Cannabis Compound Database: Showing Compound Card for Ferulic acid (CDB000044)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

1.0

Created at

2020-03-18 23:22:43 UTC

Updated at

2022-12-13 19:31:28 UTC

CannabisDB ID

CDB000044

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Ferulic acid

Description

Ferulic acid, also known as (e)-ferulate or trans-ferulate, belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing a cinnamic acid where the benzene ring is hydroxylated. Ferulic acid is a moderately weak acid (based on its pKa). Ferulic acid is a highly abundant phenolic phytochemical which is present in plant cell walls. In humans it can be readily absorbed by the small intestine and excreted through the urine. It is one of the most abundant phenolic acids in plants, varying from 5 g/kg in wheat bran to 9 g/kg in sugar-beet pulp and 50 g/kg in corn kernels. It occurs primarily in seeds and leaves both in its free form (albeit rarely) and covalently linked to lignin and other biopolymers. It is usually found as ester cross-links with polysaccharides in the cell wall, such as arabinoxylans in grasses, pectin in spinach and sugar beet, and xyloglucans in bamboo. It also can cross-link with a variety of plant proteins. Due to its phenolic nucleus and an extended side chain conjugation (carbohydrates and proteins), ferulic acid readily forms a resonance-stabilized phenoxy radical which accounts for its potent antioxidant potential. Food supplementation with curcumin and ferulic acid is considered a nutritional approach to reducing oxidative damage and amyloid pathology in Alzheimer‚Äôs disease (PMID: 17127365 , 1398220 , 15453708 , 9878519 ). Ferulic acid can be produced by a number of microbes including Pseudomonas and Saccharomyces (PMID: 8395165 ). It possesses antioxidant, anti-aging and anti-inflammatory properties. It protects the skin from damage by UV light and is used in skin care, sun care, hair care and color cosmetics.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(e)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid	ChEBI
(e)-4'-Hydroxy-3'-methoxycinnamic acid	ChEBI
(e)-4-Hydroxy-3-methoxycinnamic acid	ChEBI
(e)-Ferulic acid	ChEBI
3-(4-Hydroxy-3-methoxyphenyl)propenoic acid	ChEBI
3-Methoxy-4-hydroxy-trans-cinnamic acid	ChEBI
4-Hydroxy-3-methoxycinnamic acid	ChEBI
trans-4-Hydroxy-3-methoxycinnamic acid	ChEBI
3-Methoxy-4-hydroxy-trans-cinnamate	Kegg
4-Hydroxy-3-methoxycinnamate	Kegg
(e)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoate	Generator
(e)-4'-Hydroxy-3'-methoxycinnamate	Generator
(e)-4-Hydroxy-3-methoxycinnamate	Generator
(e)-Ferulate	Generator
3-(4-Hydroxy-3-methoxyphenyl)propenoate	Generator
trans-4-Hydroxy-3-methoxycinnamate	Generator
trans-Ferulate	Generator
Ferulate	Generator
(2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoate	HMDB
(2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid	HMDB
(e)-4-Hydroxy-3-methoxy-cinnamate	HMDB
(e)-4-Hydroxy-3-methoxy-cinnamic acid	HMDB
Ferulic acid, (e)-isomer	MeSH, HMDB
Ferulic acid, monosodium salt	MeSH, HMDB
Sodium ferulate	MeSH, HMDB
Ferulic acid, (Z)-isomer	MeSH, HMDB
8,8'-Diferulic acid	MeSH, HMDB
(2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-acrylic acid	HMDB
(2E)-3-(4-Hydroxy-3-methoxyphenyl)prop-2-enoic acid	HMDB
(E)-3-(4-Hydroxy-3-methoxyphenyl)acrylic acid	HMDB
Fumalic acid	HMDB
3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid	HMDB
3-Methoxy-4-hydroxycinnamic acid	HMDB
4'-Hydroxy-3'-methoxycinnamic acid	HMDB
Coniferic acid	HMDB
Ferulaic acid	HMDB
4’-Hydroxy-3’-methoxycinnamic acid	PhytoBank

