5,8-dihydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one

Details

• Internal ID: 89e586ac-811d-4bac-9e54-1a0d29d471bb
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 5,8-dihydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): C1=CC(=CC=C1C2=CC(=O)C3=C(O2)C(=C(C=C3O)OC4C(C(C(C(O4)CO)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C2=CC(=O)C3=C(O2)C(=C(C=C3O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O
• InChI: InChI=1S/C21H20O11/c22-7-14-16(26)18(28)19(29)21(32-14)31-13-6-11(25)15-10(24)5-12(30-20(15)17(13)27)8-1-3-9(23)4-2-8/h1-6,14,16,18-19,21-23,25-29H,7H2/t14-,16-,18+,19-,21-/m1/s1
• InChI Key: LKPJBEBGOBIWTE-GHNMMOQISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₁₁
• Molecular Weight: 448.40 g/mol
• Exact Mass: 448.10056145 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): -0.24
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• 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	-	0.9355	93.55%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.6068	60.68%
OATP2B1 inhibitior	+	0.6034	60.34%
OATP1B1 inhibitior	+	0.8755	87.55%
OATP1B3 inhibitior	+	0.9265	92.65%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.4751	47.51%
P-glycoprotein inhibitior	-	0.7617	76.17%
P-glycoprotein substrate	-	0.8235	82.35%
CYP3A4 substrate	+	0.5867	58.67%
CYP2C9 substrate	-	0.6762	67.62%
CYP2D6 substrate	-	0.8575	85.75%
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	+	0.7256	72.56%
CYP inhibitory promiscuity	-	0.7728	77.28%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7144	71.44%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.8393	83.93%
Skin irritation	-	0.8036	80.36%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5491	54.91%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.8446	84.46%
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	-	0.8027	80.27%
Acute Oral Toxicity (c)	III	0.4045	40.45%
Estrogen receptor binding	+	0.7395	73.95%
Androgen receptor binding	+	0.7563	75.63%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6071	60.71%
Aromatase binding	+	0.6983	69.83%
PPAR gamma	+	0.7831	78.31%
Honey bee toxicity	-	0.6868	68.68%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6649	66.49%
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	99.16%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.90%	94.00%
CHEMBL2581	P07339	Cathepsin D	95.86%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.25%	89.00%
CHEMBL3194	P02766	Transthyretin	93.91%	90.71%
CHEMBL220	P22303	Acetylcholinesterase	91.99%	94.45%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	91.61%	96.21%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.19%	99.15%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.68%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.38%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.85%	86.33%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	88.30%	95.78%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.97%	94.45%
CHEMBL242	Q92731	Estrogen receptor beta	85.85%	98.35%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	85.13%	95.64%
CHEMBL3401	O75469	Pregnane X receptor	84.82%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.70%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.36%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.87%	97.09%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.59%	95.89%
CHEMBL1951	P21397	Monoamine oxidase A	82.50%	91.49%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.43%	91.71%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	81.75%	83.57%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.37%	90.71%

Plants that contains it

• Rosmarinus officinalis
• Stachys alopecuros

Cross-Links

• PubChem: 101260296
• LOTUS: LTS0179034
• wikiData: Q105153192