Naringin

Details

• Internal ID: fd0456c7-8b5c-4272-99e6-1119252278ad
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: (2S)-7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=CC(=C4C(=O)CC(OC4=C3)C5=CC=C(C=C5)O)O)CO)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=CC(=C4C(=O)C[C@H](OC4=C3)C5=CC=C(C=C5)O)O)CO)O)O)O)O)O
• InChI: InChI=1S/C27H32O14/c1-10-20(32)22(34)24(36)26(37-10)41-25-23(35)21(33)18(9-28)40-27(25)38-13-6-14(30)19-15(31)8-16(39-17(19)7-13)11-2-4-12(29)5-3-11/h2-7,10,16,18,20-30,32-36H,8-9H2,1H3/t10-,16-,18+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1
• InChI Key: DFPMSGMNTNDNHN-ZPHOTFPESA-N
• Popularity: 1,247 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₂O₁₄
• Molecular Weight: 580.50 g/mol
• Exact Mass: 580.17920569 g/mol
• Topological Polar Surface Area (TPSA): 225.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): -1.17
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 6

Synonyms

• 10236-47-2
• Naringoside
• aurantiin
• (2S)-Naringin
• Naringenin 7-Rhamnoglucoside
• Naringenin 7-O-neohesperidoside
• UNII-N7TD9J649B
• N7TD9J649B
• CHEBI:28819
• Naringenin-7-beta-neohesperidoside
• EINECS 233-566-4
• 4'5-diOH-Flavone-7-rhgluc
• AI3-19008
• CHEMBL451532
• (2S)-7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
• DTXSID6022478
• NARINGENIN-7-RHAMNOGLUCOSIDE
• (S)-7-(((2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one
• 7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
• 4',5,7-Trihydroxyflavanone-7-rhamnoglucoside
• NARINGIN (USP-RS)
• NARINGIN [USP-RS]
• 5-Hydroxy-2-(4-hydroxyphenyl)-7-(2-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranosyloxy)-4-chromanon
• 7-(2-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyloxy)-2,3-dihydro-4',5,7-trihydroxyflavone
• Naringenin 7-O-alpha-L-rhamnosyl-(1->2)-beta-D-glucoside
• naringenin 7-O-(alpha-L-rhamnosyl-(1,2)-beta-D-glucoside)
• Naringenin 7-O-[alpha-L-rhamnosyl-(1->2)-beta-D-glucoside]
• C27H32O14
• MFCD00148888
• (2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside
• 4H-1-Benzopyran-4-one, 7-((2-O-(6-deoxy-alpha-L-mannapyranosyl)-beta-D-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl), (S)-
• Naringenine-7-rhamnosidoglucoside
• SR-01000736681
• naringenin-7-hesperidoside
• Naringenin 7-O-(alpha-L-rhamnosyl-(1->2)-beta-D-glucoside)
• Naringin extract
• Naringenin,(S)
• C27-H32-O14
• (S)-7-((2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)tetrahydro-2H-pyran-2-yloxy)-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one
• Naringenin Glycoside
• Naringin (Naringoside)
• NARINGIN [INCI]
• NARINGIN [MI]
• Prestwick0_000467
• Prestwick1_000467
• Prestwick2_000467
• Prestwick3_000467
• AURANTIIN [WHO-DD]
• SCHEMBL23432
• BSPBio_000574
• cid_25075
• MLS000069459
• BIDD:ER0262
• DivK1c_000247
• SPBio_002513
• BPBio1_000632
• cid_442428
• DTXCID302478
• GTPL4738
• MEGxp0_001877
• ACon1_000139
• HMS500M09
• KBio1_000247
• DFPMSGMNTNDNHN-ZPHOTFPESA-N
• NINDS_000247
• CITRUS NARINGININE [VANDF]
• HMS2231M18
• 4H-1-Benzopyran-4-one, 7-((2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-, (2S)-
• 4H-1-Benzopyran-4-one, 7-((2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-, (S)-
• HY-N0153
• BDBM50241582
• s2329
• AKOS016034302
• CCG-208591
• CS-5632
• IDI1_000247
• NCGC00142617-01
• NCGC00142617-02
• NCGC00142617-03
• AS-12929
• SMR000059108
• XN167836
• C09789
• A800566
• Q418469
• SR-01000736681-4
• SR-01000736681-5
• BRD-K02953697-001-09-2
• BRD-K02953697-002-03-3
• (2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-betaD-glucopyranoside
• (2S)-7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one
• (2S)-7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one
• (2S)-7-[(2S,4S,5S,3R,6R)-3-((2S,6S,3R,4R,5R)-3,4,5-trihydroxy-6-methyl(2H-3,4, 5,6-tetrahydropyran-2-yloxy))-4,5-dihydroxy-6-(hydroxymethyl)(2H-3,4,5,6-tetra hydropyran-2-yloxy)]-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one
• (2S)-7-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
• (S)-7-((2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-2H-pyran-2-yloxy)-tetrahydro-2H-pyran-2-yloxy)-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one
• 4H-1-Benzopyran-4-one,7-[[2-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-,(S)-
• 7-((2-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-2,3-DIHYDRO-5-HYDROXY-2-(4-HYDROXYPHENYL)-4H-1-BENZOPYRAN-4-ONE
• 7-[[2-O-(6-Deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-glucopyranosyl]oxy]-5-hydroxy-2(S)-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4777	47.77%
Caco-2	-	0.9102	91.02%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.9857	98.57%
Subcellular localzation	Mitochondria	0.6881	68.81%
OATP2B1 inhibitior	-	0.8517	85.17%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9552	95.52%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.4758	47.58%
P-glycoprotein inhibitior	-	0.9165	91.65%
P-glycoprotein substrate	-	0.6697	66.97%
CYP3A4 substrate	+	0.6479	64.79%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8479	84.79%
CYP3A4 inhibition	-	0.9358	93.58%
CYP2C9 inhibition	-	0.9271	92.71%
CYP2C19 inhibition	-	0.9330	93.30%
CYP2D6 inhibition	-	0.9643	96.43%
CYP1A2 inhibition	-	0.8830	88.30%
CYP2C8 inhibition	+	0.4936	49.36%
CYP inhibitory promiscuity	-	0.7188	71.88%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7023	70.23%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.9292	92.92%
Skin irritation	-	0.8192	81.92%
Skin corrosion	-	0.9626	96.26%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7001	70.01%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.9312	93.12%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.6977	69.77%
Acute Oral Toxicity (c)	III	0.5734	57.34%
Estrogen receptor binding	+	0.7739	77.39%
Androgen receptor binding	-	0.5890	58.90%
Thyroid receptor binding	+	0.5258	52.58%
Glucocorticoid receptor binding	-	0.4849	48.49%
Aromatase binding	+	0.5263	52.63%
PPAR gamma	+	0.7120	71.20%
Honey bee toxicity	-	0.6888	68.88%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5150	51.50%
Fish aquatic toxicity	+	0.8289	82.89%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1978	P11511	Cytochrome P450 19A1	5000 nM	IC50	PMID: 18462007
CHEMBL6089	P61088	Ubiquitin-conjugating enzyme E2 N	6662 nM; 5771 nM; 8695 nM	IC50; IC50; IC50	via CMAUP; via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.58%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.15%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.06%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.95%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.15%	89.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	92.44%	96.21%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.51%	86.33%
CHEMBL4208	P20618	Proteasome component C5	90.78%	90.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.23%	94.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	89.62%	97.36%
CHEMBL3401	O75469	Pregnane X receptor	89.33%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.00%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.63%	95.89%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	87.97%	94.80%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.87%	86.92%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.20%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.27%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.12%	99.17%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	82.21%	85.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.07%	99.23%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	80.86%	93.10%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.66%	90.71%
CHEMBL226	P30542	Adenosine A1 receptor	80.56%	95.93%

