Identification

PhytoHub ID
PHUB000588
Name
Coumaric acid (m-)
Systematic Name
3'-hydroxycinnamic acid
Synonyms
  • 3-(3-hydroxyphenyl)acrylic acid
  • 3-coumaric acid
  • 3-Hydroxycinnamic acid
  • trans-3-coumaric acid
CAS Number
588-30-7
Average Mass
164.16
Monoisotopic Mass
164.047344118
Chemical Formula
C9H8O3
IUPAC Name
m-coumaric acid
InChI Key
KKSDGJDHHZEWEP-SNAWJCMRSA-N
InChI Identifier
InChI=1S/C9H8O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-6,10H,(H,11,12)/b5-4+
SMILES
OC(=O)\C=C\C1=CC(O)=CC=C1
Structure

Calculated Properties

Solubility (ALOGPS)
1.04e+00 g/l
LogS (ALOGPS)
-2.20
LogP (ALOGPS)
1.71
Hydrogen Acceptors
3
Hydrogen Donors
2
Rotatable Bond Count
2
Polar Surface Area
57.53
Refractivity
45.040800000000004
Polarizability
16.37252332945193
Formal Charge
0
Physiological Charge
-1
pKa (strongest basic)
-5.971942929194903
pKa (strongest acidic)
3.8229114681096656
Number of Rings
1
Rule of Five
Yes
Bioavailability
Yes
Ghose Filter
Yes
Veber's Rule
No
MDDR-like Rule
No

Taxonomy

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

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", "1-hydroxy-4-unsubstituted benzenoids", "Carbonyl compounds", "Carboxylic acids", "Cinnamic acids", "Coumaric acids", "Hydrocarbon derivatives", "Monocarboxylic acids and derivatives", "Organic oxides", "Styrenes"]
External Descriptor Annotations
["3-coumaric acid"]
Substituent Names
["1-hydroxy-2-unsubstituted benzenoid", "1-hydroxy-4-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

Record IDSourceDescriptionView
ML001251MassBankLC-ESI-ITFT Spectrum - 50 % (nominal), unspecifiedView Spectra
PR100766MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecifiedView Spectra
PR100767MassBankLC-ESI-QTOF Spectrum - 30 V, unspecifiedView Spectra

