PhytoHub: Showing entry for Ferulic acid

Ferulic acid

Identification

PhytoHub ID

PHUB000608

Name

Ferulic acid

Systematic Name

4’-hydroxy-3’-methoxycinnamic acid

Synonyms

3-(4-hydroxy-3-methoxyphenyl)acrylic acid
3-Methoxy-4-hydroxycinnamic acid
4-Hydroxy-3-methoxycinnamic acid
4’-hydroxy-3’-methoxycinnamic acid
trans-ferulic acid

CAS Number

537-98-4

Average Mass

194.186

Monoisotopic Mass

194.057908802

Chemical Formula

C₁₀H₁₀O₄

IUPAC Name

ferulic acid

InChI Key

KSEBMYQBYZTDHS-HWKANZROSA-N

InChI Identifier

InChI=1S/C10H10O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+

SMILES

COC1=C(O)C=CC(\C=C\C(O)=O)=C1

Structure

Similar Structures

Calculated Properties

Solubility (ALOGPS): 9.06e-01 g/l
LogS (ALOGPS): -2.33
LogP (ALOGPS): 1.58
Hydrogen Acceptors: 4
Hydrogen Donors: 2
Rotatable Bond Count: 3
Polar Surface Area: 66.76
Refractivity: 51.50400000000002
Polarizability: 19.349332656403057
Formal Charge: 0
Physiological Charge: -1
pKa (strongest basic): -4.893961534479146
pKa (strongest acidic): 3.5753044752877954
Number of Rings: 1
Rule of Five: Yes
Bioavailability: Yes
Ghose Filter: Yes
Veber's Rule: No
MDDR-like Rule: No

External Links

ChEBI: 17620
PubChem: 445858
MetaboLights: MTBLC17620

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)

Precursor	Family	Class	Sub-class
Cyanidin 3-O-glucoside	Polyphenols	Flavonoids	Anthocyanins	Show Precursor
Caffeic acid	(Poly)phenol metabolites	Phenolic acid metabolites	Cinnamic acids	Show Precursor
5-O-Caffeoylquinic acid	Polyphenols	Phenolic acids	Hydroxycinnamic acids	Show Precursor
Orange flavanones	Polyphenols	Flavonoids	Flavanones	Show Precursor

Spectra

Record ID	Source	Description	View
JP002207	MassBank	EI-B Spectrum - -, [M]+*	View Spectra
JP007239	MassBank	EI-B Spectrum - -, [M]+*	View Spectra
JP011305	MassBank	EI-B Spectrum - -, [M]+*	View Spectra
JP011308	MassBank	EI-B Spectrum - -, [M]+*	View Spectra
KO001106	MassBank	LC-ESI-QQ Spectrum - 10 V, unspecified	View Spectra
KO001107	MassBank	LC-ESI-QQ Spectrum - 20 V, unspecified	View Spectra
KO001108	MassBank	LC-ESI-QQ Spectrum - 30 V, unspecified	View Spectra
KO001109	MassBank	LC-ESI-QQ Spectrum - 40 V, unspecified	View Spectra
KO001110	MassBank	LC-ESI-QQ Spectrum - 50 V, unspecified	View Spectra
KZ000089	MassBank	GC-EI-TOF Spectrum - -, unspecified	View Spectra
KZ000133	MassBank	GC-EI-TOF Spectrum - -, unspecified	View Spectra
OUF00227	MassBank	GC-EI-TOF Spectrum - -, unspecified	View Spectra
PR010004	MassBank	GC-EI-TOF Spectrum - -, unspecified	View Spectra
PR100004	MassBank	LC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecified	View Spectra
PR100005	MassBank	LC-ESI-QTOF Spectrum - 30 V, unspecified	View Spectra
PR100482	MassBank	LC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecified	View Spectra
PS001101	ReSpect	N/A Spectrum - 10, [M+H]+	View Spectra
PS001102	ReSpect	N/A Spectrum - 20, [M+H]+	View Spectra
PS001103	ReSpect	N/A Spectrum - 30, [M+H]+	View Spectra
PS103901	ReSpect	N/A Spectrum - 10, [M+H]+	View Spectra
PS103902	ReSpect	N/A Spectrum - 20, [M+H]+	View Spectra
PS103907	ReSpect	N/A Spectrum - 10, [M-H]-	View Spectra

