8-hydroxy-3-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-naphthalen-1-one

Details

• Internal ID: 54d35df7-24c0-48fa-aef9-80beca899e5b
• Taxonomy: Benzenoids > Naphthalenes > Phenylnaphthalenes
• IUPAC Name: 8-hydroxy-3-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-naphthalen-1-one
• SMILES (Canonical): C1C2=CC(=C(C(=C2C(=O)C=C1C3=CC=C(C=C3)O)O)C4C(C(C(C(O4)CO)O)O)O)OC5C(C(C(C(O5)CO)O)O)O
• SMILES (Isomeric): C1C2=CC(=C(C(=C2C(=O)C=C1C3=CC=C(C=C3)O)O)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
• InChI: InChI=1S/C28H32O14/c29-8-16-20(33)23(36)25(38)27(40-16)19-15(41-28-26(39)24(37)21(34)17(9-30)42-28)7-12-5-11(6-14(32)18(12)22(19)35)10-1-3-13(31)4-2-10/h1-4,6-7,16-17,20-21,23-31,33-39H,5,8-9H2/t16-,17-,20-,21-,23+,24+,25-,26-,27+,28-/m1/s1
• InChI Key: DGHRWOMWBYMIMW-JFECCKQBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₂O₁₄
• Molecular Weight: 592.50 g/mol
• Exact Mass: 592.17920569 g/mol
• Topological Polar Surface Area (TPSA): 247.00 Ų
• XlogP: -1.40
• Atomic LogP (AlogP): -2.39
• H-Bond Acceptor: 14
• H-Bond Donor: 10
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6489	64.89%
Caco-2	-	0.9242	92.42%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6000	60.00%
OATP2B1 inhibitior	-	0.7034	70.34%
OATP1B1 inhibitior	+	0.8421	84.21%
OATP1B3 inhibitior	+	0.9574	95.74%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.6117	61.17%
P-glycoprotein inhibitior	-	0.6398	63.98%
P-glycoprotein substrate	-	0.7594	75.94%
CYP3A4 substrate	+	0.6522	65.22%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8585	85.85%
CYP3A4 inhibition	-	0.9411	94.11%
CYP2C9 inhibition	-	0.8255	82.55%
CYP2C19 inhibition	-	0.7629	76.29%
CYP2D6 inhibition	-	0.8892	88.92%
CYP1A2 inhibition	-	0.8392	83.92%
CYP2C8 inhibition	+	0.7869	78.69%
CYP inhibitory promiscuity	+	0.5000	50.00%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7063	70.63%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.8980	89.80%
Skin irritation	-	0.8080	80.80%
Skin corrosion	-	0.9592	95.92%
Ames mutagenesis	+	0.5399	53.99%
Human Ether-a-go-go-Related Gene inhibition	+	0.7659	76.59%
Micronuclear	+	0.6233	62.33%
Hepatotoxicity	-	0.6446	64.46%
skin sensitisation	-	0.8400	84.00%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.8071	80.71%
Acute Oral Toxicity (c)	III	0.3899	38.99%
Estrogen receptor binding	+	0.7171	71.71%
Androgen receptor binding	+	0.6183	61.83%
Thyroid receptor binding	-	0.5287	52.87%
Glucocorticoid receptor binding	-	0.6154	61.54%
Aromatase binding	+	0.6172	61.72%
PPAR gamma	+	0.7618	76.18%
Honey bee toxicity	-	0.7572	75.72%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5051	50.51%
Fish aquatic toxicity	+	0.9338	93.38%

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	99.48%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.70%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.97%	96.09%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	92.82%	96.21%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.69%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.66%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.53%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.47%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.27%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.94%	94.00%
CHEMBL220	P22303	Acetylcholinesterase	89.87%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.19%	86.33%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	87.89%	95.78%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	87.19%	95.64%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	85.69%	91.71%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.00%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.77%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.06%	99.15%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.45%	90.71%

Plants that contains it

• Eutrema salsugineum

Cross-Links

• PubChem: 162966808
• LOTUS: LTS0266435
• wikiData: Q104978709