Sinapaldehyde glucoside

Details

• Internal ID: 751a93d2-23b0-4a3c-9651-e75c55e9176d
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: (E)-3-[3,5-dimethoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enal
• SMILES (Canonical): COC1=CC(=CC(=C1OC2C(C(C(C(O2)CO)O)O)O)OC)C=CC=O
• SMILES (Isomeric): COC1=CC(=CC(=C1O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)OC)/C=C/C=O
• InChI: InChI=1S/C17H22O9/c1-23-10-6-9(4-3-5-18)7-11(24-2)16(10)26-17-15(22)14(21)13(20)12(8-19)25-17/h3-7,12-15,17,19-22H,8H2,1-2H3/b4-3+/t12-,13-,14+,15-,17+/m1/s1
• InChI Key: OYTCTPHTVUEGCL-GCPOEHJPSA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₂O₉
• Molecular Weight: 370.40 g/mol
• Exact Mass: 370.12638228 g/mol
• Topological Polar Surface Area (TPSA): 135.00 Ų
• XlogP: -1.20
• Atomic LogP (AlogP): -0.91
• H-Bond Acceptor: 9
• H-Bond Donor: 4
• Rotatable Bonds: 7

Synonyms

• 154461-65-1
• sinapaldehydeglucoside
• sinapic aldehyde glucoside
• sinapyl aldehyde glucoside
• trans-sinapaldehyde glucoside
• CHEMBL251059
• (E)-sinapaldehyde glucopyranoside
• CHEBI:142126
• DTXSID701169886
• trans-sinapaldehyde beta-D-glucoside
• AKOS040762351
• NCGC00385983-01
• sinapyl aldehyde-4-O-beta-D-glucopyranoside
• (E)-sinapaldehyde 4-O-beta-D-glucopyranoside
• 4-O-(beta-D-glucosyl)-trans-sinapyl aldehyde
• trans-4-O-(beta-D-glucosyl)-sinapoyl aldehyde
• trans-sinapaldehyde 4-O-beta-D-glucopyranoside
• (E)-sinapic aldehyde 4-O-beta-D-glucopyranoside
• (E)-sinapyl aldehyde 4-O-beta-D-glucopyranoside
• 4-O-(beta-D-glucosyl)-4-trans-sinapyl aldehyde
• trans-sinapic aldehyde 4-O-beta-D-glucopyranoside
• trans-sinapyl aldehyde 4-O-beta-D-glucopyranoside
• 3-[3,5-Dimethoxy-4-(beta-D-glucopyranosyloxy)phenyl]propenal
• (2E)-3-[4-(beta-D-Glucopyranosyloxy)-3,5-dimethoxyphenyl]-2-propenal
• 2,6-dimethoxy-4-[(1E)-3-oxoprop-1-en-1-yl]phenyl beta-D-glucopyranoside
• (E)-3-[3,5-dimethoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enal
• NCGC00385983-01_C17H22O9_2,6-Dimethoxy-4-[(1E)-3-oxo-1-propen-1-yl]phenyl beta-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6048	60.48%
Caco-2	-	0.7666	76.66%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6192	61.92%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8767	87.67%
OATP1B3 inhibitior	+	0.9710	97.10%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.4774	47.74%
P-glycoprotein inhibitior	-	0.7887	78.87%
P-glycoprotein substrate	-	0.9132	91.32%
CYP3A4 substrate	+	0.5201	52.01%
CYP2C9 substrate	+	0.5847	58.47%
CYP2D6 substrate	-	0.8396	83.96%
CYP3A4 inhibition	-	0.7213	72.13%
CYP2C9 inhibition	-	0.8850	88.50%
CYP2C19 inhibition	-	0.8591	85.91%
CYP2D6 inhibition	-	0.8824	88.24%
CYP1A2 inhibition	-	0.8581	85.81%
CYP2C8 inhibition	-	0.6583	65.83%
CYP inhibitory promiscuity	-	0.6070	60.70%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7696	76.96%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.9555	95.55%
Skin irritation	-	0.8214	82.14%
Skin corrosion	-	0.9587	95.87%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4713	47.13%
Micronuclear	+	0.5033	50.33%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.8325	83.25%
Respiratory toxicity	-	0.7111	71.11%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	-	0.6375	63.75%
Nephrotoxicity	-	0.7519	75.19%
Acute Oral Toxicity (c)	III	0.7544	75.44%
Estrogen receptor binding	-	0.5745	57.45%
Androgen receptor binding	-	0.6140	61.40%
Thyroid receptor binding	+	0.6145	61.45%
Glucocorticoid receptor binding	+	0.5760	57.60%
Aromatase binding	-	0.5451	54.51%
PPAR gamma	+	0.6666	66.66%
Honey bee toxicity	-	0.8155	81.55%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6355	63.55%
Fish aquatic toxicity	+	0.7406	74.06%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.74%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.70%	96.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.32%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.36%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	92.20%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.02%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.64%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.25%	89.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.94%	86.92%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.83%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.21%	85.14%

Plants that contains it

• Eleutherococcus senticosus
• Magnolia champaca
• Magnolia officinalis
• Phellodendron amurense
• Syringa reticulata

Cross-Links

• PubChem: 25791064
• NPASS: NPC210478
• LOTUS: LTS0269793
• wikiData: Q74418022