Neohesperidin dihydrochalcone (NHDC) is a synthetic compound derived from the natural flavonoid naringin, found in citrus fruits. It is produced by a chemical reaction involving the hydrogenation of the double bond in the chalcone moiety of naringin. NHDC is a potent sweetener with approximately 1500-1800 times the sweetness of sucrose, making it a popular sugar substitute. It is also used in food and beverage industries for its sweetening properties. Research on NHDC has shown that it possesses various beneficial properties, including antioxidant, anti-inflammatory, and anti-diabetic activities. It has been suggested to have potential applications in treating obesity, metabolic syndrome, and cancer. Studies have focused on its mechanisms of action, including its effects on glucose metabolism, lipid profiles, and oxidative stress. NHDC is widely studied due to its low-calorie nature, potential health benefits, and applications in food and pharmaceutical industries. It is a promising candidate for natural sweetener development and has gained significant attention for its potential to improve human health and well-being.'
neohesperidin dihydrochalcone : A member of the dihydrochalcones that is 3,2',4',6'-tetrahydroxy-4-methoxydihydrochalcone attached to a neohesperidosyl residue at position 4' via glycosidic linkage. It is found in sweet orange. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]
| ID Source | ID |
|---|---|
| PubMed CID | 30231 |
| CHEMBL ID | 1159645 |
| CHEBI ID | 83535 |
| SCHEMBL ID | 909958 |
| MeSH ID | M0061501 |
| Synonym |
|---|
| 1-[4-[(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-2,6-dihydroxy-phenyl]-3-(3-hydroxy-4-methoxy-phenyl)propan-1-one |
| 20702-77-6 |
| 1-(4-((2-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranosyl)oxy)-2,6-dihydroxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)propan-1-one |
| neohesperidine dihydrochalcone |
| neosperidin dihydrochalcone |
| neohesperidin dihydrochalcone |
| NCGC00091109-01 |
| 1-propanone, 1-(4-((2-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranosyl)oxy)-2,6-dihydroxyphenyl)-3-(3-hydroxy-4-me |
| einecs 243-978-6 |
| glucopyranoside, 3,5-dihydroxy-4-(3-hydroxy-4-methoxyhydrocinnamoyl)phenyl 2-o-(6-deoxy-alpha-l-mannopyranosyl)-, beta-d- |
| 1-(4-((2-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranosyl)oxy)-2,6-dihydroxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)- |
| neohesperidin dc |
| ccris 4848 |
| nhdc |
| neohesperidin dhc |
| nci-c60764 |
| glucopyranoside, 3,5-dihydroxy-4-(3-hydroxy-4-methoxyhydrocinnamoyl)phenyl-2-o-(6-deoxy-alpha-l-mannopyranosyl)-, beta-d- |
| 3,5-dihydroxy-4-(3-hydroxy-4-methoxyhydrocinnamoyl)phenyl) 2-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranoside |
| neohesperidin dihydrochalcone, >=96%, fg |
| neohesperidin dihydrochalcone, >=95% (hplc) |
| neohesperidine dc |
| inchi=1/c28h36o15/c1-11-21(34)23(36)25(38)27(40-11)43-26-24(37)22(35)19(10-29)42-28(26)41-13-8-16(32)20(17(33)9-13)14(30)5-3-12-4-6-18(39-2)15(31)7-12/h4,6-9,11,19,21-29,31-38h,3,5,10h2,1-2h3/t11-,19+,21-,22+,23+,24-,25+,26+,27-,28+/m0/s1 |
| itvgxxminpyuhd-cuvhlrmhsa- |
| 1-[4-[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2s,3r,4r,5r,6s)-3,4,5 |
| N0675 |
| chebi:83535 , |
| CHEMBL1159645 |
| 1-[4-[(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-2,6-dihydroxyphenyl]-3-(3-hydroxy-4-methoxyphenyl)propan-1-one |
| NCGC00091109-02 |
| tox21_200303 |
| dtxsid3025706 , |
| cas-20702-77-6 |
| NCGC00257857-01 |
| dtxcid305706 |
| A814825 |
| 1-[4-[(2s,3r,4r,5r,6s)-4,5-dihydroxy-6-methyl-2-[(2r,3r,4s,5s,6r)-2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-3-yl]oxy-tetrahydropyran-3-yl]oxy-2,6-dihydroxy-phenyl]-3-(3-hydroxy-4-methoxy-phenyl)propan-1-one |
| 1-propanone, 1-(4-((2-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranosyl)oxy)-2,6-dihydroxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)- |
| unii-3x476d83qv |
| 3x476d83qv , |
| glucopyranoside, 3,5-dihydroxy-4-(3-hydroxy-4-methoxyhydrocinnamoyl)phenyl 2-o-.alpha.-l-rhamnopyranosyl- |
| 1-propanone, 1-(4-((2-o-(6-deoxy-.alpha.-l-mannopyranosyl)-.beta.-d-glucopyranosyl)oxy)-2,6-dihydroxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)- |
| glucopyranoside, 3,5-dihydroxy-4-(3-hydroxy-4-methoxyhydrocinnamoyl)phenyl 2-o-(6-deoxy-.alpha.-l-mannopyranosyl)-, .beta.-d- |
| fema no. 3811 |
| neohesperidin-dihydrochalcone [ep monograph] |
| neohesperidin dihydrochalone |
