5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one

Details

• Internal ID: b1eab35f-d5eb-45df-94b9-4163fca2aa16
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): C1=C(C=C(C(=C1O)O)O)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(C(O4)COC5C(C(C(C(O5)CO)O)O)O)O)O)O
• SMILES (Isomeric): C1=C(C=C(C(=C1O)O)O)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)CO)O)O)O)O)O)O
• InChI: InChI=1S/C27H30O18/c28-5-13-17(34)20(37)22(39)26(43-13)41-6-14-18(35)21(38)23(40)27(44-14)45-25-19(36)15-9(30)3-8(29)4-12(15)42-24(25)7-1-10(31)16(33)11(32)2-7/h1-4,13-14,17-18,20-23,26-35,37-40H,5-6H2/t13-,14+,17-,18+,20+,21-,22+,23+,26+,27-/m0/s1
• InChI Key: HUHZBMAVCTZCMX-HRYPUBINSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₈
• Molecular Weight: 642.50 g/mol
• Exact Mass: 642.14321410 g/mol
• Topological Polar Surface Area (TPSA): 306.00 Ų
• XlogP: -2.10
• Atomic LogP (AlogP): -3.01
• H-Bond Acceptor: 18
• H-Bond Donor: 12
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5736	57.36%
Caco-2	-	0.9240	92.40%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.5848	58.48%
OATP2B1 inhibitior	-	0.5606	56.06%
OATP1B1 inhibitior	+	0.8460	84.60%
OATP1B3 inhibitior	+	0.9434	94.34%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.5895	58.95%
P-glycoprotein inhibitior	-	0.5537	55.37%
P-glycoprotein substrate	-	0.6520	65.20%
CYP3A4 substrate	+	0.6187	61.87%
CYP2C9 substrate	-	0.6709	67.09%
CYP2D6 substrate	-	0.8582	85.82%
CYP3A4 inhibition	-	0.9390	93.90%
CYP2C9 inhibition	-	0.9315	93.15%
CYP2C19 inhibition	-	0.9047	90.47%
CYP2D6 inhibition	-	0.9458	94.58%
CYP1A2 inhibition	-	0.9180	91.80%
CYP2C8 inhibition	+	0.7985	79.85%
CYP inhibitory promiscuity	-	0.7526	75.26%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6848	68.48%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.8975	89.75%
Skin irritation	-	0.8255	82.55%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	+	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3784	37.84%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.9132	91.32%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.7781	77.81%
Acute Oral Toxicity (c)	IV	0.4763	47.63%
Estrogen receptor binding	+	0.8178	81.78%
Androgen receptor binding	+	0.6122	61.22%
Thyroid receptor binding	+	0.5483	54.83%
Glucocorticoid receptor binding	-	0.5120	51.20%
Aromatase binding	+	0.6239	62.39%
PPAR gamma	+	0.7501	75.01%
Honey bee toxicity	-	0.7815	78.15%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6150	61.50%
Fish aquatic toxicity	+	0.7958	79.58%

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	99.78%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.75%	89.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	95.80%	95.64%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.59%	94.00%
CHEMBL2581	P07339	Cathepsin D	93.03%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	92.25%	94.73%
CHEMBL3194	P02766	Transthyretin	91.54%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.69%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.81%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.80%	86.33%
CHEMBL2424	Q04760	Glyoxalase I	87.41%	91.67%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.48%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.96%	96.09%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	83.60%	80.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.13%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.33%	94.45%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.19%	86.92%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.27%	97.36%

Plants that contains it

• Ribes nigrum

Cross-Links

• PubChem: 162856353
• LOTUS: LTS0262062
• wikiData: Q105033794