5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[(4-hydroxyphenyl)methyl]-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one

Details

• Internal ID: c321629a-384c-402b-b82e-19b04ba35b64
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides
• IUPAC Name: 5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[(4-hydroxyphenyl)methyl]-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
• SMILES (Canonical): C1=CC(=CC=C1CC2=C(C(=C(C3=C2OC(=CC3=O)C4=CC=C(C=C4)O)O)C5C(C(C(C(O5)CO)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1CC2=C(C(=C(C3=C2OC(=CC3=O)C4=CC=C(C=C4)O)O)[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O
• InChI: InChI=1S/C28H26O11/c29-11-19-23(34)25(36)26(37)28(39-19)21-22(33)16(9-12-1-5-14(30)6-2-12)27-20(24(21)35)17(32)10-18(38-27)13-3-7-15(31)8-4-13/h1-8,10,19,23,25-26,28-31,33-37H,9,11H2/t19-,23-,25+,26-,28+/m1/s1
• InChI Key: QSEKYEYPJACWFH-JVOWPQRDSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₂₆O₁₁
• Molecular Weight: 538.50 g/mol
• Exact Mass: 538.14751164 g/mol
• Topological Polar Surface Area (TPSA): 197.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.39
• H-Bond Acceptor: 11
• H-Bond Donor: 8
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6665	66.65%
Caco-2	-	0.9392	93.92%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.5728	57.28%
OATP2B1 inhibitior	-	0.5435	54.35%
OATP1B1 inhibitior	+	0.7047	70.47%
OATP1B3 inhibitior	+	0.9709	97.09%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.8783	87.83%
P-glycoprotein inhibitior	+	0.5764	57.64%
P-glycoprotein substrate	-	0.7261	72.61%
CYP3A4 substrate	+	0.6053	60.53%
CYP2C9 substrate	-	0.5961	59.61%
CYP2D6 substrate	-	0.8222	82.22%
CYP3A4 inhibition	-	0.8310	83.10%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9240	92.40%
CYP2D6 inhibition	-	0.9476	94.76%
CYP1A2 inhibition	-	0.8355	83.55%
CYP2C8 inhibition	+	0.7453	74.53%
CYP inhibitory promiscuity	-	0.7806	78.06%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7252	72.52%
Eye corrosion	-	0.9936	99.36%
Eye irritation	-	0.8876	88.76%
Skin irritation	-	0.7691	76.91%
Skin corrosion	-	0.9606	96.06%
Ames mutagenesis	+	0.6199	61.99%
Human Ether-a-go-go-Related Gene inhibition	+	0.6951	69.51%
Micronuclear	+	0.6559	65.59%
Hepatotoxicity	-	0.7446	74.46%
skin sensitisation	-	0.8683	86.83%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.7929	79.29%
Acute Oral Toxicity (c)	IV	0.3746	37.46%
Estrogen receptor binding	+	0.7964	79.64%
Androgen receptor binding	+	0.8032	80.32%
Thyroid receptor binding	-	0.4870	48.70%
Glucocorticoid receptor binding	-	0.4881	48.81%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.7035	70.35%
Honey bee toxicity	-	0.6392	63.92%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.6921	69.21%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.02%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.82%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.92%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.28%	89.00%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	92.45%	95.17%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	90.59%	83.57%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.56%	94.45%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.23%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.72%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.22%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	86.39%	94.73%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	86.31%	91.71%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	85.97%	96.21%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	85.96%	89.23%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.25%	86.92%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	85.18%	85.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.05%	86.33%
CHEMBL1944	P08473	Neprilysin	84.54%	92.63%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.49%	95.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.45%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.10%	95.89%

Plants that contains it

• Citrullus colocynthis

Cross-Links

• PubChem: 102446088
• LOTUS: LTS0245730
• wikiData: Q105226906