1,8-dihydroxynaphthol 1-O-alpha-glucopyranoside

Details

• Internal ID: e0751551-dd72-4df9-b847-991f10afc36a
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(8-hydroxynaphthalen-1-yl)oxyoxane-3,4,5-triol
• SMILES (Canonical): C1=CC2=C(C(=C1)O)C(=CC=C2)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): C1=CC2=C(C(=C1)O)C(=CC=C2)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• InChI: InChI=1S/C16H18O7/c17-7-11-13(19)14(20)15(21)16(23-11)22-10-6-2-4-8-3-1-5-9(18)12(8)10/h1-6,11,13-21H,7H2/t11-,13-,14+,15-,16+/m1/s1
• InChI Key: AHZAHMZTRGKNPT-JZYAIQKZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₈O₇
• Molecular Weight: 322.31 g/mol
• Exact Mass: 322.10525291 g/mol
• Topological Polar Surface Area (TPSA): 120.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.28
• H-Bond Acceptor: 7
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

• CHEBI:207644
• (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(8-hydroxynaphthalen-1-yl)oxyoxane-3,4,5-triol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6630	66.30%
Caco-2	-	0.8054	80.54%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.4988	49.88%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9470	94.70%
OATP1B3 inhibitior	+	0.9492	94.92%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.9635	96.35%
P-glycoprotein inhibitior	-	0.9283	92.83%
P-glycoprotein substrate	-	0.9584	95.84%
CYP3A4 substrate	-	0.5467	54.67%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7927	79.27%
CYP3A4 inhibition	-	0.9255	92.55%
CYP2C9 inhibition	-	0.9272	92.72%
CYP2C19 inhibition	-	0.8390	83.90%
CYP2D6 inhibition	-	0.9182	91.82%
CYP1A2 inhibition	-	0.8708	87.08%
CYP2C8 inhibition	-	0.6923	69.23%
CYP inhibitory promiscuity	-	0.7734	77.34%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6060	60.60%
Eye corrosion	-	0.9926	99.26%
Eye irritation	-	0.6512	65.12%
Skin irritation	-	0.8186	81.86%
Skin corrosion	-	0.9740	97.40%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5638	56.38%
Micronuclear	+	0.5359	53.59%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	-	0.8942	89.42%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	+	0.6147	61.47%
Acute Oral Toxicity (c)	III	0.5406	54.06%
Estrogen receptor binding	-	0.6556	65.56%
Androgen receptor binding	-	0.6769	67.69%
Thyroid receptor binding	+	0.5818	58.18%
Glucocorticoid receptor binding	-	0.6310	63.10%
Aromatase binding	-	0.5299	52.99%
PPAR gamma	+	0.7283	72.83%
Honey bee toxicity	-	0.8447	84.47%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6650	66.50%
Fish aquatic toxicity	+	0.6988	69.88%

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	97.94%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.32%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.96%	96.09%
CHEMBL2581	P07339	Cathepsin D	83.67%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	83.05%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.02%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.92%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.95%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.93%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.16%	86.92%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 11427241
• LOTUS: LTS0072864
• wikiData: Q77484658