(E)-3-[3,5-dimethoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoic acid

Details

• Internal ID: b9c1e117-9ebc-4f36-abc8-4bff9ac7b1d9
• 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-enoic acid
• SMILES (Canonical): COC1=CC(=CC(=C1OC2C(C(C(C(O2)CO)O)O)O)OC)C=CC(=O)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)O
• InChI: InChI=1S/C17H22O10/c1-24-9-5-8(3-4-12(19)20)6-10(25-2)16(9)27-17-15(23)14(22)13(21)11(7-18)26-17/h3-6,11,13-15,17-18,21-23H,7H2,1-2H3,(H,19,20)/b4-3+/t11-,13-,14+,15-,17+/m1/s1
• InChI Key: KKLWTTVTWMTNBP-KYXYLJOWSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₂O₁₀
• Molecular Weight: 386.30 g/mol
• Exact Mass: 386.12129689 g/mol
• Topological Polar Surface Area (TPSA): 155.00 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): -1.02
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 7

Synonyms

• 117405-52-4
• 2-Propenoic acid, 3-[4-(beta-D-glucopyranosyloxy)-3,5-dimethoxyphenyl]-, (2E)-
• 4'-O-Glucopyranosylsinapic acid
• C02919
• sinapoyl-4-O-beta-D-glucoside
• CHEMBL3916405
• CHEBI:145341
• DTXSID801291032
• 4-O-beta-D-Glucopyranosylsinapic acid
• AKOS040736221
• trans-p-Sinapoyl-beta-D-glucopyranoside
• 4-O-beta-D-glucosyl-trans-sinapic acid
• (E)-3-[3,5-dimethoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoic acid
• 4-O-(beta-D-glucosyl)-(2E)-sinapic acid
• O(4)-(beta-D-glucosyl)-(2E)-sinapic acid
• 4-O-(beta-D-glucopyranosyl)-(2E)-sinapic acid
• (2E)-3-[4-(beta-D-glucopyranosyloxy)-3,5-dimethoxyphenyl]acrylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6048	60.48%
Caco-2	-	0.8071	80.71%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6192	61.92%
OATP2B1 inhibitior	-	0.8568	85.68%
OATP1B1 inhibitior	+	0.8940	89.40%
OATP1B3 inhibitior	+	0.9710	97.10%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.5911	59.11%
P-glycoprotein inhibitior	-	0.8099	80.99%
P-glycoprotein substrate	-	0.9226	92.26%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.8004	80.04%
CYP2D6 substrate	-	0.8631	86.31%
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	+	0.4833	48.33%
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	-	0.9443	94.43%
Skin irritation	-	0.8214	82.14%
Skin corrosion	-	0.9587	95.87%
Ames mutagenesis	-	0.7870	78.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.6818	68.18%
Micronuclear	+	0.5033	50.33%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.8325	83.25%
Respiratory toxicity	-	0.6667	66.67%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	-	0.6375	63.75%
Nephrotoxicity	-	0.7873	78.73%
Acute Oral Toxicity (c)	III	0.7544	75.44%
Estrogen receptor binding	-	0.5860	58.60%
Androgen receptor binding	-	0.5582	55.82%
Thyroid receptor binding	+	0.6331	63.31%
Glucocorticoid receptor binding	+	0.6171	61.71%
Aromatase binding	-	0.6276	62.76%
PPAR gamma	+	0.6830	68.30%
Honey bee toxicity	-	0.8410	84.10%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6455	64.55%
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
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	97.06%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.59%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.12%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.43%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.11%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.69%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.36%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.93%	85.14%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.17%	86.92%
CHEMBL3401	O75469	Pregnane X receptor	85.39%	94.73%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.01%	95.89%

Plants that contains it

• Adenopeltis serrata
• Bituminaria bituminosa
• Brassica napus
• Capsicum annuum
• Centaurea seridis
• Chrozophora tinctoria
• Cneorum pulverulentum
• Cyclamen purpurascens
• Cydonia oblonga
• Dalbergia stipulacea
• Delphinium ajacis
• Elaeagnus commutata
• Eucalyptus flocktoniae
• Flindersia brayleyana
• Heracleum sphondylium
• Jungermannia obovata
• Kummerowia striata
• Mascarenhasia arborescens
• Meconopsis napaulensis
• Merremia umbellata
• Millettia conraui
• Palafoxia rosea
• Pedicularis condensata
• Perityle vaseyi
• Phoebe formosana
• Piloselloides hirsuta
• Plectranthus garckeanus
• Porella swartziana
• Quercus mongolica
• Rheum webbianum
• Salacia chinensis
• Salvia coulteri
• Satureja cuneifolia
• Senecio flavus
• Sida cordifolia
• Solanum sisymbriifolium
• Thymbra spicata
• Turraeanthus mannii

Cross-Links

• PubChem: 5280550
• NPASS: NPC232673
• LOTUS: LTS0246013
• wikiData: Q76280931