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

Details

• Internal ID: 5bc9d948-f568-4116-9dec-a6976554a511
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 7-[(2S,3R,4S,5S,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,5-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• SMILES (Canonical): C1=CC(=CC=C1C2=C(C(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)OC5C(C(C(C(O5)CO)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O[C@H]4[C@@H]([C@H]([C@@H]([C@@H](O4)CO)O)O)O[C@H]5[C@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O)O
• InChI: InChI=1S/C27H30O16/c28-7-14-17(32)20(35)23(38)26(41-14)43-25-21(36)18(33)15(8-29)42-27(25)39-11-5-12(31)16-13(6-11)40-24(22(37)19(16)34)9-1-3-10(30)4-2-9/h1-6,14-15,17-18,20-21,23,25-33,35-38H,7-8H2/t14-,15+,17-,18-,20+,21+,23+,25-,26+,27-/m1/s1
• InChI Key: QIIWNLYXERJKDH-BYXBZGOXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₆
• Molecular Weight: 610.50 g/mol
• Exact Mass: 610.15338487 g/mol
• Topological Polar Surface Area (TPSA): 266.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -2.42
• H-Bond Acceptor: 16
• H-Bond Donor: 10
• 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	-	0.9373	93.73%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.5848	58.48%
OATP2B1 inhibitior	-	0.5582	55.82%
OATP1B1 inhibitior	+	0.9024	90.24%
OATP1B3 inhibitior	+	0.9434	94.34%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.6007	60.07%
P-glycoprotein inhibitior	-	0.7096	70.96%
P-glycoprotein substrate	-	0.6628	66.28%
CYP3A4 substrate	+	0.6456	64.56%
CYP2C9 substrate	-	0.6762	67.62%
CYP2D6 substrate	-	0.8575	85.75%
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	+	0.8202	82.02%
CYP inhibitory promiscuity	-	0.7526	75.26%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6848	68.48%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.8995	89.95%
Skin irritation	-	0.8255	82.55%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	+	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4322	43.22%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.7571	75.71%
skin sensitisation	-	0.9132	91.32%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.8977	89.77%
Acute Oral Toxicity (c)	IV	0.4763	47.63%
Estrogen receptor binding	+	0.7990	79.90%
Androgen receptor binding	+	0.6543	65.43%
Thyroid receptor binding	-	0.4937	49.37%
Glucocorticoid receptor binding	-	0.5519	55.19%
Aromatase binding	+	0.7060	70.60%
PPAR gamma	+	0.7906	79.06%
Honey bee toxicity	-	0.6915	69.15%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5350	53.50%
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	99.62%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.36%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.33%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.80%	94.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	95.57%	95.64%
CHEMBL2581	P07339	Cathepsin D	95.21%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.56%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	91.08%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.60%	86.92%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.77%	94.45%
CHEMBL3194	P02766	Transthyretin	89.03%	90.71%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	88.66%	95.78%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.53%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.69%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.44%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.42%	95.89%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.80%	96.21%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.55%	95.56%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.03%	97.36%
CHEMBL242	Q92731	Estrogen receptor beta	81.30%	98.35%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.47%	96.09%

Plants that contains it

• Crocus sativus

Cross-Links

• PubChem: 163081589
• LOTUS: LTS0046377
• wikiData: Q105221417