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

Details

• Internal ID: 049cc9a5-2e39-46c5-9021-7ec46dbc442d
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: 1-[1,6-dihydroxy-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=CC(=CC(=C2C(=C1C(=O)C)O)OC3C(C(C(C(O3)CO)O)O)O)O
• SMILES (Isomeric): CC1=CC2=CC(=CC(=C2C(=C1C(=O)C)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O
• InChI: InChI=1S/C19H22O9/c1-7-3-9-4-10(22)5-11(14(9)16(24)13(7)8(2)21)27-19-18(26)17(25)15(23)12(6-20)28-19/h3-5,12,15,17-20,22-26H,6H2,1-2H3/t12-,15-,17+,18-,19-/m1/s1
• InChI Key: VJDBDVUFFPRHSF-JZXZQAMYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₂O₉
• Molecular Weight: 394.40 g/mol
• Exact Mass: 394.12638228 g/mol
• Topological Polar Surface Area (TPSA): 157.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): -0.06
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

• NSC 362402
• 1-[1,6-dihydroxy-3-methyl-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxynaphthalen-2-yl]ethanone
• C19H22O9
• C19-H22-O9
• Compound NP-009013
• 6-Hydroxymusizin 8-O-glucoside
• AKOS040739257

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4908	49.08%
Caco-2	-	0.8523	85.23%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6127	61.27%
OATP2B1 inhibitior	-	0.5561	55.61%
OATP1B1 inhibitior	+	0.8576	85.76%
OATP1B3 inhibitior	+	0.9434	94.34%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.7660	76.60%
P-glycoprotein inhibitior	-	0.8422	84.22%
P-glycoprotein substrate	-	0.8471	84.71%
CYP3A4 substrate	+	0.5798	57.98%
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	+	0.5309	53.09%
CYP inhibitory promiscuity	-	0.7349	73.49%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7397	73.97%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.8107	81.07%
Skin irritation	-	0.8301	83.01%
Skin corrosion	-	0.9649	96.49%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6546	65.46%
Micronuclear	+	0.6033	60.33%
Hepatotoxicity	-	0.6986	69.86%
skin sensitisation	-	0.9122	91.22%
Respiratory toxicity	-	0.6556	65.56%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.6469	64.69%
Acute Oral Toxicity (c)	III	0.6437	64.37%
Estrogen receptor binding	+	0.6589	65.89%
Androgen receptor binding	-	0.5685	56.85%
Thyroid receptor binding	-	0.5437	54.37%
Glucocorticoid receptor binding	+	0.5947	59.47%
Aromatase binding	+	0.5710	57.10%
PPAR gamma	+	0.6113	61.13%
Honey bee toxicity	-	0.8405	84.05%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7000	70.00%
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	98.28%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	94.81%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.22%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.92%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.03%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.90%	89.00%
CHEMBL220	P22303	Acetylcholinesterase	87.78%	94.45%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.00%	96.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.83%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.36%	96.00%
CHEMBL2581	P07339	Cathepsin D	84.28%	98.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.77%	95.89%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.66%	96.21%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	82.56%	97.21%

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
• Rheum palmatum
• Rosa villosa
• Salvia greggii
• Senecio behnii
• Senna tora
• Sticherus quadripartitus
• Tagetes filifolia
• Tanacetum coccineum
• Verbascum densiflorum

Cross-Links

• PubChem: 100753
• NPASS: NPC142063
• LOTUS: LTS0036966
• wikiData: Q105287163