Isoferulic acid

Identification

Generic Name
Isoferulic acid
DrugBank Accession Number
DB07109
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 194.184
Monoisotopic: 194.057908808
Chemical Formula
C10H10O4
Synonyms
  • Hesperetic acid
  • Isoferulic acid
External IDs
  • NSC-51987

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids
show 5 more
Substituents
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
show 15 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
ferulic acids (CHEBI:27794)
Affected organisms
Not Available

Chemical Identifiers

UNII
XSQ2K2G7MC
CAS number
537-73-5
InChI Key
QURCVMIEKCOAJU-HWKANZROSA-N
InChI
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+
IUPAC Name
(2E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid
SMILES
COC1=C(O)C=C(\C=C\C(O)=O)C=C1

References

General References
Not Available
Human Metabolome Database
HMDB0000955
KEGG Compound
C10470
PubChem Compound
736186
PubChem Substance
99443580
ChemSpider
643318
BindingDB
50241245
ChEBI
27794
ChEMBL
CHEMBL233295
ZINC
ZINC000000156055
PDBe Ligand
4FE
Wikipedia
Isoferulic_acid
PDB Entries
3cbg

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility0.871 mg/mLALOGPS
logP1.56ALOGPS
logP1.67Chemaxon
logS-2.4ALOGPS
pKa (Strongest Acidic)3.58Chemaxon
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
Polarizability19.36 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
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-002e-0900000000-b51b390a0727d3838cab
Mass Spectrum (Electron Ionization)MSsplash10-0006-5900000000-db5f99d89dd9e349c86c
MS/MS Spectrum - Quattro_QQQ 10V, NegativeLC-MS/MSsplash10-004l-0900000000-ab3320c9d0dfcba00b6e
MS/MS Spectrum - Quattro_QQQ 25V, NegativeLC-MS/MSsplash10-001i-0900000000-2b9775043a4af5fdc064
MS/MS Spectrum - Quattro_QQQ 40V, NegativeLC-MS/MSsplash10-001i-0900000000-29fd32eacfaa52704559
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-0006-0900000000-d26e8f9f43c25710a04d
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-003r-0900000000-25d10f2b53d467937524
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-001i-0900000000-b2f1dd5274585c5f6b0b
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-001i-3900000000-2e21dbcbb598dba64525
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-001i-2900000000-7a28000b74f8c4f5b27f
MS/MS Spectrum - ESI-TOF 40V, NegativeLC-MS/MSsplash10-01p9-0920000000-7aaa9640d85177e2e6b5
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSsplash10-01p9-0920000000-7aaa9640d85177e2e6b5
MS/MS Spectrum - ESI-TOF 30V, NegativeLC-MS/MSsplash10-01p9-0920000000-7aaa9640d85177e2e6b5
MS/MS Spectrum - ESI-TOF 50V, NegativeLC-MS/MSsplash10-01p9-0920000000-7aaa9640d85177e2e6b5
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSsplash10-005l-0902100000-6fc8730bd28daa779b66
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSsplash10-005l-0902100000-6fc8730bd28daa779b66
MS/MS Spectrum - ESI-TOF 40V, NegativeLC-MS/MSsplash10-001i-0900000000-623ecba5385a03e0406b
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSsplash10-004i-0900000000-205ebeb435685d894bcf
MS/MS Spectrum - ESI-TOF 30V, NegativeLC-MS/MSsplash10-001i-0900000000-97eb2cfc1a86c4933f76
MS/MS Spectrum - ESI-TOF 50V, NegativeLC-MS/MSsplash10-001i-0900000000-49f1d1fd82311df29713
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSsplash10-005l-0902100000-6fc8730bd28daa779b66
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSsplash10-001i-0900000000-98a02290d6c361fab314
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-0900000000-d26e8f9f43c25710a04d
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-003r-0900000000-9243255b49d91db03480
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-001i-0900000000-16e965c4e3fe3823386d
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-001i-3900000000-2e21dbcbb598dba64525
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-001i-2900000000-7a28000b74f8c4f5b27f
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-001i-0900000000-623ecba5385a03e0406b
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-004i-0900000000-205ebeb435685d894bcf
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-001i-0900000000-97eb2cfc1a86c4933f76
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-001i-0900000000-49f1d1fd82311df29713
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-001i-0900000000-98a02290d6c361fab314
MS/MS Spectrum - , positiveLC-MS/MSsplash10-004s-3900000000-d57d0c2452d7165fde14
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-002b-0900000000-5e5b47827bffa960cc11
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0900000000-3c1a74b14de38c9fd2f2
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000t-0900000000-f78ef4f1c838f72646d2
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0900000000-71b8c3a4c72f7d9610f3
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-05o0-2900000000-43854b5947c41ef9fb06
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-8900000000-6159b281a58c91db9456
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-153.7124376
predicted
DarkChem Lite v0.1.0
[M-H]-154.2282376
predicted
DarkChem Lite v0.1.0
[M-H]-147.95692
predicted
DeepCCS 1.0 (2019)
[M+H]+155.0436376
predicted
DarkChem Lite v0.1.0
[M+H]+157.7287376
predicted
DarkChem Lite v0.1.0
[M+H]+150.31493
predicted
DeepCCS 1.0 (2019)
[M+Na]+153.3218376
predicted
DarkChem Lite v0.1.0
[M+Na]+154.7208376
predicted
DarkChem Lite v0.1.0
[M+Na]+156.40807
predicted
DeepCCS 1.0 (2019)

Targets

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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. [Article]

Drug created at September 15, 2010 21:18 / Updated at June 12, 2020 16:52