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

Details

• Internal ID: cfac2cff-3d49-4e7b-a20e-2ca5671c172f
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides
• IUPAC Name: 6-[(2S,3R,4S,5S,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3S,4S,5S,6S)-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)O)OC5C(C(C(C(O5)CO)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)O[C@H]5[C@H]([C@H]([C@@H]([C@@H](O5)CO)O)O)O)O)O
• InChI: InChI=1S/C27H30O15/c28-7-15-20(34)23(37)26(42-27-24(38)22(36)19(33)16(8-29)41-27)25(40-15)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-/m0/s1
• InChI Key: RQTTXGQDIROLTQ-FRMBBQOESA-N
• Popularity: 3 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	-	0.9304	93.04%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.5848	58.48%
OATP2B1 inhibitior	-	0.5550	55.50%
OATP1B1 inhibitior	+	0.8691	86.91%
OATP1B3 inhibitior	+	0.9434	94.34%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.5350	53.50%
P-glycoprotein inhibitior	-	0.6696	66.96%
P-glycoprotein substrate	-	0.7794	77.94%
CYP3A4 substrate	+	0.6350	63.50%
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	+	0.7373	73.73%
CYP inhibitory promiscuity	-	0.7526	75.26%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6848	68.48%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.9010	90.10%
Skin irritation	-	0.8255	82.55%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	+	0.5399	53.99%
Human Ether-a-go-go-Related Gene inhibition	-	0.5147	51.47%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.8821	88.21%
skin sensitisation	-	0.9132	91.32%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.8920	89.20%
Acute Oral Toxicity (c)	IV	0.4763	47.63%
Estrogen receptor binding	+	0.7887	78.87%
Androgen receptor binding	+	0.7614	76.14%
Thyroid receptor binding	+	0.5270	52.70%
Glucocorticoid receptor binding	+	0.5469	54.69%
Aromatase binding	+	0.7022	70.22%
PPAR gamma	+	0.7878	78.78%
Honey bee toxicity	-	0.6584	65.84%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
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	99.64%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.28%	98.95%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	95.87%	83.57%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.43%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.43%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.71%	99.15%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	88.54%	96.21%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.45%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.24%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.15%	86.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.90%	86.33%
CHEMBL3194	P02766	Transthyretin	87.24%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	87.15%	94.73%
CHEMBL1951	P21397	Monoamine oxidase A	86.52%	91.49%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.01%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.29%	94.45%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	82.01%	95.78%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.67%	91.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.69%	95.89%

Plants that contains it

• Cucumis sativus
• Ziziphus jujuba

Cross-Links

• PubChem: 160702278
• LOTUS: LTS0112612
• wikiData: Q105243591