(2S,4R)-4,5,6,7-tetramethoxyflavan

Details

• Internal ID: 47c069ba-1b20-4550-b6e5-48f1ac53859b
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 7-O-methylated flavonoids
• IUPAC Name: (2S,4R)-4,5,6,7-tetramethoxy-2-phenyl-3,4-dihydro-2H-chromene
• SMILES (Canonical): COC1CC(OC2=CC(=C(C(=C12)OC)OC)OC)C3=CC=CC=C3
• SMILES (Isomeric): CO[C@@H]1C[C@H](OC2=CC(=C(C(=C12)OC)OC)OC)C3=CC=CC=C3
• InChI: InChI=1S/C19H22O5/c1-20-14-10-13(12-8-6-5-7-9-12)24-15-11-16(21-2)18(22-3)19(23-4)17(14)15/h5-9,11,13-14H,10H2,1-4H3/t13-,14+/m0/s1
• InChI Key: IMKNBXLCVBCZGQ-UONOGXRCSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₂O₅
• Molecular Weight: 330.40 g/mol
• Exact Mass: 330.14672380 g/mol
• Topological Polar Surface Area (TPSA): 46.20 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 3.92
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 5

Synonyms

• (2S,4R)-4,5,6,7-tetramethoxyflavan

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9915	99.15%
Caco-2	+	0.9187	91.87%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.5607	56.07%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9387	93.87%
OATP1B3 inhibitior	+	0.9859	98.59%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7545	75.45%
P-glycoprotein inhibitior	+	0.5951	59.51%
P-glycoprotein substrate	-	0.8678	86.78%
CYP3A4 substrate	+	0.5066	50.66%
CYP2C9 substrate	-	0.8209	82.09%
CYP2D6 substrate	+	0.5823	58.23%
CYP3A4 inhibition	-	0.6830	68.30%
CYP2C9 inhibition	-	0.8903	89.03%
CYP2C19 inhibition	+	0.5581	55.81%
CYP2D6 inhibition	-	0.9004	90.04%
CYP1A2 inhibition	+	0.8323	83.23%
CYP2C8 inhibition	+	0.6841	68.41%
CYP inhibitory promiscuity	+	0.6627	66.27%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5799	57.99%
Eye corrosion	-	0.9822	98.22%
Eye irritation	-	0.8590	85.90%
Skin irritation	-	0.7660	76.60%
Skin corrosion	-	0.9748	97.48%
Ames mutagenesis	+	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8748	87.48%
Micronuclear	+	0.5018	50.18%
Hepatotoxicity	-	0.5843	58.43%
skin sensitisation	-	0.9110	91.10%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.7077	70.77%
Acute Oral Toxicity (c)	III	0.5675	56.75%
Estrogen receptor binding	+	0.7744	77.44%
Androgen receptor binding	+	0.6059	60.59%
Thyroid receptor binding	+	0.7428	74.28%
Glucocorticoid receptor binding	+	0.7358	73.58%
Aromatase binding	-	0.6592	65.92%
PPAR gamma	+	0.5524	55.24%
Honey bee toxicity	-	0.8728	87.28%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.7100	71.00%
Fish aquatic toxicity	+	0.8783	87.83%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.40%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.04%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.61%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.41%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.26%	97.14%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	86.59%	94.03%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.99%	97.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.18%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.76%	99.17%
CHEMBL2535	P11166	Glucose transporter	80.58%	98.75%
CHEMBL2803	P43403	Tyrosine-protein kinase ZAP-70	80.01%	82.50%

Plants that contains it

• Beilschmiedia zenkeri

Cross-Links

• PubChem: 44614520
• LOTUS: LTS0110578
• wikiData: Q105115736