3-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one

Details

• Internal ID: 41118bea-e8e9-43b0-a4ee-92bc9d9ea31a
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 3-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
• SMILES (Canonical): C1=C(C=C(C(=C1O)O)O)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(C(O4)CO)O)O)OC5C(C(C(O5)CO)O)O
• SMILES (Isomeric): C1=C(C=C(C(=C1O)O)O)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O[C@H]5[C@@H]([C@H]([C@H](O5)CO)O)O
• InChI: InChI=1S/C26H28O17/c27-5-13-17(34)20(37)24(43-25-21(38)18(35)14(6-28)40-25)26(41-13)42-23-19(36)15-9(30)3-8(29)4-12(15)39-22(23)7-1-10(31)16(33)11(32)2-7/h1-4,13-14,17-18,20-21,24-35,37-38H,5-6H2/t13-,14-,17-,18+,20+,21-,24-,25+,26+/m1/s1
• InChI Key: DKEIMQZQSBDMFK-KPKKTSSRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₈O₁₇
• Molecular Weight: 612.50 g/mol
• Exact Mass: 612.13264942 g/mol
• Topological Polar Surface Area (TPSA): 286.00 Ų
• XlogP: -1.00
• Atomic LogP (AlogP): -2.37
• H-Bond Acceptor: 17
• H-Bond Donor: 11
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5737	57.37%
Caco-2	-	0.9238	92.38%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6767	67.67%
OATP2B1 inhibitior	-	0.5540	55.40%
OATP1B1 inhibitior	+	0.8564	85.64%
OATP1B3 inhibitior	+	0.9453	94.53%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.4555	45.55%
P-glycoprotein inhibitior	-	0.5555	55.55%
P-glycoprotein substrate	-	0.6866	68.66%
CYP3A4 substrate	+	0.6315	63.15%
CYP2C9 substrate	-	0.6709	67.09%
CYP2D6 substrate	-	0.8582	85.82%
CYP3A4 inhibition	-	0.8613	86.13%
CYP2C9 inhibition	-	0.8849	88.49%
CYP2C19 inhibition	-	0.8109	81.09%
CYP2D6 inhibition	-	0.9082	90.82%
CYP1A2 inhibition	-	0.8791	87.91%
CYP2C8 inhibition	+	0.7662	76.62%
CYP inhibitory promiscuity	-	0.5669	56.69%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6086	60.86%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.8941	89.41%
Skin irritation	-	0.8230	82.30%
Skin corrosion	-	0.9614	96.14%
Ames mutagenesis	+	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6456	64.56%
Micronuclear	+	0.6733	67.33%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.8881	88.81%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.8492	84.92%
Acute Oral Toxicity (c)	III	0.5291	52.91%
Estrogen receptor binding	+	0.8401	84.01%
Androgen receptor binding	+	0.6760	67.60%
Thyroid receptor binding	+	0.5424	54.24%
Glucocorticoid receptor binding	-	0.4761	47.61%
Aromatase binding	+	0.6500	65.00%
PPAR gamma	+	0.7584	75.84%
Honey bee toxicity	-	0.7399	73.99%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5650	56.50%
Fish aquatic toxicity	+	0.8457	84.57%

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	99.78%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.96%	89.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	95.19%	95.64%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.49%	94.00%
CHEMBL2581	P07339	Cathepsin D	92.04%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	91.47%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.08%	99.17%
CHEMBL3194	P02766	Transthyretin	90.96%	90.71%
CHEMBL2424	Q04760	Glyoxalase I	87.85%	91.67%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.65%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.23%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	86.14%	91.49%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.18%	97.36%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.22%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.96%	94.45%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	81.48%	80.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.81%	96.09%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	80.69%	83.57%

Plants that contains it

• Phyllolobium chinense

Cross-Links

• PubChem: 162901450
• LOTUS: LTS0010377
• wikiData: Q104983114