Xanthohumol
precursor
Showing entry for Xanthohumol
Identification
- PhytoHub ID
- PHUB001402
- Name
- Xanthohumol
- Systematic Name
- Not Available
- Synonyms
- Not Available
- CAS Number
- 6754-58-1
- Average Mass
- 354.402
- Monoisotopic Mass
- 354.146723808
- Chemical Formula
- C21H22O5
- IUPAC Name
- (2E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
- InChI Key
- ORXQGKIUCDPEAJ-YRNVUSSQSA-N
- InChI Identifier
InChI=1S/C21H22O5/c1-13(2)4-10-16-18(24)12-19(26-3)20(21(16)25)17(23)11-7-14-5-8-15(22)9-6-14/h4-9,11-12,22,24-25H,10H2,1-3H3/b11-7+
- SMILES
COC1=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=C(CC=C(C)C)C(O)=C1
- Structure
Structure for Xanthohumol
Calculated Properties
- Solubility (ALOGPS)
- 5.56e-03 g/l
- LogS (ALOGPS)
- -4.80
- LogP (ALOGPS)
- 3.91
- Hydrogen Acceptors
- 5
- Hydrogen Donors
- 3
- Rotatable Bond Count
- 6
- Polar Surface Area
- 86.99000000000001
- Refractivity
- 103.5257
- Polarizability
- 38.5242701785884
- Formal Charge
- 0
- Physiological Charge
- -1
- pKa (strongest basic)
- -4.896190778259284
- pKa (strongest acidic)
- 7.010896021723353
- Number of Rings
- 2
- Rule of Five
- No
- Bioavailability
- Yes
- Ghose Filter
- Yes
- Veber's Rule
- No
- MDDR-like Rule
- No
Taxonomy as Food Phytochemical
- Family
- Polyphenols
- Class
- Miscellaneous polyphenols
- Sub-class
- Not Available
Classyfire Taxonomy
- Kingdom Name
- Organic compounds
- Class
- Linear 1,3-diarylpropanoids
- Super-class
- Phenylpropanoids and polyketides
- Sub-class
- Chalcones and dihydrochalcones
- Direct Parent Name
- 3-prenylated chalcones
- Alternative Parent Names
- ["1-hydroxy-2-unsubstituted benzenoids", "1-hydroxy-4-unsubstituted benzenoids", "2'-Hydroxychalcones", "Acryloyl compounds", "Alkyl aryl ethers", "Anisoles", "Aryl ketones", "Benzoyl derivatives", "Cinnamylphenols", "Enones", "Hydrocarbon derivatives", "Hydroxycinnamic acids and derivatives", "Methoxybenzenes", "Methoxyphenols", "Organic oxides", "Phenoxy compounds", "Resorcinols", "Styrenes", "Vinylogous acids"]
- External Descriptor Annotations
- ["Chalcones and dihydrochalcones", "aromatic ether", "chalcones", "polyphenol"]
- Substituent Names
- ["1-hydroxy-2-unsubstituted benzenoid", "1-hydroxy-4-unsubstituted benzenoid", "2'-hydroxychalcone", "3-prenylated chalcone", "Acryloyl-group", "Alkyl aryl ether", "Alpha,beta-unsaturated ketone", "Anisole", "Aromatic homomonocyclic compound", "Aryl ketone", "Benzenoid", "Benzoyl", "Cinnamylphenol", "Enone", "Ether", "Hydrocarbon derivative", "Hydroxycinnamic acid or derivatives", "Ketone", "Methoxybenzene", "Methoxyphenol", "Monocyclic benzene moiety", "Organic oxide", "Organic oxygen compound", "Organooxygen compound", "Phenol", "Phenol ether", "Phenoxy compound", "Resorcinol", "Styrene", "Vinylogous acid"]
Spectra from Online Resources
No spectra information available
Food Sources
| Name | Group | |||
|---|---|---|---|---|
| Beer | Beverages, Alcoholic | 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 | ||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Xanthohumol | 6-Prenylnaringenin | human | plasma | gut microbiota metabolite | Not Available | Not Available | Not Available | C20H20O5 | 340.131073744 | Publications | |||
| Xanthohumol | 8-Prenylnaringenin | human | plasma | host-gut microbiota co-metabolite | Not Available | Not Available | Not Available | C20H20O5 | 340.131073744 | Publications | |||
| Xanthohumol | Isoxanthohumol | human | plasma (major) | Not Available | Not Available | Not Available | Not Available | C21H22O5 | 354.146723808 | Publications |
Inter-Individual Variations in Metabolism
| Food Phytochemical | Metabolite | Effect | Value |
|---|