Isoorientin 2''-(6-O-p-coumaroyl)glucoside

Details

• Internal ID: 5ebcfab9-0a9f-4447-b740-55e351822bfa
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides
• IUPAC Name: [(2R,3S,4S,5R,6S)-6-[(2S,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-6-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): C1=CC(=CC=C1C=CC(=O)OCC2C(C(C(C(O2)OC3C(C(C(OC3C4=C(C5=C(C=C4O)OC(=CC5=O)C6=CC(=C(C=C6)O)O)O)CO)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1/C=C/C(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)O[C@@H]3[C@H]([C@@H]([C@H](O[C@H]3C4=C(C5=C(C=C4O)OC(=CC5=O)C6=CC(=C(C=C6)O)O)O)CO)O)O)O)O)O)O
• InChI: InChI=1S/C36H36O18/c37-12-23-28(44)32(48)35(54-36-33(49)31(47)29(45)24(53-36)13-50-25(43)8-3-14-1-5-16(38)6-2-14)34(52-23)27-20(42)11-22-26(30(27)46)19(41)10-21(51-22)15-4-7-17(39)18(40)9-15/h1-11,23-24,28-29,31-40,42,44-49H,12-13H2/b8-3+/t23-,24-,28-,29-,31+,32+,33-,34+,35-,36+/m1/s1
• InChI Key: MWRFISCXYNYBKS-MLUXYXKLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₃₆O₁₈
• Molecular Weight: 756.70 g/mol
• Exact Mass: 756.19016430 g/mol
• Topological Polar Surface Area (TPSA): 303.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.41
• H-Bond Acceptor: 18
• H-Bond Donor: 11
• Rotatable Bonds: 9

Synonyms

• 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-6-[2-O-[6-O-[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propen-1-yl]-beta-D-glucopyranosyl]-beta-D-glucopyranosyl]-4H-1-benzopyran-4-one
• 220948-74-3

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5570	55.70%
Caco-2	-	0.8996	89.96%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.5040	50.40%
OATP2B1 inhibitior	-	0.7079	70.79%
OATP1B1 inhibitior	+	0.8512	85.12%
OATP1B3 inhibitior	+	0.9786	97.86%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.4562	45.62%
P-glycoprotein inhibitior	+	0.6132	61.32%
P-glycoprotein substrate	-	0.5347	53.47%
CYP3A4 substrate	+	0.6890	68.90%
CYP2C9 substrate	-	0.8122	81.22%
CYP2D6 substrate	-	0.8686	86.86%
CYP3A4 inhibition	-	0.9209	92.09%
CYP2C9 inhibition	-	0.8990	89.90%
CYP2C19 inhibition	-	0.8708	87.08%
CYP2D6 inhibition	-	0.9370	93.70%
CYP1A2 inhibition	-	0.9325	93.25%
CYP2C8 inhibition	+	0.8536	85.36%
CYP inhibitory promiscuity	-	0.7843	78.43%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6850	68.50%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.9058	90.58%
Skin irritation	-	0.8335	83.35%
Skin corrosion	-	0.9579	95.79%
Ames mutagenesis	-	0.5301	53.01%
Human Ether-a-go-go-Related Gene inhibition	+	0.7070	70.70%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.8537	85.37%
skin sensitisation	-	0.8754	87.54%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.9462	94.62%
Acute Oral Toxicity (c)	IV	0.4410	44.10%
Estrogen receptor binding	+	0.7706	77.06%
Androgen receptor binding	+	0.7768	77.68%
Thyroid receptor binding	+	0.5198	51.98%
Glucocorticoid receptor binding	-	0.4818	48.18%
Aromatase binding	+	0.5975	59.75%
PPAR gamma	+	0.7113	71.13%
Honey bee toxicity	-	0.6291	62.91%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9324	93.24%

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	99.88%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.66%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	98.25%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.89%	86.33%
CHEMBL3194	P02766	Transthyretin	95.76%	90.71%
CHEMBL2581	P07339	Cathepsin D	94.69%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.69%	97.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.54%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.42%	95.56%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	89.54%	91.71%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.08%	86.92%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.23%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.84%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	86.33%	94.73%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	85.62%	83.57%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.61%	85.14%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	84.41%	80.78%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.26%	94.45%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	82.50%	83.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.21%	95.50%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	81.58%	95.78%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.66%	95.83%
CHEMBL226	P30542	Adenosine A1 receptor	80.51%	95.93%
CHEMBL5255	O00206	Toll-like receptor 4	80.49%	92.50%
CHEMBL5678	P34947	G protein-coupled receptor kinase 5	80.02%	88.00%

Plants that contains it

• Oryza sativa

Cross-Links

• PubChem: 100952215
• LOTUS: LTS0130424
• wikiData: Q105173742