2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]chromen-4-one

Details

• Internal ID: b374f35e-fd61-4c46-92a2-4a55cdbb1717
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]chromen-4-one
• SMILES (Canonical): C1C(C(C(C(O1)OCC2C(C(C(C(O2)C3=C(C4=C(C=C3O)OC(=CC4=O)C5=CC(=C(C=C5)O)O)O)O)O)O)O)O)O
• SMILES (Isomeric): C1[C@@H]([C@@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)C3=C(C4=C(C=C3O)OC(=CC4=O)C5=CC(=C(C=C5)O)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C26H28O15/c27-9-2-1-8(3-10(9)28)14-4-11(29)17-15(40-14)5-12(30)18(21(17)34)25-23(36)22(35)20(33)16(41-25)7-39-26-24(37)19(32)13(31)6-38-26/h1-5,13,16,19-20,22-28,30-37H,6-7H2/t13-,16+,19-,20+,22-,23+,24+,25-,26-/m0/s1
• InChI Key: OBBCHAQRWPNBEC-CCXXTZDOSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₈O₁₅
• Molecular Weight: 580.50 g/mol
• Exact Mass: 580.14282018 g/mol
• Topological Polar Surface Area (TPSA): 256.00 Ų
• XlogP: -2.20
• Atomic LogP (AlogP): -1.74
• H-Bond Acceptor: 15
• H-Bond Donor: 10
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4617	46.17%
Caco-2	-	0.9248	92.48%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6348	63.48%
OATP2B1 inhibitior	-	0.5566	55.66%
OATP1B1 inhibitior	+	0.8968	89.68%
OATP1B3 inhibitior	+	0.8755	87.55%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.5704	57.04%
P-glycoprotein inhibitior	-	0.6642	66.42%
P-glycoprotein substrate	-	0.6109	61.09%
CYP3A4 substrate	+	0.6459	64.59%
CYP2C9 substrate	-	0.6709	67.09%
CYP2D6 substrate	-	0.8569	85.69%
CYP3A4 inhibition	-	0.9216	92.16%
CYP2C9 inhibition	-	0.9563	95.63%
CYP2C19 inhibition	-	0.9069	90.69%
CYP2D6 inhibition	-	0.9175	91.75%
CYP1A2 inhibition	-	0.9253	92.53%
CYP2C8 inhibition	+	0.7420	74.20%
CYP inhibitory promiscuity	-	0.8943	89.43%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6832	68.32%
Eye corrosion	-	0.9935	99.35%
Eye irritation	-	0.8985	89.85%
Skin irritation	-	0.8248	82.48%
Skin corrosion	-	0.9684	96.84%
Ames mutagenesis	+	0.6336	63.36%
Human Ether-a-go-go-Related Gene inhibition	-	0.3621	36.21%
Micronuclear	+	0.6174	61.74%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.9031	90.31%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.9728	97.28%
Acute Oral Toxicity (c)	III	0.4775	47.75%
Estrogen receptor binding	+	0.7395	73.95%
Androgen receptor binding	+	0.7052	70.52%
Thyroid receptor binding	+	0.5274	52.74%
Glucocorticoid receptor binding	-	0.5140	51.40%
Aromatase binding	+	0.6223	62.23%
PPAR gamma	+	0.7341	73.41%
Honey bee toxicity	-	0.7013	70.13%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.8955	89.55%

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	99.90%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.59%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.74%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	94.46%	99.15%
CHEMBL1951	P21397	Monoamine oxidase A	94.10%	91.49%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.07%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.55%	97.09%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	90.02%	80.33%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.83%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.73%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.28%	95.56%
CHEMBL4040	P28482	MAP kinase ERK2	87.09%	83.82%
CHEMBL3401	O75469	Pregnane X receptor	86.28%	94.73%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.93%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.41%	94.45%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	81.80%	83.57%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.44%	86.92%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.98%	95.89%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	80.77%	83.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.00%	96.09%

Plants that contains it

• Swertia perennis

Cross-Links

• PubChem: 101423634
• LOTUS: LTS0076363
• wikiData: Q105188925