8-[4,5-Dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one

Details

• Internal ID: a554971a-00bb-404f-97b6-5b7033557364
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-8-O-glycosides
• IUPAC Name: 8-[4,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=C(C=C(C4=C3OC(=CC4=O)C5=CC=C(C=C5)O)O)O)CO)O)O)O)O)O
• SMILES (Isomeric): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=C(C=C(C4=C3OC(=CC4=O)C5=CC=C(C=C5)O)O)O)CO)O)O)O)O)O
• InChI: InChI=1S/C27H30O15/c1-9-18(33)20(35)22(37)26(38-9)42-25-21(36)19(34)16(8-28)40-27(25)41-23-14(32)6-12(30)17-13(31)7-15(39-24(17)23)10-2-4-11(29)5-3-10/h2-7,9,16,18-22,25-30,32-37H,8H2,1H3
• InChI Key: IWWZSSAEMJLBMM-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₅
• Molecular Weight: 594.50 g/mol
• Exact Mass: 594.15847025 g/mol
• Topological Polar Surface Area (TPSA): 245.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -1.39
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4777	47.77%
Caco-2	-	0.9201	92.01%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.9000	90.00%
Subcellular localzation	Mitochondria	0.6881	68.81%
OATP2B1 inhibitior	-	0.5651	56.51%
OATP1B1 inhibitior	+	0.8765	87.65%
OATP1B3 inhibitior	+	0.9552	95.52%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.8230	82.30%
P-glycoprotein inhibitior	-	0.6647	66.47%
P-glycoprotein substrate	-	0.5619	56.19%
CYP3A4 substrate	+	0.6423	64.23%
CYP2C9 substrate	-	0.6986	69.86%
CYP2D6 substrate	-	0.8617	86.17%
CYP3A4 inhibition	-	0.9358	93.58%
CYP2C9 inhibition	-	0.9271	92.71%
CYP2C19 inhibition	-	0.9330	93.30%
CYP2D6 inhibition	-	0.9643	96.43%
CYP1A2 inhibition	-	0.8830	88.30%
CYP2C8 inhibition	+	0.6710	67.10%
CYP inhibitory promiscuity	-	0.7188	71.88%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7023	70.23%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.9261	92.61%
Skin irritation	-	0.8192	81.92%
Skin corrosion	-	0.9626	96.26%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4111	41.11%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	-	0.9312	93.12%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.9150	91.50%
Acute Oral Toxicity (c)	III	0.5734	57.34%
Estrogen receptor binding	+	0.8176	81.76%
Androgen receptor binding	+	0.6975	69.75%
Thyroid receptor binding	+	0.5598	55.98%
Glucocorticoid receptor binding	+	0.5979	59.79%
Aromatase binding	+	0.6304	63.04%
PPAR gamma	+	0.7484	74.84%
Honey bee toxicity	-	0.6688	66.88%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6050	60.50%
Fish aquatic toxicity	+	0.8289	82.89%

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	99.17%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.56%	91.49%
CHEMBL2581	P07339	Cathepsin D	97.38%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.49%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.45%	94.00%
CHEMBL242	Q92731	Estrogen receptor beta	93.16%	98.35%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.23%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	91.29%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.01%	99.15%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.06%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.04%	86.92%
CHEMBL3194	P02766	Transthyretin	85.48%	90.71%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	84.72%	83.57%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.58%	96.21%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.38%	95.56%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	83.24%	91.71%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	81.95%	93.10%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.28%	97.09%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.71%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.46%	90.71%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.20%	97.36%

Plants that contains it

• Crataegus viridis
• Pyracantha coccinea

Cross-Links

• PubChem: 75051926
• LOTUS: LTS0208617
• wikiData: Q105121937