Vicinin 2

Details

• Internal ID: c6ca274d-a506-49d0-b02d-2eaa6dac1088
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-8-O-glycosides
• IUPAC Name: 5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]chromen-4-one
• SMILES (Canonical): C1=CC(=CC=C1C2=CC(=O)C3=C(C(=C(C(=C3O2)OC4C(C(C(C(O4)CO)O)O)O)O)OC5C(C(C(C(O5)CO)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C2=CC(=O)C3=C(C(=C(C(=C3O2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O
• InChI: InChI=1S/C27H30O17/c28-6-12-15(32)18(35)20(37)26(41-12)43-24-17(34)14-10(31)5-11(8-1-3-9(30)4-2-8)40-23(14)25(22(24)39)44-27-21(38)19(36)16(33)13(7-29)42-27/h1-5,12-13,15-16,18-21,26-30,32-39H,6-7H2/t12-,13-,15-,16-,18+,19+,20-,21-,26+,27+/m1/s1
• InChI Key: CSNXTSWTBUEIJB-PXJYGDGDSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₇
• Molecular Weight: 626.50 g/mol
• Exact Mass: 626.14829948 g/mol
• Topological Polar Surface Area (TPSA): 286.00 Ų
• XlogP: -1.70
• Atomic LogP (AlogP): -3.07
• H-Bond Acceptor: 17
• H-Bond Donor: 11
• Rotatable Bonds: 7

Synonyms

• 90456-53-4
• 2-(4-Hydroxyphenyl)-5,7-dihydroxy-6,8-bis(beta-D-glucopyranosyloxy)-4H-1-benzopyran-4-one
• 4H-1-Benzopyran-4-one, 6,8-bis(beta-D-glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-
• CHEMBL538921
• DTXSID901126527
• AKOS040763518
• 5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]chromen-4-one
• 6,8-Bis(beta-D-glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5736	57.36%
Caco-2	-	0.9241	92.41%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.5848	58.48%
OATP2B1 inhibitior	-	0.5574	55.74%
OATP1B1 inhibitior	+	0.8282	82.82%
OATP1B3 inhibitior	+	0.9434	94.34%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.6527	65.27%
P-glycoprotein inhibitior	-	0.5384	53.84%
P-glycoprotein substrate	-	0.8185	81.85%
CYP3A4 substrate	+	0.5863	58.63%
CYP2C9 substrate	-	0.6762	67.62%
CYP2D6 substrate	-	0.8575	85.75%
CYP3A4 inhibition	-	0.9390	93.90%
CYP2C9 inhibition	-	0.9315	93.15%
CYP2C19 inhibition	-	0.9047	90.47%
CYP2D6 inhibition	-	0.9458	94.58%
CYP1A2 inhibition	-	0.9180	91.80%
CYP2C8 inhibition	+	0.7177	71.77%
CYP inhibitory promiscuity	-	0.7526	75.26%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6848	68.48%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.8835	88.35%
Skin irritation	-	0.8255	82.55%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7114	71.14%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.7696	76.96%
skin sensitisation	-	0.9132	91.32%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.8187	81.87%
Acute Oral Toxicity (c)	IV	0.4763	47.63%
Estrogen receptor binding	+	0.8059	80.59%
Androgen receptor binding	+	0.7093	70.93%
Thyroid receptor binding	+	0.5736	57.36%
Glucocorticoid receptor binding	+	0.5472	54.72%
Aromatase binding	+	0.6432	64.32%
PPAR gamma	+	0.7441	74.41%
Honey bee toxicity	-	0.7137	71.37%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6350	63.50%
Fish aquatic toxicity	+	0.7958	79.58%

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	99.25%	91.11%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	96.34%	83.57%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.60%	94.00%
CHEMBL2581	P07339	Cathepsin D	95.13%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.29%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.97%	94.45%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	91.68%	95.64%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.58%	85.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.54%	99.15%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.43%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.17%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	87.84%	94.73%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	87.66%	91.71%
CHEMBL242	Q92731	Estrogen receptor beta	87.33%	98.35%
CHEMBL3194	P02766	Transthyretin	86.51%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.32%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.23%	86.33%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	86.22%	96.21%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	84.60%	95.78%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.58%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.30%	95.56%

Plants that contains it

• Achillea millefolium
• Artemisia capillaris
• Centaurea hierapolitana
• Cirsium oligophyllum
• Collinsonia japonica
• Glycyrrhiza glabra

Cross-Links

• PubChem: 5315206
• NPASS: NPC259152
• LOTUS: LTS0203509
• wikiData: Q104969455