Dihydrocaffeic acid-3'-O-glucuronide
Showing entry for Dihydrocaffeic acid-3'-O-glucuronide
Identification
- PhytoHub ID
- PHUB001204
- Name
- Dihydrocaffeic acid-3'-O-glucuronide
- Systematic Name
- 3-(4'-hydroxyphenyl)propanoic acid-3'-glucuronide
- Synonyms
- 3-(4-hydroxyphenyl)propanoic acid-3-glucuronide
- 3-(4-hydroxyphenyl)propionic acid-3-glucuronide
- 3-(4'-Hydroxyphenyl)propionic acid-3'-O-glucuronide
- dihydrocaffeic acid-3-glucuronide
- CAS Number
- Not Available
- Average Mass
- 358.299
- Monoisotopic Mass
- 358.08999678
- Chemical Formula
- C15H18O10
- IUPAC Name
- (2R,3R,4R,5S,6R)-6-[5-(2-carboxyethyl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
- InChI Key
- AELQNMHOLDHBFA-VVSAWPALSA-N
- InChI Identifier
InChI=1S/C15H18O10/c16-7-3-1-6(2-4-9(17)18)5-8(7)24-15-12(21)10(19)11(20)13(25-15)14(22)23/h1,3,5,10-13,15-16,19-21H,2,4H2,(H,17,18)(H,22,23)/t10-,11-,12+,13-,15+/m1/s1
- SMILES
O[C@H]1[C@H](O)[C@@H](OC2=C(O)C=CC(CCC(O)=O)=C2)O[C@H]([C@@H]1O)C(O)=O
- Structure
Calculated Properties
- Solubility (ALOGPS)
- 8.41e+00 g/l
- LogS (ALOGPS)
- -1.63
- LogP (ALOGPS)
- -0.09
- Hydrogen Acceptors
- 10
- Hydrogen Donors
- 6
- Rotatable Bond Count
- 6
- Polar Surface Area
- 173.98
- Refractivity
- 77.9402
- Polarizability
- 32.98813207252531
- Formal Charge
- 0
- Physiological Charge
- -2
- pKa (strongest basic)
- -3.6868279761517333
- pKa (strongest acidic)
- 3.0131597965048678
- Number of Rings
- 2
- Rule of Five
- No
- Bioavailability
- Yes
- Ghose Filter
- No
- Veber's Rule
- No
- MDDR-like Rule
- No
External Links
No external links
Taxonomy as Metabolite
- Family
- (Poly)phenol metabolites
- Class
- Phenolic acid metabolites
- Sub-class
- Phenylpropanoic acids
Taxonomy of its Food Phytochemical Precursor(s)
Food Phytochemical | Family | Class | Sub-class | |
---|---|---|---|---|
Dihydrocaffeic acid | Polyphenols | Phenolic acids | Phenolic acids subclass not specified | Show Food Phytochemical |
Caffeic acid | Polyphenols | Phenolic acids | Hydroxycinnamic acids | Show Food Phytochemical |
Orange flavanones | Polyphenols | Flavonoids | Flavanones | Show Food Phytochemical |
Black tea Flavan-3-ols | Polyphenols | Flavonoids | Flavan-3-ols | Show Food Phytochemical |
Coffee Chlorogenic acids | Polyphenols | Phenolic acids | Hydroxycinnamic acids | Show Food Phytochemical |
Yerba mate Chlorogenic acids | Polyphenols | Phenolic acids | Hydroxycinnamic acids | Show Food Phytochemical |
Coffee hydroxycinnamates | Polyphenols | Flavonoids | Hydroxycinnamic acids | Show Food Phytochemical |
Classyfire Taxonomy
- Kingdom Name
- Organic compounds
- Class
- Organooxygen compounds
- Super-class
- Organic oxygen compounds
- Sub-class
- Carbohydrates and carbohydrate conjugates
- Direct Parent Name
- Phenolic glycosides
- Alternative Parent Names
- ["1-hydroxy-2-unsubstituted benzenoids", "Acetals", "Beta hydroxy acids and derivatives", "Carbonyl compounds", "Carboxylic acids", "Dicarboxylic acids and derivatives", "Hexoses", "Hydrocarbon derivatives", "O-glucuronides", "O-glycosyl compounds", "Organic oxides", "Oxacyclic compounds", "Oxanes", "Phenol ethers", "Phenoxy compounds", "Phenylpropanoic acids", "Polyols", "Pyrans", "Secondary alcohols"]
- External Descriptor Annotations
- Not Available
- Substituent Names
- ["1-hydroxy-2-unsubstituted benzenoid", "1-o-glucuronide", "3-phenylpropanoic-acid", "Acetal", "Alcohol", "Aromatic heteromonocyclic compound", "Benzenoid", "Beta-hydroxy acid", "Carbonyl group", "Carboxylic acid", "Carboxylic acid derivative", "Dicarboxylic acid or derivatives", "Glucuronic acid or derivatives", "Hexose monosaccharide", "Hydrocarbon derivative", "Hydroxy acid", "Monocyclic benzene moiety", "Monosaccharide", "O-glucuronide", "O-glycosyl compound", "Organic oxide", "Organoheterocyclic compound", "Oxacycle", "Oxane", "Phenol", "Phenol ether", "Phenolic glycoside", "Phenoxy compound", "Polyol", "Pyran", "Secondary alcohol"]
Spectra from Online Resources
No spectra information available
Food Sources
No food source information available
Food Sources of its Food Phytochemical(s)
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 | ||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Dihydrocaffeic acid | Dihydrocaffeic acid-3'-O-glucuronide | rat | urine | Not Available | Not Available | Not Available | Not Available | C15H18O10 | 358.08999678 | Publications | |||
Caffeic acid | Dihydrocaffeic acid-3'-O-glucuronide | human | plasma | host metabolism | Not Available | Not Available | Not Available | C15H18O10 | 358.08999678 | Publications | |||
Orange flavanones | Dihydrocaffeic acid-3'-O-glucuronide | Not Available | Not Available | Not Available | Not Available | Not Available | Not Available | C15H18O10 | 358.08999678 | Detailed Intervention Studies | |||
Black tea Flavan-3-ols | Dihydrocaffeic acid-3'-O-glucuronide | human | urine | host-gut microbiota co-metabolite | Not Available | Not Available | <1% | C15H18O10 | 358.08999678 | Detailed Intervention Studies | Publications | ||
Coffee Chlorogenic acids | Dihydrocaffeic acid-3'-O-glucuronide | human | urine | host-gut microbiota co-metabolite | Not Available | Not Available | <1% | C15H18O10 | 358.08999678 | Detailed Intervention Studies | Publications | ||
Yerba mate Chlorogenic acids | Dihydrocaffeic acid-3'-O-glucuronide | human | urine | host-gut microbiota co-metabolite | Not Available | Not Available | <1% | C15H18O10 | 358.08999678 | Detailed Intervention Studies | Publications | ||
Coffee hydroxycinnamates | Dihydrocaffeic acid-3'-O-glucuronide | Not Available | Not Available | Not Available | Not Available | Not Available | Not Available | C15H18O10 | 358.08999678 | Detailed Intervention Studies |
Inter-Individual Variations in Metabolism
Food Phytochemical | Metabolite | Effect | Value | |||
---|---|---|---|---|---|---|
Coffee Chlorogenic acids | Dihydrocaffeic acid-3'-O-glucuronide | Microbiota | Effect, clusters | Publications |