Food Sources

Name	Group
American cranberry	Fruit, Berries	Publications	Show
Apple juice	Beverages, Non-alcoholic	Publications	Show
Beer	Beverages, Alcoholic	Publications	Show
Bilberry	Fruit, Berries	Publications	Show
Black mulberry	Fruit, Berries	Publications	Show
Blackberry	Fruit, Berries	Publications	Show
Blueberry	Fruit, Berries	Publications	Show
Broccoli	Vegetables, Cabbages	Publications	Show
Cocoa bean	Cocoa and cocoa products	Publications	Show
Coffee	Coffee and coffee products	Publications	Show
Common bean	Pulses and beans	Publications	Show
Common walnut	Nuts	Publications	Show
Common wheat	Cereals and cereal products	Publications	Show
Corn	Cereals and cereal products	Publications	Show
Date	Fruit, Other fruits	Publications	Show
Eggplant	Vegetables, Fruit vegetables	Publications	Show
European cranberry	Fruit, Berries	Publications	Show
Fennel	Herbs and Spices	Publications	Show
Grapefruit	Fruit, Citrus	Publications	Show
Hard wheat	Cereals and cereal products	Publications	Show
Olive, black	Fruit, Drupes	Publications	Show
Olive, green	Fruit, Drupes	Publications	Show
Orange juice	Beverages, Non-alcoholic	Publications	Show
Rapeseed	Oilseed crops	Publications	Show
Red raspberry	Fruit, Berries	Publications	Show
Rice	Cereals and cereal products	Publications	Show
Rosemary	Herbs and Spices	Publications	Show
Rye bread	Cereals and cereal products	Publications	Show
Spinach	Vegetables, Leaf vegetables	Publications	Show
Strawberry	Fruit, Berries	Publications	Show
Sweet orange	Fruit, Citrus	Publications	Show
Tarragon	Herbs and Spices	Publications	Show
Tomato	Vegetables, Fruit vegetables	Publications	Show
White wine	Beverages, Alcoholic	Publications	Show

Precursor	Food Source	Food Source Group
Caffeic acid	American cranberry	Fruit, Berries	Publications	Show
Caffeic acid	Apple	Fruit, Pomes	Publications	Show
5-O-Caffeoylquinic acid	Apple	Fruit, Pomes	Publications	Show
5-O-Caffeoylquinic acid	Apple cider	Beverages, Alcoholic	Publications	Show
Caffeic acid	Apple juice	Beverages, Non-alcoholic	Publications	Show
5-O-Caffeoylquinic acid	Apple juice	Beverages, Non-alcoholic	Publications	Show
5-O-Caffeoylquinic acid	Apricot	Fruit, Drupes	Publications	Show
Cyanidin 3-O-glucoside	Blackberry	Fruit, Berries	Publications	Show
Caffeic acid	Blackberry	Fruit, Berries	Publications	Show
5-O-Caffeoylquinic acid	Blackberry	Fruit, Berries	Publications	Show
5-O-Caffeoylquinic acid	Blackcurrant	Fruit, Berries	Publications	Show
Caffeic acid	Blueberry	Fruit, Berries	Publications	Show
5-O-Caffeoylquinic acid	Blueberry	Fruit, Berries	Publications	Show
Caffeic acid	Broccoli	Vegetables, Cabbages	Publications	Show
5-O-Caffeoylquinic acid	Broccoli	Vegetables, Cabbages	Publications	Show
Caffeic acid	Carrot	Vegetables, Root vegetables	Publications	Show
5-O-Caffeoylquinic acid	Carrot	Vegetables, Root vegetables	Publications	Show
5-O-Caffeoylquinic acid	Cherry tomato	Vegetables, Fruit vegetables	Publications	Show
Caffeic acid	Cider	Beverages, Alcoholic	Publications	Show
5-O-Caffeoylquinic acid	Cider	Beverages, Alcoholic	Publications	Show
Caffeic acid	Coffee	Coffee and coffee products	Publications	Show
5-O-Caffeoylquinic acid	Coffee	Coffee and coffee products	Publications	Show
Caffeic acid	Common wheat	Cereals and cereal products	Publications	Show
Caffeic acid	Eggplant	Vegetables, Fruit vegetables	Publications	Show
5-O-Caffeoylquinic acid	Eggplant	Vegetables, Fruit vegetables	Publications	Show
Caffeic acid	European cranberry	Fruit, Berries	Publications	Show
5-O-Caffeoylquinic acid	European cranberry	Fruit, Berries	Publications	Show
Caffeic acid	European plum	Fruit, Drupes	Publications	Show
5-O-Caffeoylquinic acid	European plum	Fruit, Drupes	Publications	Show
5-O-Caffeoylquinic acid	Globe artichoke	Vegetables, Other vegetables	Publications	Show
5-O-Caffeoylquinic acid	Green tea	Teas and herbal teas	Publications	Show
Cyanidin 3-O-glucoside	Lettuce	Vegetables, Leaf vegetables	Publications	Show
5-O-Caffeoylquinic acid	Lettuce	Vegetables, Leaf vegetables	Publications	Show
Caffeic acid	Mate	Beverages, Non-alcoholic	Publications	Show
5-O-Caffeoylquinic acid	Mate	Beverages, Non-alcoholic	Publications	Show
Cyanidin 3-O-glucoside	Olive, black	Fruit, Drupes	Publications	Show
Caffeic acid	Olive, black	Fruit, Drupes	Publications	Show
5-O-Caffeoylquinic acid	Olive, black	Fruit, Drupes	Publications	Show
Caffeic acid	Olive, green	Fruit, Drupes	Publications	Show
5-O-Caffeoylquinic acid	Peach	Fruit, Drupes	Publications	Show
Caffeic acid	Pear	Fruit, Pomes	Publications	Show
5-O-Caffeoylquinic acid	Pear	Fruit, Pomes	Publications	Show
Cyanidin 3-O-glucoside	Pomegranate juice	Beverages, Non-alcoholic	Publications	Show
5-O-Caffeoylquinic acid	Potato	Vegetables, Tubers	Publications	Show
5-O-Caffeoylquinic acid	Roasted coffee	Coffee and coffee products	Publications	Show
Cyanidin 3-O-glucoside	Strawberry	Fruit, Berries	Publications	Show
Caffeic acid	Strawberry	Fruit, Berries	Publications	Show
5-O-Caffeoylquinic acid	Strawberry	Fruit, Berries	Publications	Show
Cyanidin 3-O-glucoside	Sweet cherry	Fruit, Drupes	Publications	Show
Caffeic acid	Sweet cherry	Fruit, Drupes	Publications	Show
5-O-Caffeoylquinic acid	Sweet cherry	Fruit, Drupes	Publications	Show
Caffeic acid	Tomato	Vegetables, Fruit vegetables	Publications	Show
5-O-Caffeoylquinic acid	Tomato	Vegetables, Fruit vegetables	Publications	Show
Caffeic acid	White wine grape	Fruit, Berries	Publications	Show