Chemical Formula

C₁₀H₁₀O₄

Average Molecular Weight

194.18

Monoisotopic Molecular Weight

194.0579

IUPAC Name

(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid

Traditional Name

ferulic acid

CAS Registry Number

537-98-4

SMILES

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

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+

InChI Key

KSEBMYQBYZTDHS-HWKANZROSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acids

Alternative Parents

Substituents

Cinnamic acid
Coumaric acid or derivatives
Hydroxycinnamic acid
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Styrene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Ether
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

ferulic acids (CHEBI:17620 )
Coniferyl alcohol derivatives (C01494 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Tissue and substructures:

Epidermis

Cell and elements:

Cell:

Fibroblast

Subcellular:

Cytoplasm

Biofluid and excreta:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	168 - 171 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	1.51	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	1.58	ALOGPS
logP	1.67	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	3.77	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	51.5 m³·mol⁻¹	ChemAxon
Polarizability	19.18 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0006-5900000000-8c81de6c352294475072	2015-03-01	View Spectrum
GC-MS	Ferulic acid, 2 TMS, GC-MS Spectrum	splash10-05g4-1978000000-1097d5b300514a0489df	Spectrum
GC-MS	Ferulic acid, 2 TMS, GC-MS Spectrum	splash10-00kv-2964000000-3d20d62c97c33247cfcf	Spectrum
GC-MS	Ferulic acid, non-derivatized, GC-MS Spectrum	splash10-00ku-1965000000-ebee2a916fe97f0270a1	Spectrum
GC-MS	Ferulic acid, 2 TMS, GC-MS Spectrum	splash10-00di-9654000000-b3f1759076cffd2ac235	Spectrum
GC-MS	Ferulic acid, 2 TMS, GC-MS Spectrum	splash10-000m-3975000000-5a41c311d78f7219474c	Spectrum
GC-MS	Ferulic acid, non-derivatized, GC-MS Spectrum	splash10-0006-1900000000-5dffac87fe7c815de4ce	Spectrum
GC-MS	Ferulic acid, non-derivatized, GC-MS Spectrum	splash10-0006-2900000000-8db541bacfe47b9e0c8b	Spectrum
GC-MS	Ferulic acid, non-derivatized, GC-MS Spectrum	splash10-0006-2900000000-a338415bd30d4e62e664	Spectrum
GC-MS	Ferulic acid, non-derivatized, GC-MS Spectrum	splash10-05g4-1978000000-1097d5b300514a0489df	Spectrum
GC-MS	Ferulic acid, non-derivatized, GC-MS Spectrum	splash10-00kv-2964000000-3d20d62c97c33247cfcf	Spectrum
GC-MS	Ferulic acid, non-derivatized, GC-MS Spectrum	splash10-00ku-1965000000-ebee2a916fe97f0270a1	Spectrum
GC-MS	Ferulic acid, non-derivatized, GC-MS Spectrum	splash10-00di-9654000000-b3f1759076cffd2ac235	Spectrum
GC-MS	Ferulic acid, non-derivatized, GC-MS Spectrum	splash10-000m-3975000000-5a41c311d78f7219474c	Spectrum
GC-MS	Ferulic acid, non-derivatized, GC-MS Spectrum	splash10-00kv-1954000000-9dae07505bd18466be87	Spectrum
Predicted GC-MS	Ferulic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-002e-0900000000-d76b7991f2d90cb58bd5	Spectrum
Predicted GC-MS	Ferulic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-6094000000-b805979df23a0d890d7c	Spectrum
Predicted GC-MS	Ferulic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Ferulic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Ferulic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Ferulic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Ferulic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Ferulic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Ferulic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-004i-0900000000-d193da7a6efffdab2dbb	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00kr-7900000000-b5b8d28b28c8067c3932	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-002r-9000000000-d3616a5367a7a2a9b3c6	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positive	splash10-0006-1900000000-5dffac87fe7c815de4ce	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0006-0900000000-c173873ef0d975be6c34	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-001i-0900000000-0b9174ecaba08b2f01b9	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-001i-1900000000-eff77e27aef254928643	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-001r-9700000000-18946fad05ffb1f78a7d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-001r-9300000000-e2221a73d3d078bf6e03	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0002-0900000000-653c9a454414dd8b8b50	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-002b-0900000000-62b2ee8bf9571be3d97f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-001i-0900000000-a7cded21e6010eb8bce2	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-0900000000-c173873ef0d975be6c34	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001i-0900000000-0b9174ecaba08b2f01b9	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001i-1900000000-eff77e27aef254928643	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001r-9700000000-18946fad05ffb1f78a7d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001r-9300000000-e2221a73d3d078bf6e03	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-001i-0900000000-a7cded21e6010eb8bce2	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-002b-0900000000-cdced9ddbcdaedf2f1b9	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-0900000000-434fdd914ca34cd68f41	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0900000000-0dcbcad8bf6cb403f4f8	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0g31-5900000000-4fa9ed831b4e0d1573e5	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-29c8691e15490f8d88ac	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0900000000-e940f09e099b7acf3772	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00o1-1900000000-ee61087a069406e459c7	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, DMSO, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, DMSO, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
UDP-glucuronosyltransferase 1-1	UGT1A1	2q37	P22309	details
Sulfotransferase 1A3	SULT1A3		P0DMM9	details

