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

Details

• Internal ID: 4fddb823-b71c-4312-9c98-93e4736c0021
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides > Flavonoid 8-C-glycosides
• IUPAC Name: 5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]chromen-4-one
• SMILES (Canonical): COC1=C(C(=C2C(=O)C=C(OC2=C1C3C(C(C(CO3)O)O)O)C4=CC=C(C=C4)O)O)C5C(C(C(C(O5)CO)O)O)O
• SMILES (Isomeric): COC1=C(C(=C2C(=O)C=C(OC2=C1[C@H]3[C@@H]([C@H]([C@H](CO3)O)O)O)C4=CC=C(C=C4)O)O)[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
• InChI: InChI=1S/C27H30O14/c1-38-24-16(27-23(37)21(35)19(33)14(7-28)41-27)20(34)15-11(30)6-13(9-2-4-10(29)5-3-9)40-25(15)17(24)26-22(36)18(32)12(31)8-39-26/h2-6,12,14,18-19,21-23,26-29,31-37H,7-8H2,1H3/t12-,14+,18-,19+,21-,22+,23+,26-,27-/m0/s1
• InChI Key: IHRVJPZYTSPICL-QHTAQJPCSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₄
• Molecular Weight: 578.50 g/mol
• Exact Mass: 578.16355563 g/mol
• Topological Polar Surface Area (TPSA): 236.00 Ų
• XlogP: -1.90
• Atomic LogP (AlogP): -1.45
• H-Bond Acceptor: 14
• H-Bond Donor: 9
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6749	67.49%
Caco-2	-	0.8904	89.04%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.5157	51.57%
OATP2B1 inhibitior	-	0.5694	56.94%
OATP1B1 inhibitior	+	0.7520	75.20%
OATP1B3 inhibitior	+	0.9797	97.97%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7282	72.82%
P-glycoprotein inhibitior	-	0.5794	57.94%
P-glycoprotein substrate	-	0.5719	57.19%
CYP3A4 substrate	+	0.6479	64.79%
CYP2C9 substrate	-	0.8087	80.87%
CYP2D6 substrate	-	0.8299	82.99%
CYP3A4 inhibition	-	0.8642	86.42%
CYP2C9 inhibition	-	0.9232	92.32%
CYP2C19 inhibition	-	0.8857	88.57%
CYP2D6 inhibition	-	0.9256	92.56%
CYP1A2 inhibition	-	0.8628	86.28%
CYP2C8 inhibition	+	0.6736	67.36%
CYP inhibitory promiscuity	-	0.8076	80.76%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6744	67.44%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.9175	91.75%
Skin irritation	-	0.8140	81.40%
Skin corrosion	-	0.9557	95.57%
Ames mutagenesis	+	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6507	65.07%
Micronuclear	+	0.6159	61.59%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.9078	90.78%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.9401	94.01%
Acute Oral Toxicity (c)	III	0.7078	70.78%
Estrogen receptor binding	+	0.7535	75.35%
Androgen receptor binding	+	0.7397	73.97%
Thyroid receptor binding	-	0.5146	51.46%
Glucocorticoid receptor binding	+	0.5717	57.17%
Aromatase binding	+	0.5477	54.77%
PPAR gamma	+	0.6927	69.27%
Honey bee toxicity	-	0.7493	74.93%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	-	0.5650	56.50%

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	99.72%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.73%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.05%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.78%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.18%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.94%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.50%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.19%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.98%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.28%	96.09%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	86.76%	95.83%
CHEMBL3401	O75469	Pregnane X receptor	85.65%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.61%	99.17%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	85.57%	91.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.50%	99.15%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.38%	86.92%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	85.14%	89.23%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.29%	90.71%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	81.14%	95.64%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.13%	97.14%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.59%	95.89%

Plants that contains it

• Conchocarpus guyanensis

Cross-Links

• PubChem: 162964563
• LOTUS: LTS0141005
• wikiData: Q105113223