3-[(2S,3S,4S,5S)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-yl]oxy-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one

Details

• Internal ID: 966b7109-1046-4d3f-949e-cb3cf0c58456
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 3-[(2S,3S,4S,5S)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-yl]oxy-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=CC(=C3C(=C2)OC(=C(C3=O)OC4C(C(C(O4)C(CO)O)O)O)C5=CC(=C(C=C5)O)OC)O)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@H]([C@@H]([C@@H]([C@@H](O1)OC2=CC(=C3C(=C2)OC(=C(C3=O)O[C@H]4[C@H]([C@@H]([C@@H](O4)[C@@H](CO)O)O)O)C5=CC(=C(C=C5)O)OC)O)O)O)O
• InChI: InChI=1S/C28H32O16/c1-9-18(33)20(35)22(37)27(40-9)41-11-6-13(31)17-16(7-11)42-24(10-3-4-12(30)15(5-10)39-2)26(19(17)34)44-28-23(38)21(36)25(43-28)14(32)8-29/h3-7,9,14,18,20-23,25,27-33,35-38H,8H2,1-2H3/t9-,14-,18-,20+,21+,22+,23+,25+,27+,28+/m1/s1
• InChI Key: PSRODHPZGAPALB-NGNZGEECSA-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): 255.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -1.74
• H-Bond Acceptor: 16
• H-Bond Donor: 9
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6861	68.61%
Caco-2	-	0.9119	91.19%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6520	65.20%
OATP2B1 inhibitior	-	0.5694	56.94%
OATP1B1 inhibitior	+	0.9247	92.47%
OATP1B3 inhibitior	+	0.9274	92.74%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8001	80.01%
P-glycoprotein inhibitior	-	0.5123	51.23%
P-glycoprotein substrate	+	0.5885	58.85%
CYP3A4 substrate	+	0.6572	65.72%
CYP2C9 substrate	-	0.8740	87.40%
CYP2D6 substrate	-	0.8547	85.47%
CYP3A4 inhibition	-	0.6484	64.84%
CYP2C9 inhibition	-	0.8463	84.63%
CYP2C19 inhibition	-	0.8712	87.12%
CYP2D6 inhibition	-	0.8405	84.05%
CYP1A2 inhibition	-	0.8967	89.67%
CYP2C8 inhibition	+	0.8152	81.52%
CYP inhibitory promiscuity	-	0.5586	55.86%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6153	61.53%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.8953	89.53%
Skin irritation	-	0.8163	81.63%
Skin corrosion	-	0.9536	95.36%
Ames mutagenesis	-	0.7128	71.28%
Human Ether-a-go-go-Related Gene inhibition	+	0.7290	72.90%
Micronuclear	+	0.6933	69.33%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.8863	88.63%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.9013	90.13%
Acute Oral Toxicity (c)	III	0.7332	73.32%
Estrogen receptor binding	+	0.7501	75.01%
Androgen receptor binding	+	0.5685	56.85%
Thyroid receptor binding	-	0.5253	52.53%
Glucocorticoid receptor binding	+	0.6212	62.12%
Aromatase binding	-	0.5185	51.85%
PPAR gamma	+	0.6678	66.78%
Honey bee toxicity	-	0.7547	75.47%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.7240	72.40%

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	99.06%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.23%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.15%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.93%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.83%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.66%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.33%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.95%	99.15%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.66%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.03%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	89.74%	90.71%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.35%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	87.08%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.41%	86.92%
CHEMBL1907	P15144	Aminopeptidase N	85.38%	93.31%
CHEMBL4208	P20618	Proteasome component C5	84.87%	90.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	84.43%	97.36%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.47%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.95%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.44%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.93%	96.00%

Plants that contains it

• Erysimum siliculosum

Cross-Links

• PubChem: 162908014
• LOTUS: LTS0132834
• wikiData: Q105214365