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

Details

• Internal ID: 88adc3b1-649c-4380-b051-50af50a2743e
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 3,5-dihydroxy-2-(4-hydroxyphenyl)-7-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): C1=CC(=CC=C1C2=C(C(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O[C@@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)O
• InChI: InChI=1S/C21H20O11/c22-7-13-15(25)17(27)19(29)21(32-13)30-10-5-11(24)14-12(6-10)31-20(18(28)16(14)26)8-1-3-9(23)4-2-8/h1-6,13,15,17,19,21-25,27-29H,7H2/t13-,15-,17+,19-,21+/m1/s1
• InChI Key: YPWHZCPMOQGCDQ-WNZLTNKYSA-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: 0.70
• Atomic LogP (AlogP): -0.24
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 4

Synonyms

• 3,5-dihydroxy-2-(4-hydroxyphenyl)-7-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• NCGC00386047-01!3,5-dihydroxy-2-(4-hydroxyphenyl)-7-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5116	51.16%
Caco-2	-	0.9536	95.36%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6068	60.68%
OATP2B1 inhibitior	+	0.5966	59.66%
OATP1B1 inhibitior	+	0.8995	89.95%
OATP1B3 inhibitior	+	0.9265	92.65%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.6323	63.23%
P-glycoprotein inhibitior	-	0.8031	80.31%
P-glycoprotein substrate	-	0.7577	75.77%
CYP3A4 substrate	+	0.6096	60.96%
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	+	0.8424	84.24%
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	-	0.8597	85.97%
Skin irritation	-	0.8036	80.36%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	+	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5198	51.98%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.7321	73.21%
skin sensitisation	-	0.9122	91.22%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.8619	86.19%
Acute Oral Toxicity (c)	III	0.4045	40.45%
Estrogen receptor binding	+	0.7245	72.45%
Androgen receptor binding	+	0.6776	67.76%
Thyroid receptor binding	+	0.5374	53.74%
Glucocorticoid receptor binding	+	0.6328	63.28%
Aromatase binding	+	0.6487	64.87%
PPAR gamma	+	0.8154	81.54%
Honey bee toxicity	-	0.7532	75.32%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5850	58.50%
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	99.53%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	96.41%	91.49%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	96.22%	95.64%
CHEMBL2581	P07339	Cathepsin D	95.87%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.83%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.61%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.52%	99.15%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.32%	86.92%
CHEMBL3401	O75469	Pregnane X receptor	90.87%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.99%	97.09%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	88.89%	95.78%
CHEMBL3194	P02766	Transthyretin	88.83%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.80%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.05%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.31%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.67%	95.89%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.65%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.55%	95.56%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.36%	96.21%
CHEMBL242	Q92731	Estrogen receptor beta	80.88%	98.35%

Plants that contains it

• Artemisia vulgaris
• Euphorbia micractina
• Maclura cochinchinensis
• Maclura pomifera
• Rorippa indica
• Rosa roxburghii
• Urena lobata

Cross-Links

• PubChem: 25203835
• NPASS: NPC234452
• LOTUS: LTS0148217
• wikiData: Q105351973