5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(1S)-1-(4-hydroxyphenyl)ethyl]-8-[(2S,3R,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one

Details

• Internal ID: 77611a01-372b-438e-bccb-c5ae8a1b673c
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides > Flavonoid 8-C-glycosides
• IUPAC Name: 5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(1S)-1-(4-hydroxyphenyl)ethyl]-8-[(2S,3R,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
• SMILES (Canonical): CC(C1=CC=C(C=C1)O)C2=C(C(=C3C(=C2O)C(=O)C=C(O3)C4=CC=C(C=C4)O)C5C(C(C(C(O5)CO)O)O)O)O
• SMILES (Isomeric): C[C@@H](C1=CC=C(C=C1)O)C2=C(C(=C3C(=C2O)C(=O)C=C(O3)C4=CC=C(C=C4)O)[C@H]5[C@@H]([C@H]([C@H]([C@H](O5)CO)O)O)O)O
• InChI: InChI=1S/C29H28O11/c1-12(13-2-6-15(31)7-3-13)20-24(35)21-17(33)10-18(14-4-8-16(32)9-5-14)39-28(21)22(25(20)36)29-27(38)26(37)23(34)19(11-30)40-29/h2-10,12,19,23,26-27,29-32,34-38H,11H2,1H3/t12-,19+,23-,26-,27+,29-/m0/s1
• InChI Key: VAVVYQGVFZBLHB-QVEOQNIASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₂₈O₁₁
• Molecular Weight: 552.50 g/mol
• Exact Mass: 552.16316171 g/mol
• Topological Polar Surface Area (TPSA): 197.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 1.95
• 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	+	0.6908	69.08%
Caco-2	-	0.8943	89.43%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6674	66.74%
OATP2B1 inhibitior	+	0.5880	58.80%
OATP1B1 inhibitior	+	0.7213	72.13%
OATP1B3 inhibitior	+	0.9801	98.01%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.8986	89.86%
P-glycoprotein inhibitior	+	0.6152	61.52%
P-glycoprotein substrate	-	0.6396	63.96%
CYP3A4 substrate	+	0.5960	59.60%
CYP2C9 substrate	-	0.6089	60.89%
CYP2D6 substrate	-	0.8455	84.55%
CYP3A4 inhibition	-	0.8584	85.84%
CYP2C9 inhibition	-	0.9039	90.39%
CYP2C19 inhibition	-	0.9232	92.32%
CYP2D6 inhibition	-	0.9605	96.05%
CYP1A2 inhibition	-	0.7896	78.96%
CYP2C8 inhibition	+	0.5506	55.06%
CYP inhibitory promiscuity	-	0.7398	73.98%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7151	71.51%
Eye corrosion	-	0.9933	99.33%
Eye irritation	-	0.8794	87.94%
Skin irritation	-	0.7901	79.01%
Skin corrosion	-	0.9508	95.08%
Ames mutagenesis	+	0.5992	59.92%
Human Ether-a-go-go-Related Gene inhibition	+	0.8450	84.50%
Micronuclear	+	0.6259	62.59%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.8925	89.25%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.7250	72.50%
Acute Oral Toxicity (c)	III	0.4784	47.84%
Estrogen receptor binding	+	0.8480	84.80%
Androgen receptor binding	+	0.7857	78.57%
Thyroid receptor binding	+	0.5904	59.04%
Glucocorticoid receptor binding	+	0.7107	71.07%
Aromatase binding	-	0.5352	53.52%
PPAR gamma	+	0.6177	61.77%
Honey bee toxicity	-	0.6929	69.29%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.7028	70.28%

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	99.24%	91.11%
CHEMBL2581	P07339	Cathepsin D	99.18%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.28%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	92.37%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.77%	85.14%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	91.60%	90.71%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	91.09%	89.23%
CHEMBL242	Q92731	Estrogen receptor beta	90.92%	98.35%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.89%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.31%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.72%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.20%	95.56%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	88.54%	93.10%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	88.47%	85.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.24%	86.33%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	86.53%	96.21%
CHEMBL4040	P28482	MAP kinase ERK2	86.28%	83.82%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.95%	99.17%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	83.79%	83.10%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.75%	86.92%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.50%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.16%	97.09%
CHEMBL3038469	P24941	CDK2/Cyclin A	82.01%	91.38%

Plants that contains it

• Cucumis sativus

Cross-Links

• PubChem: 162950401
• LOTUS: LTS0188330
• wikiData: Q105283020