Vicenin-2

Details

Top
Internal ID bfe5f1d0-8c3d-43c4-a714-d5db0e9a604e
Taxonomy Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides > Flavonoid 8-C-glycosides
IUPAC Name 5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
SMILES (Canonical) C1=CC(=CC=C1C2=CC(=O)C3=C(C(=C(C(=C3O2)C4C(C(C(C(O4)CO)O)O)O)O)C5C(C(C(C(O5)CO)O)O)O)O)O
SMILES (Isomeric) C1=CC(=CC=C1C2=CC(=O)C3=C(C(=C(C(=C3O2)C4C(C(C(C(O4)CO)O)O)O)O)C5C(C(C(C(O5)CO)O)O)O)O)O
InChI InChI=1S/C27H30O15/c28-6-12-17(32)21(36)23(38)26(41-12)15-19(34)14-10(31)5-11(8-1-3-9(30)4-2-8)40-25(14)16(20(15)35)27-24(39)22(37)18(33)13(7-29)42-27/h1-5,12-13,17-18,21-24,26-30,32-39H,6-7H2
InChI Key FIAAVMJLAGNUKW-UHFFFAOYSA-N
Popularity 71 references in papers

Physical and Chemical Properties

Top
Molecular Formula C27H30O15
Molecular Weight 594.50 g/mol
Exact Mass 594.15847025 g/mol
Topological Polar Surface Area (TPSA) 267.00 Ų
XlogP -2.30
Atomic LogP (AlogP) -2.39
H-Bond Acceptor 15
H-Bond Donor 11
Rotatable Bonds 5

Synonyms

Top
Vicenin
Vicenin-2
Violantin
Apigenin 6,8-di-glucopyranoside
5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
4H-1-Benzopyran-4-one, 6,8-di-beta-D-glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-
6,8-di-c-glucosylapigenin
Compound NP-000002
6,8-di-C-glucosyl-4',5,7-trihydroxyflavone
Apigenin 6,8-di-C-glucoside
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

Top
2D Structure of Vicenin-2

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.6251 62.51%
Caco-2 - 0.9152 91.52%
Blood Brain Barrier - 0.6500 65.00%
Human oral bioavailability - 0.7857 78.57%
Subcellular localzation Mitochondria 0.5454 54.54%
OATP2B1 inhibitior - 0.5548 55.48%
OATP1B1 inhibitior + 0.7711 77.11%
OATP1B3 inhibitior + 0.9752 97.52%
MATE1 inhibitior - 0.8200 82.00%
OCT2 inhibitior - 0.8250 82.50%
BSEP inhibitior + 0.6705 67.05%
P-glycoprotein inhibitior - 0.5691 56.91%
P-glycoprotein substrate - 0.8398 83.98%
CYP3A4 substrate + 0.5621 56.21%
CYP2C9 substrate - 0.6194 61.94%
CYP2D6 substrate - 0.8416 84.16%
CYP3A4 inhibition - 0.8760 87.60%
CYP2C9 inhibition - 0.9182 91.82%
CYP2C19 inhibition - 0.9102 91.02%
CYP2D6 inhibition - 0.9445 94.45%
CYP1A2 inhibition - 0.8801 88.01%
CYP2C8 inhibition + 0.6604 66.04%
CYP inhibitory promiscuity - 0.7721 77.21%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.6914 69.14%
Eye corrosion - 0.9937 99.37%
Eye irritation - 0.8867 88.67%
Skin irritation - 0.7949 79.49%
Skin corrosion - 0.9613 96.13%
Ames mutagenesis + 0.6329 63.29%
Human Ether-a-go-go-Related Gene inhibition + 0.7423 74.23%
Micronuclear + 0.6459 64.59%
Hepatotoxicity - 0.7446 74.46%
skin sensitisation - 0.8739 87.39%
Respiratory toxicity + 0.6222 62.22%
Reproductive toxicity + 0.7444 74.44%
Mitochondrial toxicity + 0.6625 66.25%
Nephrotoxicity - 0.6787 67.87%
Acute Oral Toxicity (c) IV 0.4242 42.42%
Estrogen receptor binding + 0.7148 71.48%
Androgen receptor binding + 0.7374 73.74%
Thyroid receptor binding - 0.5169 51.69%
Glucocorticoid receptor binding - 0.5206 52.06%
Aromatase binding + 0.6474 64.74%
PPAR gamma + 0.7165 71.65%
Honey bee toxicity - 0.7665 76.65%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.6300 63.00%
Fish aquatic toxicity + 0.6549 65.49%

Targets

Top

Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
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 99.35% 91.11%
CHEMBL2581 P07339 Cathepsin D 98.05% 98.95%
CHEMBL1806 P11388 DNA topoisomerase II alpha 94.61% 89.00%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 92.73% 94.00%
CHEMBL3401 O75469 Pregnane X receptor 89.61% 94.73%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.95% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 86.89% 95.56%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 86.20% 99.15%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 85.69% 86.92%
CHEMBL3137262 O60341 LSD1/CoREST complex 84.08% 97.09%
CHEMBL5284 Q96RR4 CaM-kinase kinase beta 82.75% 89.23%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 82.70% 96.21%
CHEMBL3060 Q9Y345 Glycine transporter 2 82.26% 99.17%
CHEMBL2288 Q13526 Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 81.97% 91.71%
CHEMBL2107 P61073 C-X-C chemokine receptor type 4 81.76% 93.10%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 81.13% 90.71%
CHEMBL242 Q92731 Estrogen receptor beta 80.62% 98.35%
CHEMBL2553 Q15418 Ribosomal protein S6 kinase alpha 1 80.51% 85.11%

Cross-Links

Top
PubChem 3084407
LOTUS LTS0255367
wikiData Q104387517