(2R)-7-hydroxy-2-(4-hydroxyphenyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one

Details

• Internal ID: 22a41b54-94f4-4d77-b8cd-ecc09fb796e6
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides
• IUPAC Name: (2R)-7-hydroxy-2-(4-hydroxyphenyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
• SMILES (Canonical): C1C(OC2=C(C1=O)C(=CC(=C2)O)OC3C(C(C(C(O3)CO)O)O)O)C4=CC=C(C=C4)O
• SMILES (Isomeric): C1[C@@H](OC2=C(C1=O)C(=CC(=C2)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C4=CC=C(C=C4)O
• InChI: InChI=1S/C21H22O10/c22-8-16-18(26)19(27)20(28)21(31-16)30-15-6-11(24)5-14-17(15)12(25)7-13(29-14)9-1-3-10(23)4-2-9/h1-6,13,16,18-24,26-28H,7-8H2/t13-,16-,18-,19+,20-,21-/m1/s1
• InChI Key: MFQIWHVVFBCURA-KYSZGLPYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₁₀
• Molecular Weight: 434.40 g/mol
• Exact Mass: 434.12129689 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.02
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

• 19253-00-0
• Naringenin 5-O-beta-D-glucopyranoside
• (2R)-7-hydroxy-2-(4-hydroxyphenyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
• CHEMBL2152489
• DTXSID80967364
• (2R)-(-)-Naringenin 5-O-|A-D-glucopyranoside
• 7-Hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-5-yl hexopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5116	51.16%
Caco-2	-	0.9349	93.49%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.9143	91.43%
Subcellular localzation	Mitochondria	0.6068	60.68%
OATP2B1 inhibitior	-	0.5685	56.85%
OATP1B1 inhibitior	+	0.9240	92.40%
OATP1B3 inhibitior	+	0.9265	92.65%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.6483	64.83%
P-glycoprotein inhibitior	-	0.7095	70.95%
P-glycoprotein substrate	-	0.8794	87.94%
CYP3A4 substrate	+	0.5808	58.08%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8143	81.43%
CYP3A4 inhibition	-	0.9193	91.93%
CYP2C9 inhibition	-	0.9296	92.96%
CYP2C19 inhibition	-	0.9289	92.89%
CYP2D6 inhibition	-	0.9513	95.13%
CYP1A2 inhibition	-	0.9084	90.84%
CYP2C8 inhibition	-	0.5600	56.00%
CYP inhibitory promiscuity	-	0.7728	77.28%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7144	71.44%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.8812	88.12%
Skin irritation	-	0.8036	80.36%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	-	0.5454	54.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6020	60.20%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.9122	91.22%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.6193	61.93%
Acute Oral Toxicity (c)	III	0.4045	40.45%
Estrogen receptor binding	+	0.7159	71.59%
Androgen receptor binding	+	0.5459	54.59%
Thyroid receptor binding	+	0.5256	52.56%
Glucocorticoid receptor binding	+	0.5576	55.76%
Aromatase binding	+	0.6009	60.09%
PPAR gamma	+	0.7497	74.97%
Honey bee toxicity	-	0.7400	74.00%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6049	60.49%
Fish aquatic toxicity	+	0.8218	82.18%

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	99.01%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.75%	97.09%
CHEMBL2581	P07339	Cathepsin D	94.50%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.67%	96.09%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	92.20%	96.21%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.44%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.11%	94.45%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.49%	86.92%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.32%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.65%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.61%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	85.60%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.58%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.58%	95.89%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	83.88%	95.78%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	82.53%	85.00%
CHEMBL4208	P20618	Proteasome component C5	82.04%	90.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.64%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.90%	99.23%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	80.31%	90.93%

Plants that contains it

• Abies nephrolepis
• Alstonia rostrata
• Asteriscus aquaticus
• Betula pendula subsp. mandshurica
• Capparis spinosa var. ovata
• Charpentiera obovata
• Cinnamomum subavenium
• Croton montevidensis
• Datisca glomerata
• Dioscorea olfersiana
• Ecballium elaterium
• Elaeodendron papillosum
• Helichrysum arenarium
• Helichrysum armenium
• Helichrysum auriceps
• Hubertia tomentosa
• Leionema dentatum
• Ligustrum obtusifolium
• Lotus ucrainicus
• Myristica cagayanensis
• Nothofagus fusca
• Phyllanthus oligospermus
• Polygonum pubescens
• Prunus persica
• Pseudowintera colorata
• Quercus imbricaria
• Rhodiola crenulata
• Scrophularia koelzii
• Spiracantha cornifolia
• Strychnos nux-vomica
• Vaccinium vitis-idaea
• Vincetoxicum tanakae

Cross-Links

• PubChem: 3083618
• NPASS: NPC72649
• ChEMBL: CHEMBL2152489
• LOTUS: LTS0098718
• wikiData: Q82949957