2-Hydroxybenzalpyruvate

Identification

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Name
2-Hydroxybenzalpyruvate
Accession Number
DB08636
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
Not Available
CAS number
90293-62-2
Weight
Average: 192.1681
Monoisotopic: 192.042258744
Chemical Formula
C10H8O4
InChI Key
HMXOGGUFCBUALL-AATRIKPKSA-N
InChI
InChI=1S/C10H8O4/c11-8-4-2-1-3-7(8)5-6-9(12)10(13)14/h1-6,11H,(H,13,14)/b6-5+
IUPAC Name
(3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoic acid
SMILES
OC(=O)C(=O)\C=C\C1=CC=CC=C1O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
U2-hydroxychromene-2-carboxylate isomeraseNot 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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Compound
C06203
PubChem Compound
5280911
PubChem Substance
99445107
ChemSpider
4444428
ChEBI
59354
HET
TOH

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 Solubility0.623 mg/mLALOGPS
logP1.86ALOGPS
logP2.12ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)2.93ChemAxon
pKa (Strongest Basic)-6.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity50.39 m3·mol-1ChemAxon
Polarizability18.48 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9508
Blood Brain Barrier+0.6423
Caco-2 permeable+0.5212
P-glycoprotein substrateNon-substrate0.677
P-glycoprotein inhibitor INon-inhibitor0.948
P-glycoprotein inhibitor IINon-inhibitor0.9734
Renal organic cation transporterNon-inhibitor0.9302
CYP450 2C9 substrateNon-substrate0.7986
CYP450 2D6 substrateNon-substrate0.9157
CYP450 3A4 substrateNon-substrate0.7191
CYP450 1A2 substrateNon-inhibitor0.9509
CYP450 2C9 inhibitorNon-inhibitor0.7709
CYP450 2D6 inhibitorNon-inhibitor0.9192
CYP450 2C19 inhibitorNon-inhibitor0.8728
CYP450 3A4 inhibitorNon-inhibitor0.935
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9354
Ames testNon AMES toxic0.96
CarcinogenicityNon-carcinogens0.8992
BiodegradationReady biodegradable0.7722
Rat acute toxicity1.5021 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9738
hERG inhibition (predictor II)Non-inhibitor0.9683
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-MSNot Available
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

Taxonomy

Description
This compound belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. These are compounds containing an cinnamic acid (or a derivative thereof) 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 and derivatives
Alternative Parents
Styrenes / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Alpha-keto acids and derivatives / Enones / Alpha-hydroxy ketones / Acryloyl compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides
show 1 more
Substituents
Hydroxycinnamic acid or derivatives / Styrene / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Alpha-keto acid / Benzenoid / Monocyclic benzene moiety / Keto acid / Acryloyl-group
show 13 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
2-oxo monocarboxylic acid (CHEBI:59354)

Targets

Kind
Protein
Organism
Pseudomonas putida
Pharmacological action
Unknown
General Function
Protein disulfide oxidoreductase activity
Specific Function
Involved in the naphthalene catabolic pathway. Catalyzes the reversible glutathione-dependent isomerization of 2-hydroxychromene-2-carboxylate (HCCA) to trans-O-hydroxybenzylidenepyruvate (THBPA).
Gene Name
nahD
Uniprot ID
Q51948
Uniprot Name
2-hydroxychromene-2-carboxylate isomerase
Molecular Weight
23061.0 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 15:33 / Updated on August 02, 2019 08:28