Identification

PhytoHub ID
PHUB000622
Name
Isoferulic acid
Systematic Name
3’-Hydroxy-4’-methoxycinnamic acid
Synonyms
  • 3-(3-hydroxy-4-methoxyphenyl)acrylic acid
  • 3-hydroxy-4-methoxycinnamic acid
  • hesperetate
  • Hesperetic acid
CAS Number
537-73-5
Average Mass
194.186
Monoisotopic Mass
194.057908802
Chemical Formula
C10H10O4
IUPAC Name
isoferulic acid
InChI Key
QURCVMIEKCOAJU-HWKANZROSA-N
InChI Identifier
InChI=1S/C10H10O4/c1-14-9-4-2-7(6-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+
SMILES
COC1=C(O)C=C(\C=C\C(O)=O)C=C1
Structure

Calculated Properties

Solubility (ALOGPS)
8.71e-01 g/l
LogS (ALOGPS)
-2.35
LogP (ALOGPS)
1.56
Hydrogen Acceptors
4
Hydrogen Donors
2
Rotatable Bond Count
3
Polar Surface Area
66.76
Refractivity
51.50400000000001
Polarizability
19.407828698621252
Formal Charge
0
Physiological Charge
-1
pKa (strongest basic)
-4.889780750650177
pKa (strongest acidic)
3.5754283041637582
Number of Rings
1
Rule of Five
Yes
Bioavailability
Yes
Ghose Filter
Yes
Veber's Rule
No
MDDR-like Rule
No

Taxonomy as Metabolite

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

Taxonomy of its Precursor(s)

PrecursorFamilyClassSub-class
Caffeic acid(Poly)phenol metabolitesPhenolic acid metabolitesCinnamic acidsShow Precursor
5-O-Caffeoylquinic acidPolyphenolsPhenolic acidsHydroxycinnamic acidsShow Precursor
Dihydrocaffeic acid(Poly)phenol metabolitesPhenolic acid metabolitesPhenylpropanoic acidsShow Precursor
Orange flavanonesPolyphenolsFlavonoidsFlavanonesShow Precursor

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", "Alkyl aryl ethers", "Anisoles", "Carbonyl compounds", "Carboxylic acids", "Cinnamic acids", "Coumaric acids and derivatives", "Hydrocarbon derivatives", "Methoxybenzenes", "Methoxyphenols", "Monocarboxylic acids and derivatives", "Organic oxides", "Phenoxy compounds", "Styrenes"]
External Descriptor Annotations
["ferulic acids"]
Substituent Names
["1-hydroxy-2-unsubstituted benzenoid", "1-hydroxy-4-unsubstituted benzenoid", "Alkyl aryl ether", "Anisole", "Aromatic homomonocyclic compound", "Benzenoid", "Carbonyl group", "Carboxylic acid", "Carboxylic acid derivative", "Cinnamic acid", "Coumaric acid or derivatives", "Ether", "Hydrocarbon derivative", "Hydroxycinnamic acid", "Methoxybenzene", "Methoxyphenol", "Monocarboxylic acid or derivatives", "Monocyclic benzene moiety", "Organic oxide", "Organic oxygen compound", "Organooxygen compound", "Phenol", "Phenol ether", "Phenoxy compound", "Styrene"]

Spectra

Record IDSourceDescriptionView
JP002207MassBankEI-B Spectrum - -, [M]+*View Spectra
KO001211MassBankLC-ESI-QQ Spectrum - 10 V, unspecifiedView Spectra
KO001212MassBankLC-ESI-QQ Spectrum - 20 V, unspecifiedView Spectra
KO001213MassBankLC-ESI-QQ Spectrum - 30 V, unspecifiedView Spectra
KO001214MassBankLC-ESI-QQ Spectrum - 40 V, unspecifiedView Spectra
KO001215MassBankLC-ESI-QQ Spectrum - 50 V, unspecifiedView Spectra

Food Sources

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
Dihydrocaffeic acidBlueberryFruit, BerriesShow
Caffeic acidBroccoliVegetables, Cabbages PublicationsShow
5-O-Caffeoylquinic acidBroccoliVegetables, Cabbages PublicationsShow
Dihydrocaffeic acidBroccoliVegetables, CabbagesShow
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
Dihydrocaffeic acidCiderBeverages, AlcoholicShow
Caffeic acidCoffeeCoffee and coffee products PublicationsShow
5-O-Caffeoylquinic acidCoffeeCoffee and coffee products PublicationsShow
Dihydrocaffeic acidCoffeeCoffee and coffee productsShow
Caffeic acidCommon wheatCereals and cereal products PublicationsShow
Dihydrocaffeic acidCommon wheatCereals and cereal productsShow
Dihydrocaffeic acidCornCereals and cereal productsShow
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
Dihydrocaffeic acidGrapesFruit, BerriesShow
5-O-Caffeoylquinic acidGreen teaTeas and herbal teas PublicationsShow
Dihydrocaffeic acidLemonFruit, CitrusShow
5-O-Caffeoylquinic acidLettuceVegetables, Leaf vegetables PublicationsShow
Dihydrocaffeic acidLettuceVegetables, Leaf vegetablesShow
Dihydrocaffeic acidLimeFruit, CitrusShow
Caffeic acidMateBeverages, Non-alcoholic PublicationsShow
5-O-Caffeoylquinic acidMateBeverages, Non-alcoholic PublicationsShow
Caffeic acidOlive, blackFruit, Drupes PublicationsShow
5-O-Caffeoylquinic acidOlive, blackFruit, Drupes PublicationsShow
Dihydrocaffeic acidOlive, blackFruit, Drupes PublicationsShow
Caffeic acidOlive, greenFruit, Drupes PublicationsShow
Dihydrocaffeic acidOlive, greenFruit, Drupes PublicationsShow
5-O-Caffeoylquinic acidPeachFruit, Drupes PublicationsShow
Caffeic acidPearFruit, Pomes PublicationsShow
5-O-Caffeoylquinic acidPearFruit, Pomes PublicationsShow
5-O-Caffeoylquinic acidPotatoVegetables, Tubers PublicationsShow
5-O-Caffeoylquinic acidRoasted coffeeCoffee and coffee products PublicationsShow
Dihydrocaffeic acidSpinachVegetables, Leaf vegetablesShow
Caffeic acidStrawberryFruit, Berries PublicationsShow
5-O-Caffeoylquinic acidStrawberryFruit, Berries 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
Dihydrocaffeic acidWheat breadCereals and cereal productsShow
Caffeic acidWhite wine grapeFruit, Berries PublicationsShow

Metabolism

PrecursorMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
Caffeic acid Isoferulic acidhuman ratfaeces, plasma, urinehost metabolismNot AvailableNot AvailableC10H10O4194.057908802 Publications
5-O-Caffeoylquinic acid Isoferulic acidraturinehost metabolismNot AvailableNot AvailableC10H10O4194.057908802
Dihydrocaffeic acid Isoferulic acidraturineNot AvailableNot AvailableNot AvailableC10H10O4194.057908802
Orange flavanones Isoferulic acidhumanurinegut microbiota metaboliteNot AvailableNot Available1-5%C10H10O4194.057908802 Detailed Intervention Studies

Inter-Individual Variations Metabolism

No inter-individual variations available

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