3-[(2R,3S,4S,5S)-3,4-dihydroxy-5-[(1S)-1-hydroxyethyl]oxolan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-7-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one

Details

• Internal ID: c076105b-057e-431b-a2c4-a3539f97a949
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 3-[(2R,3S,4S,5S)-3,4-dihydroxy-5-[(1S)-1-hydroxyethyl]oxolan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-7-[(2R,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(C)O)O)O)C5=CC=C(C=C5)O)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](C)O)O)O)C5=CC=C(C=C5)O)O)O)O)O
• InChI: InChI=1S/C27H30O14/c1-9(28)23-20(34)22(36)27(40-23)41-25-18(32)16-14(30)7-13(38-26-21(35)19(33)17(31)10(2)37-26)8-15(16)39-24(25)11-3-5-12(29)6-4-11/h3-10,17,19-23,26-31,33-36H,1-2H3/t9-,10+,17+,19-,20-,21-,22-,23-,26+,27+/m0/s1
• InChI Key: PUXKQFMZRYJBBE-LKKHWDDJSA-N
• Popularity: 0 references 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: 0.50
• Atomic LogP (AlogP): -0.72
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8754	87.54%
Caco-2	-	0.9087	90.87%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7664	76.64%
OATP2B1 inhibitior	-	0.5522	55.22%
OATP1B1 inhibitior	+	0.9220	92.20%
OATP1B3 inhibitior	+	0.7894	78.94%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.8388	83.88%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	-	0.5201	52.01%
CYP3A4 substrate	+	0.6410	64.10%
CYP2C9 substrate	-	0.7354	73.54%
CYP2D6 substrate	-	0.8607	86.07%
CYP3A4 inhibition	+	0.6222	62.22%
CYP2C9 inhibition	-	0.6749	67.49%
CYP2C19 inhibition	-	0.5000	50.00%
CYP2D6 inhibition	-	0.8317	83.17%
CYP1A2 inhibition	-	0.5184	51.84%
CYP2C8 inhibition	+	0.7278	72.78%
CYP inhibitory promiscuity	+	0.6929	69.29%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4717	47.17%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.8931	89.31%
Skin irritation	-	0.7168	71.68%
Skin corrosion	-	0.9444	94.44%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3908	39.08%
Micronuclear	+	0.9300	93.00%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.8590	85.90%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.8481	84.81%
Acute Oral Toxicity (c)	III	0.4675	46.75%
Estrogen receptor binding	+	0.6962	69.62%
Androgen receptor binding	+	0.6646	66.46%
Thyroid receptor binding	+	0.5357	53.57%
Glucocorticoid receptor binding	+	0.6208	62.08%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.7016	70.16%
Honey bee toxicity	-	0.7458	74.58%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6650	66.50%
Fish aquatic toxicity	+	0.9681	96.81%

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	99.24%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.71%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.99%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.94%	85.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	96.21%	99.15%
CHEMBL1951	P21397	Monoamine oxidase A	94.49%	91.49%
CHEMBL3401	O75469	Pregnane X receptor	93.51%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.98%	94.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	91.95%	90.71%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	91.14%	95.64%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.59%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.54%	96.09%
CHEMBL242	Q92731	Estrogen receptor beta	88.06%	98.35%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.90%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.03%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.19%	94.45%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	84.87%	95.78%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.43%	99.17%
CHEMBL4208	P20618	Proteasome component C5	83.51%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.74%	95.89%
CHEMBL2179	P04062	Beta-glucocerebrosidase	81.26%	85.31%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	81.10%	93.65%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.09%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.55%	99.23%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.06%	97.36%

Plants that contains it

• Anthocercis viscosa
• Cyphanthera tasmanica
• Datura discolor
• Datura ferox
• Datura innoxia
• Datura metel
• Duboisia myoporoides
• Physalis minima
• Physalis peruviana
• Prunus spinosa
• Scopolia carniolica
• Solandra maxima
• Solanum betaceum

Cross-Links

• PubChem: 162890784
• LOTUS: LTS0267395
• wikiData: Q27262615