1-[1-hydroxy-3-methyl-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxynaphthalen-2-yl]ethanone

Details

• Internal ID: 0893460a-9d31-46d7-9980-a4efbc6c8329
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: 1-[1-hydroxy-3-methyl-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxynaphthalen-2-yl]ethanone
• SMILES (Canonical): CC1=CC2=C(C(=CC=C2)OC3C(C(C(C(O3)CO)O)O)O)C(=C1C(=O)C)O
• SMILES (Isomeric): CC1=CC2=C(C(=CC=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C(=C1C(=O)C)O
• InChI: InChI=1S/C19H22O8/c1-8-6-10-4-3-5-11(14(10)16(23)13(8)9(2)21)26-19-18(25)17(24)15(22)12(7-20)27-19/h3-6,12,15,17-20,22-25H,7H2,1-2H3/t12-,15-,17+,18-,19-/m1/s1
• InChI Key: FZUPKYUANHOYBD-JZXZQAMYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₂O₈
• Molecular Weight: 378.40 g/mol
• Exact Mass: 378.13146766 g/mol
• Topological Polar Surface Area (TPSA): 137.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 0.24
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4908	49.08%
Caco-2	-	0.8232	82.32%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6127	61.27%
OATP2B1 inhibitior	-	0.5637	56.37%
OATP1B1 inhibitior	+	0.8755	87.55%
OATP1B3 inhibitior	+	0.9434	94.34%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.6630	66.30%
P-glycoprotein inhibitior	-	0.8624	86.24%
P-glycoprotein substrate	-	0.8444	84.44%
CYP3A4 substrate	+	0.5918	59.18%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8669	86.69%
CYP3A4 inhibition	-	0.8689	86.89%
CYP2C9 inhibition	-	0.9263	92.63%
CYP2C19 inhibition	-	0.9137	91.37%
CYP2D6 inhibition	-	0.9341	93.41%
CYP1A2 inhibition	-	0.6791	67.91%
CYP2C8 inhibition	+	0.5591	55.91%
CYP inhibitory promiscuity	-	0.7349	73.49%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7397	73.97%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.8901	89.01%
Skin irritation	-	0.8301	83.01%
Skin corrosion	-	0.9649	96.49%
Ames mutagenesis	+	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5151	51.51%
Micronuclear	+	0.6033	60.33%
Hepatotoxicity	-	0.6518	65.18%
skin sensitisation	-	0.9122	91.22%
Respiratory toxicity	-	0.6333	63.33%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.6439	64.39%
Acute Oral Toxicity (c)	III	0.6437	64.37%
Estrogen receptor binding	+	0.6573	65.73%
Androgen receptor binding	-	0.5839	58.39%
Thyroid receptor binding	-	0.5116	51.16%
Glucocorticoid receptor binding	+	0.5838	58.38%
Aromatase binding	+	0.6441	64.41%
PPAR gamma	+	0.6287	62.87%
Honey bee toxicity	-	0.8729	87.29%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	0.8540	85.40%

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	98.35%	91.11%
CHEMBL220	P22303	Acetylcholinesterase	98.20%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	95.18%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.45%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.20%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.96%	86.33%
CHEMBL2581	P07339	Cathepsin D	89.36%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.68%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.65%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.62%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.58%	95.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.06%	96.95%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.75%	95.50%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	80.20%	97.21%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.06%	99.15%

Plants that contains it

• Albizia myriophylla
• Amphorogyne spicata
• Anaphalis lactea
• Anchusa azurea
• Balanophora laxiflora
• Benincasa hispida
• Carduus tenuiflorus
• Chaiturus marrubiastrum
• Cryptochilus strictus
• Degenia velebitica
• Delphinium nuttallianum
• Delphinium virgatum
• Dillenia indica
• Dipsacus dipsacoides
• Erythrophleum ivorense
• Grangea maderaspatana
• Helichrysum chionosphaerum
• Jacquemontia paniculata
• Leptocereus quadricostatus
• Lespedeza tomentosa
• Lupinus argenteus subsp. argenteus
• Mandragora officinarum
• Metrodorea nigra
• Nepeta granatensis
• Onobrychis arenaria
• Petunia inflata
• Phedimus selskanianus
• Photinia serratifolia
• Pittocaulon praecox
• Quercus rubra
• Rheum officinale
• Rosa villosa
• Rumex nepalensis
• Rumex patientia
• Salvia greggii
• Senecio behnii
• Sticherus quadripartitus
• Tagetes filifolia
• Tanacetum coccineum
• Verbascum densiflorum

Cross-Links

• PubChem: 5319972
• NPASS: NPC216752
• LOTUS: LTS0072500
• wikiData: Q105005184