI Key: XMWZSFFOJPSCLZ-VAPFXODJSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₂O₆
• Molecular Weight: 452.50 g/mol
• Exact Mass: 452.21988874 g/mol
• Topological Polar Surface Area (TPSA): 85.20 Ų
• XlogP: 6.50
• Atomic LogP (AlogP): 6.06
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9687	96.87%
Caco-2	-	0.5892	58.92%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7177	71.77%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8935	89.35%
OATP1B3 inhibitior	+	0.8732	87.32%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7564	75.64%
BSEP inhibitior	+	0.9390	93.90%
P-glycoprotein inhibitior	+	0.8777	87.77%
P-glycoprotein substrate	-	0.6816	68.16%
CYP3A4 substrate	+	0.6285	62.85%
CYP2C9 substrate	-	0.7977	79.77%
CYP2D6 substrate	-	0.7912	79.12%
CYP3A4 inhibition	-	0.5392	53.92%
CYP2C9 inhibition	-	0.5118	51.18%
CYP2C19 inhibition	+	0.6670	66.70%
CYP2D6 inhibition	-	0.6670	66.70%
CYP1A2 inhibition	+	0.7857	78.57%
CYP2C8 inhibition	+	0.5385	53.85%
CYP inhibitory promiscuity	+	0.6947	69.47%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7665	76.65%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.8372	83.72%
Skin irritation	-	0.7769	77.69%
Skin corrosion	-	0.9416	94.16%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7248	72.48%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.5948	59.48%
skin sensitisation	-	0.8398	83.98%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.7773	77.73%
Acute Oral Toxicity (c)	III	0.3502	35.02%
Estrogen receptor binding	+	0.8986	89.86%
Androgen receptor binding	+	0.6095	60.95%
Thyroid receptor binding	+	0.6102	61.02%
Glucocorticoid receptor binding	+	0.8382	83.82%
Aromatase binding	+	0.5467	54.67%
PPAR gamma	+	0.8530	85.30%
Honey bee toxicity	-	0.7654	76.54%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9955	99.55%

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	99.28%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.68%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.79%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.63%	94.45%
CHEMBL2581	P07339	Cathepsin D	95.58%	98.95%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	94.29%	92.68%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.52%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.08%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.85%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.22%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.77%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.45%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	87.82%	94.73%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.09%	92.94%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.90%	99.23%
CHEMBL4208	P20618	Proteasome component C5	84.60%	90.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.08%	90.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.77%	94.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.33%	86.92%
CHEMBL2535	P11166	Glucose transporter	82.29%	98.75%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.46%	96.00%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	81.16%	92.08%

Plants that contains it

• Paulownia tomentosa

Cross-Links

• PubChem: 24854121
• NPASS: NPC226025
• ChEMBL: CHEMBL3581355
• LOTUS: LTS0235835
• wikiData: Q105331478