(Z)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]ethyl]prop-2-enamide

Details

• Internal ID: d28f5ab5-514b-471f-b8b1-810eafb21aa1
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: (Z)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]ethyl]prop-2-enamide
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CC(=O)NCCC2=CC=C(C=C2)OC3C(C(C(C(O3)CO)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)/C=C\C(=O)NCCC2=CC=C(C=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O
• InChI: InChI=1S/C24H29NO9/c1-32-18-12-15(4-8-17(18)27)5-9-20(28)25-11-10-14-2-6-16(7-3-14)33-24-23(31)22(30)21(29)19(13-26)34-24/h2-9,12,19,21-24,26-27,29-31H,10-11,13H2,1H3,(H,25,28)/b9-5-/t19-,21-,22+,23-,24-/m1/s1
• InChI Key: VVTVHDZQFUALQV-LSYRUTCLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₉NO₉
• Molecular Weight: 475.50 g/mol
• Exact Mass: 475.18423150 g/mol
• Topological Polar Surface Area (TPSA): 158.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): -0.05
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5744	57.44%
Caco-2	-	0.8921	89.21%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.5445	54.45%
OATP2B1 inhibitior	-	0.8575	85.75%
OATP1B1 inhibitior	+	0.8992	89.92%
OATP1B3 inhibitior	+	0.9539	95.39%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.8188	81.88%
P-glycoprotein inhibitior	-	0.4881	48.81%
P-glycoprotein substrate	-	0.5391	53.91%
CYP3A4 substrate	+	0.6376	63.76%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8437	84.37%
CYP3A4 inhibition	-	0.8028	80.28%
CYP2C9 inhibition	-	0.8080	80.80%
CYP2C19 inhibition	-	0.8777	87.77%
CYP2D6 inhibition	-	0.6063	60.63%
CYP1A2 inhibition	-	0.8673	86.73%
CYP2C8 inhibition	+	0.8052	80.52%
CYP inhibitory promiscuity	-	0.7880	78.80%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6943	69.43%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.9517	95.17%
Skin irritation	-	0.7782	77.82%
Skin corrosion	-	0.9457	94.57%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	+	0.6300	63.00%
Hepatotoxicity	-	0.9073	90.73%
skin sensitisation	-	0.8790	87.90%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.9384	93.84%
Acute Oral Toxicity (c)	III	0.7454	74.54%
Estrogen receptor binding	+	0.5974	59.74%
Androgen receptor binding	+	0.6572	65.72%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6139	61.39%
Aromatase binding	-	0.5668	56.68%
PPAR gamma	+	0.6884	68.84%
Honey bee toxicity	-	0.7547	75.47%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	-	0.7438	74.38%

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	99.73%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.03%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	97.12%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	96.80%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.06%	86.33%
CHEMBL2581	P07339	Cathepsin D	93.94%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.17%	89.00%
CHEMBL4208	P20618	Proteasome component C5	91.35%	90.00%
CHEMBL3437	Q16853	Amine oxidase, copper containing	90.52%	94.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	88.94%	95.50%
CHEMBL3401	O75469	Pregnane X receptor	88.39%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.93%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.58%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.55%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.90%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.59%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.41%	94.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.98%	90.71%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.83%	92.62%
CHEMBL3194	P02766	Transthyretin	80.77%	90.71%

Plants that contains it

• Stephania longa

Cross-Links

• PubChem: 45258990
• LOTUS: LTS0268338
• wikiData: Q105297888