Vanicoside B

Details

• Internal ID: 8c65a33f-864e-4fe0-97d2-ea1bf521039c
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
• IUPAC Name: [(2R,3R,4S,5S)-3-hydroxy-4-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-5-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxymethyl]oxan-2-yl]oxyoxolan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CC(=O)OCC2C(C(C(C(O2)OC3(C(C(C(O3)COC(=O)C=CC4=CC=C(C=C4)O)O)OC(=O)C=CC5=CC=C(C=C5)O)COC(=O)C=CC6=CC=C(C=C6)O)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)/C=C/C(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@H](O2)O[C@]3([C@H]([C@@H]([C@H](O3)COC(=O)/C=C/C4=CC=C(C=C4)O)O)OC(=O)/C=C/C5=CC=C(C=C5)O)COC(=O)/C=C/C6=CC=C(C=C6)O)O)O)O)O
• InChI: InChI=1S/C49H48O20/c1-62-36-24-31(8-19-35(36)53)12-22-40(55)63-25-37-43(58)45(60)46(61)48(66-37)69-49(27-65-41(56)21-10-29-4-15-33(51)16-5-29)47(67-42(57)23-11-30-6-17-34(52)18-7-30)44(59)38(68-49)26-64-39(54)20-9-28-2-13-32(50)14-3-28/h2-24,37-38,43-48,50-53,58-61H,25-27H2,1H3/b20-9+,21-10+,22-12+,23-11+/t37-,38-,43-,44-,45+,46-,47+,48-,49+/m1/s1
• InChI Key: ALSDWGAQQGXOHC-PWYSLETCSA-N
• Popularity: 10 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₉H₄₈O₂₀
• Molecular Weight: 956.90 g/mol
• Exact Mass: 956.27389392 g/mol
• Topological Polar Surface Area (TPSA): 304.00 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 2.49
• H-Bond Acceptor: 20
• H-Bond Donor: 8
• Rotatable Bonds: 18

Synonyms

• 155179-21-8
• C49H48O20
• C49-H48-O20
• CHEMBL492323
• SCHEMBL3366349
• DTXSID401317941
• HY-N9561
• AKOS040763269
• LS-71606
• CS-0201356
• [(2R,3R,4S,5S)-3-hydroxy-4-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-5-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxymethyl]oxan-2-yl]oxyoxolan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7530	75.30%
Caco-2	-	0.8772	87.72%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7750	77.50%
OATP2B1 inhibitior	-	0.8609	86.09%
OATP1B1 inhibitior	+	0.8619	86.19%
OATP1B3 inhibitior	+	0.9553	95.53%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9111	91.11%
P-glycoprotein inhibitior	+	0.7445	74.45%
P-glycoprotein substrate	-	0.6476	64.76%
CYP3A4 substrate	+	0.6637	66.37%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8583	85.83%
CYP3A4 inhibition	-	0.8440	84.40%
CYP2C9 inhibition	-	0.7419	74.19%
CYP2C19 inhibition	-	0.6894	68.94%
CYP2D6 inhibition	-	0.9109	91.09%
CYP1A2 inhibition	-	0.8571	85.71%
CYP2C8 inhibition	+	0.8568	85.68%
CYP inhibitory promiscuity	-	0.7239	72.39%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5872	58.72%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.9061	90.61%
Skin irritation	-	0.8495	84.95%
Skin corrosion	-	0.9446	94.46%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7985	79.85%
Micronuclear	+	0.5148	51.48%
Hepatotoxicity	-	0.8625	86.25%
skin sensitisation	-	0.8012	80.12%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.9212	92.12%
Acute Oral Toxicity (c)	III	0.6812	68.12%
Estrogen receptor binding	+	0.8203	82.03%
Androgen receptor binding	+	0.7078	70.78%
Thyroid receptor binding	+	0.5787	57.87%
Glucocorticoid receptor binding	+	0.6338	63.38%
Aromatase binding	+	0.5637	56.37%
PPAR gamma	+	0.7254	72.54%
Honey bee toxicity	-	0.7139	71.39%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9564	95.64%

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	99.52%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.05%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.53%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.25%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.20%	95.56%
CHEMBL3194	P02766	Transthyretin	92.94%	90.71%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	92.07%	89.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.81%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	91.74%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.58%	99.17%
CHEMBL4208	P20618	Proteasome component C5	88.00%	90.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.02%	95.50%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.68%	85.14%
CHEMBL2535	P11166	Glucose transporter	85.54%	98.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.09%	97.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	84.62%	97.36%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	82.06%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.02%	91.19%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.89%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.78%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.40%	95.89%
CHEMBL2179	P04062	Beta-glucocerebrosidase	81.01%	85.31%

Plants that contains it

• Persicaria pensylvanica
• Polygonum perfoliatum
• Reynoutria sachalinensis

Cross-Links

• PubChem: 10033855
• NPASS: NPC7145
• LOTUS: LTS0114722
• wikiData: Q104399643