Vitexin-4invertedexclamationmarka-o-glucoside

Details

• Internal ID: ce2e65b0-57e4-4c95-9633-bafc1f8ba32e
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-8-O-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]oxy-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)OC4C(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)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/C27H30O16/c28-7-15-18(34)20(36)22(38)26(40-15)43-25-21(37)19(35)16(8-29)41-27(25)42-23-13(33)5-11(31)17-12(32)6-14(39-24(17)23)9-1-3-10(30)4-2-9/h1-6,15-16,18-22,25-31,33-38H,7-8H2/t15-,16-,18-,19-,20+,21+,22-,25-,26+,27+/m1/s1
• InChI Key: FHPGRJSWCJSVEN-OWNIHXIWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₆
• Molecular Weight: 610.50 g/mol
• Exact Mass: 610.15338487 g/mol
• Topological Polar Surface Area (TPSA): 266.00 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): -2.42
• H-Bond Acceptor: 16
• H-Bond Donor: 10
• Rotatable Bonds: 7

Synonyms

• Vitexin-4 inverted exclamation marka-o-glucoside
• 8-(((2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5736	57.36%
Caco-2	-	0.9266	92.66%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.5848	58.48%
OATP2B1 inhibitior	-	0.5562	55.62%
OATP1B1 inhibitior	+	0.8942	89.42%
OATP1B3 inhibitior	+	0.9434	94.34%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.6958	69.58%
P-glycoprotein inhibitior	-	0.5958	59.58%
P-glycoprotein substrate	-	0.7521	75.21%
CYP3A4 substrate	+	0.6218	62.18%
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	+	0.6774	67.74%
CYP inhibitory promiscuity	-	0.7526	75.26%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6848	68.48%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.9134	91.34%
Skin irritation	-	0.8255	82.55%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4004	40.04%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.8071	80.71%
skin sensitisation	-	0.9132	91.32%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.8519	85.19%
Acute Oral Toxicity (c)	IV	0.4763	47.63%
Estrogen receptor binding	+	0.8188	81.88%
Androgen receptor binding	+	0.7391	73.91%
Thyroid receptor binding	+	0.5421	54.21%
Glucocorticoid receptor binding	-	0.4803	48.03%
Aromatase binding	+	0.6940	69.40%
PPAR gamma	+	0.7505	75.05%
Honey bee toxicity	-	0.6377	63.77%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6250	62.50%
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	99.16%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.71%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.77%	89.00%
CHEMBL2581	P07339	Cathepsin D	94.65%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	93.94%	91.49%
CHEMBL242	Q92731	Estrogen receptor beta	92.91%	98.35%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.16%	99.15%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	90.75%	83.57%
CHEMBL3194	P02766	Transthyretin	89.79%	90.71%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.58%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.67%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.47%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	87.77%	94.73%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	85.72%	96.21%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.11%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.57%	97.09%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	82.20%	95.78%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.44%	91.71%
CHEMBL3922	P50579	Methionine aminopeptidase 2	81.39%	97.28%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.02%	95.56%

Plants that contains it

• Derris reticulata
• Eucalyptus ovata
• Gentiana arisanensis
• Gratiola officinalis
• Panzerina lanata
• Setaria italica
• Solanum dulcamara

Cross-Links

• PubChem: 57387656
• NPASS: NPC58950
• LOTUS: LTS0133354
• wikiData: Q104995373