5,7-Dihydroxy-2-(4-hydroxyphenyl)-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-(3,4,5-trihydroxyoxan-2-yl)chromen-4-one

Details

• Internal ID: 15b77aa3-6bd4-4bb6-876d-c9deb9356541
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides > Flavonoid 8-C-glycosides
• IUPAC Name: 5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-(3,4,5-trihydroxyoxan-2-yl)chromen-4-one
• SMILES (Canonical): C1C(C(C(C(O1)C2=C3C(=C(C(=C2O)C4C(C(C(C(O4)CO)O)O)O)O)C(=O)C=C(O3)C5=CC=C(C=C5)O)O)O)O
• SMILES (Isomeric): C1C(C(C(C(O1)C2=C3C(=C(C(=C2O)C4C(C(C(C(O4)CO)O)O)O)O)C(=O)C=C(O3)C5=CC=C(C=C5)O)O)O)O
• InChI: InChI=1S/C26H28O14/c27-6-13-18(32)21(35)23(37)26(40-13)15-19(33)14-10(29)5-12(8-1-3-9(28)4-2-8)39-24(14)16(20(15)34)25-22(36)17(31)11(30)7-38-25/h1-5,11,13,17-18,21-23,25-28,30-37H,6-7H2
• InChI Key: MMDUKUSNQNWVET-UHFFFAOYSA-N
• Popularity: 22 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₈O₁₄
• Molecular Weight: 564.50 g/mol
• Exact Mass: 564.14790556 g/mol
• Topological Polar Surface Area (TPSA): 247.00 Ų
• XlogP: -2.20
• Atomic LogP (AlogP): -1.75
• H-Bond Acceptor: 14
• H-Bond Donor: 10
• Rotatable Bonds: 4

Synonyms

• 5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-(3,4,5-trihydroxyoxan-2-yl)chromen-4-one
• 207461-10-7
• Vicenin -3
• 51938-32-0
• Compound NP-000004
• MLS000876755
• MEGxp0_000003
• CHEMBL1537012
• ACon1_001811
• CHEBI:139467
• HMS2271I13
• AKOS040740192
• NCGC00180115-01
• SMR000440577
• FT-0777369
• 6-b-D-Glucopyranosyl-8-b-D-ribopyranosylapigenin
• 6-beta-D-Glucopyranosyl-8-beta-D-ribopyranosylapigenin
• BRD-A73892391-001-01-4

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6857	68.57%
Caco-2	-	0.9187	91.87%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.4570	45.70%
OATP2B1 inhibitior	-	0.5523	55.23%
OATP1B1 inhibitior	+	0.7874	78.74%
OATP1B3 inhibitior	+	0.9676	96.76%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.6452	64.52%
P-glycoprotein inhibitior	-	0.5932	59.32%
P-glycoprotein substrate	-	0.6583	65.83%
CYP3A4 substrate	+	0.6172	61.72%
CYP2C9 substrate	-	0.6194	61.94%
CYP2D6 substrate	-	0.8416	84.16%
CYP3A4 inhibition	-	0.8741	87.41%
CYP2C9 inhibition	-	0.9567	95.67%
CYP2C19 inhibition	-	0.9398	93.98%
CYP2D6 inhibition	-	0.9294	92.94%
CYP1A2 inhibition	-	0.9102	91.02%
CYP2C8 inhibition	+	0.6484	64.84%
CYP inhibitory promiscuity	-	0.8877	88.77%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6898	68.98%
Eye corrosion	-	0.9945	99.45%
Eye irritation	-	0.8879	88.79%
Skin irritation	-	0.7949	79.49%
Skin corrosion	-	0.9607	96.07%
Ames mutagenesis	+	0.6666	66.66%
Human Ether-a-go-go-Related Gene inhibition	+	0.6796	67.96%
Micronuclear	+	0.6459	64.59%
Hepatotoxicity	-	0.7196	71.96%
skin sensitisation	-	0.8677	86.77%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.8903	89.03%
Acute Oral Toxicity (c)	III	0.4064	40.64%
Estrogen receptor binding	+	0.7228	72.28%
Androgen receptor binding	+	0.7345	73.45%
Thyroid receptor binding	-	0.5268	52.68%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	+	0.6166	61.66%
PPAR gamma	+	0.7221	72.21%
Honey bee toxicity	-	0.7506	75.06%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	-	0.4350	43.50%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2392	P06746	DNA polymerase beta	17782.8 nM	Potency	via CMAUP
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	4466.8 nM	Potency	via CMAUP
CHEMBL2608	P10253	Lysosomal alpha-glucosidase	28183.8 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.64%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.55%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.09%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.74%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.26%	97.09%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	90.40%	89.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.00%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.03%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	86.83%	94.73%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.44%	90.71%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	86.09%	95.83%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.37%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.10%	94.45%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	83.88%	85.11%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.84%	86.92%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	83.49%	93.10%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	83.35%	91.71%
CHEMBL220	P22303	Acetylcholinesterase	82.98%	94.45%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	82.77%	95.64%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	81.33%	80.33%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.17%	96.21%

Plants that contains it

• Achillea collina
• Achillea roseo-alba
• Artemisia annua
• Carlina corymbosa
• Centaurea melitensis
• Cydonia oblonga
• Eleusine indica
• Glycyrrhiza glabra
• Glycyrrhiza inflata
• Gratiola officinalis
• Iris domestica
• Linum grandiflorum
• Liparis condylobulbon
• Neoraputia paraensis
• Nervilia fordii
• Oryza sativa
• Salvia blepharophylla
• Scleropyrum pentandrum
• Seriphidium herba-alba
• Trichophorum cespitosum
• Vitex lucens

Cross-Links

• PubChem: 3550102
• NPASS: NPC326592
• ChEMBL: CHEMBL1537012
• LOTUS: LTS0218423
• wikiData: Q104171826