NAV

2-Oxo-3-Pentenoic Acid

Identification

Generic Name
2-Oxo-3-Pentenoic Acid
DrugBank Accession Number
DB02005
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 114.0993
Monoisotopic: 114.031694058
Chemical Formula
C5H6O3
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
U2-hydroxymuconate tautomeraseNot AvailablePseudomonas putida
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
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Keto acids and derivatives
Sub Class
Short-chain keto acids and derivatives
Direct Parent
Short-chain keto acids and derivatives
Alternative Parents
Methyl-branched fatty acids / Unsaturated fatty acids / Alpha-keto acids and derivatives / Enones / Alpha-hydroxy ketones / Acryloyl compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives
Substituents
Acryloyl-group / Aliphatic acyclic compound / Alpha,beta-unsaturated ketone / Alpha-hydroxy ketone / Alpha-keto acid / Branched fatty acid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Enone
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
IWARWSDDJHGZOW-IHWYPQMZSA-N
InChI
InChI=1S/C5H6O3/c1-2-3-4(6)5(7)8/h2-3H,1H3,(H,7,8)/b3-2-
IUPAC Name
(3Z)-2-oxopent-3-enoic acid
SMILES
[H]\C(C)=C(/[H])C(=O)C(O)=O

References

General References
Not Available
PubChem Compound
5289089
PubChem Substance
46504701
ChemSpider
4451123
PDBe Ligand
OXP
PDB Entries
1bjp

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 Solubility19.8 mg/mLALOGPS
logP0.77ALOGPS
logP1.21Chemaxon
logS-0.76ALOGPS
pKa (Strongest Acidic)3.13Chemaxon
pKa (Strongest Basic)-9.7Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area54.37 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity28.31 m3·mol-1Chemaxon
Polarizability10.5 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9879
Blood Brain Barrier+0.9394
Caco-2 permeable-0.6455
P-glycoprotein substrateNon-substrate0.7912
P-glycoprotein inhibitor INon-inhibitor0.9244
P-glycoprotein inhibitor IINon-inhibitor0.9366
Renal organic cation transporterNon-inhibitor0.9491
CYP450 2C9 substrateNon-substrate0.7713
CYP450 2D6 substrateNon-substrate0.9396
CYP450 3A4 substrateNon-substrate0.7604
CYP450 1A2 substrateNon-inhibitor0.9651
CYP450 2C9 inhibitorNon-inhibitor0.9383
CYP450 2D6 inhibitorNon-inhibitor0.9661
CYP450 2C19 inhibitorNon-inhibitor0.9706
CYP450 3A4 inhibitorNon-inhibitor0.978
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9853
Ames testNon AMES toxic0.6767
CarcinogenicityCarcinogens 0.5187
BiodegradationReady biodegradable0.8522
Rat acute toxicity2.0407 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9847
hERG inhibition (predictor II)Non-inhibitor0.9826
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-MSsplash10-016u-9000000000-ebe3b293dd4c0df20818
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014l-9000000000-2695a599edb5307c03cd
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-9000000000-04598d27631c94e68a38
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-cbfee20c16d6edf30e45
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-4d6c3f89a1c5ee1a1041
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0gb9-9000000000-94ac57aaf902dbbb9c57
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udl-9000000000-0dba352ccadb35ad25c8
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-127.15573
predicted
DeepCCS 1.0 (2019)
[M+H]+129.83534
predicted
DeepCCS 1.0 (2019)
[M+Na]+138.65305
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. 2-hydroxymuconate tautomerase
Kind
Protein
Organism
Pseudomonas putida
Pharmacological action
Unknown
General Function
Isomerase activity
Specific Function
Catalyzes the ketonization of 2-hydroxymuconate stereoselectively to yield 2-oxo-3-hexenedioate.
Gene Name
xylH
Uniprot ID
Q01468
Uniprot Name
2-hydroxymuconate tautomerase
Molecular Weight
6941.95 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52