Ferulic acid

Identification

Name
Ferulic acid
Accession Number
DB07767
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
NSC-2821 / NSC-51986 / NSC-674320
Categories
UNII
AVM951ZWST
CAS number
1135-24-6
Weight
Average: 194.184
Monoisotopic: 194.057908808
Chemical Formula
C10H10O4
InChI Key
KSEBMYQBYZTDHS-HWKANZROSA-N
InChI
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+
IUPAC Name
(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid
SMILES
COC1=CC(\C=C\C(O)=O)=CC=C1O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UEndo-1,4-beta-xylanase YNot AvailableClostridium thermocellum
UEndo-1,4-beta-xylanase ZNot AvailableClostridium thermocellum (strain ATCC 27405 / DSM 1237)
UEst1eNot AvailableButyrivibrio proteoclasticus
UO-methyltransferaseNot AvailableSynechocystis sp. (strain PCC 6803 / Kazusa)
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(1,2,6,7-3H)TestosteroneThe therapeutic efficacy of Ferulic acid can be increased when used in combination with (1,2,6,7-3H)Testosterone.
(R)-warfarinThe risk or severity of bleeding can be increased when Ferulic acid is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Ferulic acid is combined with (S)-Warfarin.
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid may increase the hypotensive activities of Ferulic acid.
1-TestosteroneThe therapeutic efficacy of Ferulic acid can be increased when used in combination with 1-Testosterone.
18-methyl-19-nortestosteroneThe therapeutic efficacy of Ferulic acid can be increased when used in combination with 18-methyl-19-nortestosterone.
4-hydroxycoumarinThe risk or severity of bleeding can be increased when Ferulic acid is combined with 4-hydroxycoumarin.
4-HydroxytestosteroneThe therapeutic efficacy of Ferulic acid can be increased when used in combination with 4-Hydroxytestosterone.
5beta-dihydrotestosteroneThe therapeutic efficacy of Ferulic acid can be increased when used in combination with 5beta-dihydrotestosterone.
AbciximabThe risk or severity of bleeding can be increased when Abciximab is combined with Ferulic acid.
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0000954
KEGG Compound
C01494
PubChem Compound
445858
PubChem Substance
99444238
ChemSpider
393368
BindingDB
50214744
ChEBI
17620
ChEMBL
CHEMBL32749
HET
FER
Wikipedia
Ferulic_acid
PDB Entries
1gkl / 1gw2 / 1gwt / 1jt2 / 1kyz / 1uwc / 2bjh / 2bnj / 2wtn / 3cbg
show 10 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.906 mg/mLALOGPS
logP1.58ALOGPS
logP1.67ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)3.77ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity51.5 m3·mol-1ChemAxon
Polarizability19.18 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9614
Blood Brain Barrier-0.5305
Caco-2 permeable+0.7183
P-glycoprotein substrateNon-substrate0.5662
P-glycoprotein inhibitor INon-inhibitor0.9018
P-glycoprotein inhibitor IINon-inhibitor0.8895
Renal organic cation transporterNon-inhibitor0.9086
CYP450 2C9 substrateNon-substrate0.7464
CYP450 2D6 substrateNon-substrate0.8922
CYP450 3A4 substrateNon-substrate0.6289
CYP450 1A2 substrateNon-inhibitor0.7513
CYP450 2C9 inhibitorNon-inhibitor0.5793
CYP450 2D6 inhibitorNon-inhibitor0.9588
CYP450 2C19 inhibitorNon-inhibitor0.6276
CYP450 3A4 inhibitorNon-inhibitor0.924
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7745
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.9076
BiodegradationReady biodegradable0.7554
Rat acute toxicity1.4314 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9754
hERG inhibition (predictor II)Non-inhibitor0.9575
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-05g4-1978000000-1097d5b300514a0489df
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-00kv-2964000000-3d20d62c97c33247cfcf
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-00ku-1965000000-ebee2a916fe97f0270a1
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-00di-9654000000-b3f1759076cffd2ac235
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-000m-3975000000-5a41c311d78f7219474c
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0006-1900000000-5dffac87fe7c815de4ce
GC-MS Spectrum - EI-BGC-MSsplash10-0006-2900000000-8db541bacfe47b9e0c8b
GC-MS Spectrum - EI-BGC-MSsplash10-0006-2900000000-a338415bd30d4e62e664
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-05g4-1978000000-1097d5b300514a0489df
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00kv-2964000000-3d20d62c97c33247cfcf
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00ku-1965000000-ebee2a916fe97f0270a1
