8-[(2S,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]-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-one

Details

• Internal ID: 629cd9ec-a227-44a8-b4d9-292ff491ced4
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides > Flavonoid 8-C-glycosides
• IUPAC Name: 8-[(2S,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]-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-one
• SMILES (Canonical): COC1=C(C=CC(=C1)C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)C4C(C(C(C(O4)CO)O)O)OC5C(C(C(C(O5)CO)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)[C@H]4C([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
• InChI: InChI=1S/C28H32O16/c1-40-15-4-9(2-3-10(15)31)14-6-13(34)18-11(32)5-12(33)19(25(18)41-14)26-27(23(38)21(36)16(7-29)42-26)44-28-24(39)22(37)20(35)17(8-30)43-28/h2-6,16-17,20-24,26-33,35-39H,7-8H2,1H3/t16-,17+,20+,21+,22-,23-,24-,26-,27?,28-/m0/s1
• InChI Key: CUIBWAIUPCYNQR-GRNIEWGASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₂O₁₆
• Molecular Weight: 624.50 g/mol
• Exact Mass: 624.16903493 g/mol
• Topological Polar Surface Area (TPSA): 266.00 Ų
• XlogP: -1.40
• Atomic LogP (AlogP): -2.08
• 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	-	0.5457	54.57%
Caco-2	-	0.9238	92.38%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.5961	59.61%
OATP2B1 inhibitior	-	0.5765	57.65%
OATP1B1 inhibitior	+	0.8692	86.92%
OATP1B3 inhibitior	+	0.9786	97.86%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7753	77.53%
P-glycoprotein inhibitior	-	0.5906	59.06%
P-glycoprotein substrate	-	0.6258	62.58%
CYP3A4 substrate	+	0.6309	63.09%
CYP2C9 substrate	-	0.8389	83.89%
CYP2D6 substrate	-	0.8501	85.01%
CYP3A4 inhibition	-	0.9437	94.37%
CYP2C9 inhibition	-	0.9060	90.60%
CYP2C19 inhibition	-	0.8926	89.26%
CYP2D6 inhibition	-	0.9515	95.15%
CYP1A2 inhibition	-	0.9150	91.50%
CYP2C8 inhibition	+	0.6727	67.27%
CYP inhibitory promiscuity	-	0.7142	71.42%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6642	66.42%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9126	91.26%
Skin irritation	-	0.8320	83.20%
Skin corrosion	-	0.9606	96.06%
Ames mutagenesis	-	0.5093	50.93%
Human Ether-a-go-go-Related Gene inhibition	-	0.3744	37.44%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.8500	85.00%
skin sensitisation	-	0.9324	93.24%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.7826	78.26%
Acute Oral Toxicity (c)	III	0.6678	66.78%
Estrogen receptor binding	+	0.8305	83.05%
Androgen receptor binding	+	0.7143	71.43%
Thyroid receptor binding	+	0.5164	51.64%
Glucocorticoid receptor binding	+	0.6308	63.08%
Aromatase binding	+	0.6029	60.29%
PPAR gamma	+	0.7189	71.89%
Honey bee toxicity	-	0.7125	71.25%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.6698	66.98%

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	99.11%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.57%	94.00%
CHEMBL2581	P07339	Cathepsin D	95.96%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.98%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.78%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.25%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.59%	86.92%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.05%	99.15%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	88.44%	96.21%
CHEMBL3401	O75469	Pregnane X receptor	86.78%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.32%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.17%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.85%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.58%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.91%	96.00%
CHEMBL1951	P21397	Monoamine oxidase A	80.71%	91.49%

Plants that contains it

• Setaria italica

Cross-Links

• PubChem: 163186448
• LOTUS: LTS0066215
• wikiData: Q104970277