(2S,4S,6R)-2-[(1S)-1-hydroxy-2-(4-hydroxyphenyl)ethyl]-6-(4-hydroxy-3-methoxyphenyl)oxan-4-ol

Details

• Internal ID: 570e649e-0b57-4f1c-82a6-1d2716cde64a
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids
• IUPAC Name: (2S,4S,6R)-2-[(1S)-1-hydroxy-2-(4-hydroxyphenyl)ethyl]-6-(4-hydroxy-3-methoxyphenyl)oxan-4-ol
• SMILES (Canonical): COC1=C(C=CC(=C1)C2CC(CC(O2)C(CC3=CC=C(C=C3)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)[C@H]2C[C@@H](C[C@H](O2)[C@H](CC3=CC=C(C=C3)O)O)O)O
• InChI: InChI=1S/C20H24O6/c1-25-19-9-13(4-7-16(19)23)18-10-15(22)11-20(26-18)17(24)8-12-2-5-14(21)6-3-12/h2-7,9,15,17-18,20-24H,8,10-11H2,1H3/t15-,17-,18+,20-/m0/s1
• InChI Key: UKFYIKOSRJMAAB-BOLBYERCSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₆
• Molecular Weight: 360.40 g/mol
• Exact Mass: 360.15728848 g/mol
• Topological Polar Surface Area (TPSA): 99.40 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.29
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9488	94.88%
Caco-2	-	0.7314	73.14%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.8594	85.94%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8847	88.47%
OATP1B3 inhibitior	+	0.9083	90.83%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	-	0.6707	67.07%
P-glycoprotein substrate	-	0.6213	62.13%
CYP3A4 substrate	+	0.5671	56.71%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4800	48.00%
CYP3A4 inhibition	-	0.9239	92.39%
CYP2C9 inhibition	-	0.7778	77.78%
CYP2C19 inhibition	+	0.6136	61.36%
CYP2D6 inhibition	-	0.8373	83.73%
CYP1A2 inhibition	-	0.7810	78.10%
CYP2C8 inhibition	+	0.6997	69.97%
CYP inhibitory promiscuity	+	0.5110	51.10%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.6236	62.36%
Eye corrosion	-	0.9842	98.42%
Eye irritation	-	0.8596	85.96%
Skin irritation	-	0.7781	77.81%
Skin corrosion	-	0.9439	94.39%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7716	77.16%
Micronuclear	+	0.6159	61.59%
Hepatotoxicity	-	0.6500	65.00%
skin sensitisation	-	0.8787	87.87%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.7802	78.02%
Acute Oral Toxicity (c)	III	0.6768	67.68%
Estrogen receptor binding	+	0.6883	68.83%
Androgen receptor binding	+	0.5515	55.15%
Thyroid receptor binding	+	0.5490	54.90%
Glucocorticoid receptor binding	-	0.4820	48.20%
Aromatase binding	-	0.5447	54.47%
PPAR gamma	+	0.5456	54.56%
Honey bee toxicity	-	0.8102	81.02%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.8605	86.05%

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	98.93%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.94%	91.11%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	95.07%	96.95%
CHEMBL2581	P07339	Cathepsin D	94.65%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.41%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	93.63%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.25%	94.45%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	91.21%	97.21%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.84%	99.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	89.77%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.74%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.93%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.05%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.88%	97.14%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.57%	90.71%
CHEMBL2535	P11166	Glucose transporter	85.29%	98.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.16%	95.56%
CHEMBL3438	Q05513	Protein kinase C zeta	85.06%	88.48%
CHEMBL4208	P20618	Proteasome component C5	84.67%	90.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.94%	99.15%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.37%	92.62%
CHEMBL1255126	O15151	Protein Mdm4	81.68%	90.20%
CHEMBL242	Q92731	Estrogen receptor beta	81.03%	98.35%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.86%	89.00%

Plants that contains it

• Alnus hirsuta
• Juglans mandshurica
• Rhoiptelea chiliantha

Cross-Links

• PubChem: 46184734
• LOTUS: LTS0212642
• wikiData: Q105274514