(2S,5S)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: db1032fe-1ae4-4d5a-a7f2-88f2f94791f6
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Anthocyanins > Anthocyanidin-3-O-glycosides
• IUPAC Name: (2S,5S)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): C1=CC(=C(C=C1C2=[O+]C3=CC(=CC(=C3C=C2OC4C(C(C(C(O4)CO)O)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C2=[O+]C3=CC(=CC(=C3C=C2O[C@H]4C(C([C@@H](C(O4)CO)O)O)O)O)O)O)O
• InChI: InChI=1S/C21H20O11/c22-7-16-17(27)18(28)19(29)21(32-16)31-15-6-10-12(25)4-9(23)5-14(10)30-20(15)8-1-2-11(24)13(26)3-8/h1-6,16-19,21-22,27-29H,7H2,(H3-,23,24,25,26)/p+1/t16?,17-,18?,19?,21-/m1/s1
• InChI Key: RKWHWFONKJEUEF-NPUISUJTSA-O
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₁O₁₁+
• Molecular Weight: 449.40 g/mol
• Exact Mass: 449.10838648 g/mol
• Topological Polar Surface Area (TPSA): 181.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): 0.38
• H-Bond Acceptor: 10
• H-Bond Donor: 8
• Rotatable Bonds: 4

Synonyms

• LMPK12010110

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8136	81.36%
Caco-2	-	0.8921	89.21%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Nucleus	0.4412	44.12%
OATP2B1 inhibitior	+	0.5876	58.76%
OATP1B1 inhibitior	+	0.9309	93.09%
OATP1B3 inhibitior	+	0.9404	94.04%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.7183	71.83%
P-glycoprotein inhibitior	-	0.6860	68.60%
P-glycoprotein substrate	-	0.8592	85.92%
CYP3A4 substrate	+	0.5715	57.15%
CYP2C9 substrate	-	0.8060	80.60%
CYP2D6 substrate	-	0.8268	82.68%
CYP3A4 inhibition	-	0.9550	95.50%
CYP2C9 inhibition	-	0.9002	90.02%
CYP2C19 inhibition	-	0.8426	84.26%
CYP2D6 inhibition	-	0.9191	91.91%
CYP1A2 inhibition	-	0.8856	88.56%
CYP2C8 inhibition	+	0.8164	81.64%
CYP inhibitory promiscuity	-	0.7819	78.19%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6532	65.32%
Eye corrosion	-	0.9919	99.19%
Eye irritation	-	0.7073	70.73%
Skin irritation	-	0.8047	80.47%
Skin corrosion	-	0.9630	96.30%
Ames mutagenesis	-	0.5137	51.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.4694	46.94%
Micronuclear	+	0.6359	63.59%
Hepatotoxicity	-	0.8321	83.21%
skin sensitisation	-	0.9067	90.67%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.7457	74.57%
Acute Oral Toxicity (c)	III	0.4439	44.39%
Estrogen receptor binding	+	0.7517	75.17%
Androgen receptor binding	+	0.6917	69.17%
Thyroid receptor binding	+	0.5977	59.77%
Glucocorticoid receptor binding	+	0.7298	72.98%
Aromatase binding	+	0.7175	71.75%
PPAR gamma	+	0.7415	74.15%
Honey bee toxicity	-	0.7367	73.67%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5449	54.49%
Fish aquatic toxicity	+	0.7666	76.66%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL284	P27487	Dipeptidyl peptidase IV	420 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.30%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	96.01%	91.49%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	94.22%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.22%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.14%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.39%	94.00%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	88.82%	95.78%
CHEMBL2581	P07339	Cathepsin D	88.59%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.42%	99.17%
CHEMBL3194	P02766	Transthyretin	86.69%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.35%	86.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.75%	92.94%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	84.66%	89.62%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.24%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.52%	97.09%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.60%	95.83%

Plants that contains it

• Acer opalus
• Acer platanoides
• Achillea crithmifolia
• Ajuga reptans
• Allium cepa
• Allium sativum
• Allium schoenoprasum
• Amelanchier alnifolia
• Amelanchier bartramiana
• Aronia melanocarpa
• Berberis vulgaris
• Brownea ariza
• Camellia polyodonta
• Camellia sinensis
• Chaenomeles speciosa
• Chrysanthemum indicum
• Cichorium intybus
• Cichorium pumilum
• Clarkia speciosa
• Cornus suecica
• Cyclamen persicum
• Cynomorium coccineum
• Dacrycarpus dacrydioides
• Daucus carota
• Dracula chimaera
• Dyckia niederleinii
• Echinacea pallida
• Erythrina fusca
• Euphorbia tirucalli
• Eurya japonica
• Fragaria × ananassa
• Geranium sylvaticum
• Glycine max
• Gossypium hirsutum
• Helianthus annuus
• Hibiscus syriacus
• Keckiella lemmonii
• Litchi chinensis
• Lobelia chinensis
• Malus sylvestris
• Morus alba
• Oenothera affinis
• Oenothera odorata
• Oryza sativa
• Oxalis reclinata
• Paeonia suffruticosa
• Penstemon serrulatus
• Petunia exserta
• Phalaris arundinacea
• Phaseolus vulgaris
• Phleum pratense
• Phragmites australis
• Pieris japonica
• Pistacia lentiscus
• Pistia stratiotes
• Podocarpus totara
• Populus deltoides
• Populus tremula
• Prunus cerasus
• Prunus domestica
• Prunus serotina
• Punica granatum
• Puya coerulea
• Rheum rhabarbarum
• Rheum tataricum
• Rhododendron simsii
• Ribes nigrum
• Rosa platyacantha
• Rubus chingii
• Rubus coreanus
• Rubus idaeus
• Sambucus canadensis
• Sambucus nigra
• Sanguisorba officinalis
• Secale cereale
• Speranskia tuberculata
• Tanacetum cinerariifolium
• Tradescantia pallida
• Tricyrtis formosana
• Vaccinium angustifolium
• Vaccinium arboreum
• Vaccinium corymbosum
• Vaccinium macrocarpon
• Vaccinium myrtillus
• Vaccinium oxycoccos
• Vaccinium uliginosum
• Visnea mocanera
• Vitis vinifera
• Zea mays

Cross-Links

• PubChem: 44256715
• NPASS: NPC164614
• LOTUS: LTS0221391
• wikiData: Q104252558