7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-one

Details

• Internal ID: dd9fb7f4-ac32-4887-b494-4a1769817127
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-one
• SMILES (Canonical): COC1=C(C=CC(=C1)C2=CC(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)OC5C(C(C(C(O5)CO)O)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C2=CC(=O)C3=C(C=C(C=C3O2)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]([C@H](O5)CO)O)O)O)O)O
• InChI: InChI=1S/C28H32O16/c1-39-16-4-10(2-3-12(16)31)15-7-14(33)20-13(32)5-11(6-17(20)41-15)40-28-26(24(37)22(35)19(9-30)43-28)44-27-25(38)23(36)21(34)18(8-29)42-27/h2-7,18-19,21-32,34-38H,8-9H2,1H3/t18-,19-,21-,22-,23-,24+,25-,26-,27+,28-/m1/s1
• InChI Key: PRAAWOPIZHEJGG-ZTXLZDAFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₂O₁₆
• Molecular Weight: 624.50 g/mol
• Exact Mass: 624.16903493 g/mol
• Topological Polar Surface Area (TPSA): 255.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -2.12
• H-Bond Acceptor: 16
• H-Bond Donor: 9
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5457	54.57%
Caco-2	-	0.9137	91.37%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.5961	59.61%
OATP2B1 inhibitior	-	0.7058	70.58%
OATP1B1 inhibitior	+	0.9395	93.95%
OATP1B3 inhibitior	+	0.9786	97.86%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.5504	55.04%
P-glycoprotein inhibitior	-	0.6421	64.21%
P-glycoprotein substrate	-	0.5833	58.33%
CYP3A4 substrate	+	0.6165	61.65%
CYP2C9 substrate	-	0.8485	84.85%
CYP2D6 substrate	-	0.8501	85.01%
CYP3A4 inhibition	-	0.9437	94.37%
CYP2C9 inhibition	-	0.9060	90.60%
CYP2C19 inhibition	-	0.8926	89.26%
CYP2D6 inhibition	-	0.9515	95.15%
CYP1A2 inhibition	-	0.9150	91.50%
CYP2C8 inhibition	+	0.7323	73.23%
CYP inhibitory promiscuity	-	0.7142	71.42%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6642	66.42%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9154	91.54%
Skin irritation	-	0.8320	83.20%
Skin corrosion	-	0.9606	96.06%
Ames mutagenesis	-	0.5292	52.92%
Human Ether-a-go-go-Related Gene inhibition	+	0.6892	68.92%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.9000	90.00%
skin sensitisation	-	0.9324	93.24%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.8509	85.09%
Acute Oral Toxicity (c)	III	0.6678	66.78%
Estrogen receptor binding	+	0.8452	84.52%
Androgen receptor binding	+	0.5952	59.52%
Thyroid receptor binding	-	0.5118	51.18%
Glucocorticoid receptor binding	-	0.4855	48.55%
Aromatase binding	+	0.6618	66.18%
PPAR gamma	+	0.7808	78.08%
Honey bee toxicity	-	0.6644	66.44%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.6698	66.98%

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	99.32%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.51%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.13%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.85%	89.00%
CHEMBL2581	P07339	Cathepsin D	94.10%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.36%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.42%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.93%	96.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.80%	86.92%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	89.90%	96.21%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.79%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	89.21%	91.49%
CHEMBL3194	P02766	Transthyretin	88.91%	90.71%
CHEMBL220	P22303	Acetylcholinesterase	88.40%	94.45%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.66%	97.36%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.46%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	87.07%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.66%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.80%	94.45%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	84.68%	95.78%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.26%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.14%	97.09%
CHEMBL1907	P15144	Aminopeptidase N	81.24%	93.31%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.78%	96.00%

Plants that contains it

• Sideritis grandiflora

Cross-Links

• PubChem: 21721981
• LOTUS: LTS0240827
• wikiData: Q105213562