3-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one

Details

• Internal ID: 5982ea32-0f45-47c1-90cd-0018b7482315
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 3-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)O)OC5C(C(C(O5)CO)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O[C@H]5[C@@H]([C@H]([C@@H](O5)CO)O)O)O)O
• InChI: InChI=1S/C26H28O16/c27-6-14-17(32)20(35)22(37)25(40-14)38-9-4-12(31)16-13(5-9)39-23(8-1-2-10(29)11(30)3-8)24(19(16)34)42-26-21(36)18(33)15(7-28)41-26/h1-5,14-15,17-18,20-22,25-33,35-37H,6-7H2/t14-,15+,17-,18+,20+,21-,22-,25-,26+/m1/s1
• InChI Key: WYROMXDQWJEWEB-OACVLVRCSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₈O₁₆
• Molecular Weight: 596.50 g/mol
• Exact Mass: 596.13773480 g/mol
• Topological Polar Surface Area (TPSA): 266.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -2.43
• H-Bond Acceptor: 16
• H-Bond Donor: 10
• 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	-	0.9282	92.82%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6767	67.67%
OATP2B1 inhibitior	-	0.5514	55.14%
OATP1B1 inhibitior	+	0.9497	94.97%
OATP1B3 inhibitior	+	0.9453	94.53%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.6542	65.42%
P-glycoprotein inhibitior	-	0.5588	55.88%
P-glycoprotein substrate	-	0.8212	82.12%
CYP3A4 substrate	+	0.6085	60.85%
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	+	0.8217	82.17%
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	-	0.8807	88.07%
Skin irritation	-	0.8230	82.30%
Skin corrosion	-	0.9614	96.14%
Ames mutagenesis	+	0.7136	71.36%
Human Ether-a-go-go-Related Gene inhibition	+	0.7115	71.15%
Micronuclear	+	0.6733	67.33%
Hepatotoxicity	-	0.6946	69.46%
skin sensitisation	-	0.8881	88.81%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.8177	81.77%
Acute Oral Toxicity (c)	III	0.5291	52.91%
Estrogen receptor binding	+	0.7559	75.59%
Androgen receptor binding	+	0.6658	66.58%
Thyroid receptor binding	-	0.4942	49.42%
Glucocorticoid receptor binding	-	0.5147	51.47%
Aromatase binding	+	0.5407	54.07%
PPAR gamma	+	0.7254	72.54%
Honey bee toxicity	-	0.7224	72.24%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5950	59.50%
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	99.56%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	96.67%	91.49%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	95.66%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.55%	89.00%
CHEMBL2581	P07339	Cathepsin D	94.65%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.22%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	89.92%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.80%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.61%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.46%	86.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.01%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.86%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.68%	94.45%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	86.94%	95.78%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.26%	96.09%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	85.25%	95.64%
CHEMBL3194	P02766	Transthyretin	84.50%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.31%	95.56%

Plants that contains it

• Carthamus lanatus
• Vicia lens

Cross-Links

• PubChem: 102145595
• NPASS: NPC7096
• LOTUS: LTS0133703
• wikiData: Q105322502