8-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxychromen-4-one

Details

• Internal ID: 07e74e20-120a-48d4-adfc-c2196e2ac05d
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides > Flavonoid 8-C-glycosides
• IUPAC Name: 8-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxychromen-4-one
• SMILES (Canonical): COC1=C(C2=C(C(=C1)O)C(=O)C=C(O2)C3=CC=C(C=C3)O)C4C(C(C(C(O4)CO)O)O)OC5C(C(C(O5)CO)O)O
• SMILES (Isomeric): COC1=C(C2=C(C(=C1)O)C(=O)C=C(O2)C3=CC=C(C=C3)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](O5)CO)O)O
• InChI: InChI=1S/C27H30O14/c1-37-15-7-13(32)18-12(31)6-14(10-2-4-11(30)5-3-10)38-24(18)19(15)25-26(22(35)20(33)16(8-28)39-25)41-27-23(36)21(34)17(9-29)40-27/h2-7,16-17,20-23,25-30,32-36H,8-9H2,1H3/t16-,17-,20-,21+,22+,23-,25+,26-,27+/m1/s1
• InChI Key: LAEOJCQTNYZDKY-ADDDRJKVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₄
• Molecular Weight: 578.50 g/mol
• Exact Mass: 578.16355563 g/mol
• Topological Polar Surface Area (TPSA): 225.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): -1.14
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5974	59.74%
Caco-2	-	0.9096	90.96%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.6848	68.48%
OATP2B1 inhibitior	-	0.7066	70.66%
OATP1B1 inhibitior	+	0.8556	85.56%
OATP1B3 inhibitior	+	0.9746	97.46%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8585	85.85%
P-glycoprotein inhibitior	-	0.6074	60.74%
P-glycoprotein substrate	-	0.6351	63.51%
CYP3A4 substrate	+	0.6479	64.79%
CYP2C9 substrate	-	0.8389	83.89%
CYP2D6 substrate	-	0.8501	85.01%
CYP3A4 inhibition	-	0.8638	86.38%
CYP2C9 inhibition	-	0.8003	80.03%
CYP2C19 inhibition	-	0.7529	75.29%
CYP2D6 inhibition	-	0.9197	91.97%
CYP1A2 inhibition	-	0.8921	89.21%
CYP2C8 inhibition	+	0.6957	69.57%
CYP inhibitory promiscuity	+	0.5065	50.65%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5707	57.07%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9281	92.81%
Skin irritation	-	0.8306	83.06%
Skin corrosion	-	0.9548	95.48%
Ames mutagenesis	+	0.5936	59.36%
Human Ether-a-go-go-Related Gene inhibition	-	0.4030	40.30%
Micronuclear	+	0.6833	68.33%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.8970	89.70%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.7080	70.80%
Acute Oral Toxicity (c)	III	0.7481	74.81%
Estrogen receptor binding	+	0.8087	80.87%
Androgen receptor binding	+	0.7862	78.62%
Thyroid receptor binding	+	0.5248	52.48%
Glucocorticoid receptor binding	+	0.6405	64.05%
Aromatase binding	+	0.6302	63.02%
PPAR gamma	+	0.7114	71.14%
Honey bee toxicity	-	0.6875	68.75%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.7431	74.31%

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	98.95%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.08%	94.00%
CHEMBL2581	P07339	Cathepsin D	96.89%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.73%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.70%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.49%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.38%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.48%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.34%	99.17%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	88.26%	96.21%
CHEMBL3401	O75469	Pregnane X receptor	85.82%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.23%	99.15%
CHEMBL3194	P02766	Transthyretin	83.79%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.61%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.20%	97.14%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.15%	95.89%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.48%	96.09%

Plants that contains it

• Gnetum africanum

Cross-Links

• PubChem: 14583623
• LOTUS: LTS0014413
• wikiData: Q105148606