(2S)-2-(3,5-dihydroxyphenyl)-5,6-dihydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one

Details

• Internal ID: d9bb456c-cc90-4973-8ac8-c5dc6431a561
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: (2S)-2-(3,5-dihydroxyphenyl)-5,6-dihydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
• SMILES (Canonical): C1C(OC2=CC(=C(C(=C2C1=O)O)O)OC3C(C(C(C(O3)CO)O)O)O)C4=CC(=CC(=C4)O)O
• SMILES (Isomeric): C1[C@H](OC2=CC(=C(C(=C2C1=O)O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C4=CC(=CC(=C4)O)O
• InChI: InChI=1S/C21H22O12/c22-6-14-17(27)19(29)20(30)21(33-14)32-13-5-12-15(18(28)16(13)26)10(25)4-11(31-12)7-1-8(23)3-9(24)2-7/h1-3,5,11,14,17,19-24,26-30H,4,6H2/t11-,14+,17+,19-,20+,21+/m0/s1
• InChI Key: DUGVPRQGQKRYOM-LBNJVWSVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₁₂
• Molecular Weight: 466.40 g/mol
• Exact Mass: 466.11112613 g/mol
• Topological Polar Surface Area (TPSA): 207.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): -0.61
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5116	51.16%
Caco-2	-	0.9361	93.61%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.6068	60.68%
OATP2B1 inhibitior	-	0.5565	55.65%
OATP1B1 inhibitior	+	0.8997	89.97%
OATP1B3 inhibitior	+	0.9265	92.65%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.6468	64.68%
P-glycoprotein inhibitior	-	0.7384	73.84%
P-glycoprotein substrate	-	0.8617	86.17%
CYP3A4 substrate	+	0.5803	58.03%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8398	83.98%
CYP3A4 inhibition	-	0.9193	91.93%
CYP2C9 inhibition	-	0.9296	92.96%
CYP2C19 inhibition	-	0.9289	92.89%
CYP2D6 inhibition	-	0.9513	95.13%
CYP1A2 inhibition	-	0.9084	90.84%
CYP2C8 inhibition	-	0.5983	59.83%
CYP inhibitory promiscuity	-	0.7728	77.28%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7144	71.44%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.8373	83.73%
Skin irritation	-	0.8036	80.36%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3883	38.83%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.7750	77.50%
skin sensitisation	-	0.9122	91.22%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.5776	57.76%
Acute Oral Toxicity (c)	III	0.4045	40.45%
Estrogen receptor binding	+	0.7864	78.64%
Androgen receptor binding	-	0.4896	48.96%
Thyroid receptor binding	+	0.5705	57.05%
Glucocorticoid receptor binding	+	0.5703	57.03%
Aromatase binding	+	0.5638	56.38%
PPAR gamma	+	0.7837	78.37%
Honey bee toxicity	-	0.7228	72.28%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6249	62.49%
Fish aquatic toxicity	+	0.8218	82.18%

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	99.30%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.91%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.49%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.95%	89.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	91.16%	96.21%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.33%	94.45%
CHEMBL2581	P07339	Cathepsin D	89.47%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.63%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.42%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.24%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.58%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.22%	86.92%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.12%	95.89%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	84.28%	95.64%
CHEMBL4208	P20618	Proteasome component C5	83.78%	90.00%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	82.14%	95.78%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.74%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	81.40%	94.73%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.08%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.78%	99.23%

Plants that contains it

• Lippia origanoides

Cross-Links

• PubChem: 163014749
• LOTUS: LTS0163520
• wikiData: Q104989222