Plants that contains it

• Ageratum conyzoides
• Agnorhiza bolanderi
• Ailanthus integrifolia
• Anaxagorea crassipetala
• Araujia sericifera
• Arnica nevadensis
• Artemisia gmelinii
• Astragalus mongholicus
• Beyeria sulcata var. brevipes
• Bursaria spinosa
• Centaurea spinosa
• Chamaecytisus austriacus
• Chloranthus tianmushanensis
• Chromolaena odorata
• Chromolaena pulchella
• Cicer arietinum
• Citrus × aurantium
• Citrus deliciosa
• Citrus japonica
• Citrus latipes
• Citrus maxima
• Citrus medica
• Citrus trifoliata
• Coriandrum sativum
• Craibia grandiflora
• Crocus sativus
• Dendrosenecio kilimanjari
• Dipterocarpus alatus
• Drosera peltata
• Echinops amplexicaulis
• Euphorbia condylocarpa
• Ficus formosana
• Gardenia fosbergii
• Glycyrrhiza
• Hedysarum polybotrys
• Helianthus annuus
• Helianthus maximiliani
• Helianthus niveus
• Holarrhena pubescens
• Ilex affinis
• Isodon umbrosus
• Kaempferia pulchra
• Litogyne gariepina
• Medicago sativa
• Morus alba
• Odixia angusta
• Onopordum illyricum
• Origanum majoricum
• Podocarpus fasciculus
• Portulaca oleracea
• Prosopis glandulosa
• Prunus laurocerasus
• Prunus mume
• Pteris plumieri
• Pyrrosia serpens
• Quercus cerris
• Rheum officinale
• Rheum palmatum
• Rheum tanguticum
• Rhododendron dauricum
• Ribes nigrum
• Rosmarinus officinalis
• Salvia officinalis
• Scutellaria barbata
• Senecio squalidus
• Seriphidium cinum
• Sesbania punicea
• Simira eliezeriana
• Sorbus pallescens
• Stenostomum lucidum
• Styphnolobium japonicum
• Syzygium jambos
• Taxodium huegelii
• Tripterygium wilfordii
• Vitex madiensis
• Vitis vinifera

Cross-Links

• PubChem: 442428
• NPASS: NPC142860
• ChEMBL: CHEMBL451532
• LOTUS: LTS0165229
• wikiData: Q418469