(2Z,4E)-3-chloro-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid

Identification

Generic Name
(2Z,4E)-3-chloro-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
DrugBank Accession Number
DB07516
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 252.65
Monoisotopic: 252.018936483
Chemical Formula
C12H9ClO4
Synonyms
Not Available

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 / Halogenated fatty acids / Unsaturated fatty acids / Vinylogous halides / Enones / Acryloyl compounds / Vinyl chlorides / Monocarboxylic acids and derivatives
show 5 more
Substituents
Acryloyl-group / Alpha,beta-unsaturated ketone / Aromatic homomonocyclic compound / Aryl ketone / Benzenoid / Benzoyl / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Chloroalkene
show 19 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
IBJDCVXDXGFGIO-FKTQTOOFSA-N
InChI
InChI=1S/C12H9ClO4/c13-9(11(15)12(16)17)6-7-10(14)8-4-2-1-3-5-8/h1-7,15H,(H,16,17)/b7-6+,11-9-
IUPAC Name
(2Z,4E)-3-chloro-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
SMILES
OC(=O)C(\O)=C(\Cl)/C=C/C(=O)C1=CC=CC=C1

References

General References
Not Available
PubChem Compound
17749729
PubChem Substance
99443987
ChemSpider
22376702
ZINC
ZINC000100035584
PDBe Ligand
C1E
PDB Entries
2rht / 4lxh

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 Solubility0.0692 mg/mLALOGPS
logP2.1ALOGPS
logP1.96Chemaxon
logS-3.6ALOGPS
pKa (Strongest Acidic)3.05Chemaxon
pKa (Strongest Basic)-6.8Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area74.6 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity65.43 m3·mol-1Chemaxon
Polarizability23.75 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9401
Blood Brain Barrier+0.7917
Caco-2 permeable-0.531
P-glycoprotein substrateNon-substrate0.6893
P-glycoprotein inhibitor INon-inhibitor0.9672
P-glycoprotein inhibitor IINon-inhibitor0.987
Renal organic cation transporterNon-inhibitor0.939
CYP450 2C9 substrateNon-substrate0.8398
CYP450 2D6 substrateNon-substrate0.9304
CYP450 3A4 substrateNon-substrate0.697
CYP450 1A2 substrateNon-inhibitor0.5902
CYP450 2C9 inhibitorNon-inhibitor0.835
CYP450 2D6 inhibitorNon-inhibitor0.8967
CYP450 2C19 inhibitorNon-inhibitor0.8319
CYP450 3A4 inhibitorNon-inhibitor0.8998
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9598
Ames testNon AMES toxic0.5935
CarcinogenicityNon-carcinogens0.7144
BiodegradationNot ready biodegradable0.599
Rat acute toxicity1.8849 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9833
hERG inhibition (predictor II)Non-inhibitor0.9536
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-MSsplash10-0a4i-9770000000-ca7b553ade117f7dfa5a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ufr-1950000000-a844ce6eddae2cb52bda
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-1920000000-5589dda8a531ce97be9a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9600000000-995cb73a7f2109552c0c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a6r-0900000000-ca98f7bb462a14ace55d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9300000000-5f22a1412881e30697f0
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0pdi-5900000000-b4c7c31670e90abd7041
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]-158.88354
predicted
DeepCCS 1.0 (2019)
[M+H]+161.24156
predicted
DeepCCS 1.0 (2019)
[M+Na]+167.3347
predicted
DeepCCS 1.0 (2019)

Targets

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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 21:23 / Updated at June 12, 2020 16:52