Sinensin

Details

• Internal ID: d9938202-4042-4076-b876-a5ea0a831bc3
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: (2R,3R)-3,5-dihydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
• SMILES (Canonical): C1=CC(=CC=C1C2C(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=C1[C@@H]2[C@H](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/C21H22O11/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/h1-6,13,15,17-25,27-29H,7H2/t13-,15-,17+,18+,19-,20-,21-/m1/s1
• InChI Key: UDIXYHJHYVDNOG-JUIPTLLLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₁₁
• Molecular Weight: 450.40 g/mol
• Exact Mass: 450.11621151 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -1.05
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 4

Synonyms

• 28189-90-4
• (2R,3R)-3,5-dihydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
• Aromadendrin 7-glucoside
• aromadendrin 7-O-glucoside
• CHEBI:167531
• AKOS032948915

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5116	51.16%
Caco-2	-	0.9387	93.87%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.6068	60.68%
OATP2B1 inhibitior	-	0.5542	55.42%
OATP1B1 inhibitior	+	0.8963	89.63%
OATP1B3 inhibitior	+	0.9265	92.65%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	-	0.7816	78.16%
P-glycoprotein substrate	-	0.9148	91.48%
CYP3A4 substrate	+	0.5798	57.98%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8512	85.12%
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	+	0.4941	49.41%
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	-	0.8267	82.67%
Skin irritation	-	0.8036	80.36%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	-	0.5354	53.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4719	47.19%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.9122	91.22%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.6382	63.82%
Acute Oral Toxicity (c)	III	0.4045	40.45%
Estrogen receptor binding	+	0.6259	62.59%
Androgen receptor binding	+	0.5490	54.90%
Thyroid receptor binding	+	0.5876	58.76%
Glucocorticoid receptor binding	-	0.5141	51.41%
Aromatase binding	+	0.6322	63.22%
PPAR gamma	+	0.7102	71.02%
Honey bee toxicity	-	0.7710	77.10%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5950	59.50%
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	99.11%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.94%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	91.94%	94.73%
CHEMBL2581	P07339	Cathepsin D	91.67%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.83%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.77%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.44%	96.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.19%	86.92%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.03%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.59%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.04%	86.33%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	85.72%	96.21%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.54%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.76%	99.17%
CHEMBL1951	P21397	Monoamine oxidase A	82.31%	91.49%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.60%	99.23%

Plants that contains it

• Abies nephrolepis
• Calicotome villosa
• Cornus mas
• Crocus chrysanthus
• Genista pichisermolliana
• Helichrysum arenarium
• Ipomoea muricata
• Pseudotsuga menziesii

Cross-Links

• PubChem: 10456395
• NPASS: NPC300569
• LOTUS: LTS0058080
• wikiData: Q105270382