| neohesperidin-dihydrochalcone |
| neohesperidine dihydrochalcone [fcc] |
| neohesperidin dihydrochalone [fhfi] |
| neohesperidin dihydrochalcone [inci] |
| 1-(4-((2-o-(6-deoxy-.alpha.-l-mannopyranosyl)-.beta.-d-dihydrochalcone glucopyranosyl)oxy)-2,6-dihydroxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)propan-1-one |
| neohesperidin dihydrochalcone [mi] |
| neohesperidin dihydrochalcone [usp-rs] |
| hesperetin dihydrochalcone-4'-.beta.-neohesperidoside |
| neohesperidine dihydrochalcone [usp-rs] |
| citrosa |
| AKOS015895239 |
| 1-(4-((2-o-[6-deoxy-alpha-l-mannopyranosyl]-beta-d-glucopyranosyl)oxy)-2,6-dihydroxyphenyl)-3-[3-hydroxy-4-methoxyphenyl]-1-propanone |
| S2331 |
| 3,5-dihydroxy-4-[3-(3-hydroxy-4-methoxyphenyl)propanoyl]phenyl 2-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranoside |
| ITVGXXMINPYUHD-CUVHLRMHSA-N |
| SCHEMBL909958 |
| Q-201457 |
| neohesperidine |
| AC-34860 |
| neosperidin-dihydrochalcone |
| neohesperidin dihydrochalcone, analytical standard |
| HY-N0154 |
| sr-01000883756 |
| SR-01000883756-1 |
| CS-6419 |
| 1-(4-(((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)-2,6-dihydroxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)propan-1-one |
| neohesperidin dihydrochalcone, united states pharmacopeia (usp) reference standard |
| neohesperidindihydrochalcone |
| neohesperidin dihydrochalcone, european pharmacopoeia (ep) reference standard |
| NCGC00091109-04 |
| 1-propanone, 1-[4-[[2-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranosyl]oxy]-2,6-dihydroxyphenyl]-3-(3-hydroxy-4-methoxyphenyl)- |
| Q424595 |
| 1-(4-((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)-2,6-dihydroxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)propan-1-one |
| AS-15190 |
| BRD-K61032563-001-02-9 |
| HMS3884H13 |
| CCG-270237 |
Neohesperidin dihydrochalcone (NHDC) is a sweetener, which interacts with the transmembrane domain (TMD) of the T1R3 subunit of the human sweet taste receptor. It has unique properties and applications for the food, beverage, pharmaceutical, and animal feed industries.
| Excerpt | Reference | Relevance |
|---|---|---|
| " This developed method is successfully used in the pharmacokinetic and tissue distribution study of NHDC in rats." | ( Application of a liquid chromatography-tandem mass spectrometry method to the pharmacokinetics, bioavailability and tissue distribution of neohesperidin dihydrochalcone in rats. Jianshe, M; Pan, Y; Shi, S; Wang, X; Xiang, Z; Zheng, X, 2014) | 0.6 |
| Excerpt | Reference | Relevance |
|---|---|---|
| " This study was aimed at developing a high sensitive and selective liquid chromatography-tandem mass spectrometry method to quantify neohesperidin dihydrochalcone (NHDC) in rat plasma and tissues for pharmacokinetic, bioavailability and tissue distribution studies." | ( Application of a liquid chromatography-tandem mass spectrometry method to the pharmacokinetics, bioavailability and tissue distribution of neohesperidin dihydrochalcone in rats. Jianshe, M; Pan, Y; Shi, S; Wang, X; Xiang, Z; Zheng, X, 2014) | 0.81 |
| "The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs." | ( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019) | 0.51 |
| Role | Description |
|---|---|
| environmental contaminant | Any minor or unwanted substance introduced into the environment that can have undesired effects. |
| xenobiotic | A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means. |
| plant metabolite | Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. |
| sweetening agent | Substance that sweeten food, beverages, medications, etc. |
| [role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Class | Description |
|---|---|
| neohesperidoside | A glycoside containing alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranosyl residue as the sugar unit. |
| disaccharide derivative | A carbohydrate derivative that is formally obtained from a disaccharide. |
| dihydrochalcones | Any ketone that is 1,3-diphenylpropanone and its derivatives obtained by substitution. |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Chain A, Cruzipain | Trypanosoma cruzi | Potency | 39.8107 | 0.0020 | 14.6779 | 39.8107 | AID1476 |
| Luciferase | Photinus pyralis (common eastern firefly) | Potency | 79.9007 | 0.0072 | 15.7588 | 89.3584 | AID1224835 |
| RAR-related orphan receptor gamma | Mus musculus (house mouse) | Potency | 0.9718 | 0.0060 | 38.0041 | 19,952.5996 | AID1159521 |
