NAV

(2E,4E)-2-Hydroxy-6-oxo-6-phenyl-2,4-hexadienoic acid

Identification

Generic Name
(2E,4E)-2-Hydroxy-6-oxo-6-phenyl-2,4-hexadienoic acid
DrugBank Accession Number
DB07915
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 218.2054
Monoisotopic: 218.057908808
Chemical Formula
C12H10O4
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-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolaseNot AvailableBurkholderia xenovorans (strain LB400)
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 medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Keto acids and derivatives
Sub Class
Medium-chain keto acids and derivatives
Direct Parent
Medium-chain keto acids and derivatives
Alternative Parents
Benzoyl derivatives / Aryl ketones / Hydroxy fatty acids / Unsaturated fatty acids / Enones / Acryloyl compounds / Monocarboxylic acids and derivatives / Enols / Carboxylic acids / Organic oxides
show 1 more
Substituents
Acryloyl-group / Alpha,beta-unsaturated ketone / Aromatic homomonocyclic compound / Aryl ketone / Benzenoid / Benzoyl / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Enol
show 12 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
RDRDHXDYMGUCKE-VCABWLAWSA-N
InChI
InChI=1S/C12H10O4/c13-10(9-5-2-1-3-6-9)7-4-8-11(14)12(15)16/h1-8,14H,(H,15,16)/b7-4+,11-8+
IUPAC Name
(2E,4E)-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
SMILES
OC(=O)C(\O)=C/C=C/C(=O)C1=CC=CC=C1

References

General References
Not Available
PubChem Substance
99444386
ChemSpider
16188846
ZINC
ZINC000100036081
PDBe Ligand
HPZ
PDB Entries
2puj

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 Solubility0.359 mg/mLALOGPS
logP1.63ALOGPS
logP1.72Chemaxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.25Chemaxon
pKa (Strongest Basic)-6.1Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area74.6 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity60.71 m3·mol-1Chemaxon
Polarizability21.7 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8583
Blood Brain Barrier+0.6344
Caco-2 permeable-0.5815
P-glycoprotein substrateNon-substrate0.6448
P-glycoprotein inhibitor INon-inhibitor0.9542
P-glycoprotein inhibitor IINon-inhibitor0.9853
Renal organic cation transporterNon-inhibitor0.9379
CYP450 2C9 substrateNon-substrate0.8587
CYP450 2D6 substrateNon-substrate0.9384
CYP450 3A4 substrateNon-substrate0.7455
CYP450 1A2 substrateNon-inhibitor0.834
CYP450 2C9 inhibitorNon-inhibitor0.8373
CYP450 2D6 inhibitorNon-inhibitor0.95
CYP450 2C19 inhibitorNon-inhibitor0.957
CYP450 3A4 inhibitorNon-inhibitor0.9384
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9543
Ames testNon AMES toxic0.9181
CarcinogenicityNon-carcinogens0.7922
BiodegradationReady biodegradable0.8809
Rat acute toxicity1.4253 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9771
hERG inhibition (predictor II)Non-inhibitor0.967
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-MSsplash10-0kmi-5930000000-3768455e82d1848e5092
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0aos-2920000000-d7fea4de108f0785fbe9
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0600-3900000000-361553a6cfc429f52187
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-1900000000-31ba791ce086449bc706
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0aor-3900000000-9ca6dd6b1346daa2161f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0kdi-6900000000-42048d70bed0a71063d1
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0gdm-9500000000-91c3bb6c959d5b7a0667
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]-152.65273
predicted
DeepCCS 1.0 (2019)
[M+H]+155.01073
predicted
DeepCCS 1.0 (2019)
[M+Na]+161.10387
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. 2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase
Kind
Protein
Organism
Burkholderia xenovorans (strain LB400)
Pharmacological action
Unknown
General Function
2-hydroxy-6-oxonona-2,4-dienedioate hydrolase activity
Specific Function
Catalyzes an unusual C-C bond hydrolysis of 2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid (HOPDA) to produce benzoic acid and 2-hydroxy-2,4-pentadienoic acid (HPD).
Gene Name
bphD
Uniprot ID
P47229
Uniprot Name
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase
Molecular Weight
32029.435 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 21:26 / Updated at June 12, 2020 16:52