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

Details

• Internal ID: 51a18238-1ca6-4100-9d9c-c013562c3618
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides
• IUPAC Name: 6-[(2S,3R,4S,5R,6R)-3-[(2S,3S,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-5-hydroxy-2-(4-hydroxyphenyl)-7,8-dimethoxychromen-4-one
• SMILES (Canonical): COC1=C(C(=C2C(=O)C=C(OC2=C1OC)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=C1OC)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/C28H32O15/c1-38-21-17(19(34)16-13(32)7-14(41-22(16)25(21)39-2)11-3-5-12(31)6-4-11)23-24(20(35)18(33)15(8-29)42-23)43-27-26(36)28(37,9-30)10-40-27/h3-7,15,18,20,23-24,26-27,29-31,33-37H,8-10H2,1-2H3/t15-,18+,20+,23+,24-,26-,27+,28+/m1/s1
• InChI Key: WRJOTXXNFMIKBB-RVFHNPSISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₂O₁₅
• Molecular Weight: 608.50 g/mol
• Exact Mass: 608.17412031 g/mol
• Topological Polar Surface Area (TPSA): 234.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -1.13
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6634	66.34%
Caco-2	-	0.8811	88.11%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6223	62.23%
OATP2B1 inhibitior	-	0.8494	84.94%
OATP1B1 inhibitior	+	0.8171	81.71%
OATP1B3 inhibitior	+	0.9601	96.01%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9337	93.37%
P-glycoprotein inhibitior	-	0.4294	42.94%
P-glycoprotein substrate	+	0.5157	51.57%
CYP3A4 substrate	+	0.6883	68.83%
CYP2C9 substrate	-	0.8346	83.46%
CYP2D6 substrate	-	0.8537	85.37%
CYP3A4 inhibition	-	0.8178	81.78%
CYP2C9 inhibition	-	0.9078	90.78%
CYP2C19 inhibition	-	0.8665	86.65%
CYP2D6 inhibition	-	0.9193	91.93%
CYP1A2 inhibition	-	0.8977	89.77%
CYP2C8 inhibition	+	0.7055	70.55%
CYP inhibitory promiscuity	-	0.7651	76.51%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5686	56.86%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.9170	91.70%
Skin irritation	-	0.8182	81.82%
Skin corrosion	-	0.9454	94.54%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6511	65.11%
Micronuclear	+	0.6733	67.33%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.8795	87.95%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.7596	75.96%
Acute Oral Toxicity (c)	III	0.6977	69.77%
Estrogen receptor binding	+	0.8252	82.52%
Androgen receptor binding	+	0.7731	77.31%
Thyroid receptor binding	+	0.6160	61.60%
Glucocorticoid receptor binding	+	0.7630	76.30%
Aromatase binding	+	0.6965	69.65%
PPAR gamma	+	0.7828	78.28%
Honey bee toxicity	-	0.7353	73.53%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.7109	71.09%

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	99.69%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.92%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.36%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.02%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.96%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.33%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.47%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.35%	97.09%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	90.13%	83.57%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.26%	86.92%
CHEMBL226	P30542	Adenosine A1 receptor	86.71%	95.93%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.40%	97.14%
CHEMBL3922	P50579	Methionine aminopeptidase 2	86.27%	97.28%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.59%	95.83%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.04%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.96%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.65%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	84.44%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.34%	99.15%
CHEMBL6175	Q9H3R0	Lysine-specific demethylase 4C	83.29%	96.69%
CHEMBL2803	P43403	Tyrosine-protein kinase ZAP-70	81.69%	82.50%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	80.52%	95.53%
CHEMBL242	Q92731	Estrogen receptor beta	80.39%	98.35%

Plants that contains it

• Abrus precatorius

Cross-Links

• PubChem: 163067810
• LOTUS: LTS0010614
• wikiData: Q105311348