2,3,4,5-tetramethoxy-6-[(1R)-1-methoxy-3-phenylpropyl]phenol

Details

• Internal ID: c6e96d16-df02-412c-abb9-2197dc76a9ca
• Taxonomy: Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Cinnamylphenols
• IUPAC Name: 2,3,4,5-tetramethoxy-6-[(1R)-1-methoxy-3-phenylpropyl]phenol
• SMILES (Canonical): COC1=C(C(=C(C(=C1C(CCC2=CC=CC=C2)OC)O)OC)OC)OC
• SMILES (Isomeric): COC1=C(C(=C(C(=C1[C@@H](CCC2=CC=CC=C2)OC)O)OC)OC)OC
• InChI: InChI=1S/C20H26O6/c1-22-14(12-11-13-9-7-6-8-10-13)15-16(21)18(24-3)20(26-5)19(25-4)17(15)23-2/h6-10,14,21H,11-12H2,1-5H3/t14-/m1/s1
• InChI Key: GPIKQDSOFNVIMH-CQSZACIVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₆
• Molecular Weight: 362.40 g/mol
• Exact Mass: 362.17293854 g/mol
• Topological Polar Surface Area (TPSA): 66.40 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.75
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9741	97.41%
Caco-2	+	0.8182	81.82%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8575	85.75%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9009	90.09%
OATP1B3 inhibitior	+	0.9178	91.78%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.7849	78.49%
P-glycoprotein inhibitior	+	0.6928	69.28%
P-glycoprotein substrate	-	0.7142	71.42%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.6092	60.92%
CYP2D6 substrate	+	0.4755	47.55%
CYP3A4 inhibition	-	0.8336	83.36%
CYP2C9 inhibition	-	0.7904	79.04%
CYP2C19 inhibition	+	0.8053	80.53%
CYP2D6 inhibition	-	0.8070	80.70%
CYP1A2 inhibition	+	0.5631	56.31%
CYP2C8 inhibition	-	0.5793	57.93%
CYP inhibitory promiscuity	+	0.5380	53.80%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7343	73.43%
Carcinogenicity (trinary)	Non-required	0.6823	68.23%
Eye corrosion	-	0.9825	98.25%
Eye irritation	-	0.8363	83.63%
Skin irritation	-	0.7118	71.18%
Skin corrosion	-	0.9259	92.59%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7192	71.92%
Micronuclear	-	0.7941	79.41%
Hepatotoxicity	+	0.5556	55.56%
skin sensitisation	-	0.8750	87.50%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	-	0.5111	51.11%
Mitochondrial toxicity	-	0.7125	71.25%
Nephrotoxicity	-	0.8952	89.52%
Acute Oral Toxicity (c)	III	0.7111	71.11%
Estrogen receptor binding	+	0.7511	75.11%
Androgen receptor binding	+	0.5837	58.37%
Thyroid receptor binding	+	0.7184	71.84%
Glucocorticoid receptor binding	+	0.6919	69.19%
Aromatase binding	-	0.7682	76.82%
PPAR gamma	+	0.6323	63.23%
Honey bee toxicity	-	0.8960	89.60%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.6700	67.00%
Fish aquatic toxicity	+	0.9126	91.26%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.32%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.27%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.88%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.03%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.68%	99.17%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	87.83%	94.08%
CHEMBL5939	Q9NZ08	Endoplasmic reticulum aminopeptidase 1	86.31%	100.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.12%	95.50%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	85.69%	94.62%
CHEMBL3192	Q9BY41	Histone deacetylase 8	84.99%	93.99%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.38%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	81.30%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.07%	94.45%

Plants that contains it

• Lindera erythrocarpa

Cross-Links

• PubChem: 162858371
• LOTUS: LTS0238599
• wikiData: Q105014847