| aldehyde dehydrogenase 1 family, member A1 | Homo sapiens (human) | Potency | 35.4813 | 0.0112 | 12.4002 | 100.0000 | AID1030 |
| retinoic acid nuclear receptor alpha variant 1 | Homo sapiens (human) | Potency | 63.9037 | 0.0030 | 41.6115 | 22,387.1992 | AID1159552; AID1159555 |
| retinoid X nuclear receptor alpha | Homo sapiens (human) | Potency | 24.6133 | 0.0008 | 17.5051 | 59.3239 | AID1159527 |
| Histone H2A.x | Cricetulus griseus (Chinese hamster) | Potency | 80.2447 | 0.0391 | 47.5451 | 146.8240 | AID1224845 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1296008 | Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening | 2020 | SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1 | Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening. |
| AID1346987 | P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen | 2019 | Molecular pharmacology, 11, Volume: 96, Issue:5 | A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. |
| AID1347159 | Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay | 2020 | Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49 | Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors. |
| AID1347160 | Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors | 2020 | Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49 | Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors. |
| AID1346986 | P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen | 2019 | Molecular pharmacology, 11, Volume: 96, Issue:5 | A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. |
| AID977602 | Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM | 2013 | Molecular pharmacology, Jun, Volume: 83, Issue:6 | Structure-based identification of OATP1B1/3 inhibitors. |
| AID90088 | Sensory evaluation was done for sweetness at a concentration of 250 p.p.m. against compound potency calculated on a molar basis. | 1985 | Journal of medicinal chemistry, Jan, Volume: 28, Issue:1 | Diterpenoid sweeteners. Synthesis and sensory evaluation of stevioside analogues with improved organoleptic properties. |
| AID90264 | Sensory evaluation was done at a concentration of 250 p.p.m. against other properties. | 1985 | Journal of medicinal chemistry, Jan, Volume: 28, Issue:1 | Diterpenoid sweeteners. Synthesis and sensory evaluation of stevioside analogues with improved organoleptic properties. |
| AID90226 | Sensory evaluation was done for sweetness at a concentration of 250 p.p.m. against compound potency calculated on weight basis. | 1985 | Journal of medicinal chemistry, Jan, Volume: 28, Issue:1 | Diterpenoid sweeteners. Synthesis and sensory evaluation of stevioside analogues with improved organoleptic properties. |
| AID977599 | Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM | 2013 | Molecular pharmacology, Jun, Volume: 83, Issue:6 | Structure-based identification of OATP1B1/3 inhibitors. |
| AID90266 | Sensory evaluation was done at a concentration of 250 p.p.m. against property of sweetness. | 1985 | Journal of medicinal chemistry, Jan, Volume: 28, Issue:1 | Diterpenoid sweeteners. Synthesis and sensory evaluation of stevioside analogues with improved organoleptic properties. |
| AID90265 | Sensory evaluation was done at a concentration of 250 p.p.m. against property of bitterness. | 1985 | Journal of medicinal chemistry, Jan, Volume: 28, Issue:1 | Diterpenoid sweeteners. Synthesis and sensory evaluation of stevioside analogues with improved organoleptic properties. |
| AID89764 | Sensory evaluation was done for sweetness at a concentration of 250 p.p.m. against sample intensity relative to 10% sucrose. | 1985 | Journal of medicinal chemistry, Jan, Volume: 28, Issue:1 | Diterpenoid sweeteners. Synthesis and sensory evaluation of stevioside analogues with improved organoleptic properties. |
| AID1159550 | Human Phosphogluconate dehydrogenase (6PGD) Inhibitor Screening | 2015 | Nature cell biology, Nov, Volume: 17, Issue:11 | 6-Phosphogluconate dehydrogenase links oxidative PPP, lipogenesis and tumour growth by inhibiting LKB1-AMPK signalling. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 7 (14.58) | 18.7374 |
| 1990's | 4 (8.33) | 18.2507 |
| 2000's | 12 (25.00) | 29.6817 |
| 2010's | 15 (31.25) | 24.3611 |
| 2020's | 10 (20.83) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.
| This Compound (41.88) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 3 (6.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 47 (94.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||