[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-(4-hydroxy-3,5-dimethoxyphenyl)-7-methoxy-5-oxochromen-3-yl]oxyoxan-2-yl]methyl 3-(4-hydroxyphenyl)prop-2-enoate

Details

• Internal ID: 9620b289-8e90-4909-a91a-9c45925332cb
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid 3-O-p-coumaroyl glycosides
• IUPAC Name: [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-(4-hydroxy-3,5-dimethoxyphenyl)-7-methoxy-5-oxochromen-3-yl]oxyoxan-2-yl]methyl 3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=CC(=O)C2=CC(=C(OC2=C1)C3=CC(=C(C(=C3)OC)O)OC)OC4C(C(C(C(O4)COC(=O)C=CC5=CC=C(C=C5)O)O)O)O
• SMILES (Isomeric): COC1=CC(=O)C2=CC(=C(OC2=C1)C3=CC(=C(C(=C3)OC)O)OC)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)COC(=O)C=CC5=CC=C(C=C5)O)O)O)O
• InChI: InChI=1S/C33H32O14/c1-41-19-12-21(35)20-14-25(32(45-22(20)13-19)17-10-23(42-2)28(37)24(11-17)43-3)46-33-31(40)30(39)29(38)26(47-33)15-44-27(36)9-6-16-4-7-18(34)8-5-16/h4-14,26,29-31,33-34,37-40H,15H2,1-3H3/t26-,29-,30+,31-,33-/m1/s1
• InChI Key: BORANEKYFOUAHQ-XAEVNMDXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₃₂O₁₄
• Molecular Weight: 652.60 g/mol
• Exact Mass: 652.17920569 g/mol
• Topological Polar Surface Area (TPSA): 200.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 2.29
• H-Bond Acceptor: 14
• H-Bond Donor: 5
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5530	55.30%
Caco-2	-	0.8793	87.93%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.5729	57.29%
OATP2B1 inhibitior	+	0.5676	56.76%
OATP1B1 inhibitior	+	0.8276	82.76%
OATP1B3 inhibitior	+	0.9478	94.78%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8686	86.86%
P-glycoprotein inhibitior	+	0.7381	73.81%
P-glycoprotein substrate	+	0.5149	51.49%
CYP3A4 substrate	+	0.6727	67.27%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8600	86.00%
CYP3A4 inhibition	-	0.9007	90.07%
CYP2C9 inhibition	-	0.8872	88.72%
CYP2C19 inhibition	-	0.9236	92.36%
CYP2D6 inhibition	-	0.9301	93.01%
CYP1A2 inhibition	-	0.9344	93.44%
CYP2C8 inhibition	+	0.8436	84.36%
CYP inhibitory promiscuity	-	0.7459	74.59%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6348	63.48%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9217	92.17%
Skin irritation	-	0.8375	83.75%
Skin corrosion	-	0.9543	95.43%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7784	77.84%
Micronuclear	+	0.7092	70.92%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	-	0.9161	91.61%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.8997	89.97%
Acute Oral Toxicity (c)	III	0.5848	58.48%
Estrogen receptor binding	+	0.8258	82.58%
Androgen receptor binding	+	0.7438	74.38%
Thyroid receptor binding	+	0.5597	55.97%
Glucocorticoid receptor binding	+	0.7875	78.75%
Aromatase binding	+	0.5387	53.87%
PPAR gamma	+	0.6616	66.16%
Honey bee toxicity	-	0.7606	76.06%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9530	95.30%

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	98.77%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.78%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.91%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.02%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.96%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.34%	99.17%
CHEMBL2581	P07339	Cathepsin D	93.08%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.82%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.10%	95.56%
CHEMBL3194	P02766	Transthyretin	90.89%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.43%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	86.95%	94.73%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.40%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.18%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.58%	97.09%
CHEMBL2002	P12268	Inosine-5'-monophosphate dehydrogenase 2	84.35%	98.21%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.03%	95.89%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.95%	97.36%
CHEMBL4208	P20618	Proteasome component C5	80.83%	90.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.62%	90.71%

Plants that contains it

• Catharanthus roseus

Cross-Links

• PubChem: 163191711
• LOTUS: LTS0259820
• wikiData: Q104939407