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

Details

• Internal ID: 19127b5e-c0fa-44e5-98cd-f779f0685fd9
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides > Flavonoid 8-C-glycosides
• IUPAC Name: 8-[(2S,3R,4S,5S,6S)-3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3C(C(C(OC3C4=C(C=C(C5=C4OC(=CC5=O)C6=CC=C(C=C6)OC)O)O)CO)O)O)CO)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2O[C@@H]3[C@H]([C@@H]([C@@H](O[C@H]3C4=C(C=C(C5=C4OC(=CC5=O)C6=CC=C(C=C6)OC)O)O)CO)O)O)CO)O)O)O)O)O
• InChI: InChI=1S/C34H42O19/c1-11-22(40)25(43)28(46)33(48-11)53-32-27(45)24(42)19(10-36)51-34(32)52-31-26(44)23(41)18(9-35)50-30(31)21-15(38)7-14(37)20-16(39)8-17(49-29(20)21)12-3-5-13(47-2)6-4-12/h3-8,11,18-19,22-28,30-38,40-46H,9-10H2,1-2H3/t11-,18-,19+,22-,23+,24+,25+,26-,27-,28-,30-,31+,32+,33-,34-/m0/s1
• InChI Key: AQRHLFGVMFUVHW-ZTTQCJTHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₄₂O₁₉
• Molecular Weight: 754.70 g/mol
• Exact Mass: 754.23202911 g/mol
• Topological Polar Surface Area (TPSA): 304.00 Ų
• XlogP: -2.20
• Atomic LogP (AlogP): -2.93
• H-Bond Acceptor: 19
• H-Bond Donor: 11
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5623	56.23%
Caco-2	-	0.9070	90.70%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.5984	59.84%
OATP2B1 inhibitior	-	0.7203	72.03%
OATP1B1 inhibitior	+	0.8322	83.22%
OATP1B3 inhibitior	+	0.9748	97.48%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.6616	66.16%
P-glycoprotein inhibitior	-	0.5447	54.47%
P-glycoprotein substrate	-	0.5447	54.47%
CYP3A4 substrate	+	0.6594	65.94%
CYP2C9 substrate	-	0.8555	85.55%
CYP2D6 substrate	-	0.8543	85.43%
CYP3A4 inhibition	-	0.9284	92.84%
CYP2C9 inhibition	-	0.9208	92.08%
CYP2C19 inhibition	-	0.9124	91.24%
CYP2D6 inhibition	-	0.9531	95.31%
CYP1A2 inhibition	-	0.9232	92.32%
CYP2C8 inhibition	+	0.6206	62.06%
CYP inhibitory promiscuity	-	0.7113	71.13%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7032	70.32%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9197	91.97%
Skin irritation	-	0.8442	84.42%
Skin corrosion	-	0.9614	96.14%
Ames mutagenesis	+	0.5035	50.35%
Human Ether-a-go-go-Related Gene inhibition	+	0.7796	77.96%
Micronuclear	+	0.6633	66.33%
Hepatotoxicity	-	0.8500	85.00%
skin sensitisation	-	0.9340	93.40%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.9102	91.02%
Acute Oral Toxicity (c)	III	0.7041	70.41%
Estrogen receptor binding	+	0.8562	85.62%
Androgen receptor binding	+	0.7276	72.76%
Thyroid receptor binding	+	0.5187	51.87%
Glucocorticoid receptor binding	+	0.5683	56.83%
Aromatase binding	+	0.6051	60.51%
PPAR gamma	+	0.7223	72.23%
Honey bee toxicity	-	0.7163	71.63%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.7167	71.67%

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	99.60%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.64%	94.00%
CHEMBL1951	P21397	Monoamine oxidase A	97.40%	91.49%
CHEMBL2581	P07339	Cathepsin D	97.13%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.74%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	94.07%	86.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.06%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.42%	99.15%
CHEMBL3714130	P46095	G-protein coupled receptor 6	93.05%	97.36%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.76%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	89.42%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.92%	85.14%
CHEMBL1907	P15144	Aminopeptidase N	86.91%	93.31%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.09%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.12%	97.09%
CHEMBL4208	P20618	Proteasome component C5	82.47%	90.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.35%	96.21%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	82.24%	81.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.15%	96.00%
CHEMBL308	P06493	Cyclin-dependent kinase 1	81.68%	91.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.88%	95.89%

Plants that contains it

• Peganum harmala

Cross-Links

• PubChem: 162998076
• LOTUS: LTS0004436
• wikiData: Q104917016