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-9654000000-b3f1759076cffd2ac235
GC-MS Spectrum - GC-MSGC-MSsplash10-000m-3975000000-5a41c311d78f7219474c
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00kv-1954000000-9dae07505bd18466be87
Mass Spectrum (Electron Ionization)MSsplash10-0006-5900000000-8c81de6c352294475072
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-004i-0900000000-d193da7a6efffdab2dbb
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-00kr-7900000000-b5b8d28b28c8067c3932
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-002r-9000000000-d3616a5367a7a2a9b3c6
MS/MS Spectrum - EI-B (HITACHI M-52) , PositiveLC-MS/MSsplash10-0006-1900000000-5dffac87fe7c815de4ce
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-0006-0900000000-c173873ef0d975be6c34
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-001i-0900000000-0b9174ecaba08b2f01b9
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-001i-1900000000-eff77e27aef254928643
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-001r-9700000000-18946fad05ffb1f78a7d
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-001r-9300000000-e2221a73d3d078bf6e03
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-0002-0900000000-653c9a454414dd8b8b50
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, PositiveLC-MS/MSsplash10-002b-0900000000-62b2ee8bf9571be3d97f
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-001i-0900000000-a7cded21e6010eb8bce2
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-0900000000-c173873ef0d975be6c34
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-001i-0900000000-0b9174ecaba08b2f01b9
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-001i-1900000000-eff77e27aef254928643
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-001r-9700000000-18946fad05ffb1f78a7d
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-001r-9300000000-e2221a73d3d078bf6e03
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-001i-0900000000-a7cded21e6010eb8bce2
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-002b-0900000000-cdced9ddbcdaedf2f1b9
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-002b-0900000000-df06f7f58486ac25c21b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0002-0900000000-653c9a454414dd8b8b50
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-002b-0900000000-62b2ee8bf9571be3d97f
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-000j-0900000000-1ef88466d8544694f557
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-000j-0900000000-bb82c87030f6232d5663
MS/MS Spectrum - , positiveLC-MS/MSsplash10-002b-2921111101-6d1aa599f0f132a3695d
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as hydroxycinnamic acids. These 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
Coumaric acids and derivatives / Cinnamic acids / Methoxyphenols / Styrenes / Phenoxy compounds / Methoxybenzenes / Anisoles / Alkyl aryl ethers / 1-hydroxy-2-unsubstituted benzenoids / Monocarboxylic acids and derivatives
show 4 more
Substituents
Cinnamic acid / Coumaric acid or derivatives / Hydroxycinnamic acid / Methoxyphenol / Phenoxy compound / Anisole / Methoxybenzene / Styrene / Phenol ether / 1-hydroxy-2-unsubstituted benzenoid
show 14 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
ferulic acids (CHEBI:17620) / Coniferyl alcohol derivatives (C01494)

Targets

Kind
Protein
Organism
Clostridium thermocellum
Pharmacological action
Unknown
General Function
Endo-1,4-beta-xylanase activity
Specific Function
Not Available
Gene Name
xynY
Uniprot ID
P51584
Uniprot Name
Endo-1,4-beta-xylanase Y
Molecular Weight
119671.86 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Clostridium thermocellum (strain ATCC 27405 / DSM 1237)
Pharmacological action
Unknown
General Function
Xylan endo-1,3-beta-xylosidase activity
Specific Function
Not Available
Gene Name
xynZ
Uniprot ID
P10478
Uniprot Name
Endo-1,4-beta-xylanase Z
Molecular Weight
92262.3 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Butyrivibrio proteoclasticus
Pharmacological action
Unknown
General Function
Not Available
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
D2YW37
Uniprot Name
Est1e
Molecular Weight
28020.97 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Synechocystis sp. (strain PCC 6803 / Kazusa)
Pharmacological action
Unknown
General Function
O-methyltransferase activity
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
Q55813
Uniprot Name
O-methyltransferase
Molecular Weight
24312.805 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on September 15, 2010 15:25 / Updated on November 02, 2018 06:38