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
para-coumaric 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

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

Taxonomy as Precursor

Family
(Poly)phenol metabolites
Class
Phenolic acid metabolites
Sub-class
Cinnamic acids

Taxonomy as Metabolite

Metabolite Family
Not Available
Metabolite Class
Not Available
Metabolite Sub-class
Not Available

Taxonomy of its Precursor(s)

PrecursorFamilyClassSub-class
NaringeninPolyphenolsFlavonoidsFlavanonesShow Precursor
Orange flavanonesPolyphenolsFlavonoidsFlavanonesShow Precursor

Spectra

Record IDSourceDescriptionView
JP007236MassBankEI-B Spectrum - -, [M]+*View Spectra
JP011903MassBankEI-B Spectrum - -, [M]+*View Spectra
KO000406MassBankLC-ESI-QQ Spectrum - 10 V, unspecifiedView Spectra
KO000407MassBankLC-ESI-QQ Spectrum - 20 V, unspecifiedView Spectra
KO000408MassBankLC-ESI-QQ Spectrum - 30 V, unspecifiedView Spectra
KO000409MassBankLC-ESI-QQ Spectrum - 40 V, unspecifiedView Spectra
KO000410MassBankLC-ESI-QQ Spectrum - 50 V, unspecifiedView Spectra
OUF00416MassBankGC-EI-TOF Spectrum - -, unspecifiedView Spectra
PR100261MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecifiedView Spectra
PR100685MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecifiedView Spectra
PR100894MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecifiedView Spectra
PR100895MassBankLC-ESI-QTOF Spectrum - 30 V, unspecifiedView Spectra

Food Sources

NameGroup
American cranberryFruit, Berries PublicationsShow
AppleFruit, Pomes PublicationsShow
Apple ciderBeverages, Alcoholic PublicationsShow
Apple juiceBeverages, Non-alcoholic PublicationsShow
BeerBeverages, Alcoholic PublicationsShow
BlackberryFruit, Berries PublicationsShow
CoffeeCoffee and coffee products PublicationsShow
European cranberryFruit, Berries PublicationsShow
Olive, blackFruit, Drupes PublicationsShow
Olive, greenFruit, Drupes PublicationsShow
Orange juiceBeverages, Non-alcoholic PublicationsShow
PeanutNuts PublicationsShow
StrawberryFruit, Berries PublicationsShow
TomatoVegetables, Fruit vegetables PublicationsShow
Wheat breadCereals and cereal products PublicationsShow
PrecursorFood SourceFood Source Group
NaringeninCherry tomatoVegetables, Fruit vegetables PublicationsShow
NaringeninGrapefruitFruit, Citrus PublicationsShow
NaringeninGrapefruit juiceBeverages, Non-alcoholic PublicationsShow
NaringeninSweet orangeFruit, Citrus PublicationsShow
NaringeninTomatoVegetables, Fruit vegetables PublicationsShow

Metabolism

PrecursorMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
Coumaric acid (p-) 3-Phenylpropionic acidhumanNot Availablegut microbiota metaboliteNot AvailableNot AvailableC9H10O2150.068079562 Publications
Coumaric acid (p-) Benzoic acidhumanurinegut microbiota metaboliteNot AvailableNot AvailableC7H6O2122.036779433
Coumaric acid (p-) Coumaric acid-4'-O-glucuronideratplasmaNot AvailableNot AvailableNot AvailableC15H16O9340.079432095 Publications
Coumaric acid (p-) coumaric acid-4′-sulfateratplasmaNot AvailableNot AvailableNot AvailableC9H8O6S244.2233596 Publications
Coumaric acid (p-) Coumaric acid sulfoglucuronide (p-)ratplasmaNot AvailableNot AvailableNot AvailableC15H16O12S420.3492191 Publications
Coumaric acid (p-) Hippuric acidhumanplasma, urinehost-gut microbiota co-metaboliteNot AvailableNot AvailableC9H9NO3179.058243154 Publications
Coumaric acid (p-) Phloretic acidhumanurinehost metabolismNot AvailableNot AvailableC9H10O3166.062994182 Publications
Coumaric acid (p-) p-Hydroxybenzoic acidhumanurineNot AvailableNot AvailableNot AvailableC7H6O3138.031694053 Publications
Naringenin Coumaric acid (p-)raturineNot AvailableNot AvailableNot AvailableC9H8O3164.047344118 Publications
Orange flavanones Coumaric acid (p-)humanurinegut microbiota metaboliteNot AvailableNot AvailableC9H8O3164.047344118 Detailed Intervention Studies

Inter-Individual Variations Metabolism

No inter-individual variations available

Back