(2R,3S)-2-[3-hydroxy-4-methoxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]chromane-3,5,7-triol

Details

• Internal ID: a1630d99-5f39-4ab7-8adc-b35f89130d11
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides
• IUPAC Name: (2R,3S)-2-[3-hydroxy-4-methoxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-3,4-dihydro-2H-chromene-3,5,7-triol
• SMILES (Canonical): COC1=C(C=C(C=C1OC2C(C(C(C(O2)CO)O)O)O)C3C(CC4=C(C=C(C=C4O3)O)O)O)O
• SMILES (Isomeric): COC1=C(C=C(C=C1O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)[C@@H]3[C@H](CC4=C(C=C(C=C4O3)O)O)O)O
• InChI: InChI=1S/C22H26O12/c1-31-21-12(26)2-8(20-13(27)6-10-11(25)4-9(24)5-14(10)32-20)3-15(21)33-22-19(30)18(29)17(28)16(7-23)34-22/h2-5,13,16-20,22-30H,6-7H2,1H3/t13-,16+,17+,18-,19+,20+,22+/m0/s1
• InChI Key: FHINLKPLNHTRNY-JLLDPRJFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₆O₁₂
• Molecular Weight: 482.40 g/mol
• Exact Mass: 482.14242626 g/mol
• Topological Polar Surface Area (TPSA): 199.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): -0.97
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 5

Synonyms

• (2R,3S)-2-[3-hydroxy-4-methoxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]chromane-3,5,7-triol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5173	51.73%
Caco-2	-	0.8678	86.78%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.4822	48.22%
OATP2B1 inhibitior	-	0.7151	71.51%
OATP1B1 inhibitior	+	0.8301	83.01%
OATP1B3 inhibitior	+	0.9688	96.88%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.5737	57.37%
P-glycoprotein inhibitior	-	0.7206	72.06%
P-glycoprotein substrate	-	0.7555	75.55%
CYP3A4 substrate	+	0.6057	60.57%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7447	74.47%
CYP3A4 inhibition	-	0.9315	93.15%
CYP2C9 inhibition	-	0.9376	93.76%
CYP2C19 inhibition	-	0.9166	91.66%
CYP2D6 inhibition	-	0.9171	91.71%
CYP1A2 inhibition	-	0.9170	91.70%
CYP2C8 inhibition	+	0.6139	61.39%
CYP inhibitory promiscuity	-	0.8348	83.48%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6425	64.25%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.9225	92.25%
Skin irritation	-	0.8126	81.26%
Skin corrosion	-	0.9555	95.55%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8032	80.32%
Micronuclear	+	0.6359	63.59%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.9250	92.50%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.6977	69.77%
Acute Oral Toxicity (c)	III	0.6924	69.24%
Estrogen receptor binding	+	0.7532	75.32%
Androgen receptor binding	-	0.5346	53.46%
Thyroid receptor binding	+	0.6740	67.40%
Glucocorticoid receptor binding	+	0.5506	55.06%
Aromatase binding	+	0.5518	55.18%
PPAR gamma	+	0.6837	68.37%
Honey bee toxicity	-	0.8033	80.33%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	-	0.4637	46.37%

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	99.57%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.33%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.48%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.07%	85.14%
CHEMBL2581	P07339	Cathepsin D	88.86%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.42%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.96%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.27%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	85.80%	94.73%
CHEMBL4208	P20618	Proteasome component C5	85.13%	90.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.10%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.87%	94.00%
CHEMBL2535	P11166	Glucose transporter	83.48%	98.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.23%	95.56%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	81.25%	82.38%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.92%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.38%	96.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.30%	95.83%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.16%	97.14%

Plants that contains it

• Gymnosporia senegalensis

Cross-Links

• PubChem: 476782
• LOTUS: LTS0045535
• wikiData: Q104667207