Hesperidin

Details

• Internal ID: e8029768-9f52-4424-b7c1-91c6f88e3236
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: (2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-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): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=CC(=C4C(=O)C[C@H](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/t10-,17-,19+,21-,22+,23+,24-,25+,26+,27+,28+/m0/s1
• InChI Key: QUQPHWDTPGMPEX-QJBIFVCTSA-N
• Popularity: 1,922 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

• 520-26-3
• Cirantin
• Hesperidoside
• Hesperidine
• Hesper bitabs
• Hesperetin 7-rhamnoglucoside
• Hesperetin 7-rutinoside
• Hesperetin-rutinosid
• Ciratin
• Hesperidin, (2S)-
• (S)-(-)-Hesperidin
• USAF CF-3
• Hesperidin, (S)-(-)-
• NSC 44184
• CCRIS 3940
• EINECS 208-288-1
• (2S)-Hesperidin
• UNII-E750O06Y6O
• BRN 0075140
• DIOSVEIN
• Hesperetin-7-O-rhamnoglucoside
• DTXSID9044328
• Hesperetin-7-rutinoside
• CHEBI:28775
• E750O06Y6O
• Hesperetin 7-O-rutinoside
• Hesperitin-7-rhamnoglucoside
• (2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-2,3-dihydrochromen-4-one
• 3',5'-Dihydroxy-4'-methoxy-7-rutinosyloxyflavan-4-on
• MLS001304066
• DTXCID7024328
• EC 208-288-1
• 5-18-05-00218 (Beilstein Handbook Reference)
• Hesperidin (JAN)
• Hesperetin, 7-(6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside)
• NSC-44184
• (2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside
• (S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)chroman-4-one
• 4H-1-Benzopyran-4-one, 7-((6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,3-dihydo-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-, (S)-
• 5-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-((6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranosyl)oxy)-4-chromanon
• 7-((6-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one, (S)-
• 7-(6-O-Desoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyloxy)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-chromanon
• SMR000718775
• HESPERIDIN [JAN]
• MFCD00075663
• Glucopyranoside, hesperetin-7 6-O-(6-deoxy-alpha-L-mannopyranosyl)-, beta-D-
• HESPERIDIN (MART.)
• HESPERIDIN [MART.]
• HESPERIDIN (USP-RS)
• HESPERIDIN [USP-RS]
• (2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one
• (s)-7-[[6-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4h-1-benzopyran-4-one
• 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)-
• Aurantiamarin (Methyl Hesperidin)
• 3',5'-DIHYDROXY-4'-METHOXY-7-RUTINOSYLOXYFLAVAN-4-ONE
• hesperetin 7-(6-O-alpha-L-rhamnopyranosyl)-beta-D-glucopyranoside
• NSC44184
• Hesperidin 2S
• 2S, Hesperidin
• (2S)-5-hydroxy-2-(3-hydroxy-4-methoxy-phenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chroman-4-one
• 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)-, (2S)-
• Hesperitin-7-rutinoside
• Hesperetin 7 Rutinoside
• SR-01000799145
• Hesperetin 7 Rhamnoglucoside
• Hesperidina
• 7-Rhamnoglucoside, Hesperetin
• Hesperidin,(S)
• NCGC00016481-01
• (2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 6-O-(6-deoxy-a-L-mannopyranosyl)-ss-D-glucopyranoside
• (2S)-7-[[6-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one (Hesperidin)
• (S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)methyl)tetrahydro-2H-pyran-2-yloxy)chroman-4-one
• CAS-520-26-3
• Hesperetin Glycoside
• C28H34O15
• HESPERIDEN Powder
• Hesperidin, >=80%
• HESPERIDIN [MI]
• DIOSMIN [NDI]
• Prestwick3_000400
• HESPERIDIN [INCI]
• HESPERIDIN [VANDF]
• D0I9HF
• D0N6KM
• HESPERIDIN [WHO-DD]
• SCHEMBL94586
• BSPBio_000619
• cid_10621
• Hesperidin, analytical standard
• BPBio1_000681
• CHEMBL449317
• NDI 590 [FDMS]
• BCBcMAP01_000136
• BDBM61776
• NDI 590
• 2H-pyran-2-yloxy)chroman-4-one
• QUQPHWDTPGMPEX-QJBIFVCTSA-N
• HMS2096O21
• HMS2233I03
• HMS3713O21
• 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)-
• Tox21_110448
• s2309
• AKOS015895450
• CCG-208580
• CS-5631
• CS-O-01636
• DB04703
• KS-5308
• C28-H34-O15
• SMP1_000149
• NCGC00179501-01
• HY-15337
• LS-74767
• AB00513829
• H0049
• C09755
• D01038
• (S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-
• EN300-7419024
• Q385937
• Hesperidin, primary pharmaceutical reference standard
• methyltetrahydro-2H-pyran-2-yloxy)methyl)tetrahydro-
• SR-01000799145-4
• SR-01000799145-5
• SR-01000799145-7
• 7-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-
• BRD-K38903228-001-02-8
• BRD-K38903228-001-13-5
• Hesperidin, European Pharmacopoeia (EP) Reference Standard
• Hesperidin, Pharmaceutical Secondary Standard; Certified Reference Material
• Flavanone, 3',5,7-trihydroxy-4'-methoxy-, 7-(6-O-alpha-L-rhamnosyl-D-glucoside)
• (2S)-2-(4-methoxy-3-oxidanyl-phenyl)-7-[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5R,6S)-6-methyl-3,4,5-tris(oxidanyl)oxan-2-yl]oxymethyl]-3,4,5-tris(oxidanyl)oxan-2-yl]oxy-5-oxidanyl-2,3-dihydrochromen-4-one
• (2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-2-oxanyl]oxymethyl]-2-oxanyl]oxy]-3,4-dihydro-2H-1-benzopyran-4-one
• (2S)-7-((6-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-2,3-DIHYDRO-5-HYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)-4H-1-BENZOPYRAN-4-ONE
• (2S)-7-((6-O-(6-DEOXY-alpha-L-MANNOPYRANOSYL)-beta-D-GLUCOPYRANOSYL)OXY)-2,3-DIHYDRO-5-HYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)-4H-1-BENZOPYRAN-4-ONE
• (S)-7-[[6-O-(6-Deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one
• 4H-1-benzopirano-4-ona, 7-[[6-O-(6-deoxi-alfa-L-manopiranosil)-beta-D-glucopiranosil] oxi]-2,3-dihidro-5-hidroxi-2-(3-hidroxi-4-metoxifenil)-, (2S)-
• 4H-1-BENZOPYRAN-4-ONE, 7-((6-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-2,3-DIHYDO-5-HYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)-, (S)-
• 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)-, (2S)-
• 5-HYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)-7-((6-O-.ALPHA.-L-RHAMNOPYRANOSYL-.BETA.-D-GLUCOPYRANOSYL)OXY)-4-CHROMANON

