Naringin
precursor
Showing entry for Naringin
Identification
- PhytoHub ID
- PHUB000389
- Name
- Naringin
- Systematic Name
- Not Available
- Synonyms
- Naringenin 7-O-neohesperidoside
- Naringenin 7-O-rhamnoglucoside
- CAS Number
- Not Available
- Average Mass
- 580.539
- Monoisotopic Mass
- 580.17920571
- Chemical Formula
- C27H32O14
- IUPAC Name
- 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
- InChI Key
- DFPMSGMNTNDNHN-JJLSSNRUSA-N
- InChI Identifier
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
- SMILES
C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2OC2=CC(O)=C3C(=O)CC(OC3=C2)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O
- Structure
Structure for Naringin
Calculated Properties
- Solubility (ALOGPS)
- 4.06e+00 g/l
- LogS (ALOGPS)
- -2.16
- LogP (ALOGPS)
- -0.24
- Hydrogen Acceptors
- 14
- Hydrogen Donors
- 8
- Rotatable Bond Count
- 6
- Polar Surface Area
- 225.05999999999997
- Refractivity
- 134.30380000000002
- Polarizability
- 56.864154507353646
- Formal Charge
- 0
- Physiological Charge
- 0
- pKa (strongest basic)
- -2.981092569339441
- pKa (strongest acidic)
- 8.579343855596704
- Number of Rings
- 5
- Rule of Five
- No
- Bioavailability
- No
- Ghose Filter
- No
- Veber's Rule
- No
- MDDR-like Rule
- Yes
Taxonomy as Food Phytochemical
- Family
- Polyphenols
- Class
- Flavonoids
- Sub-class
- Flavanones
Classyfire Taxonomy
- Kingdom Name
- Organic compounds
- Class
- Flavonoids
- Super-class
- Phenylpropanoids and polyketides
- Sub-class
- Flavonoid glycosides
- Direct Parent Name
- Flavonoid-7-O-glycosides
- Alternative Parent Names
- ["1-hydroxy-2-unsubstituted benzenoids", "1-hydroxy-4-unsubstituted benzenoids", "4'-hydroxyflavonoids", "5-hydroxyflavonoids", "Acetals", "Alkyl aryl ethers", "Aryl alkyl ketones", "Benzene and substituted derivatives", "Chromones", "Disaccharides", "Flavanones", "Hydrocarbon derivatives", "O-glycosyl compounds", "Organic oxides", "Oxacyclic compounds", "Oxanes", "Phenolic glycosides", "Polyols", "Primary alcohols", "Secondary alcohols", "Vinylogous acids"]
- External Descriptor Annotations
- Not Available
- Substituent Names
- ["1-benzopyran", "1-hydroxy-2-unsubstituted benzenoid", "1-hydroxy-4-unsubstituted benzenoid", "4'-hydroxyflavonoid", "5-hydroxyflavonoid", "Acetal", "Alcohol", "Alkyl aryl ether", "Aromatic heteropolycyclic compound", "Aryl alkyl ketone", "Aryl ketone", "Benzenoid", "Benzopyran", "Chromane", "Chromone", "Disaccharide", "Ether", "Flavan", "Flavanone", "Flavonoid-7-o-glycoside", "Glycosyl compound", "Hydrocarbon derivative", "Hydroxyflavonoid", "Ketone", "Monocyclic benzene moiety", "O-glycosyl compound", "Organic oxide", "Organic oxygen compound", "Organoheterocyclic compound", "Organooxygen compound", "Oxacycle", "Oxane", "Phenol", "Phenolic glycoside", "Polyol", "Primary alcohol", "Secondary alcohol", "Vinylogous acid"]
Spectra from Phytohub
| Spectrum Type | Instrument Type | Technology | Ion Mode | Collision Energy | View | |
|---|---|---|---|---|---|---|
| LC-MS/MS | LC-ESI-QFT | Thermo Fisher Scientific Q-Exactive HF | Negative | 35V | View Spectrum | |
| LC-MS/MS | LC-ESI-QFT | Thermo Fisher Scientific Q-Exactive HF | Positive | 35V | View Spectrum | |
| LC-MS/MS | LC-ESI-QFT | Thermo Fisher Scientific Q-Exactive HF | Negative | 45V | View Spectrum | |
| LC-MS/MS | LC-ESI-QFT | Thermo Fisher Scientific Q-Exactive HF | Negative | 65V | View Spectrum | |
| LC-MS/MS | LC-ESI-QFT | Thermo Fisher Scientific Q-Exactive HF | Positive | 45V | View Spectrum | |
| LC-MS/MS | LC-ESI-QFT | Thermo Fisher Scientific Q-Exactive HF | Positive | 65V | View Spectrum | |
| Predicted LC-MS/MS | Not Available | Predicted by CFM-ID | Positive | 10V | View Spectrum | |
