5,7-dihydroxy-2-[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-6-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one

Details

• Internal ID: 363db767-fb5c-4b5c-83f4-a56b29e0a894
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides
• IUPAC Name: 5,7-dihydroxy-2-[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-6-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
• SMILES (Canonical): COC1=C(C=CC(=C1)C2=CC(=O)C3=C(O2)C=C(C(=C3O)C4C(C(C(C(O4)CO)O)O)O)O)OC5C(C(C(C(O5)CO)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C2=CC(=O)C3=C(O2)C=C(C(=C3O)[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]([C@H](O5)CO)O)O)O
• InChI: InChI=1S/C28H32O16/c1-40-14-4-9(2-3-12(14)43-28-26(39)24(37)21(34)17(8-30)44-28)13-5-10(31)18-15(41-13)6-11(32)19(22(18)35)27-25(38)23(36)20(33)16(7-29)42-27/h2-6,16-17,20-21,23-30,32-39H,7-8H2,1H3/t16-,17-,20-,21-,23+,24+,25+,26-,27+,28-/m1/s1
• InChI Key: VAOOAPRSEDZAEV-CCQODMIESA-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): 266.00 Ų
• XlogP: -1.60
• 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	-	0.5457	54.57%
Caco-2	-	0.9071	90.71%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.5961	59.61%
OATP2B1 inhibitior	-	0.7025	70.25%
OATP1B1 inhibitior	+	0.8569	85.69%
OATP1B3 inhibitior	+	0.9786	97.86%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.6651	66.51%
P-glycoprotein inhibitior	-	0.4421	44.21%
P-glycoprotein substrate	-	0.5947	59.47%
CYP3A4 substrate	+	0.6311	63.11%
CYP2C9 substrate	-	0.8389	83.89%
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	+	0.7816	78.16%
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	-	0.9139	91.39%
Skin irritation	-	0.8320	83.20%
Skin corrosion	-	0.9606	96.06%
Ames mutagenesis	+	0.5099	50.99%
Human Ether-a-go-go-Related Gene inhibition	+	0.7415	74.15%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.9324	93.24%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.9135	91.35%
Acute Oral Toxicity (c)	III	0.6678	66.78%
Estrogen receptor binding	+	0.8115	81.15%
Androgen receptor binding	+	0.6237	62.37%
Thyroid receptor binding	-	0.5178	51.78%
Glucocorticoid receptor binding	+	0.5402	54.02%
Aromatase binding	+	0.5684	56.84%
PPAR gamma	+	0.7268	72.68%
Honey bee toxicity	-	0.7052	70.52%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7200	72.00%
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	98.49%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.92%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.40%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.11%	85.14%
CHEMBL220	P22303	Acetylcholinesterase	95.87%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.47%	89.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	92.19%	96.21%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.02%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.21%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.16%	86.92%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.30%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	85.36%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.33%	99.15%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.07%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.03%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.85%	96.00%

Plants that contains it

• Cucumis sativus

Cross-Links

• PubChem: 163049412
• LOTUS: LTS0258729
• wikiData: Q105282872