[(2R,3S,4S,5S,6R)-2-(acetyloxymethyl)-6-[(3,4-dihydroxyphenyl)methoxymethyl]-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Details

• Internal ID: 992f3f21-b006-4334-9e59-21206e87b993
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2R,3S,4S,5S,6R)-2-(acetyloxymethyl)-6-[(3,4-dihydroxyphenyl)methoxymethyl]-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(OC(C2OC(=O)C=CC3=CC(=C(C=C3)O)O)COC(=O)C)COCC4=CC(=C(C=C4)O)O)OC5C(C(C(C(O5)CO)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)O)O)COC(=O)C)COCC4=CC(=C(C=C4)O)O)O[C@H]5[C@@H]([C@H]([C@H]([C@H](O5)CO)O)O)O)O)O)O
• InChI: InChI=1S/C37H48O21/c1-15-27(45)29(47)31(49)36(53-15)58-35-33(56-26(44)8-5-17-3-6-19(40)21(42)9-17)25(14-52-16(2)39)54-24(13-51-12-18-4-7-20(41)22(43)10-18)34(35)57-37-32(50)30(48)28(46)23(11-38)55-37/h3-10,15,23-25,27-38,40-43,45-50H,11-14H2,1-2H3/b8-5+/t15-,23+,24+,25+,27-,28-,29+,30-,31+,32+,33-,34-,35+,36-,37-/m0/s1
• InChI Key: XLZBZHHNPMBBNW-NVBKABIASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₄₈O₂₁
• Molecular Weight: 828.80 g/mol
• Exact Mass: 828.26880854 g/mol
• Topological Polar Surface Area (TPSA): 331.00 Ų
• XlogP: -2.10
• Atomic LogP (AlogP): -2.62
• H-Bond Acceptor: 21
• H-Bond Donor: 11
• Rotatable Bonds: 14

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6191	61.91%
Caco-2	-	0.8916	89.16%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.9143	91.43%
Subcellular localzation	Mitochondria	0.7392	73.92%
OATP2B1 inhibitior	-	0.7242	72.42%
OATP1B1 inhibitior	+	0.8507	85.07%
OATP1B3 inhibitior	+	0.9450	94.50%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.9134	91.34%
P-glycoprotein inhibitior	+	0.6155	61.55%
P-glycoprotein substrate	-	0.6050	60.50%
CYP3A4 substrate	+	0.6669	66.69%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8770	87.70%
CYP3A4 inhibition	-	0.8792	87.92%
CYP2C9 inhibition	-	0.8928	89.28%
CYP2C19 inhibition	-	0.9078	90.78%
CYP2D6 inhibition	-	0.9167	91.67%
CYP1A2 inhibition	-	0.8920	89.20%
CYP2C8 inhibition	+	0.7044	70.44%
CYP inhibitory promiscuity	-	0.9123	91.23%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.7841	78.41%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.9138	91.38%
Skin irritation	-	0.8513	85.13%
Skin corrosion	-	0.9573	95.73%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7218	72.18%
Micronuclear	-	0.6226	62.26%
Hepatotoxicity	-	0.8875	88.75%
skin sensitisation	-	0.8506	85.06%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.8993	89.93%
Acute Oral Toxicity (c)	III	0.6558	65.58%
Estrogen receptor binding	+	0.7949	79.49%
Androgen receptor binding	-	0.6045	60.45%
Thyroid receptor binding	+	0.5212	52.12%
Glucocorticoid receptor binding	+	0.5497	54.97%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.7072	70.72%
Honey bee toxicity	-	0.6172	61.72%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5045	50.45%
Fish aquatic toxicity	+	0.9669	96.69%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.73%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.71%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.76%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.33%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.40%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	94.51%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.18%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.87%	96.00%
CHEMBL2581	P07339	Cathepsin D	93.30%	98.95%
CHEMBL3194	P02766	Transthyretin	88.05%	90.71%
CHEMBL226	P30542	Adenosine A1 receptor	88.01%	95.93%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.11%	96.95%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.74%	95.50%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.13%	86.92%
CHEMBL3714130	P46095	G-protein coupled receptor 6	84.61%	97.36%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.94%	97.09%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.62%	95.89%
CHEMBL4208	P20618	Proteasome component C5	83.44%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.92%	94.45%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	82.40%	94.80%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.13%	95.56%

Plants that contains it

• Markhamia stipulata

Cross-Links

• PubChem: 163106577
• LOTUS: LTS0086733
• wikiData: Q105330571