[(2R,3S,4S,5R,6S)-6-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[2-(4-hydroxyphenyl)-7-methoxy-4-oxo-5,6-dihydrochromen-6-yl]oxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate

Details

• Internal ID: 188d9db4-5253-4964-825b-8e6d798d3dbd
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2R,3S,4S,5R,6S)-6-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[2-(4-hydroxyphenyl)-7-methoxy-4-oxo-5,6-dihydrochromen-6-yl]oxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=CC2=C(CC1C3C(C(C(C(O3)CO)O)O)OC4C(C(C(C(O4)COC(=O)C=CC5=CC(=C(C(=C5)OC)O)OC)O)O)O)C(=O)C=C(O2)C6=CC=C(C=C6)O
• SMILES (Isomeric): COC1=CC2=C(CC1[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)COC(=O)/C=C/C5=CC(=C(C(=C5)OC)O)OC)O)O)O)C(=O)C=C(O2)C6=CC=C(C=C6)O
• InChI: InChI=1S/C39H44O18/c1-50-24-14-25-20(22(42)13-23(54-25)18-5-7-19(41)8-6-18)12-21(24)37-38(35(48)32(45)28(15-40)55-37)57-39-36(49)34(47)33(46)29(56-39)16-53-30(43)9-4-17-10-26(51-2)31(44)27(11-17)52-3/h4-11,13-14,21,28-29,32-41,44-49H,12,15-16H2,1-3H3/b9-4+/t21?,28-,29-,32-,33-,34+,35+,36-,37+,38-,39+/m1/s1
• InChI Key: CWJDZOMEXBVUKZ-IPMPBZIISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₄₄O₁₈
• Molecular Weight: 800.80 g/mol
• Exact Mass: 800.25276455 g/mol
• Topological Polar Surface Area (TPSA): 270.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): -0.17
• H-Bond Acceptor: 18
• H-Bond Donor: 8
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4828	48.28%
Caco-2	-	0.8823	88.23%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.5603	56.03%
OATP2B1 inhibitior	-	0.7171	71.71%
OATP1B1 inhibitior	+	0.8224	82.24%
OATP1B3 inhibitior	+	0.9608	96.08%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.5546	55.46%
P-glycoprotein inhibitior	+	0.6909	69.09%
P-glycoprotein substrate	+	0.6397	63.97%
CYP3A4 substrate	+	0.7072	70.72%
CYP2C9 substrate	-	0.8188	81.88%
CYP2D6 substrate	-	0.8627	86.27%
CYP3A4 inhibition	-	0.9212	92.12%
CYP2C9 inhibition	-	0.8132	81.32%
CYP2C19 inhibition	-	0.8656	86.56%
CYP2D6 inhibition	-	0.9458	94.58%
CYP1A2 inhibition	-	0.8960	89.60%
CYP2C8 inhibition	+	0.8308	83.08%
CYP inhibitory promiscuity	-	0.7032	70.32%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6577	65.77%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9098	90.98%
Skin irritation	-	0.8318	83.18%
Skin corrosion	-	0.9522	95.22%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4045	40.45%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	-	0.7966	79.66%
skin sensitisation	-	0.8751	87.51%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.8921	89.21%
Acute Oral Toxicity (c)	III	0.5604	56.04%
Estrogen receptor binding	+	0.8029	80.29%
Androgen receptor binding	+	0.7335	73.35%
Thyroid receptor binding	+	0.5535	55.35%
Glucocorticoid receptor binding	+	0.6859	68.59%
Aromatase binding	+	0.5953	59.53%
PPAR gamma	+	0.7236	72.36%
Honey bee toxicity	-	0.6623	66.23%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9244	92.44%

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	99.72%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.48%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	98.04%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.65%	86.33%
CHEMBL2581	P07339	Cathepsin D	96.24%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.47%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.19%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.96%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.13%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.76%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.80%	94.00%
CHEMBL3194	P02766	Transthyretin	89.31%	90.71%
CHEMBL5255	O00206	Toll-like receptor 4	87.72%	92.50%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.09%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.54%	99.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.97%	95.89%
CHEMBL3922	P50579	Methionine aminopeptidase 2	85.74%	97.28%
CHEMBL226	P30542	Adenosine A1 receptor	85.27%	95.93%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.12%	94.45%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.60%	94.33%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.45%	90.71%
CHEMBL4630	O14757	Serine/threonine-protein kinase Chk1	83.44%	97.03%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.17%	91.71%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.20%	97.14%

Plants that contains it

• Ziziphus jujuba

Cross-Links

• PubChem: 5321319
• NPASS: NPC203171