(2S,3S,4S)-4-[4-hydroxy-3-[2-hydroxy-5-[[(3S,4R,5S)-3-hydroxy-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl]-3-methoxyphenyl]-5-methoxyphenyl]-2,3-bis(hydroxymethyl)-7-methoxy-3,4-dihydro-1H-naphthalene-2,6-diol

Details

• Internal ID: 79e7f18b-43da-464c-af02-9108617a2980
• Taxonomy: Lignans, neolignans and related compounds > Aryltetralin lignans > 9,9p-dihydroxyaryltetralin lignans
• IUPAC Name: (2S,3S,4S)-4-[4-hydroxy-3-[2-hydroxy-5-[[(3S,4R,5S)-3-hydroxy-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl]-3-methoxyphenyl]-5-methoxyphenyl]-2,3-bis(hydroxymethyl)-7-methoxy-3,4-dihydro-1H-naphthalene-2,6-diol
• SMILES (Canonical): COC1=CC(=CC(=C1O)C2=C(C(=CC(=C2)C3C(C(CC4=CC(=C(C=C34)O)OC)(CO)O)CO)OC)O)CC5(COC(C5CO)C6=CC(=C(C=C6)O)OC)O
• SMILES (Isomeric): COC1=CC(=CC(=C1O)C2=C(C(=CC(=C2)[C@@H]3[C@H]([C@@](CC4=CC(=C(C=C34)O)OC)(CO)O)CO)OC)O)C[C@]5(CO[C@@H]([C@H]5CO)C6=CC(=C(C=C6)O)OC)O
• InChI: InChI=1S/C40H46O14/c1-50-31-10-21(5-6-29(31)44)38-28(17-42)40(49,19-54-38)14-20-7-25(36(46)33(8-20)52-3)26-9-22(11-34(53-4)37(26)47)35-24-13-30(45)32(51-2)12-23(24)15-39(48,18-43)27(35)16-41/h5-13,27-28,35,38,41-49H,14-19H2,1-4H3/t27-,28-,35+,38-,39-,40-/m1/s1
• InChI Key: TZQIHCIPTUUXIJ-KZFJUJRZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₄₆O₁₄
• Molecular Weight: 750.80 g/mol
• Exact Mass: 750.28875614 g/mol
• Topological Polar Surface Area (TPSA): 228.00 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 2.88
• H-Bond Acceptor: 14
• H-Bond Donor: 9
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9053	90.53%
Caco-2	-	0.8500	85.00%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6649	66.49%
OATP2B1 inhibitior	-	0.5727	57.27%
OATP1B1 inhibitior	+	0.8642	86.42%
OATP1B3 inhibitior	+	0.9651	96.51%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9725	97.25%
P-glycoprotein inhibitior	+	0.7859	78.59%
P-glycoprotein substrate	+	0.5713	57.13%
CYP3A4 substrate	+	0.6951	69.51%
CYP2C9 substrate	-	0.6048	60.48%
CYP2D6 substrate	-	0.6611	66.11%
CYP3A4 inhibition	-	0.8287	82.87%
CYP2C9 inhibition	-	0.8213	82.13%
CYP2C19 inhibition	-	0.7172	71.72%
CYP2D6 inhibition	-	0.9202	92.02%
CYP1A2 inhibition	-	0.7423	74.23%
CYP2C8 inhibition	+	0.8501	85.01%
CYP inhibitory promiscuity	-	0.6772	67.72%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5671	56.71%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.9099	90.99%
Skin irritation	-	0.8116	81.16%
Skin corrosion	-	0.9476	94.76%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9057	90.57%
Micronuclear	+	0.5400	54.00%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.8648	86.48%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.7729	77.29%
Acute Oral Toxicity (c)	III	0.5384	53.84%
Estrogen receptor binding	+	0.8638	86.38%
Androgen receptor binding	+	0.7471	74.71%
Thyroid receptor binding	+	0.6377	63.77%
Glucocorticoid receptor binding	+	0.7980	79.80%
Aromatase binding	+	0.6418	64.18%
PPAR gamma	+	0.7400	74.00%
Honey bee toxicity	-	0.7685	76.85%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.8950	89.50%

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	99.68%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.24%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.80%	97.09%
CHEMBL2581	P07339	Cathepsin D	94.25%	98.95%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	94.24%	95.17%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.31%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.57%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.87%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.68%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	91.50%	92.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.15%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.55%	99.15%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.26%	92.94%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.08%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.68%	85.14%
CHEMBL4208	P20618	Proteasome component C5	84.92%	90.00%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	83.23%	85.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.44%	94.45%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	82.44%	89.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.29%	89.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.17%	97.28%
CHEMBL5555	O00767	Acyl-CoA desaturase	81.74%	97.50%
CHEMBL3820	P35557	Hexokinase type IV	81.14%	91.96%
CHEMBL4581	P52732	Kinesin-like protein 1	81.14%	93.18%
CHEMBL2535	P11166	Glucose transporter	80.59%	98.75%

Plants that contains it

• Cerbera manghas

Cross-Links

• PubChem: 14539965
• LOTUS: LTS0050227
• wikiData: Q105268330