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

Details

• Internal ID: 37132c47-b2df-4a42-9236-03a494a5b059
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides > Flavonoid 8-C-glycosides
• IUPAC Name: 8-[(3S,4S,5S)-3-[(2S,3S)-2,3-dihydroxy-5-(hydroxymethyl)cyclohexyl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-6-[(3S,4S,5S)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(3S,4S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• SMILES (Canonical): C1C(CC(C(C1O)O)OC2C(C(C(OC2C3=C4C(=C(C(=C3O)C5C(C(C(C(O5)CO)O)O)OC6C(C(C(C(O6)CO)O)O)O)O)C(=O)C=C(O4)C7=CC=C(C=C7)O)CO)O)O)CO
• SMILES (Isomeric): C1[C@@H]([C@@H](C(CC1CO)O[C@H]2[C@H]([C@@H](C(OC2C3=C4C(=C(C(=C3O)C5[C@H]([C@H]([C@@H](C(O5)CO)O)O)OC6[C@H]([C@H](C(C(O6)CO)O)O)O)O)C(=O)C=C(O4)C7=CC=C(C=C7)O)CO)O)O)O)O
• InChI: InChI=1S/C40H52O23/c41-8-12-5-16(47)25(48)18(6-12)59-38-32(55)27(50)20(10-43)61-37(38)24-30(53)23(29(52)22-15(46)7-17(58-35(22)24)13-1-3-14(45)4-2-13)36-39(33(56)28(51)19(9-42)60-36)63-40-34(57)31(54)26(49)21(11-44)62-40/h1-4,7,12,16,18-21,25-28,31-34,36-45,47-57H,5-6,8-11H2/t12?,16-,18?,19?,20?,21?,25-,26?,27+,28+,31-,32-,33-,34-,36?,37?,38-,39-,40?/m0/s1
• InChI Key: GZKQOEANSITMGN-HJRWFDEZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₅₂O₂₃
• Molecular Weight: 900.80 g/mol
• Exact Mass: 900.28993790 g/mol
• Topological Polar Surface Area (TPSA): 396.00 Ų
• XlogP: -4.40
• Atomic LogP (AlogP): -5.05
• H-Bond Acceptor: 23
• H-Bond Donor: 16
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4890	48.90%
Caco-2	-	0.8979	89.79%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.9000	90.00%
Subcellular localzation	Mitochondria	0.5627	56.27%
OATP2B1 inhibitior	-	0.8490	84.90%
OATP1B1 inhibitior	+	0.8271	82.71%
OATP1B3 inhibitior	+	0.9196	91.96%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7688	76.88%
P-glycoprotein inhibitior	+	0.6089	60.89%
P-glycoprotein substrate	-	0.5757	57.57%
CYP3A4 substrate	+	0.6843	68.43%
CYP2C9 substrate	-	0.6278	62.78%
CYP2D6 substrate	-	0.8462	84.62%
CYP3A4 inhibition	-	0.9250	92.50%
CYP2C9 inhibition	-	0.9629	96.29%
CYP2C19 inhibition	-	0.9230	92.30%
CYP2D6 inhibition	-	0.9229	92.29%
CYP1A2 inhibition	-	0.9257	92.57%
CYP2C8 inhibition	+	0.7212	72.12%
CYP inhibitory promiscuity	-	0.9036	90.36%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7172	71.72%
Eye corrosion	-	0.9939	99.39%
Eye irritation	-	0.8994	89.94%
Skin irritation	-	0.8286	82.86%
Skin corrosion	-	0.9694	96.94%
Ames mutagenesis	+	0.5799	57.99%
Human Ether-a-go-go-Related Gene inhibition	+	0.7774	77.74%
Micronuclear	+	0.5474	54.74%
Hepatotoxicity	-	0.7571	75.71%
skin sensitisation	-	0.9072	90.72%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.8039	80.39%
Acute Oral Toxicity (c)	III	0.4544	45.44%
Estrogen receptor binding	+	0.8048	80.48%
Androgen receptor binding	+	0.7674	76.74%
Thyroid receptor binding	-	0.5194	51.94%
Glucocorticoid receptor binding	-	0.6340	63.40%
Aromatase binding	+	0.6055	60.55%
PPAR gamma	+	0.7121	71.21%
Honey bee toxicity	-	0.6078	60.78%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.8235	82.35%

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	99.70%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.06%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.17%	97.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.02%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.63%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.42%	89.00%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	90.26%	94.23%
CHEMBL1951	P21397	Monoamine oxidase A	90.05%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.76%	86.33%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	89.38%	83.57%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.17%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.99%	94.45%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	86.33%	96.21%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.32%	95.89%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.04%	95.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.91%	95.89%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	84.62%	94.62%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.03%	95.83%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.50%	99.15%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	80.51%	95.78%
CHEMBL3891	P07384	Calpain 1	80.11%	93.04%

Plants that contains it

• Ephedra aphylla

Cross-Links

• PubChem: 162817294
• LOTUS: LTS0088226
• wikiData: Q105024429