Coumaric acid (p-)
precursor
Showing entry for Coumaric acid (p-)
Identification
- PhytoHub ID
- PHUB000590
- Name
- Coumaric acid (p-)
- Systematic Name
- 4'-hydroxycinnamic acid
- Synonyms
- (4-hydroxyphenyl)acrylic acid
- 4-coumaric acid
- 4-Hydroxycinnamic acid
- p-coumaric acid
- trans-4-hydroxycinnamic acid
- CAS Number
- 501-98-4
- Average Mass
- 164.16
- Monoisotopic Mass
- 164.047344118
- Chemical Formula
- C9H8O3
- IUPAC Name
- (2E)-3-(4-hydroxyphenyl)prop-2-enoic acid
- InChI Key
- NGSWKAQJJWESNS-ZZXKWVIFSA-N
- InChI Identifier
InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+
- SMILES
OC(=O)\C=C\C1=CC=C(O)C=C1
- Structure
Structure for Coumaric acid (p-)
Calculated Properties
- Solubility (ALOGPS)
- 1.02e+00 g/l
- LogS (ALOGPS)
- -2.21
- LogP (ALOGPS)
- 1.74
- Hydrogen Acceptors
- 3
- Hydrogen Donors
- 2
- Rotatable Bond Count
- 2
- Polar Surface Area
- 57.53
- Refractivity
- 45.040800000000004
- Polarizability
- 16.431404823804833
- Formal Charge
- 0
- Physiological Charge
- -1
- pKa (strongest basic)
- -5.954717586543568
- pKa (strongest acidic)
- 3.810198948389013
- Number of Rings
- 1
- Rule of Five
- Yes
- Bioavailability
- Yes
- Ghose Filter
- Yes
- Veber's Rule
- No
- MDDR-like Rule
- No
External Links
- ChEBI
- 32374
- PubChem
- 637542
- MetaboLights
- MTBLC32374
- PeakForestCompound
- 000454
Taxonomy as Food Phytochemical
- Family
- Polyphenols
- Class
- Phenolic acids
- Sub-class
- Hydroxycinnamic acids
Taxonomy as Metabolite
- Metabolite Family
- (Poly)phenol metabolites
- Metabolite Class
- Phenolic acid metabolites
- Metabolite Sub-class
- Cinnamic acids
Taxonomy of its Food Phytochemical Precursor(s)
| Food Phytochemical | Family | Class | Sub-class | |
|---|---|---|---|---|
| Naringenin | Polyphenols | Flavonoids | Flavanones | Show Food Phytochemical |
| Orange flavanones | Polyphenols | Flavonoids | Flavanones | Show Food Phytochemical |
Classyfire Taxonomy
- Kingdom Name
- Organic compounds
- Class
- Cinnamic acids and derivatives
- Super-class
- Phenylpropanoids and polyketides
- Sub-class
- Hydroxycinnamic acids and derivatives
- Direct Parent Name
- Hydroxycinnamic acids
- Alternative Parent Names
- ["1-hydroxy-2-unsubstituted benzenoids", "Carbonyl compounds", "Carboxylic acids", "Cinnamic acids", "Coumaric acids", "Hydrocarbon derivatives", "Monocarboxylic acids and derivatives", "Organic oxides", "Styrenes"]
- External Descriptor Annotations
- ["4-coumaric acid", "Paracoumaryl alcohol derivatives"]
- Substituent Names
- ["1-hydroxy-2-unsubstituted benzenoid", "Aromatic homomonocyclic compound", "Benzenoid", "Carbonyl group", "Carboxylic acid", "Carboxylic acid derivative", "Cinnamic acid", "Coumaric acid", "Coumaric acid or derivatives", "Hydrocarbon derivative", "Hydroxycinnamic acid", "Monocarboxylic acid or derivatives", "Monocyclic benzene moiety", "Organic oxide", "Organic oxygen compound", "Organooxygen compound", "Phenol", "Styrene"]
Spectra from Online Resources
| Record ID | Source | Description | View |
|---|---|---|---|
| JP007236 | MassBank | EI-B Spectrum - -, [M]+* | View Spectra |
| JP011903 | MassBank | EI-B Spectrum - -, [M]+* | View Spectra |
| KO000406 | MassBank | LC-ESI-QQ Spectrum - 10 V, unspecified | View Spectra |
| KO000407 | MassBank | LC-ESI-QQ Spectrum - 20 V, unspecified | View Spectra |
| KO000408 | MassBank | LC-ESI-QQ Spectrum - 30 V, unspecified | View Spectra |
| KO000409 | MassBank | LC-ESI-QQ Spectrum - 40 V, unspecified | View Spectra |
| KO000410 | MassBank | LC-ESI-QQ Spectrum - 50 V, unspecified | View Spectra |
| OUF00416 | MassBank | GC-EI-TOF Spectrum - -, unspecified | View Spectra |
| PR100261 | MassBank | LC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecified | View Spectra |