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
CHEMBL1795098	Q9GZU7	Carboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 1	20733 nM	IC50	via CMAUP
CHEMBL2392	P06746	DNA polymerase beta	44668.4 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

• Aesculus turbinata
• Agathosma betulina
• Agnorhiza bolanderi
• Allium fistulosum
• Alnus alnobetula
• Anaxagorea crassipetala
• Araujia sericifera
• Argyreia nervosa
• Arnica nevadensis
• Artemisia capillaris
• Artemisia gmelinii
• Artocarpus styracifolius
• Asterolasia squamuligera
• Baccharis magellanica
• Betula pendula
• Beyeria sulcata var. brevipes
• Boronia inconspicua
• Bursaria spinosa
• Calicotome villosa
• Camchaya loloana
• Catharanthus roseus
• Chloranthus tianmushanensis
• Chromolaena odorata
• Chromolaena pulchella
• Chrysanthemum morifolium
• Cinnamomum chekiangense
• Cirsium arvense
• Cirsium arvense var. integrifolium
• Citrus × aurantium
• Citrus deliciosa
• Citrus hystrix
• Citrus maxima
• Citrus medica
• Citrus trifoliata
• Clinopodium laxiflorum
• Codonopsis pilosula
• Craibia grandiflora
• Cyanthillium cinereum
• Cyclopia falcata
• Dendrobium moniliforme
• Dendrosenecio kilimanjari
• Dimorphotheca fruticosa
• Dipterocarpus alatus
• Dorstenia mannii
• Drosera peltata
• Drummondita calida
• Echinops amplexicaulis
• Eriostemon cynobiformis
• Erysimum siliculosum
• Eschenbachia japonica
• Euphrasia stricta
• Ficus formosana
• Flindersia acuminata
• Flindersia collina
• Flindersia laevicarpa
• Flindersia xanthoxyla
• Forsythia giraldiana
• Forsythia suspensa
• Forsythia viridissima
• Gardenia fosbergii
• Glinus oppositifolius
• Grona styracifolia
• Humulus lupulus
• Hypericum perforatum
• Hypericum reflexum
• Ilex affinis
• Ipomoea nil
• Isodon umbrosus
• Kaempferia pulchra
• Kaempferia rotunda
• Krameria erecta
• Litogyne gariepina
• Lobelia chinensis
• Markhamia stipulata
• Mentha × piperita
• Mentha arvensis
• Mentha canadensis
• Mentha longifolia
• Moringa oleifera
• Myrtus communis
• Nepeta tenuifolia
• Nicotiana alata
• Odixia angusta
• Perovskia atriplicifolia
• Philotheca rhomboidea
• Philotheca tomentella
• Pilocarpus trachylophus
• Pluchea dioscoridis
• Polygonatum odoratum
• Portulaca oleracea
• Prosopis glandulosa
• Prunus laurocerasus
• Prunus mume
• Pteris plumieri
• Pyrola rotundifolia
• Quercus cerris
• Reynoutria multiflora
• Rheum officinale
• Rheum palmatum
• Rheum tanguticum
• Rosmarinus officinalis
• Rubus chingii
• Salvia officinalis
• Scutellaria barbata
• Senecio sandersonii
• Senecio squalidus
• Seriphidium cinum
• Sesbania punicea
• Sideritis soluta
• Sideritis trojana
• Sidneya tenuifolia
• Sigesbeckia glabrescens
• Sigesbeckia pubescens
• Simira eliezeriana
• Sorbus pallescens
• Stenostomum lucidum
• Stevia alpina
• Styphnolobium japonicum
• Swertia diluta
• Taraxacum coreanum
• Taraxacum mongolicum
• Taraxacum officinale
• Taraxacum platycarpum
• Taraxacum sinicum
• Taxodium huegelii
• Tetradium daniellii
• Thymus quinquecostatus
• Thymus vulgaris
• Valeriana officinalis
• Verbascum phlomoides
• Vinca minor
• Viola arvensis
• Vitex madiensis
• Zanthoxylum avicennae
• Zanthoxylum bungeanum
• Zanthoxylum dipetalum
• Zanthoxylum gilletii
• Zanthoxylum nitidum
• Zanthoxylum rhoifolium
• Zanthoxylum scandens
• Zanthoxylum schinifolium
• Zanthoxylum sprucei
• Zanthoxylum zanthoxyloides
• Ziziphus jujuba var. spinosa

Cross-Links

• PubChem: 10621
• NPASS: NPC79056
• ChEMBL: CHEMBL449317
• LOTUS: LTS0261835
• wikiData: Q385937