4H-1-Benzopyran-4-one, 7-[[6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-, (S)-

Details

• Internal ID: 064e539b-5d96-42ee-818e-56035b227492
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-[3,4,5-trihydroxy-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]oxan-2-yl]oxy-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=CC(=C4C(=O)CC(OC4=C3)C5=CC(=C(C=C5)OC)O)O)O)O)O)O)O)O
• SMILES (Isomeric): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=CC(=C4C(=O)CC(OC4=C3)C5=CC(=C(C=C5)OC)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C28H34O15/c1-10-21(32)23(34)25(36)27(40-10)39-9-19-22(33)24(35)26(37)28(43-19)41-12-6-14(30)20-15(31)8-17(42-18(20)7-12)11-3-4-16(38-2)13(29)5-11/h3-7,10,17,19,21-30,32-37H,8-9H2,1-2H3
• InChI Key: QUQPHWDTPGMPEX-UHFFFAOYSA-N
• Popularity: 4,268 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₄O₁₅
• Molecular Weight: 610.60 g/mol
• Exact Mass: 610.18977037 g/mol
• Topological Polar Surface Area (TPSA): 234.00 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): -1.16
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

• Hesperitin-7-rhamnoglucoside
• NSC44184
• MFCD00075663
• Hesperetin, 7-(6-O-(6-deoxy-.alpha.-L-mannopyranosyl))-.beta.-D-glucopyranoside)
• Hesperetin, 7-[6-O-(6-deoxy-.alpha.-L-mannopyranosyl)]-.beta.-D-glucopyranoside)
• Hesperetin-7-O-rutinoside
• Usaf cf-3 f1 gluco rhamno
• SCHEMBL765367
• CHEMBL1535112
• SCHEMBL22946699
• DTXSID50859444
• HMS3370H06
• HMS3373M16
• HMS3656E03
• 4H-1-Benzopyran-4-one, 7-[[6-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-, (S)-
• AKOS024282619
• NCGC00017348-02
• NCGC00142526-01
• 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-{3,4,5-trihydroxy-6-[(3,4,5-trihydro xy-6-methyl(2H-3,4,5,6-tetrahydropyran-2-yloxy))methyl](2H-3,4,5,6-tetrahydrop yran-2-yloxy)}chroman-4-one
• AC-13980
• AC-34057
• SY059206
• B0005-464965
• Glucopyranoside, hesperetin-7(6-O-(6-deoxy-.alpha.-L-mannopyranosyl))-, .beta.-D-
• 5-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl 6-O-(6-deoxyhexopyranosyl)hexopyranoside
• 5-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 6-O-(6-deoxyhexopyranosyl)hexopyranoside, (S)- #
• WLN: T66 BO EVT&J CR CQ DO1& GQ IO- BT6OTJ CQ DQ EQ F1O- BT6OTJ CQ DQ EQ F1 GLUCO RHAMNO

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4777	47.77%
Caco-2	-	0.8816	88.16%
Blood Brain Barrier	-	0.9250	92.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6902	69.02%
OATP2B1 inhibitior	-	0.8556	85.56%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7312	73.12%
P-glycoprotein inhibitior	-	0.9166	91.66%
P-glycoprotein substrate	-	0.5059	50.59%
CYP3A4 substrate	+	0.6304	63.04%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8428	84.28%
CYP3A4 inhibition	-	0.8619	86.19%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.5841	58.41%
CYP inhibitory promiscuity	-	0.6670	66.70%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6995	69.95%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.9143	91.43%
Skin irritation	-	0.8249	82.49%
Skin corrosion	-	0.9594	95.94%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7299	72.99%
Micronuclear	+	0.7492	74.92%
Hepatotoxicity	-	0.9000	90.00%
skin sensitisation	-	0.9436	94.36%
Respiratory toxicity	-	0.7778	77.78%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	-	0.6625	66.25%
Nephrotoxicity	-	0.7217	72.17%
Acute Oral Toxicity (c)	III	0.6904	69.04%
Estrogen receptor binding	+	0.7993	79.93%
Androgen receptor binding	-	0.8129	81.29%
Thyroid receptor binding	+	0.5588	55.88%
Glucocorticoid receptor binding	+	0.5657	56.57%
Aromatase binding	-	0.4857	48.57%
PPAR gamma	+	0.7229	72.29%
Honey bee toxicity	-	0.7222	72.22%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5549	55.49%
Fish aquatic toxicity	+	0.8477	84.77%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	31622.8 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	99.06%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.63%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.02%	94.00%
CHEMBL2581	P07339	Cathepsin D	94.61%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.61%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.38%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.27%	89.00%
CHEMBL4208	P20618	Proteasome component C5	91.35%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.98%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.77%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.44%	85.14%
CHEMBL3714130	P46095	G-protein coupled receptor 6	86.46%	97.36%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.97%	99.17%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	85.56%	96.21%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	84.62%	95.78%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.62%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	84.49%	94.73%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	84.44%	94.80%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.37%	99.23%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.72%	86.92%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.85%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.63%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.35%	96.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.04%	90.71%

Plants that contains it

• Calicotome villosa
• Cirsium arvense
• Citrus × aurantium
• Citrus deliciosa
• Citrus maxima
• Citrus medica
• Citrus trifoliata
• Codonopsis pilosula
• Cyclopia falcata
• Flindersia acuminata
• Flindersia collina
• Flindersia laevicarpa
• Flindersia xanthoxyla
• Forsythia suspensa
• Forsythia viridissima
• Grona styracifolia
• Hypericum perforatum
• Lobelia chinensis
• Mentha × piperita
• Mentha arvensis
• Mentha canadensis
• Mentha longifolia
• Nepeta tenuifolia
• Perovskia atriplicifolia
• Philotheca rhomboidea
• Polygonatum odoratum
• Portulaca oleracea
• Prunus mume
• Reynoutria multiflora
• Rheum officinale
• Rheum palmatum
• Rheum tanguticum
• Rosmarinus officinalis
• Scutellaria barbata
• Sigesbeckia glabrescens
• Sigesbeckia pubescens
• Styphnolobium japonicum
• Taraxacum coreanum
• Taraxacum mongolicum
• Taraxacum officinale
• Taraxacum platycarpum
• Taraxacum sinicum
• Thymus quinquecostatus
• Thymus vulgaris
• Verbascum phlomoides
• Zanthoxylum avicennae
• Zanthoxylum bungeanum
• Zanthoxylum dipetalum
• Zanthoxylum gilletii
• Zanthoxylum leprieurii
• Zanthoxylum schinifolium
• Zanthoxylum zanthoxyloides

Cross-Links

• PubChem: 3594
• NPASS: NPC44328
• ChEMBL: CHEMBL1535112
• LOTUS: LTS0011065
• wikiData: Q104196220