| Predicted LC-MS/MS | Not Available | Predicted by CFM-ID | Positive | 20V | View Spectrum | |
| Predicted LC-MS/MS | Not Available | Predicted by CFM-ID | Positive | 40V | View Spectrum | |
| Predicted LC-MS/MS | Not Available | Predicted by CFM-ID | Negative | 10V | View Spectrum | |
| Predicted LC-MS/MS | Not Available | Predicted by CFM-ID | Negative | 20V | View Spectrum | |
| Predicted LC-MS/MS | Not Available | Predicted by CFM-ID | Negative | 40V | View Spectrum |
Food Sources
| Name | Group | |||
|---|---|---|---|---|
| Grapefruit | Fruit, Citrus | Publications | Show | |
| Grapefruit juice | Beverages, Non-alcoholic | Publications | Show | |
| Lemon | Fruit, Citrus | Publications | Show | |
| Lime | Fruit, Citrus | Publications | Show | |
| Sour orange | Fruit, Citrus | Publications | Show | |
| Sweet orange | Fruit, Citrus | Publications | Show |
Role as Biomarker of intake
No roles as Biomarker of intake found
Metabolism
| Food Phytochemical | Metabolite | Species | Biofluids | Origin | TMax | CMax | Urinary Excretion | Formula | Monoisotopic mass | ||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Naringin | Eriodictyol | Not Available | Not Available | Not Available | Not Available | Not Available | Not Available | C15H12O6 | 288.063388106 | Detailed Intervention Studies | |||
| Naringin | Naringenin | human | plasma, urine | gut microbiota metabolite | Not Available | Not Available | Not Available | C15H12O5 | 272.068473486 | Detailed Intervention Studies | Publications | ||
| Naringin | Naringin | human | urine | unchanged | Not Available | Not Available | Not Available | C27H32O14 | 580.17920571 | Detailed Intervention Studies | Publications | ||
| Naringin | Phloretic acid | human | plasma | host metabolism | Not Available | Not Available | Not Available | C9H10O3 | 166.062994182 | Publications | |||
| Naringin | 3-Phenylpropionic acid | human | plasma | gut microbiota metabolite | Not Available | Not Available | Not Available | C9H10O2 | 150.068079562 | Publications | |||
| Naringin | Eriodictyol sulfate | Not Available | Not Available | Not Available | Not Available | Not Available | Not Available | C15H12O9S | 368.3194001 | Detailed Intervention Studies | |||
| Naringin | Naringenin-4'-glucuronide | human | urine | host metabolism | Not Available | Not Available | Not Available | C21H20O11 | 448.100561464 | Detailed Intervention Studies | Publications | ||
| Naringin | Naringenin-7-glucuronide | human | urine | host-gut microbiota co-metabolite | Not Available | Not Available | Not Available | C21H20O11 | 448.100561464 | Detailed Intervention Studies | Publications | ||
| Naringin | Naringenin-diglucuronide | Not Available | Not Available | Not Available | Not Available | Not Available | Not Available | C27H28O17 | 624.5095093 | Detailed Intervention Studies | |||
| Naringin | Naringenin-sulfoglucuronide | human | urine | host metabolism | Not Available | Not Available | Not Available | C21H20O14S | 528.4459545 | Detailed Intervention Studies | Publications | ||
| Naringin | Naringenin-5-glucuronide | human | urine | host metabolism | Not Available | Not Available | Not Available | C21H20O11 | 448.100561464 | Detailed Intervention Studies | Publications | ||
| Naringin | Naringenin-7- sulfate | human | urine | host metabolism | Not Available | Not Available | Not Available | C15H12O8S | 352.02528852 | Detailed Intervention Studies | Publications | ||
| Naringin | Naringenin-4'-sulfate | human | urine | host metabolism | Not Available | Not Available | Not Available | C15H12O8S | 352.02528852 | Detailed Intervention Studies | Publications |
Inter-Individual Variations in Metabolism
| Food Phytochemical | Metabolite | Effect | Value |
|---|