Neohesperidin

Details

• Internal ID: fe337dd1-f2d3-497c-b3e4-58f94932c7fe
• 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-(3-hydroxy-4-methoxyphenyl)-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)OC)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)OC)O)O)CO)O)O)O)O)O
• InChI: InChI=1S/C28H34O15/c1-10-21(33)23(35)25(37)27(39-10)43-26-24(36)22(34)19(9-29)42-28(26)40-12-6-14(31)20-15(32)8-17(41-18(20)7-12)11-3-4-16(38-2)13(30)5-11/h3-7,10,17,19,21-31,33-37H,8-9H2,1-2H3/t10-,17-,19+,21-,22+,23+,24-,25+,26+,27-,28+/m0/s1
• InChI Key: ARGKVCXINMKCAZ-UZRWAPQLSA-N
• Popularity: 171 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: -0.50
• Atomic LogP (AlogP): -1.16
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

• 13241-33-3
• OA5C88H3L0
• CHEBI:59016
• Hesperetin 7-O-neohesperidoside
• (S)-7-(((2-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
• FEMA NO. 4799
• DTXSID60927668
• (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-(3-hydroxy-4-methoxyphenyl)-2,3-dihydrochromen-4-one
• (2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 2-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranoside
• 4H-1-Benzopyran-4-one, 7-((2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-, (S)-
• (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-(3-hydroxy-4-methoxyphenyl)-2,3-dihydrochromen-4-one
• RefChem:165257
• GlyTouCan:G20283LL
• DTXCID101527365
• G20283LL
• 236-216-9
• 7-(4,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl)oxy-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydrochromen-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-(3-hydroxy-4-methoxyphenyl)-, (2S)-
• (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-(3-hydroxy-4-methoxyphenyl)chroman-4-one
• NSC 31048
• Neohesperdin
• Neohesperidin (Standard)
• AC1L9CTW
• Neohesperidin, >=90%
• (2S)-NEOHESPERIDIN
• UNII-OA5C88H3L0
• Hesperetin-7-neohesperidoside
• SCHEMBL121675
• NEOHESPERIDIN [USP-RS]
• CHEMBL506398
• orb1305092
• SCHEMBL31514531
• HY-N0101R
• Neohesperidin, analytical standard
• HY-N0101
• MSK40166
• EINECS 236-216-9
• AKOS015899387
• CS-6413
• ON08130
• BRN 0074945
• SMP1_000209
• AS-75238
• C09806
• 5-18-05-00219 (Beilstein Handbook Reference)
• Q18609455
• Neohesperidin, United States Pharmacopeia (USP) Reference Standard
• (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-(3-hydroxy-4-methoxy-phenyl)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-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
• (S)-4 inverted exclamation marka-Methoxy-3 inverted exclamation marka,5,7-trihydroxyflavanone-7-[2-O-(|A-L-rhamnopyranosyl)-|A-D-glucopyranoside]
• 4H-1-Benzopyran-4-one, 2,3-dihydro-7-((2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-, (S)-
• 4H-1-BENZOPYRAN-4-ONE, 7-((2-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-2,3-DIHYDRO-5-HYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)-, (2S)-
• 4H-1-BENZOPYRAN-4-ONE, 7-((2-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-2,3-DIHYDRO-5-HYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)-, (S)-
• 4H-1-Benzopyran-4-one, 7-[[2-O-(6-deoxy-|A-L-mannopyranosyl)-|A-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-, (2S)-
• FLAVANONE, 3',5,7-TRIHYDROXY-4'-METHOXY-, 7-(2-O-.ALPHA.-L-RHAMNOPYRANOSYL-.BETA.-D-GLUCOPYRANOSIDE)
• Hesperetin-7-O-neohesperidoside;3',5,7-Trihydroxy-4'-methoxyflavanone-7-O-(2-O-?-L-rhamnopyranosyl)-?-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5074	50.74%
Caco-2	-	0.8912	89.12%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.9571	95.71%
Subcellular localzation	Mitochondria	0.6238	62.38%
OATP2B1 inhibitior	-	0.8551	85.51%
OATP1B1 inhibitior	+	0.9442	94.42%
OATP1B3 inhibitior	+	0.9678	96.78%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.6196	61.96%
P-glycoprotein inhibitior	-	0.8224	82.24%
P-glycoprotein substrate	-	0.5386	53.86%
CYP3A4 substrate	+	0.6590	65.90%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8479	84.79%
CYP3A4 inhibition	-	0.8862	88.62%
CYP2C9 inhibition	-	0.9258	92.58%
CYP2C19 inhibition	-	0.9329	93.29%
CYP2D6 inhibition	-	0.9457	94.57%
CYP1A2 inhibition	-	0.9089	90.89%
CYP2C8 inhibition	+	0.5719	57.19%
CYP inhibitory promiscuity	-	0.7195	71.95%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7238	72.38%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9260	92.60%
Skin irritation	-	0.8305	83.05%
Skin corrosion	-	0.9609	96.09%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7929	79.29%
Micronuclear	+	0.6733	67.33%
Hepatotoxicity	-	0.8625	86.25%
skin sensitisation	-	0.9389	93.89%
Respiratory toxicity	-	0.6333	63.33%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.7422	74.22%
Acute Oral Toxicity (c)	III	0.6799	67.99%
Estrogen receptor binding	+	0.8039	80.39%
Androgen receptor binding	-	0.7668	76.68%
Thyroid receptor binding	+	0.5609	56.09%
Glucocorticoid receptor binding	-	0.4672	46.72%
Aromatase binding	-	0.5356	53.56%
PPAR gamma	+	0.6894	68.94%
Honey bee toxicity	-	0.6569	65.69%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.7522	75.22%

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	99.23%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.20%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.93%	94.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	94.29%	96.21%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.03%	86.33%
CHEMBL2581	P07339	Cathepsin D	93.98%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.98%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.94%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.66%	95.89%
CHEMBL4208	P20618	Proteasome component C5	91.18%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.90%	95.56%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.05%	97.36%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.28%	86.92%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.78%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.03%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.49%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.36%	94.45%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	83.96%	95.78%
CHEMBL1951	P21397	Monoamine oxidase A	83.45%	91.49%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.00%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	81.90%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.45%	99.23%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	81.30%	94.80%
CHEMBL2243	O00519	Anandamide amidohydrolase	80.86%	97.53%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.02%	90.71%

Plants that contains it

• Ageratina tomentella
• Caralluma stalagmifera
• Citrus × aurantium
• Citrus × aurantium nothof. deliciosa
• Citrus maxima
• Citrus medica
• Citrus trifoliata
• Drymaria cordata
• Euthamia graminifolia
• Ficus nervosa
• Pogostemon cablin
• Prosopis cineraria
• Rubus xanthocarpus
• Styphnolobium japonicum
• Uncaria hirsuta

Cross-Links

• PubChem: 442439
• NPASS: NPC105095
• LOTUS: LTS0129178
• wikiData: Q18609455