| PR100685 | MassBank | LC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecified | View Spectra |
| PR100894 | MassBank | LC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecified | View Spectra |
| PR100895 | MassBank | LC-ESI-QTOF Spectrum - 30 V, unspecified | View Spectra |
Food Sources
| Name | Group | |||
|---|---|---|---|---|
| American cranberry | Fruit, Berries | Publications | Show | |
| Apple | Fruit, Pomes | Publications | Show | |
| Apple cider | Beverages, Alcoholic | Publications | Show | |
| Apple juice | Beverages, Non-alcoholic | Publications | Show | |
| Beer | Beverages, Alcoholic | Publications | Show | |
| Blackberry | Fruit, Berries | Publications | Show | |
| Coffee | Coffee and coffee products | Publications | Show | |
| European cranberry | Fruit, Berries | Publications | Show | |
| Olive, black | Fruit, Drupes | Publications | Show | |
| Olive, green | Fruit, Drupes | Publications | Show | |
| Orange juice | Beverages, Non-alcoholic | Publications | Show | |
| Peanut | Nuts | Publications | Show | |
| Strawberry | Fruit, Berries | Publications | Show | |
| Tomato | Vegetables, Fruit vegetables | Publications | Show | |
| Wheat bread | Cereals and cereal products | Publications | Show |
Food Sources of its Food Phytochemical(s)
| Food Phytochemical | Food Source | Food Source Group | |||
|---|---|---|---|---|---|
| Naringenin | Cherry tomato | Vegetables, Fruit vegetables | Publications | Show | |
| Naringenin | Grapefruit | Fruit, Citrus | Publications | Show | |
| Naringenin | Grapefruit juice | Beverages, Non-alcoholic | Publications | Show | |
| Naringenin | Sweet orange | Fruit, Citrus | Publications | Show | |
| Naringenin | Tomato | Vegetables, Fruit vegetables | 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 | ||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Coumaric acid (p-) | p-Hydroxybenzoic acid | human | urine | Not Available | Not Available | Not Available | Not Available | C7H6O3 | 138.031694053 | Publications | |||
| Coumaric acid (p-) | Benzoic acid | human | urine | gut microbiota metabolite | Not Available | Not Available | Not Available | C7H6O2 | 122.036779433 | ||||
| Coumaric acid (p-) | Phloretic acid | human | urine | host metabolism | Not Available | Not Available | Not Available | C9H10O3 | 166.062994182 | Publications | |||
| Coumaric acid (p-) | 3-Phenylpropionic acid | human | Not Available | gut microbiota metabolite | Not Available | Not Available | Not Available | C9H10O2 | 150.068079562 | Publications | |||
| Coumaric acid (p-) | Hippuric acid | human | plasma, urine | host-gut microbiota co-metabolite | Not Available | Not Available | Not Available | C9H9NO3 | 179.058243154 | Publications | |||
| Coumaric acid (p-) | Coumaric acid-4'-O-glucuronide | rat | plasma | Not Available | Not Available | Not Available | Not Available | C15H16O9 | 340.079432095 | Publications | |||
| Coumaric acid (p-) | coumaric acid-4′-sulfate | rat | plasma | Not Available | Not Available | Not Available | Not Available | C9H8O6S | 244.004159152 | Publications | |||
| Coumaric acid (p-) | Coumaric acid sulfoglucuronide (p-) | rat | plasma | Not Available | Not Available | Not Available | Not Available | C15H16O12S | 420.3492191 | Publications | |||
| Naringenin | Coumaric acid (p-) | rat | urine | Not Available | Not Available | Not Available | Not Available | C9H8O3 | 164.047344118 | Publications | |||
| Orange flavanones | Coumaric acid (p-) | human | urine | gut microbiota metabolite | Not Available | Not Available | Not Available | C9H8O3 | 164.047344118 | Detailed Intervention Studies |
Inter-Individual Variations Metabolism
No data on inter-individual variations available