(2R,3S,4S,5R,6S)-2-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-6-[4-[(5R)-5-hydroxy-7-(4-hydroxyphenyl)heptyl]phenoxy]oxane-3,4,5-triol

Details

• Internal ID: d65d5867-972f-4440-9dbd-45f5ba7334eb
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids
• IUPAC Name: (2R,3S,4S,5R,6S)-2-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-6-[4-[(5R)-5-hydroxy-7-(4-hydroxyphenyl)heptyl]phenoxy]oxane-3,4,5-triol
• SMILES (Canonical): C1C(C(C(O1)OCC2C(C(C(C(O2)OC3=CC=C(C=C3)CCCCC(CCC4=CC=C(C=C4)O)O)O)O)O)O)(CO)O
• SMILES (Isomeric): C1[C@@]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=CC=C(C=C3)CCCC[C@H](CCC4=CC=C(C=C4)O)O)O)O)O)O)(CO)O
• InChI: InChI=1S/C30H42O12/c31-16-30(38)17-40-29(27(30)37)39-15-23-24(34)25(35)26(36)28(42-23)41-22-13-8-18(9-14-22)3-1-2-4-20(32)10-5-19-6-11-21(33)12-7-19/h6-9,11-14,20,23-29,31-38H,1-5,10,15-17H2/t20-,23-,24-,25+,26-,27+,28-,29-,30-/m1/s1
• InChI Key: LWKTZNWGJCDICZ-JDJSMUMXSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₂O₁₂
• Molecular Weight: 594.60 g/mol
• Exact Mass: 594.26762677 g/mol
• Topological Polar Surface Area (TPSA): 199.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): -0.26
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 14

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7641	76.41%
Caco-2	-	0.8730	87.30%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8075	80.75%
OATP2B1 inhibitior	-	0.8599	85.99%
OATP1B1 inhibitior	+	0.9084	90.84%
OATP1B3 inhibitior	+	0.9447	94.47%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.7249	72.49%
P-glycoprotein inhibitior	+	0.6642	66.42%
P-glycoprotein substrate	+	0.5641	56.41%
CYP3A4 substrate	+	0.6778	67.78%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8058	80.58%
CYP3A4 inhibition	-	0.9023	90.23%
CYP2C9 inhibition	-	0.8699	86.99%
CYP2C19 inhibition	-	0.8244	82.44%
CYP2D6 inhibition	-	0.8892	88.92%
CYP1A2 inhibition	-	0.9058	90.58%
CYP2C8 inhibition	+	0.6458	64.58%
CYP inhibitory promiscuity	-	0.8839	88.39%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5401	54.01%
Eye corrosion	-	0.9923	99.23%
Eye irritation	-	0.9172	91.72%
Skin irritation	-	0.8122	81.22%
Skin corrosion	-	0.9563	95.63%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7564	75.64%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.8593	85.93%
skin sensitisation	-	0.8907	89.07%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.7363	73.63%
Acute Oral Toxicity (c)	III	0.5751	57.51%
Estrogen receptor binding	+	0.7483	74.83%
Androgen receptor binding	+	0.6266	62.66%
Thyroid receptor binding	+	0.5251	52.51%
Glucocorticoid receptor binding	+	0.5878	58.78%
Aromatase binding	+	0.6283	62.83%
PPAR gamma	+	0.6250	62.50%
Honey bee toxicity	-	0.7101	71.01%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.7550	75.50%
Fish aquatic toxicity	+	0.7530	75.30%

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	99.34%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	98.14%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.35%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.87%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.45%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.88%	98.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	92.91%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.86%	95.89%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	92.10%	94.62%
CHEMBL242	Q92731	Estrogen receptor beta	90.34%	98.35%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	89.75%	94.97%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.40%	94.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	86.41%	100.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.71%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.50%	95.56%
CHEMBL3437	Q16853	Amine oxidase, copper containing	84.31%	94.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.85%	86.92%
CHEMBL4581	P52732	Kinesin-like protein 1	83.39%	93.18%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	83.16%	97.21%
CHEMBL5939	Q9NZ08	Endoplasmic reticulum aminopeptidase 1	83.05%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.98%	86.33%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.88%	95.83%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.79%	92.94%
CHEMBL2514	O95665	Neurotensin receptor 2	82.65%	100.00%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	82.43%	85.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.04%	96.95%
CHEMBL2179	P04062	Beta-glucocerebrosidase	81.67%	85.31%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.89%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	80.36%	94.73%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	80.32%	92.32%

Plants that contains it

• Acer triflorum

Cross-Links

• PubChem: 10393688
• LOTUS: LTS0059950
• wikiData: Q105158371