[(3R,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4,5-dihydroxy-2-[[(2R,3R,4R,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Details

• Internal ID: ad5873b2-4bd4-49a9-bbf2-2d607b593175
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(3R,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4,5-dihydroxy-2-[[(2R,3R,4R,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OCCC3=CC(=C(C=C3)O)O)O)O)OC(=O)C=CC4=CC(=C(C=C4)O)O)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OCC2[C@@H]([C@@H]([C@H]([C@@H](O2)OCCC3=CC(=C(C=C3)O)O)O)O)OC(=O)/C=C/C4=CC(=C(C=C4)O)O)O)O)O
• InChI: InChI=1S/C29H36O15/c1-13-22(35)23(36)25(38)29(42-13)41-12-20-27(44-21(34)7-4-14-2-5-16(30)18(32)10-14)24(37)26(39)28(43-20)40-9-8-15-3-6-17(31)19(33)11-15/h2-7,10-11,13,20,22-33,35-39H,8-9,12H2,1H3/b7-4+/t13-,20?,22+,23-,24-,25-,26-,27+,28-,29-/m1/s1
• InChI Key: DTOUWTJYUCZJQD-PBFVCFKESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₆O₁₅
• Molecular Weight: 624.60 g/mol
• Exact Mass: 624.20542044 g/mol
• Topological Polar Surface Area (TPSA): 245.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): -1.02
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 10

Synonyms

• AC-1400

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7422	74.22%
Caco-2	-	0.9035	90.35%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.8295	82.95%
OATP2B1 inhibitior	-	0.8520	85.20%
OATP1B1 inhibitior	+	0.8921	89.21%
OATP1B3 inhibitior	+	0.9423	94.23%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8518	85.18%
P-glycoprotein inhibitior	-	0.5512	55.12%
P-glycoprotein substrate	-	0.6512	65.12%
CYP3A4 substrate	+	0.6387	63.87%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8696	86.96%
CYP3A4 inhibition	-	0.8916	89.16%
CYP2C9 inhibition	-	0.6602	66.02%
CYP2C19 inhibition	-	0.7703	77.03%
CYP2D6 inhibition	-	0.8769	87.69%
CYP1A2 inhibition	-	0.7757	77.57%
CYP2C8 inhibition	+	0.6912	69.12%
CYP inhibitory promiscuity	-	0.5420	54.20%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6274	62.74%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.9180	91.80%
Skin irritation	-	0.8400	84.00%
Skin corrosion	-	0.9534	95.34%
Ames mutagenesis	-	0.6070	60.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.6633	66.33%
Micronuclear	-	0.6267	62.67%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.8042	80.42%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	-	0.7000	70.00%
Nephrotoxicity	-	0.9620	96.20%
Acute Oral Toxicity (c)	III	0.8082	80.82%
Estrogen receptor binding	+	0.7580	75.80%
Androgen receptor binding	-	0.7239	72.39%
Thyroid receptor binding	-	0.4926	49.26%
Glucocorticoid receptor binding	+	0.5955	59.55%
Aromatase binding	+	0.5659	56.59%
PPAR gamma	+	0.6846	68.46%
Honey bee toxicity	-	0.7316	73.16%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.8693	86.93%

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	99.60%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.11%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.36%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.91%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	94.47%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.17%	89.00%
CHEMBL3194	P02766	Transthyretin	93.62%	90.71%
CHEMBL2581	P07339	Cathepsin D	93.15%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.86%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.82%	99.17%
CHEMBL4208	P20618	Proteasome component C5	88.03%	90.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.11%	97.36%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.05%	96.95%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.16%	86.92%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	85.61%	80.78%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	83.52%	96.37%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.48%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.34%	95.89%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.25%	94.80%

Plants that contains it

• Forsythia suspensa
• Rehmannia glutinosa

Cross-Links

• PubChem: 45358127
• NPASS: NPC105610