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Cannabis Cultivar	Status	Value	Reference	Details
Alien Dawg	Detected and Quantified	0.0213 mg/g dry wt	David S. Wishart,...	details
Gabriola	Detected and Quantified	0.0108 mg/g dry wt	David S. Wishart,...	details
Island Honey	Detected and Quantified	0.0135 mg/g dry wt	David S. Wishart,...	details
Quadra	Detected and Quantified	0.00985 mg/g dry wt	David S. Wishart,...	details
Sensi Star	Detected and Quantified	0.0114 mg/g dry wt	David S. Wishart,...	details
Tangerine Dream	Detected and Quantified	0.0132 mg/g dry wt	David S. Wishart,...	details

External Links

HMDB ID

HMDB0000954

DrugBank ID

DB07767

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Ferulic_Acid

METLIN ID

4156

PubChem Compound

445858

PDB ID

Not Available

ChEBI ID

17620

References

General References

Mancuso C, Scapagini G, Curro D, Giuffrida Stella AM, De Marco C, Butterfield DA, Calabrese V: Mitochondrial dysfunction, free radical generation and cellular stress response in neurodegenerative disorders. Front Biosci. 2007 Jan 1;12:1107-23. doi: 10.2741/2130. [PubMed:17127365 ]
Graf E: Antioxidant potential of ferulic acid. Free Radic Biol Med. 1992 Oct;13(4):435-48. doi: 10.1016/0891-5849(92)90184-i. [PubMed:1398220 ]
Fukuoka K, Sawabe A, Sugimoto T, Koga M, Okuda H, Kitayama T, Shirai M, Komai K, Komemushi S, Matsuda K: Inhibitory actions of several natural products on proliferation of rat vascular smooth muscle cells induced by Hsp60 from Chlamydia pneumoniae J138. J Agric Food Chem. 2004 Oct 6;52(20):6326-9. doi: 10.1021/jf0351164. [PubMed:15453708 ]
Bourne LC, Rice-Evans C: Bioavailability of ferulic acid. Biochem Biophys Res Commun. 1998 Dec 18;253(2):222-7. doi: 10.1006/bbrc.1998.9681. [PubMed:9878519 ]
Huang Z, Dostal L, Rosazza JP: Microbial transformations of ferulic acid by Saccharomyces cerevisiae and Pseudomonas fluorescens. Appl Environ Microbiol. 1993 Jul;59(7):2244-50. [PubMed:8395165 ]

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Enzyme Details

2. Sulfotransferase 1A3

General function:: sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:: SULT1A3
Uniprot ID:: P0DMM9
Molecular weight:: 34195.96

Showing Compound Card for Ferulic acid (CDB000044)

Structure for CDB000044 (Ferulic acid)

Enzymes