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

Details

• Internal ID: d5ff11bc-0b91-427d-8c0a-035805552353
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides
• IUPAC Name: 6-[(2S,3S,4R,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• SMILES (Canonical): C1=CC(=CC=C1C2=CC(=O)C3=C(O2)C=C(C(=C3O)C4C(C(C(C(O4)CO)O)OC5C(C(C(C(O5)CO)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C2=CC(=O)C3=C(O2)C=C(C(=C3O)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O)O
• InChI: InChI=1S/C27H30O15/c28-7-15-19(33)22(36)23(37)27(41-15)42-26-20(34)16(8-29)40-25(24(26)38)18-12(32)6-14-17(21(18)35)11(31)5-13(39-14)9-1-3-10(30)4-2-9/h1-6,15-16,19-20,22-30,32-38H,7-8H2/t15-,16-,19-,20-,22+,23-,24+,25+,26+,27+/m1/s1
• InChI Key: RRZDYPCTVWWHHW-ASOIEMBXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₅
• Molecular Weight: 594.50 g/mol
• Exact Mass: 594.15847025 g/mol
• Topological Polar Surface Area (TPSA): 256.00 Ų
• XlogP: -1.40
• Atomic LogP (AlogP): -2.08
• H-Bond Acceptor: 15
• H-Bond Donor: 10
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5736	57.36%
Caco-2	-	0.9289	92.89%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.5848	58.48%
OATP2B1 inhibitior	-	0.5538	55.38%
OATP1B1 inhibitior	+	0.8718	87.18%
OATP1B3 inhibitior	+	0.9434	94.34%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	-	0.6360	63.60%
P-glycoprotein substrate	-	0.7608	76.08%
CYP3A4 substrate	+	0.6378	63.78%
CYP2C9 substrate	-	0.6643	66.43%
CYP2D6 substrate	-	0.8569	85.69%
CYP3A4 inhibition	-	0.9390	93.90%
CYP2C9 inhibition	-	0.9315	93.15%
CYP2C19 inhibition	-	0.9047	90.47%
CYP2D6 inhibition	-	0.9458	94.58%
CYP1A2 inhibition	-	0.9180	91.80%
CYP2C8 inhibition	+	0.7696	76.96%
CYP inhibitory promiscuity	-	0.7526	75.26%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6848	68.48%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.8983	89.83%
Skin irritation	-	0.8255	82.55%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	+	0.5299	52.99%
Human Ether-a-go-go-Related Gene inhibition	-	0.4061	40.61%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.8696	86.96%
skin sensitisation	-	0.9132	91.32%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.8867	88.67%
Acute Oral Toxicity (c)	IV	0.4763	47.63%
Estrogen receptor binding	+	0.7877	78.77%
Androgen receptor binding	+	0.7466	74.66%
Thyroid receptor binding	+	0.5157	51.57%
Glucocorticoid receptor binding	-	0.4754	47.54%
Aromatase binding	+	0.6535	65.35%
PPAR gamma	+	0.7807	78.07%
Honey bee toxicity	-	0.6483	64.83%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.7958	79.58%

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	99.70%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.03%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.67%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.39%	89.00%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	95.33%	83.57%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.58%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.71%	99.15%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	89.89%	96.21%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.50%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.16%	86.92%
CHEMBL3401	O75469	Pregnane X receptor	86.65%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.20%	94.45%
CHEMBL3194	P02766	Transthyretin	84.75%	90.71%
CHEMBL1951	P21397	Monoamine oxidase A	84.38%	91.49%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	83.26%	95.78%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.01%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.50%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.37%	95.89%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.31%	91.71%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.20%	90.71%

Plants that contains it

• Isatis tinctoria
• Zanthoxylum schinifolium

Cross-Links

• PubChem: 102352204
• LOTUS: LTS0039455
• wikiData: Q105029514