Bovine Metabolome Database: Showing metabocard for trans-Ferulic acid (BMDB0000954)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:39:06 UTC

Update Date

2020-06-04 20:00:53 UTC

BMDB ID

BMDB0000954

Secondary Accession Numbers

BMDB00954

Metabolite Identification

Common Name

trans-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 an cinnamic acid where the benzene ring is hydroxylated. Ferulic acid exists in all living species, ranging from bacteria to plants to humans. Based on a literature review a significant number of articles have been published on Ferulic acid.

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

194.184

Monoisotopic Molecular Weight

194.057908808

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

Status

Expected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm

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	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-05g4-1978000000-1097d5b300514a0489df	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00kv-2964000000-3d20d62c97c33247cfcf	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00ku-1965000000-ebee2a916fe97f0270a1	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00di-9654000000-b3f1759076cffd2ac235	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-000m-3975000000-5a41c311d78f7219474c	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-1900000000-5dffac87fe7c815de4ce	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-2900000000-8db541bacfe47b9e0c8b	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-2900000000-a338415bd30d4e62e664	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-05g4-1978000000-1097d5b300514a0489df	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00kv-2964000000-3d20d62c97c33247cfcf	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00ku-1965000000-ebee2a916fe97f0270a1	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9654000000-b3f1759076cffd2ac235	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-000m-3975000000-5a41c311d78f7219474c	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00kv-1954000000-9dae07505bd18466be87	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-002e-0900000000-d76b7991f2d90cb58bd5	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00di-6094000000-b805979df23a0d890d7c	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-004i-0900000000-d193da7a6efffdab2dbb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00kr-7900000000-b5b8d28b28c8067c3932	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-002r-9000000000-d3616a5367a7a2a9b3c6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positive	splash10-0006-1900000000-5dffac87fe7c815de4ce	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0006-0900000000-c173873ef0d975be6c34	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-001i-0900000000-0b9174ecaba08b2f01b9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-001i-1900000000-eff77e27aef254928643	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-001r-9700000000-18946fad05ffb1f78a7d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-001r-9300000000-e2221a73d3d078bf6e03	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0002-0900000000-653c9a454414dd8b8b50	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-002b-0900000000-62b2ee8bf9571be3d97f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-001i-0900000000-a7cded21e6010eb8bce2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-0900000000-c173873ef0d975be6c34	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001i-0900000000-0b9174ecaba08b2f01b9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001i-1900000000-eff77e27aef254928643	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001r-9700000000-18946fad05ffb1f78a7d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001r-9300000000-e2221a73d3d078bf6e03	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-001i-0900000000-a7cded21e6010eb8bce2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-002b-0900000000-cdced9ddbcdaedf2f1b9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-0900000000-434fdd914ca34cd68f41	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0900000000-0dcbcad8bf6cb403f4f8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0g31-5900000000-4fa9ed831b4e0d1573e5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-29c8691e15490f8d88ac	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0900000000-e940f09e099b7acf3772	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00o1-1900000000-ee61087a069406e459c7	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-0006-5900000000-8c81de6c352294475072	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, DMSO-d6, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, DMSO, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, DMSO, experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Epidermis
Fibroblasts

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Epidermis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Fibroblasts	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000954

DrugBank ID

DB07767

Phenol Explorer Compound ID

FooDB 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

Synthesis Reference

Ou, Shiyi; Zhang, Jing; Bao, Huiyan; Zhang, Ning; Li, Aijun. Method for preparing oligosaccharide and trans-ferulic acid. Faming Zhuanli Shenqing Gongkai Shuomingshu (2003), 8 pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for trans-Ferulic acid (BMDB0000954)

Structure for BMDB0000954 (trans-Ferulic acid)