Food Sources

NameGroup
BlackberryFruit, Berries PublicationsShow
BlueberryFruit, Berries PublicationsShow
BroccoliVegetables, CabbagesShow
CiderBeverages, AlcoholicShow
CoffeeCoffee and coffee productsShow
GrapesFruit, BerriesShow
LettuceVegetables, Leaf vegetablesShow
Olive, blackFruit, Drupes PublicationsShow
Olive, greenFruit, Drupes PublicationsShow
SpinachVegetables, Leaf vegetablesShow
PrecursorFood SourceFood Source Group
Caffeic acidAmerican cranberryFruit, Berries PublicationsShow
Caffeic acidAppleFruit, Pomes PublicationsShow
5-O-Caffeoylquinic acidAppleFruit, Pomes PublicationsShow
5-O-Caffeoylquinic acidApple ciderBeverages, Alcoholic PublicationsShow
Caffeic acidApple juiceBeverages, Non-alcoholic PublicationsShow
5-O-Caffeoylquinic acidApple juiceBeverages, Non-alcoholic PublicationsShow
5-O-Caffeoylquinic acidApricotFruit, Drupes PublicationsShow
Caffeic acidBlackberryFruit, Berries PublicationsShow
5-O-Caffeoylquinic acidBlackberryFruit, Berries PublicationsShow
5-O-Caffeoylquinic acidBlackcurrantFruit, Berries PublicationsShow
Caffeic acidBlueberryFruit, Berries PublicationsShow
5-O-Caffeoylquinic acidBlueberryFruit, Berries PublicationsShow
Caffeic acidBroccoliVegetables, Cabbages PublicationsShow
5-O-Caffeoylquinic acidBroccoliVegetables, Cabbages PublicationsShow
Caffeic acidCarrotVegetables, Root vegetables PublicationsShow
5-O-Caffeoylquinic acidCarrotVegetables, Root vegetables PublicationsShow
5-O-Caffeoylquinic acidCherry tomatoVegetables, Fruit vegetables PublicationsShow
Caffeic acidCiderBeverages, Alcoholic PublicationsShow
5-O-Caffeoylquinic acidCiderBeverages, Alcoholic PublicationsShow
Caffeic acidCoffeeCoffee and coffee products PublicationsShow
5-O-Caffeoylquinic acidCoffeeCoffee and coffee products PublicationsShow
Rosmarinic acidCommon oreganoHerbs and Spices PublicationsShow
Rosmarinic acidCommon sageHerbs and Spices PublicationsShow
Rosmarinic acidCommon thymeHerbs and Spices PublicationsShow
Caffeic acidCommon wheatCereals and cereal products PublicationsShow
Caffeic acidEggplantVegetables, Fruit vegetables PublicationsShow
5-O-Caffeoylquinic acidEggplantVegetables, Fruit vegetables PublicationsShow
Caffeic acidEuropean cranberryFruit, Berries PublicationsShow
5-O-Caffeoylquinic acidEuropean cranberryFruit, Berries PublicationsShow
Caffeic acidEuropean plumFruit, Drupes PublicationsShow
5-O-Caffeoylquinic acidEuropean plumFruit, Drupes PublicationsShow
5-O-Caffeoylquinic acidGlobe artichokeVegetables, Other vegetables PublicationsShow
5-O-Caffeoylquinic acidGreen teaTeas and herbal teas PublicationsShow
5-O-Caffeoylquinic acidLettuceVegetables, Leaf vegetables PublicationsShow
Caffeic acidMateBeverages, Non-alcoholic PublicationsShow
5-O-Caffeoylquinic acidMateBeverages, Non-alcoholic PublicationsShow
Rosmarinic acidMentha (Mint)Herbs and Spices PublicationsShow
Caffeic acidOlive, blackFruit, Drupes PublicationsShow
5-O-Caffeoylquinic acidOlive, blackFruit, Drupes PublicationsShow
Caffeic acidOlive, greenFruit, Drupes PublicationsShow
5-O-Caffeoylquinic acidPeachFruit, Drupes PublicationsShow
Caffeic acidPearFruit, Pomes PublicationsShow
5-O-Caffeoylquinic acidPearFruit, Pomes PublicationsShow
Rosmarinic acidPeppermintHerbs and Spices PublicationsShow
5-O-Caffeoylquinic acidPotatoVegetables, Tubers PublicationsShow
5-O-Caffeoylquinic acidRoasted coffeeCoffee and coffee products PublicationsShow
Rosmarinic acidRosemaryHerbs and Spices PublicationsShow
Caffeic acidStrawberryFruit, Berries PublicationsShow
5-O-Caffeoylquinic acidStrawberryFruit, Berries PublicationsShow
Rosmarinic acidSweet basilHerbs and Spices PublicationsShow
Caffeic acidSweet cherryFruit, Drupes PublicationsShow
5-O-Caffeoylquinic acidSweet cherryFruit, Drupes PublicationsShow
Caffeic acidTomatoVegetables, Fruit vegetables PublicationsShow
5-O-Caffeoylquinic acidTomatoVegetables, Fruit vegetables PublicationsShow
Caffeic acidWhite wine grapeFruit, Berries PublicationsShow

Metabolism

PrecursorMetaboliteSpeciesBiofluidsOriginFormulaMonoisotopic mass
Coumaric acid (m-) 3-Hydroxyhippuric acidraturineNot AvailableC9H9NO4195.053157774 Publications
Coumaric acid (m-) Coumaric acid glucuronide (m-)raturineNot AvailableC15H16O9340.2869145 Publications
Caffeic acid Coumaric acid (m-)raturinegut microbiota metaboliteC9H8O3164.047344118 Publications
5-O-Caffeoylquinic acid Coumaric acid (m-)ratplasma, urinegut microbiota metaboliteC9H8O3164.047344118 Publications
Rosmarinic acid Coumaric acid (m-)ratplasma, urineNot AvailableC9H8O3164.047344118 Publications
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