Vitexin 2''-O-beta-D-glucoside

Details

• Internal ID: c5f2e69a-7401-415a-b188-3766ca253e84
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides > Flavonoid 8-C-glycosides
• IUPAC Name: 8-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• SMILES (Canonical): C1=CC(=CC=C1C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)C4C(C(C(C(O4)CO)O)O)OC5C(C(C(C(O5)CO)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O
• InChI: InChI=1S/C27H30O15/c28-7-15-20(35)22(37)26(42-27-23(38)21(36)19(34)16(8-29)41-27)25(40-15)18-12(32)5-11(31)17-13(33)6-14(39-24(17)18)9-1-3-10(30)4-2-9/h1-6,15-16,19-23,25-32,34-38H,7-8H2/t15-,16-,19-,20-,21+,22+,23-,25+,26-,27+/m1/s1
• InChI Key: FYTOTHFWELWOCG-OAFKVUNRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₅
• Molecular Weight: 594.50 g/mol
• Exact Mass: 594.15847025 g/mol
• Topological Polar Surface Area (TPSA): 256.00 Ų
• XlogP: -1.40
• Atomic LogP (AlogP): -2.08
• H-Bond Acceptor: 15
• H-Bond Donor: 10
• Rotatable Bonds: 6

Synonyms

• Flavosativaside
• 61360-94-9
• Vitexin 2''-glucoside
• 2''-O-Glucosylvitexin
• 8-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• (1S)-1,5-anhydro-1-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]-2-O-beta-D-glucopyranosyl-D-glucitol
• 4H-1-Benzopyran-4-one, 8-(2-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)-5,7-dihydroxy-2-(4-hydroxyphenyl)-
• AC1NQXCK
• C04024
• CHEBI:16631
• DTXSID10415065
• AKOS040734648
• Q27102008

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5736	57.36%
Caco-2	-	0.9328	93.28%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.9143	91.43%
Subcellular localzation	Mitochondria	0.5848	58.48%
OATP2B1 inhibitior	-	0.5543	55.43%
OATP1B1 inhibitior	+	0.8775	87.75%
OATP1B3 inhibitior	+	0.9434	94.34%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.7988	79.88%
P-glycoprotein inhibitior	-	0.6087	60.87%
P-glycoprotein substrate	-	0.7774	77.74%
CYP3A4 substrate	+	0.6196	61.96%
CYP2C9 substrate	-	0.6643	66.43%
CYP2D6 substrate	-	0.8569	85.69%
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	+	0.6790	67.90%
CYP inhibitory promiscuity	-	0.7526	75.26%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6848	68.48%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.9074	90.74%
Skin irritation	-	0.8255	82.55%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	+	0.5499	54.99%
Human Ether-a-go-go-Related Gene inhibition	-	0.4001	40.01%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.8821	88.21%
skin sensitisation	-	0.9132	91.32%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.7339	73.39%
Acute Oral Toxicity (c)	IV	0.4763	47.63%
Estrogen receptor binding	+	0.8153	81.53%
Androgen receptor binding	+	0.7716	77.16%
Thyroid receptor binding	+	0.5370	53.70%
Glucocorticoid receptor binding	-	0.4641	46.41%
Aromatase binding	+	0.7117	71.17%
PPAR gamma	+	0.7523	75.23%
Honey bee toxicity	-	0.6691	66.91%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
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	99.21%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.59%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.68%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.70%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	90.36%	91.49%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.80%	99.15%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.62%	86.92%
CHEMBL3401	O75469	Pregnane X receptor	88.38%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.33%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.75%	86.33%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	86.77%	96.21%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	85.42%	83.57%
CHEMBL3194	P02766	Transthyretin	84.83%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.44%	99.17%
CHEMBL242	Q92731	Estrogen receptor beta	83.39%	98.35%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.65%	97.09%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.25%	91.71%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	82.24%	89.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.34%	94.45%
CHEMBL3038469	P24941	CDK2/Cyclin A	81.09%	91.38%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.86%	95.83%

Plants that contains it

• Adonis aleppica
• Beta vulgaris
• Cannabis sativa
• Cycas circinalis
• Fissistigma oldhamii
• Glinus lotoides
• Lycium chinense
• Podocarpus nivalis
• Ranunculus ficaria
• Ruscus aculeatus
• Setaria italica
• Silene dioica
• Vepris heterophylla
• Vitex negundo
• Vitex negundo var. cannabifolia

Cross-Links

• PubChem: 5280641
• NPASS: NPC89390
• LOTUS: LTS0248756
• wikiData: Q27102008