Metabolism

Precursor	Metabolite	Species	Biofluids	Origin	TMax	CMax	Urinary Excretion	Formula	Monoisotopic mass
Ferulic acid	3-(3'-Hydroxyphenyl)propionic acid	human rat	plasma, urine	gut microbiota metabolite	Not Available	Not Available		C₉H₁₀O₃	166.062994182
Ferulic acid	3',4'-Dihydroxyphenylacetic acid	human in vitro (human) rat	urine	gut microbiota metabolite	Not Available	Not Available		C₈H₈O₄	168.042258738		Publications
Ferulic acid	veratric acid	human	plasma, urine	host metabolism	Not Available	Not Available		C₉H₁₀O₄	182.057908802		Publications
Ferulic acid	3-Hydroxybenzoic acid	human rat	plasma, urine	gut microbiota metabolite	Not Available	Not Available		C₇H₆O₃	138.031694053		Publications
Ferulic acid	3-Phenylpropionic acid	human	plasma	gut microbiota metabolite	Not Available	Not Available		C₉H₁₀O₂	150.068079562
Ferulic acid	Dihydrocaffeic acid	human	urine	gut microbiota metabolite	Not Available	Not Available		C₉H₁₀O₄	182.057908802
Ferulic acid	Dihydroferulic acid	rat	urine	Not Available	Not Available	Not Available		C₁₀H₁₂O₄	196.073558866		Publications
Ferulic acid	Ferulic acid-4'-O-glucuronide	rat	urine	Not Available	Not Available	Not Available		C₁₆H₁₈O₁₀	370.08999678		Publications
Ferulic acid	Ferulic acid-4'-sulfate	rat	plasma	Not Available	Not Available	Not Available		C₁₀H₁₀O₇S	274.014723836		Publications
Ferulic acid	Ferulic acid sulfoglucuronide	rat	plasma	Not Available	Not Available	Not Available		C₁₆H₁₈O₁₃S	450.375513		Publications
Ferulic acid	Feruloylglycine	rat	urine	Not Available	Not Available	Not Available		C₁₂H₁₃NO₅	251.079372523		Publications
Ferulic acid	Hippuric acid	human	plasma, urine	host-gut microbiota co-metabolite	Not Available	Not Available		C₉H₉NO₃	179.058243154		Publications
Ferulic acid	Vanillic acid	human rat	urine	Not Available	Not Available	Not Available		C₈H₈O₄	168.042258738		Publications
Ferulic acid	Vanilloyl-glycine	rat	urine	Not Available	Not Available	Not Available		C₁₀H₁₁NO₅	225.063722458		Publications
Ferulic acid	Phloretic acid	human	urine	host metabolism	Not Available	Not Available		C₉H₁₀O₃	166.062994182
Ferulic acid	p-Hydroxybenzoic acid	human	plasma, urine	Not Available	Not Available	Not Available		C₇H₆O₃	138.031694053		Publications
Ferulic acid	Protocatechuic acid	human	plasma, urine	Not Available	Not Available	Not Available		C₇H₆O₄	154.026608673		Publications
Cyanidin 3-O-glucoside	Ferulic acid	human	faeces, serum, urine	Not Available	Not Available	Not Available		C₁₀H₁₀O₄	194.057908802		Publications
Caffeic acid	Ferulic acid	human rat	plasma, urine	host metabolism	Not Available	Not Available		C₁₀H₁₀O₄	194.057908802		Publications
5-O-Caffeoylquinic acid	Ferulic acid	rat	plasma, urine	host metabolism	Not Available	Not Available		C₁₀H₁₀O₄	194.057908802		Publications
Orange flavanones	Ferulic acid	human	plasma, urine	gut microbiota metabolite	1h-3h	<20 nmol/L	1-5%	C₁₀H₁₀O₄	194.057908802	Detailed Intervention Studies	Publications

Inter-Individual Variations Metabolism

No inter-individual variations available

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Showing entry for Ferulic acid