3-[4,5-Dihydroxy-6-(hydroxymethyl)-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one

Details

• Internal ID: 66ec3705-1fe7-4cdc-8376-0c2f312f62c0
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 3-[4,5-dihydroxy-6-(hydroxymethyl)-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• SMILES (Canonical): C1=CC(=CC=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(C(O4)CO)O)O)OC5C(C(C(C(O5)CO)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(C(O4)CO)O)O)OC5C(C(C(C(O5)CO)O)O)O)O
• InChI: InChI=1S/C27H30O16/c28-7-14-17(33)20(36)22(38)26(40-14)43-25-21(37)18(34)15(8-29)41-27(25)42-24-19(35)16-12(32)5-11(31)6-13(16)39-23(24)9-1-3-10(30)4-2-9/h1-6,14-15,17-18,20-22,25-34,36-38H,7-8H2
• InChI Key: LKZDFKLGDGSGEO-UHFFFAOYSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₆
• Molecular Weight: 610.50 g/mol
• Exact Mass: 610.15338487 g/mol
• Topological Polar Surface Area (TPSA): 266.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -2.42
• H-Bond Acceptor: 16
• H-Bond Donor: 10
• Rotatable Bonds: 7

Synonyms

• SMR000440707
• 3-[4,5-dihydroxy-6-(hydroxymethyl)-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• Lilyn
• MEGxp0_001275
• CHEMBL1375795
• ACon1_001443
• BDBM95768
• CHEBI:139414
• cid_13647412
• HMS2271H06
• FT-0697937
• FT-0778285
• BRD-A08304061-001-01-9
• 3-[[4,5-dihydroxy-6-(hydroxymethyl)-3-[[3,4,5-trihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-2-oxanyl]oxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-1-benzopyran-4-one
• 3-[4,5-dihydroxy-6-methylol-3-(3,4,5-trihydroxy-6-methylol-tetrahydropyran-2-yl)oxy-tetrahydropyran-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)chromone
• 3-[6-(hydroxymethyl)-3-[6-(hydroxymethyl)-3,4,5-tris(oxidanyl)oxan-2-yl]oxy-4,5-bis(oxidanyl)oxan-2-yl]oxy-2-(4-hydroxyphenyl)-5,7-bis(oxidanyl)chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5736	57.36%
Caco-2	-	0.9273	92.73%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.5848	58.48%
OATP2B1 inhibitior	-	0.5537	55.37%
OATP1B1 inhibitior	+	0.8877	88.77%
OATP1B3 inhibitior	+	0.9434	94.34%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.7364	73.64%
P-glycoprotein inhibitior	-	0.5835	58.35%
P-glycoprotein substrate	-	0.6926	69.26%
CYP3A4 substrate	+	0.6416	64.16%
CYP2C9 substrate	-	0.6762	67.62%
CYP2D6 substrate	-	0.8575	85.75%
CYP3A4 inhibition	-	0.9390	93.90%
CYP2C9 inhibition	-	0.9315	93.15%
CYP2C19 inhibition	-	0.9047	90.47%
CYP2D6 inhibition	-	0.9458	94.58%
CYP1A2 inhibition	-	0.9180	91.80%
CYP2C8 inhibition	+	0.8314	83.14%
CYP inhibitory promiscuity	-	0.7526	75.26%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6848	68.48%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.8974	89.74%
Skin irritation	-	0.8255	82.55%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	+	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4406	44.06%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.6696	66.96%
skin sensitisation	-	0.9132	91.32%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.7913	79.13%
Acute Oral Toxicity (c)	IV	0.4763	47.63%
Estrogen receptor binding	+	0.8287	82.87%
Androgen receptor binding	+	0.7213	72.13%
Thyroid receptor binding	+	0.5209	52.09%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	+	0.7028	70.28%
PPAR gamma	+	0.7765	77.65%
Honey bee toxicity	-	0.7096	70.96%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5650	56.50%
Fish aquatic toxicity	+	0.7958	79.58%

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	99.36%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.65%	89.00%
CHEMBL2581	P07339	Cathepsin D	95.32%	98.95%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	95.09%	95.64%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.90%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	90.07%	94.73%
CHEMBL1951	P21397	Monoamine oxidase A	89.34%	91.49%
CHEMBL3194	P02766	Transthyretin	89.30%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.95%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.23%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.70%	94.45%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.92%	99.15%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.12%	86.92%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	85.65%	95.78%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.46%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.77%	96.09%
CHEMBL242	Q92731	Estrogen receptor beta	81.47%	98.35%

Plants that contains it

• Alangium chinense
• Alangium kurzii
• Allium tuberosum
• Brassica napus
• Camellia sinensis
• Carthamus lanatus
• Carthamus tinctorius
• Crocus antalyensis
• Crocus sativus
• Equisetum hyemale
• Equisetum ramosissimum subsp. debile
• Hosta ventricosa
• Hydrangea macrophylla
• Iochroma gesnerioides
• Lilium candidum
• Meconopsis quintuplinervia
• Phytolacca thyrsiflora
• Rhodiola rosea
• Rosa rugosa
• Solanum incanum
• Styphnolobium japonicum
• Trigonella foenum-graecum

Cross-Links

• PubChem: 13647412
• LOTUS: LTS0225418
• wikiData: Q105153362