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

Details

• Internal ID: 8132d931-31e7-4452-8316-812f5e4a34ba
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavones
• IUPAC Name: 3-[(2S,3R,4R,5S,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(2S,3R,4R,5S,6R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
• SMILES (Canonical): C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(OC(C(C4O)O)OC5C(OC(C(C5O)O)O)CO)CO)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O[C@H]4[C@@H](O[C@H]([C@H]([C@H]4O)O)O[C@H]5[C@@H](O[C@H]([C@H]([C@H]5O)O)O)CO)CO)O)O
• InChI: InChI=1S/C27H30O17/c28-6-14-24(18(35)20(37)26(39)41-14)44-27-21(38)19(36)23(15(7-29)42-27)43-25-17(34)16-12(33)4-9(30)5-13(16)40-22(25)8-1-2-10(31)11(32)3-8/h1-5,14-15,18-21,23-24,26-33,35-39H,6-7H2/t14-,15-,18+,19+,20-,21-,23-,24-,26+,27-/m0/s1
• InChI Key: XQULESVJCDHYBO-OQWFBBMDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₇
• Molecular Weight: 626.50 g/mol
• Exact Mass: 626.14829948 g/mol
• Topological Polar Surface Area (TPSA): 286.00 Ų
• XlogP: -2.30
• Atomic LogP (AlogP): -2.71
• 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	-	0.5808	58.08%
Caco-2	-	0.9256	92.56%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6103	61.03%
OATP2B1 inhibitior	-	0.5588	55.88%
OATP1B1 inhibitior	+	0.9078	90.78%
OATP1B3 inhibitior	+	0.9368	93.68%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.5735	57.35%
P-glycoprotein inhibitior	-	0.5460	54.60%
P-glycoprotein substrate	-	0.6855	68.55%
CYP3A4 substrate	+	0.6596	65.96%
CYP2C9 substrate	-	0.8309	83.09%
CYP2D6 substrate	-	0.8512	85.12%
CYP3A4 inhibition	-	0.8854	88.54%
CYP2C9 inhibition	-	0.8879	88.79%
CYP2C19 inhibition	-	0.9022	90.22%
CYP2D6 inhibition	-	0.9223	92.23%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	+	0.8632	86.32%
CYP inhibitory promiscuity	-	0.6058	60.58%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6810	68.10%
Eye corrosion	-	0.9923	99.23%
Eye irritation	-	0.8839	88.39%
Skin irritation	-	0.8226	82.26%
Skin corrosion	-	0.9682	96.82%
Ames mutagenesis	+	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4299	42.99%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.5196	51.96%
skin sensitisation	-	0.8996	89.96%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.8731	87.31%
Acute Oral Toxicity (c)	III	0.4142	41.42%
Estrogen receptor binding	+	0.7987	79.87%
Androgen receptor binding	+	0.7416	74.16%
Thyroid receptor binding	+	0.5291	52.91%
Glucocorticoid receptor binding	-	0.5242	52.42%
Aromatase binding	+	0.6495	64.95%
PPAR gamma	+	0.7541	75.41%
Honey bee toxicity	-	0.6467	64.67%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.7814	78.14%

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%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.25%	89.00%
CHEMBL2581	P07339	Cathepsin D	94.19%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.58%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.20%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	90.39%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.21%	86.92%
CHEMBL3194	P02766	Transthyretin	89.05%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.66%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	88.65%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.62%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.51%	99.17%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	84.97%	95.78%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.40%	95.56%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	83.66%	95.64%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.48%	95.83%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.15%	96.09%

Plants that contains it

• Parthenocissus tricuspidata

Cross-Links

• PubChem: 163029236
• LOTUS: LTS0026868
• wikiData: Q105340059