[(2R,3R,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate

Details

• Internal ID: f406d7d8-22f6-4acd-8395-f28894694042
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2R,3R,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(OC(C2OC(=O)C=CC3=CC(=C(C=C3)OC)O)CO)OCCC4=CC(=C(C=C4)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H](O[C@@H]([C@H]2OC(=O)/C=C/C3=CC(=C(C=C3)OC)O)CO)OCCC4=CC(=C(C=C4)O)O)O)O)O)O
• InChI: InChI=1S/C30H38O15/c1-14-23(36)24(37)25(38)30(42-14)45-28-26(39)29(41-10-9-16-3-6-17(32)18(33)11-16)43-21(13-31)27(28)44-22(35)8-5-15-4-7-20(40-2)19(34)12-15/h3-8,11-12,14,21,23-34,36-39H,9-10,13H2,1-2H3/b8-5+/t14-,21+,23-,24+,25+,26+,27+,28+,29+,30-/m0/s1
• InChI Key: RMJYDWRKVAGFGZ-CPPDSBOHSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₃₈O₁₅
• Molecular Weight: 638.60 g/mol
• Exact Mass: 638.22107050 g/mol
• Topological Polar Surface Area (TPSA): 234.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): -0.71
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 11

Synonyms

• AC1O52VJ
• SCHEMBL5918043
• DTXSID60424288
• NSC729646
• NSC-729646
• (2R,3R,4R,5R,6R)-6-(3,4-Dihydroxyphenethoxy)-5-hydroxy-2-(hydroxymethyl)-4-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-3-yl (E)-3-(3-hydroxy-4-methoxyphenyl)acrylate
• .beta.-D-Glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl 3-O-(6-deoxy-.alpha.-L-mannopyranosyl)-4-O-[(2E)-3-(3-hydroxy-4-methoxyphenyl)-1-oxo-2-propenyl]-
• [(2R,3R,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-3-yl] (E)-3-(3-hydroxy-4-methoxy-phenyl)prop-2-enoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7808	78.08%
Caco-2	-	0.8955	89.55%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.7406	74.06%
OATP2B1 inhibitior	-	0.8602	86.02%
OATP1B1 inhibitior	+	0.8843	88.43%
OATP1B3 inhibitior	+	0.9571	95.71%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.7501	75.01%
P-glycoprotein inhibitior	-	0.5352	53.52%
P-glycoprotein substrate	+	0.5230	52.30%
CYP3A4 substrate	+	0.6709	67.09%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8611	86.11%
CYP3A4 inhibition	-	0.8552	85.52%
CYP2C9 inhibition	-	0.7968	79.68%
CYP2C19 inhibition	-	0.8381	83.81%
CYP2D6 inhibition	-	0.8929	89.29%
CYP1A2 inhibition	-	0.8885	88.85%
CYP2C8 inhibition	+	0.7923	79.23%
CYP inhibitory promiscuity	-	0.6452	64.52%
UGT catelyzed	+	0.6362	63.62%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.7121	71.21%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.9230	92.30%
Skin irritation	-	0.8430	84.30%
Skin corrosion	-	0.9583	95.83%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7064	70.64%
Micronuclear	-	0.6367	63.67%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.8413	84.13%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	-	0.6375	63.75%
Nephrotoxicity	-	0.9512	95.12%
Acute Oral Toxicity (c)	III	0.7950	79.50%
Estrogen receptor binding	+	0.8000	80.00%
Androgen receptor binding	-	0.6770	67.70%
Thyroid receptor binding	+	0.5597	55.97%
Glucocorticoid receptor binding	+	0.6556	65.56%
Aromatase binding	-	0.5073	50.73%
PPAR gamma	+	0.6617	66.17%
Honey bee toxicity	-	0.6523	65.23%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.6850	68.50%

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%
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.10%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.52%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.31%	96.00%
CHEMBL3194	P02766	Transthyretin	94.95%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.59%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.44%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	94.23%	91.49%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	93.16%	86.92%
CHEMBL2581	P07339	Cathepsin D	88.37%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	87.27%	94.73%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	85.80%	80.78%
CHEMBL3714130	P46095	G-protein coupled receptor 6	84.69%	97.36%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.67%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.04%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.34%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.76%	95.89%
CHEMBL4208	P20618	Proteasome component C5	80.58%	90.00%

Plants that contains it

• Acanthus ebracteatus
• Buddleja davidii
• Digitalis purpurea
• Euphrasia stricta
• Fernandoa adenophylla
• Firmiana simplex
• Globularia davisiana
• Globularia dumulosa
• Globularia orientalis
• Lamium purpureum
• Leonurus persicus
• Marrubium alysson
• Marrubium velutinum
• Pedicularis nordmanniana
• Penstemon secundiflorus
• Penstemon serrulatus
• Phtheirospermum japonicum
• Plantago major
• Santisukia kerrii
• Scutellaria orientalis
• Scutellaria prostrata
• Scutellaria salviifolia
• Sideritis lyciae
• Sideritis perfoliata
• Stachytarpheta cayennensis
• Verbena brasiliensis
• Volkameria inermis

Cross-Links

• PubChem: 6476334
• LOTUS: LTS0218569
• wikiData: Q82236802