6-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-5,8-dihydroxy-2-(4-hydroxyphenyl)-7-methoxychromen-4-one

Details

• Internal ID: 112afe08-88ae-46e3-93c8-d2cc07ef6163
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides
• IUPAC Name: 6-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-5,8-dihydroxy-2-(4-hydroxyphenyl)-7-methoxychromen-4-one
• SMILES (Canonical): COC1=C(C(=C2C(=O)C=C(OC2=C1O)C3=CC=C(C=C3)O)O)C4C(C(C(C(O4)CO)O)O)OC5C(C(CO5)(CO)O)O
• SMILES (Isomeric): COC1=C(C(=C2C(=O)C=C(OC2=C1O)C3=CC=C(C=C3)O)O)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O[C@H]5[C@@H]([C@](CO5)(CO)O)O
• InChI: InChI=1S/C27H30O15/c1-38-21-16(18(33)15-12(31)6-13(40-22(15)20(21)35)10-2-4-11(30)5-3-10)23-24(19(34)17(32)14(7-28)41-23)42-26-25(36)27(37,8-29)9-39-26/h2-6,14,17,19,23-26,28-30,32-37H,7-9H2,1H3/t14-,17-,19+,23+,24-,25+,26+,27-/m1/s1
• InChI Key: ZWDZHRULMLSHPW-FFCLRUJESA-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): 245.00 Ų
• XlogP: -1.00
• Atomic LogP (AlogP): -1.43
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6754	67.54%
Caco-2	-	0.8982	89.82%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6254	62.54%
OATP2B1 inhibitior	-	0.5752	57.52%
OATP1B1 inhibitior	+	0.8100	81.00%
OATP1B3 inhibitior	+	0.9655	96.55%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8864	88.64%
P-glycoprotein inhibitior	-	0.4863	48.63%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6930	69.30%
CYP2C9 substrate	-	0.8346	83.46%
CYP2D6 substrate	-	0.8537	85.37%
CYP3A4 inhibition	-	0.8418	84.18%
CYP2C9 inhibition	-	0.8860	88.60%
CYP2C19 inhibition	-	0.8296	82.96%
CYP2D6 inhibition	-	0.9113	91.13%
CYP1A2 inhibition	-	0.9060	90.60%
CYP2C8 inhibition	+	0.7216	72.16%
CYP inhibitory promiscuity	-	0.7811	78.11%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5250	52.50%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9131	91.31%
Skin irritation	-	0.8131	81.31%
Skin corrosion	-	0.9457	94.57%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6499	64.99%
Micronuclear	+	0.6733	67.33%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.8821	88.21%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.7769	77.69%
Acute Oral Toxicity (c)	III	0.6985	69.85%
Estrogen receptor binding	+	0.8304	83.04%
Androgen receptor binding	+	0.7596	75.96%
Thyroid receptor binding	+	0.5636	56.36%
Glucocorticoid receptor binding	+	0.7067	70.67%
Aromatase binding	+	0.7090	70.90%
PPAR gamma	+	0.7752	77.52%
Honey bee toxicity	-	0.7091	70.91%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.6644	66.44%

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	99.75%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.67%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.47%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.61%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.35%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.73%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.16%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.05%	97.09%
CHEMBL3922	P50579	Methionine aminopeptidase 2	87.40%	97.28%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.38%	86.92%
CHEMBL226	P30542	Adenosine A1 receptor	87.16%	95.93%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.95%	97.14%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.48%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.87%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.77%	99.23%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.25%	95.83%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.82%	99.15%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	82.91%	83.57%
CHEMBL6175	Q9H3R0	Lysine-specific demethylase 4C	81.74%	96.69%
CHEMBL242	Q92731	Estrogen receptor beta	81.38%	98.35%
CHEMBL3401	O75469	Pregnane X receptor	80.55%	94.73%

Plants that contains it

• Abrus precatorius

Cross-Links

• PubChem: 163034502
• LOTUS: LTS0170058
• wikiData: Q105384845